june 2024 to issue a ruling. chief justice roberts: next in case 22-842, national rifle association of america v. vullo. mr. cole? mr. cole: mr. chief justice, and may it please the court, government officials are free to urge people not to support political groups they oppose, but they cannot use their regulatory might to add "or else" to that request. respondent vullo did just that, not content to rely on the force of her ideas, she used the coercive power of her office. in february 2018 she told lloyds, the insurance underwriter, that she would go easy on its unrelated insurance violations if it aided her campaign to weaken the nra by

halting all duties with the group. lloyds agreed. six weeks later she issued guidance letters and a press release directing the thousands of banks and insurance companies that she directly overseas to cut off their ties with the nra, not because of any alleged illegality, but because they promote guns. in the accompanying press release vullo's boss and codefendant, governor andrew cuomo, said he directed vullo to issue the guidance because doing business with the nra "sends the wrong message." shortly thereafter, vullo extracted legally binding consent orders from the nra's three principal insurance providers barring them from ever providing insurance to the group ever again no matter how lawfully they do so. these actions worked as multiple financial institutions refused to do business with the nra, citing vullo's threats. this was not about enforcing insurance law or government

speech. it was a campaign by the state's highest political officials to use their power to coerce a a boycott of a political advocacy organization because they disagreed with its advocacy. governor cuomo essentially conceded as much in two tweets responding to this lawsuit in which he said, "the regulations new york put in place are working. we are forcing the nra into financial jeopardy. we won't stop until we shut them down. it is time to put the gun lobby out of business. #bankruptthenra." the only question is whether these allegations taken as a whole plausibly plead a first amendment claim. because vullo chose coercion over persuasion, they do. i welcome the court's questions. justice thomas: mr. cole, what is the protected speech that you allege has been suppressed?

mr. cole: promoting guns. advocating for gun rights. sending the wrong message. it is precisely the speech of the nra which caused mr. col and cuomo -- which caused vullo and cuomo to decide to target their partners and seek to coerce them into boycotting the nra. they are seeking to penalize the nra because of its speech advocating for gun rights. justice thomas: so your argument is that the sanctions on a third party suppressed the speech of nra? mr. cole: your honor, the court's first amendment restrictions does not require proof of suppression, it requires proof of burden. it is legal to propose on dollars fine -- a $1 fine. here we have actually alleged --

it has cost the nra millions of dollars as a result of the kinds of coercion that has been put in place here, and the nra like any other advocacy group relies on banks, relies on insurance companies to be able to do their business. and what is the business? political advocacy. justice kagan: isn't the issue of coercion different than the first amendment question? you are relying i think bantam books, is that correct? mr. cole: yes. >> as i read that case, there were two things going on. there was unconstitutional prior restraint, and the court recognized that, and there was the limitation of the unconstitutional restraint through the means of government coercion. so if i'm right about that in terms of how we should be thinking about bantam books, then don't we have two different questions here, the first being did vullo actually coerce any regulated entities to do

something vis-a-vis the nra, and then was that something a violation of the nra's first amendment rights, say through retaliation or censorship, the two first amendment theories i pick up from your complaint? mr. cole: justice jackson, i think what bantam books stands for is government officials are free to encourage people to take down speech or to penalize a group. what they are not free to do is to use coercion to that end. here there is no question on this record that they encouraged people to punish the nra precisely because, and only because of its political views. justice jackson: no, i understand that -- no, no, but there are two different pieces, right? you have to show there is coercion, and you allege that, but you also have to show that that coercion resulted in a first amendment violation.

bantam books is saying you can't do indirectly what you -- right, what you can't do directly. but the direct thinking bantam books was prior restraint. this here doesn't look like prior restraint, so what is your -- this is justice thomas's question again, what is your theory of the first amendment? mr. cole: again, it is the same answer as to justice thomas. of course the first amendment prohibits absolute censorship or suppression of speech, but it also prohibits the imposition of any burden on speech because of its content. even if the government denies a contract to an entity because it disapproves of -- justice jackson: right, but isn't the hard part figuring out whether or not the burden is being imposed because the content of the speech or because of the conduct? that is where we have to be really careful about what you are alleging is a first amendment problem, because the government can regulate conduct. mr. cole: i agree, and if this was a case where the government had said the nra is violating the law left and right and we

have to respond to that, and here are the legal obligations, that would be one thing. that is not what they said. they said "we want to shut the nra down, we want to put the gun lobby out of business." the title of the guidance letters that she issues are guidance regarding the nra and other gun-promotion organizations. the whole guidance is saying i don't like the fact that people use guns, i don't like the fact that people advocate for the use of guns, we need to stop this, we need -- justice jackson: isn't that her motivation? that sounds to me more like a retaliation kind of first amendment theory, as opposed to something that is happening in bantam books, which is pressure being applied to actual entit ies that themselves are speech distributors, so that those entities are censoring the speech in their power because

they are the kinds of things, but distributors, etc. -- book distributors, etc. these are insurance companies who are being pressured, so it is at least attenuated in that sense, the impact on speech, correct? mr. cole: so if the government were providing insurance, you have a contract -- let's say provides some sort of insurance to advocacy organizations and said "we will give insurance to some but we are not going to give it to advocacy organizations that disagree with us and promote guns." that would be a clear violation of the first amendment. it would not be censorship, it would not be suppression, but it would be a penalty imposed because of the viewpoint expressed by the organization. in this case, maria vullo herself and governor cuomo made it absolutely clear both enclosed-door -- both in closed-door meetings with lloyd's and public guidance letters and in tweets that they were singling out the nra not for insurance law violations.

they were singling out the nra because it promoted guns and they were against the promotion of guns. they can advocate against the promotion of guns, they can encourage people not to support groups like the nra. what they can't do is invoke the coercive authority of the office. look at the guidance letters. she could have written an op-ed if she was moved by the problems of gun violence. what she didn't. she -- but she didn't. she invoke her unique statutory authority to issue guidance letters. what are guidance letters? according to respondent, they are designed to help regulate -- tell regulated entities their obligations. in the guidance letter she goes on for four paragraphs about how bad guns are in the fifth paragraph says "in light of the above, we urge you to reconsider your relations with the nra and other gun promotion organizations." no evidence that other gun promotion organizations are involved in any insurance illegality or anything. "and reconsider your risks and manage those risks, take prompt

action." and then she issues a press release that same date in which she says cut your ties. justice barrett: are you asking the court to break any new ground in this case? mr. cole: absolutely not. this is about as square corners of the bantam books case as you can imagine. justice barrett: how does your understanding of bantam books differ if at all from respondent s in sg? mr. cole: sg is in support of our side on this case, reversal on the merits question. do believe you have to demonstrate coercion, you have to demonstrate some coercive threat, some invocation of regulatory adverse action. we have that here. we have it with the insurance law enforcement, we have it with the invocation of reputational risk. reputational risk -- she didn't gestate guns are bad -- didn't just say guns are bad, you

should reconsider your relationship with the nra. she said guns are bad and you should reconsider -- justice kagan: that idea of reputational risk is a real idea. it wasn't invented for the nra. there is a view that bank regulators have that companies are supposed to look at their reputational risks. mr. cole: right. justice kagan: so how do we know -- obviously a lot about guns in that letter, but it might be that gun advocacy groups, gun companies do impose reputational risks of the kind that bank regulators are concerned about. so, how do we know? mr. cole: i don't think you actually have to make that decision, justice kagan. the question under bantam books, there is two elements of bantam books -- did the government urge third parties to penalize or suppress speech, one, and two, did they use coercion to effectuate that encouragement?

the invocation of reputational risk is the use of coercion whether or not it is in fact a reputational risk or not. it is still the use of the coercive authority of the state to encourage these entities to punish the nra because of its speech, to cut their ties. that is number one. number two, look at the lloyd's meeting. there is no discussion about reputational risk there. justice kagan: i put the lloyd's meeting in a different category, it was really more interested -- this is a closer one. if reputational risk is a real thing, and gun companies or gun advocacy groups imposed that kind of reputational risk, isn't it a bank regulator's job to point that out? mr. cole: so, it may well be -- inventor books the court says there is a safe harbor for genuine advice about law enforcement. this was not genuine advice about law enforcement.

why would she spend four paragraphs denouncing guns -- that has nothing to do with whether there is reputational risk, that has everything to do with what she said in the meeting with lloyd's she was trying to do, leverage her authority to weaken the nra because she disagreed with its political viewpoints. so yes, reputational risk if he was deployed in a contract-neutral way to address conduct that raises reputational risk, that is one thing. if you use it -- it is a very broad term -- if you use it to target a particular political group because you disagree with its point of view anyone announced that in your -- in the very document in which you are doing it and in the press release in which, again, andrew cuomo says "i directed her to issue the guidance because doing business with the nra sends the wrong message," that does not create reputational risk. it supports an organization that i as governor disagree with. and he can disagree with it, he

can urge people not to support it. what he can't do is, again, invoke the coercive power of the state in this way. and whether or not there is a reputational risk or not, i don't think ultimately changes the outcome if you are using coercive authority. take bantam books. suppose inventive books the commission had, instead of sending the police to visit and say, hey, how's it going, take the books down, they said we are going to send the police to the bookstores that continue to sell these books and issue code violations. and they found code violations and enforced to this code violations against those bookstores. that would be illegal activity. the code violations is illegal activity. there is nothing illegitimate about looking into code violations, but if you are doing it to give coercive power to a government effort to encourage a third party to suppress speech,

it violates the first amendment. justice barrett: mr. cole, speaking of violations, your friends on the other site claim you have not made the adequate showing for retaliation claim. how do you visiting wish been debugged -- distinguish inventive books -- is it just a pleading choice? mr. cole: this is a question about whether the first amendment, the scope of the first amendment was violated by these actions. it's about whether there was a particular remedy, particular damages remedy. we have an injunctive relief claim in this case which continues to be live and which would, i think, a properly required taking down the guidance letters which remain on the new york dfs website to this day warning businesses not to do business with the nra. so the injunctive claim takes it out altogether. i don't think it is appropriate.

this is the case -- remember, where the government officials have adopted an official policy of targeting speech on a matter of concern, public concern for retaliation, that is a straightforward toleration case, not healthy. the requirements don't apply. i think -- this case would have to go forward. but i don't think it was appropriate. it wasn't raised in the op, and they waive the argument. finally i would say -- hartman were identified as narrow exceptions for the criminal context. it has never extended to the administrative law enforcement context, and there would be very serious questions about doing that.

we have clearly made out a case -- all you have to demonstrate is as justice alito was saying that you have identified that they have targeted you for some adverse action and they did so in the substantial motivating factor was your speech. they have admitted as much in public statements as well as private back door meetings. we clearly need to mount healthy and it would be open to them on a child to say we have alternative theories -- on a trial to say we have alternative theories. those are open to them on the trial. chief justice roberts: justice thomas? justice alito? justice alito: on the question of the meaning of coercion, i can think on the spectrum -- one end of the spectrum, a government official says, look,

suppress this speech, and if you don't do it, i have legal weapons i can use against you and i'm going to punish you for using those. very clear coercion. at the other end, the government official who has no authority to do anything for any practical purposes to that entity that the government official is speaking to says you should do this, it would be a good thing to do, you would be a good citizen if you did it. in between, there are a lot of different gradations, particularly when the official making this request has that power, and you have to assume the person or the entity to whom or to which the request is being made does matter. just as i am sure that these insurance companies were well aware of the power of ms. vullo. how do you define when it goes too far along that line? mr. cole: so, i do think that

the power of the official over those to whom she is speaking is a relevant factor in this assessment. but the assessment at the end of the day, what a reasonable person in the situation feel that the government is coercing it, that it is applying some sort of threat of action against it. so the mere fact that someone exercises regulatory power over you i don't think is sufficient. but when combined with what you have here, exclusive intent to punish a group because of its advocacy and the invocation of the very tools she has to make life miserable for them, you are not managing reputational risk. we might fine you, or you have these technical insurance infections where you might go after your partners and require them to never provide you affinity insurance ever again. this is on the first end of the

spectrum that you identified, justice alito. i agree there are hard cases than the middle, and that is true of any standard that at the end of the day looks at coercion, knowing the context of confessions. there are hard lines to draw. this is not. justice jackson the solicitor -- justice alito: the solicitor general urges us not to consider the enforcement actions against lloyd's and chubbs and the consent decrees, and it argues that the district court held that those actions are entitled to absolute prosecutorial immunity, and petitioner has not challenged that holding here. do you want to comment on that? mr. cole: yes, thank you. respondent never asserted absolute immunity with respect to the bantam books, the first amendment claims in this case. absolute immunity was asserted

with respect to a separate enforcement claim. they chose with respect to the first amendment comes to only assert qualified immunity. it was not asserted below, it was not asserted in the court of appeals, it was not raised in the bio, it is not appropriate for this court to decide at this stage. chief justice roberts: just a certain -- justice sotomayor? justice sotomayor: tell me -- i'm going to ask sg this question -- how do we write this case for you that would differ from how you think the sg would write it? justice barrett asked whether you are breaking new ground, and you said "i'm not." but it seems to me you are trying to in the way you are putting this. there is a lot about the guidance letters that you agree standing on their own would be ok. i'm still not sure that if the

february 18 meeting had not happened that standing alone, that guidance letter as written would necessarily be coercion. i'm not sure the consent decrees could be viewed as a selective prosecution when there is no question, i don't believe, that the carry guard had provisions, carry guard insurance policies had provisions that violated new york law. they reimbursed for criminal activity and they reimbursed for intentional acts, which new york insurance law clearly says you can't do. so standing alone, none of these things might be coercive. i see this as in light of the february 18 meeting. these things now, which is how the district court ruled. so how would you write it

differently than the district court did, number one, and number two, how would you write it differently than the sg did? mr. cole: i would write it that bantam books holds that when government officials encourage third parties to penalize a speaker because of its views, they cannot use coercion to further that end. here, respondent -- justice sotomayor: and what -- mr. cole: the threat implicit and explicit, my friend agree they can be implicit and exquisite, of course of -- implicit and exquisite, of course, of government action, that is coercion. and here she exquisitely threatened that to lloyd's, she says "i will go easy on you if you cut ties on the nra," same as i will go hard on you if you don't cut ties to the nra. she invoked her authority to punish organizations, financial institutions, with respect to

failure to manage reputational risk, and made it clear that what she meant by "manage reputational risk" was cut your ties with the nra. and then she very shortly thereafter announced these consent orders with three of the nra's principal insurance providers in which she not only punishes them for insurance infractions, but imposes an extraordinary ban, a lifetime ban in perpetuity. these organizations can never provide affinity insurance to the nra even if every t's crossed and every i is dotted under new york law. with respect to chubb, one of the three, she got them to agree to not provide insurance to the nra anywhere in the country, not just in new york. she has no jurisdiction out there. when you look at those three, under bantam books you have to look at the government's action as a whole. you see that she encouraged

third parties -- justice sotomayor: you still haven't told me how you're going to write it -- mr. cole: the only difference between the sg and us is the sg says the guidance letters might be a closer question but they support the allegation that you targeted this group and sought to use coercion. and then they say with respect to the consent letter there was absolute immunity, but as i had the discussion with justice alito, they didn't asserted absolute immunity with respect to the first amendment claim that comes out of the consent letter. justice sotomayor: thank you. chief justice roberts: justice kagan? justice gorsuch? justice gorsuch: we've gone back and forth all morning about the standard. but you have a first amendment retaliation claim in this case, and we often look at retaliation in the title vii context. just the matter you described, the effect it would have on a reasonable person in the circumstances do you see any daylight between those two standards?

mr. cole: in terms of defining what constitutes adverse action? justice gorsuch: right. mr. cole: i'm not sure that there is. i don't know that for this case one has to look very hard to see adverse action, when you see a concerted campaign, milling dollars f -- million-dollar fines, and explicit threat to a major insurance provider, we are going to go hard on you if you don't cut your ties with the nra . in that context this is clearly an adverse action under title vii, under any english-language understanding. justice gorsuch: retaliation is a familiar concept in a lot of our case law. mr. cole: and i think, look -- justice gorsuch: they have gray-area cases, all of them. mr. cole: bantam books and retaliation are slightly different in the way they conceptualize the first amendment violation. bantam books encouraging a third party to punish speech with

coercion. justice gorsuch: can we look at the lloyd's incident in isolation? you have a complaint, you have to take inferences in your favor. certainly don't want to be limited on remand up to arguing just the lloyd's incident as her case. mr. cole: well, that's right. right now the most significant harm to the nra is that the dfs continues to maintain on its website these guidance letters which essentially put a scarlet letter on the nra with respect to every bank and insurance company in new york. those should be taken down. we would urge you both for purposes of guidance to others and because it matters to the ultimate remedy in this case to address the meaning of -- meeting of lloyd's, the guidance

letters, and the subsequent enforcement action. the other thing i would say about the meeting with lloyd's was it was in private. it was in private. the nra might have suffered some damages vis-a-vis lloyd's, with respect to that meeting, but the real damage in terms of putting the scarlet letter on the nra comes from her public actions and governor cuomo's public actions to issue these guidance letters. so i would urge you to address the whole picture here, to reinforce bantam books, and to reverse on the merits. chief justice roberts: justice kavanaugh? justice kavanaugh: quickly, your view on the four-part test? mr. cole: i think it is fine. justice kavanaugh: about all i need. [laughter] mr. cole: i think -- justice kavanaugh: you can explain. mr. cole: the ultimate inquiry is has the government engaged in

coercion, has it invoked its coercive authority in some way, shape, or form? justice kavanaugh: what if new york went to insurance companies and said we don't want you to continue ensuring gun manufacturers or sellers? for the same reasons, how does that constitutional analysis work? mr. cole: that wouldn't be a first amendment problem -- justice kavanaugh: would it be anything? mr. cole: it might be a second amendment problem, i don't know. not sure it would. if the government's coercion is focused on conduct rather than speech, then it is not a first amendment -- justice kavanaugh: my last question, on bantam books, this is a little bit unusual, obviously, because it is not -- the government is not going to a communications company, bookstore, social-media company, to say take on that speech, but it is going to an insurance company. but i take your point that bantam books, as long as the

ultimate action is against speech, it doesn't matter that the intermediary is not itself a speech business. mr. cole: yeah, i think the key is the use of the third party to punish the target. for example, bantam books, if they said we are going to get those providers of insurance to stop providing insurance, it wouldn't be the same problem. justice kavanaugh: thank you. chief justice roberts: justice barrett? justice barrett: going to give you a chance to address your friend on the other side's argument that we lack jurisdiction because of the qualified immunity question, they also say that the claim for injunction is no longer in the case because you didn't cross-appeal it. i want to give you a chance to address that. mr. cole: this court did not divest itself of jurisdiction when they granted the case and ask for briefing on only one of the questions presented. if the court reverses on the first amendment ground, it would be totally appropriate to send it back to the second circuit to reconsider the qualified immunity question, which is

respondent result argued in the second circuit inexorably intertwined with the merit determination. the court's assessment of the merits is the basic disregard of what happened at lloyd's, adopting every inference in favor of vullo and against the nra with respect to the guidance letters. all of that infected not just the merit determination, but the qualified immunity determination. the court has jurisdiction over the case. it can reverse on the question it took up. justice barrett: what about the injunction? mr. cole: there is no final order. there is no final judgment. we have the right to appeal that and we will appeal that when there is a final judgment. this is an interlocutory appeal from the qualified immunity holding only. we have no obligation to cross-appeal. chief justice roberts: justice jackson? justice jackson: justice kavanaugh picked up on what i think might be a critical listings in, and i'm trying to understand it.

he said here we have a situation in which the government is not asking on a company that is itself in the business of speech, which is true. unlike bantam books, where it was. and so what i'm worried about is your position ultimately reducing to any time regulator enforces the law against an entity that does business with an advocacy organization, we have a first amendment violation. because it seemed like your answer to him was, well, what get this into the first amendment column, unlike other scenarios, is that the nra advocates for guns and it is an advocacy organization, and so action taken against it makes it a first amendment violation. even though the government was not coercing the speech itself in the same way as bantam books. so how do we avoid a world in which advocacy organizations are exempt from regulation?

mr. cole: so we are definitely not asking for an advocacy organization exception for regulation, or even from wrigley and of third parties. what bantam books requires is that -- or even from regulation of third parties. what bantam books requires is that the government encourage parties to punish speech -- justice jackson: but it's not -- forgive me, but it is not punishing speech, it is censoring speech. mr. cole: it's true in bantam books it was about censoring speech, but again, i -- justice jackson: but why isn't that relevant? justice gorsuch suggests you might have a retaliation claim, which is a species of first amendment. you allege it in this case and that mix perfect sense. they are punishing me because of my speech, that is retaliation. censorship is something different, and what i'm suggesting is that bantam books is basically a censorship case, that what they are doing is forcing these companies to take down or remove speech that the

government objects to. and that i don't quite see happening here, as opposed to the other theory that you do allege, which is they don't like what it is that we do and they are using the levers of government to prevent us from operating. mr. cole: and if there were a distinction in the first amendment between censorship and burgeoning speech because of its content -- burgeoning speech because of its content, that might be correct. but there is no such distinction. the first amendment requires strict scrutiny when the government censors speech because it doesn't like its content, when it burdens speech because it doesn't like its content. in this case it's not to burden rather than sensor. -- it sought to burden rather than sensor. but that does not in any way alter the logic of bantam books, the way bantam books has been applied for 60 years. it has been applied consistently to situations in which government official -- justice jackson: i have never seen any other situation like this.

all the other bantam books situations -- mr. cole: no, i don't think so. backpage is a seventh circuit decision by judge posner, very similar, a sheriff who didn't like what a particular social-media platform was doing, and what he did was encourage credit-card companies not to do business with that platform. justice jackson: all right, thank you. chief justice roberts: thank you, counsel. >> thank you, mr. chief justice,, please the court. government officials may criticize speech deems harmful and persuades it is not to support that speech. government officials may not take that resection against private parties to coerce those parties to penalize a speaker. taking the petitioner's allegations as true, that is what the respondent did here. in the lloyd's meeting she especially sought to bring an enforcement action against

lloyd's unless lloyd's sees providing assistance to gun groups. the court should find a strict ford first amendment violation under bantam books, but in recognizing the first amendment claims here, the court should take care to avoid suggesting any new limits on the government's ability to speak in the public or its ability to provide ordinary equal guidance to regulated entities. i welcome the questions. justice thomas: could the government rather than coerce a third-party, simply entice them to reach the same suppression -- do the exact same thing and suppress speech? mr. mcdowell: it depends, justice thomas, on what you mean by entice. justice thomas: what is the difference? mr. mcdowell: bloom requires that encouragement overwhelm the judgment of intermediary, -- justice thomas: and what would that look like in this case. mr. mcdowell: in this case, i think you could think of the

offer of leniency that vullo made it to lloyd's as either a form of significant encouragement, saying we will go easy on you for legal violations, or as a threat basically saying we will bring these enforcement actions against you if you do not stop doing business with gun groups. coercion and significant encouragement are two sides of the same coin, as mr. fletcher said earlier. chief justice roberts: counsel, considerable overlap with the first case. can you articulate what the differences are with your position in this case and the position in the prior case? mr. mcdowell: there are no differences as to the legal principles. the difference here is there is a specific course of threat, particularly in the lloyd's meeting, where she threaten adverse action in the form of enforcement action so that lloyd's would comply with the specific instruction to cut ties with all gun groups, especially the nra. whereas in murphy the plaintiffs did not identify any instance in

which the government official threatened to take adverse action against a social-media company and to get the social-media company to engage in content moderation. they pointed to generic references to legislative reforms untethered to any content moderation. chief justice roberts: so you are focusing on the specificity of the government action, or what? mr. mcdowell: in murphy there was no threat of all, no threat of adverse action at all. there was talks of legislative reforms, but they were not connected to any specific instruction. coercion in our view requires a threat of adverse action connected to a specific instruction such that it is saying if you don't do x, we will do y to you. and that was not in the record in murphy. it is in the record according to the complaint here with respect to the lloyd's meeting in particular. chief justice roberts: so does that mean that the new york officials could have achieved what they wanted to achieve if they hadn't done it in such a ham-handed manner? instead of having the meeting

with lloyd's, they just gave speeches about guns, how bad the nra is, they spoke about social backlash against guns and those who advocate for gun rights in the wake of the terrible parkland shooting, but all that they don't mention anything about any regulatory authority, and then after harping on that for a while, they made a general statements about the importance of every insurance company taking into account reputational risk, and then they sit back and they see whether that achieves the desired result? basically that is what your position is, isn't it? mr. mcdowell: no, your honor -- justice alito: if what they did is what i just outlined, with that be a violation of bantam books? mr. mcdowell: probably not because there would be an

attenuation between the legal consequences and the instruction with a message. we think the guidance letters are permissible government speech because those paragraphs involve criticisms of the nra and urging third parties not to support the nra. that is the classic form of government speech that falls within long-standing tradition. president reagan expressly criticize the kkk and urged citizens not to support or associate with kkk. that is for the first four paragraphs are doing. justice alito: well, if they had said everything in those first four paragraphs in some other format, it would be a different matter. but this is a guidance letter. you understand what a guidance letter is about, right? mr. mcdowell: i take the point that the fact that it is in a guidance letter is highly unusual. you would expect to see this in an op-ed or press conference. but without the fifth paragraph there is no indication of an adverse action at all. the first four paragraphs alone, although unusual, would be permissible government speech.

justice alito: they were ham-handed about this. people up in new york, they don't understand how to do this. if you do it in a more sophisticated manner you can achieve what you want to achieve. mr. mcdowell: i don't know, justice alito, because i don't know that insurance companies and banks would feel that there will was overborne or they were at risk of experiencing adverse action in your hypothetical. that is the question, are the parties able to exercise their own independent judgment? justice alito: i mean, seriously can you think that sophisticated insurance committees are not taking into account adverse risks? they probably heard about the parkland shooting in the aftermath of it. you think they hadn't already taken this into account? didn't they already know all the power that ms. vullo had over them? mr. mcdowell: they certainly knew about the authority the fs had, but without the invocation of that authority and tying that to a specific instruction like we have in the guidance letters come i don't think we would get to coercion.

justice gorsuch: you agree the fifth paragraph changes the calculus? mr. mcdowell: yes, your honor, but i want to make something clear, this has to be considered alongside a press release and the tweets. that is one unit of governmental communication. we would not look at guidance letters alone. we will look at guidance letters particularly as a way to reinforce allegations about the lloyd's meeting rather than considering the guidance letters as a standalone matter. justice kagan: why are you -- justice gorsuch: sorry, just to finish up. do you view this as justice barrett asked as a clear-cut case under existing law? mr. mcdowell: yes, your honor, the lloyd's meeting. justice kagan: why were you concerned with looking at the guidance letters and, nation with every thing else? what would be wrong with looking at the guidance letters alone given that there is this fifth paragraph? mr. mcdowell: the fifth paragraph takes you pretty far and you're not saying -- we are not saying it is not possible to conclude that would be a threat alone. in the same 24-hour period, they

were discussing the same thing come and i think he press release is measurably more explicit. it "urges businesses to join companies that have discontinued arrangements with the nra and to take prompt action to manage the risks." so it is pointing back to the risk-management obligations in the guidance letter and it is putting it into one sentence to make it clear, and the cuomo tweet says "the nra is and ask for missed organization" and he is urging comfort -- is an extremist organization and is urging companies to reconsider ties. to focus on the guidance letter alone, it could allow plaintiffs to cobble together first amendment claims by pointing to disparate statement of government speech and trying to connect them up to invocations of legal obligations. it is easier for because it is in one document, but that is the but a concern, and these are unusual documents, the guidance letters. it is harder to determine in isolation because it is odd to see this given speech in a guidance document.

justice alito: if this case goes back to trial, do you claim that the guidance letters and enforcement actions would not be relevant and admissible? mr. mcdowell: no, your honor, we think the guidance letters would be relevant. they reinforce the plausibility -- justice alito: what about the consent decrees? what about the enforcement actions of the consent decrees? mr. mcdowell: the district court held that she was entitled to absolute immunity we think they were targeting conduct because they appeared to be based on bona fide violations of new york insurance law, so we don't see a free-speech concern independently. but i think that the lloyd's consent decree could appear on the plausibility of the allegations with respect to the lloyd's meeting in the following way --there is a term in the lloyd's consent decree that broadly bands lloyd-- bans lloyd's from even lawful business with the nra, and that sheds light on the plausibility of the allegation that vullo was trying to coerce lloyd's from

stopping lawful business with them. justice alito: has this court ever held that every federal and state officer who is the head of an executive department or the head of an independent regulatory agency with enforcement powers has absolute immunity? mr. mcdowell: no, your honor. but the holding of the district court was that this -- she was exercising a prosecutorial function with respect to the enforcement act -- justice alito: have we ever held that all of those officials have absolute prospect oil immunity? mr. mcdow -- prosecutorial immunity. mr. mcdowell: no, we are not taking a position on that. chief justice roberts: justice thomas? justice alito? justice sotomayor: i already previewed what my question would be. how do you see them writing the opinion and how do you want it and tell me what the differences are and why are they important? mr. mcdowell: our first order of preference is to use the guidance letters as a way to reinforce the plausibility of the allegations about the

lloyd's meeting and to hinge the first amendment analysis on the lloyd's meeting, because that is an explicit threat, straightforward way of resolving this case. as i said, the guidance letters reinforce the plausibility of those allegations because the guidance letters were sent not only to insurance companies, but also to banks, and there is no suggestion that the nra was doing unlawful business with banks. and of course the guidance letters also expressly urge insurance companies and banks to cut all ties with the nra, not just lawful business. those aspects of the guidance letters reinforce the allegation that in the lloyd's meeting she was trying to coerce lloyd's to stop all of its business with gun groups, not just your target unlawful conduct -- to target unlawful conduct. chief justice roberts: justice kagan? just as gorsuch? justice barrett? justice jackson: one quick clarification -- you say the lloyd's meeting is an explicit threat, fine. what is next in terms of proof?

don't they have to show something about her motivation? mr. mcdowell: so, justice jackson, that gets to something mr. cole was talking about. there are two aspects to the claim, the coercion question and the first amendment home question. here the first amendment harm was based on viewpoint discrimination. it would have to show that she was motivated by targeting a particular viewpoint as opposed to targeting of conduct. we just think that the complaint alleges that is what her motive was because on page 223 it says -- it says and most exquisitely, 223, -- explicity, 223, position appendix, she was trying to get them to aid the campaign against gun groups. there was a focus on the speech aspect of the nra as opposed any conduct. justice jackson: thank you. chief justice roberts: thank you, counsel. mr. katyal? mr. katyal: thank you, mr. chief justice, and may please the court -- the key factor in this case is the conceded illegal conduct, as justice sotomayor or

said, the three insurers of the nra broke the law selling intentional criminal act insurance, and all of the product they offered were unlawful because the nra refused to get a license. that is why bantam books is miles away from this case and it is why the court below found qualified immunity protects vullo. in this posture, between the invidious coercion asserted or the obvious explanation she was enforcing the law, is coercion possible? when a legal action is present, the plausibility burden is higher. to use mr. cole's frame, the government is more likely responding to conduct, not speech, and 4 separate doctrines explain why. plausibility rules are " especially important in suits were government asserts qualified immunity because they must not be deterred nor distracted from discovery."

second, the presumption of regularity is at its height. third, absolute immunity protects forstmann action. and forth, causation is difficult. that is particularly after parkland, were many businesses that ms. vullo has no control over severed ties with the nra. where this court to accept this thin complaint, it would empower strike suits to enjoin valid enforcement and open sensitive discovery. that is why the court's traditional test is right. a government official crosses the line from coercion to persuasion when they are threatening as opposed to encouraging, and two, there is no objectively reasonable basis for their action. the nra can't meet that test and that is why they are seeking to weaponize the first amendment and exempt themselves from the rules that govern you and me simply because they are a controversial speaker. i welcome the court's questions. justice thomas: would you spend

just a small amount of time explaining why you think the conduct, all of this, is infected by, i guess, the one illegal insurance product involved here? mr. katyal: so, justice thomas, our position and ms. vullo's position is it is not one illegal insurance product, it is all legal. the attachments of the complaints attach the consent orders which make that clear. the nra never got a license for all of the affinity products. it is their burden to prove -- in other words, unlawful insurance product is in the complaint, they never identified in the complaint. we spent a huge amount of time on this and call them out. to this day they have not explained one lawful product that was ever issued by these three insurers. and that is why we think if you are asking yourself is there an obvious likely explanation for what is going on, that is what it is. that is why the consent orders

-- justice sotomayor: sorry, these affinity programs could have been altered, and these consent decrees and what she was seeking was a ban even of potentially lawful affinity programs. i mean, if they had taken out the intentionality provision or the criminal activity provision and just insured for accidents with guns or things like that, those would have been lawful. but she went further and said you can't even have -- mr. katyal: dfs and regulators do that all the time, justice sotomayor. there are two buckets of serious illegal activity that ms. vullo isolated and are issued in the consent orders by name. one is the prohibition of intentional act insurance, sometimes called murder insurance. that violates public policy and new york and all most every state. second, the fact that nra was doing almost all of these affinity product without a license. just without a license alone, dfs routinely imposes massive

sanctions including lifetime bans. for example, metlife, which we cite in our brief, in 2014 offered the same thing, unlicensed insurance with a partner, lifetime ban. lifetime bans are not unusual. you could have a lifetime band for a meeting. it only happens in these cases if the nra ever decided that they wanted to get a license and offer a lawful plan can they seek a modification of the consent order. but there is nothing unusual whatsoever about a punishment like this. what is unusual is to allow some strike suit like this. remember, this case was filed during the investigation in may 2018 in order to stop it from going forward. the consent order then happened, and so now they are here trying to effectively undo that enforcement action. and the worry here -- it is not just about this case, it is about any case, because everyone can allege -- stop a plea

negotiation or consent negotiation by saying you are retaliating against me. if you just think about what dinesh d'souza said publicly in the filings or michael avenatti, i am being retaliated against because of me, my speech. that is the danger and that is why there has always been an objective unreasonability standard. mr. cole says don't worry, the nra will never do this, we have only filed one suit on bantam books before in our history and it is this one. that is wrong. in five minutes of research we found another case, the nra's suit, san francisco, on exactly that there he. at least 10 of the briefs admit that they want to do this to open up lawsuits for when chick-fil-a -- >> mr. katyal, what do you do about your friend's argument not

raising this in the district court of the court of appeals? mr. katyal: a couple of arguments, the absolute immunity claim? chief justice roberts:, i'm sorry, yes. mr. katyal: first of all, everything i said before does not turn on absolute immunity or not. i'm explaining why this wasn't coercive, what happened in either the lloyd's meeting or the consent orders. we do think there is a separate argument about absolute immunity and there is a good reason to reach it. it was ventilated down below and it is squarely before this court. here is what the district court said. vullo's decision to enter into the consent orders and the precise terms are all entitled to absolute immunity because they are prosecutorial actions premised on enforcement decisions intimately associated with the judicial process. it's fair, as he says, we raise that in these elective enforcement claim, but not the

first amendment went, but there is good reason for that because at that point in the district court, there first amendment claims were focused entirely on the letters and the press release, and absolute immunity were not claiming attended to those acts. we are saying it explained what happens in the consent orders and in the lloyd's meeting. justice kavanaugh: mr. katyal, it's a bit jarring, i guess, for me that the solicitor general's on the other side from you in this case, given that the solicitor general represents the united states and the last case as a very strong interest in not expanding bantam books. so, how should we think about that? mr. katyal: yeah, i don't want to characterize their motivations or anything. i just think ultimately when they get to -- their test is not different than our test. i think we are all basically in agreement that, for example, the second circuit got it right. the second circuit's test is

government officials cannot use regulatory powers to coercing entities from refining from protected speech -- justice kavanaugh: are you ok with that four-part test? mr. katyal: absolutely we do have to insist on objective reasonability when you are dealing with enforcement actions. that second prong that i started with. because otherwise you are opening the door to anyone -- anyone would be highly incentivized if they are the target of an investigation to say i am being retaliated against. so you need to show objective unreasonability, and it is here where claims fall apart. they were doing massively illegal things. new york enforces that all the time. time. if a complaint said something like jaywalking and you are not enforcing it except against us that is not this complaint. chief justice roberts: it seems

like we are all in agreement a law is clearly established. it is just a matter of application. is that right? mr. katyal: i think the law is clearly established in terms of what i read to you, the second circuit standing. chief justice roberts: it is clearly established. mr. katyal: the concern is you open the door to people filing strike suits against enforcement actions all the time. it is not the meeting with lloyd's or the consent orders themselves. you have to read that in light of the guidance letters. we think you should look at them altogether as the solicitor general says. justice gorsuch: i think the meeting itself is enough. mr. katyal: that meeting is enough. every plea negotiation is enough. they are done in secret behind closed doors. that is the natural give and

take. what vullo said according to their own allegations is we have goods on you and we are willing to look past some to make a resolution. it is true that she and governor cuomo have said things about the nra. there is nothing that ties that give and take in the complaint. certainly not plausibly so to the feelings about the nra. the tweets my friend has been referring to by governor cuomo are not even in the complaint. i think it is very natural that in a meeting about resolving these issues you will say i will look past some issues in order to strike the resolution. that is all that is. >> can i ask you about the standards again? suppose i agree with you that illegality was at the heart of what was going on, that all of the products were illegal.

let's assume i agree with you on that. doesn't that coalesce to coercion -- doesn't that go less to coercion than whether or not that coercion of the third-party affected a violation of the first amendment? the fact that the business was illegal does not necessarily mean the february meeting was not coercive. government action in enforcing the law is coercion. isn't it just that she had a good defense to the argument that there is a problem under the first amendment? mr. katyal: your last sentence -- the same point you made in the first argument. coercion is not illegal. the government coerces all the time. what makes it illegal is if you are retaliating against someone speech. justice jackson: you concede

that in this case? that if she was coursing them under these circumstances it was retaliation? mr. katyal: no. we think it was an exercise of legitimate law enforcement. that has direct evidence. this is not a prosecution that would ordinarily be brought. this is rather a selective targeting of me. justice jackson: that is a summary judgment stage. mr. katyal: it can be done here. the selective enforcement claim was thrown out. our point is in order to them to state a claim, and you have to plead and prove, that is the language, she said it four times in the decision. this complaint does not plead and prove that enforcement would not be ordinarily done. what they have said in the complaint is we have some comparisons, the optometrists

association, the new york city bar offers insurance and i against they allege there are technical violations. none of these folks are doing what the naa was -- what the nra was doing. >> you are shifting the burden to them. all they need to know is show the desire to suppress speech was a motivating factor. they do not have to prove that burden in a regulatory action could have been taken even if ms. vullo did not have this motivation. mr. katyal: i think it directly says no to that. because allegations against enforcement are so easy to allege and difficult to disprove and because it bumps up against the presumption of regularity and because it opens the door to massive discovery into sensitive government files and because it incentivizes people to make controversial speech and then claim an exemption, it is in the

pleading itself. that is consistent with the similar things set outside of the retaliation. justice alito: suppose the allegation was we had a meeting with ms. vullo and she pulled out a pistol and held it to our heads and said i will blow your brains out unless you stop writing insurance for the nra. that would not be enough to allege a violation because she might have taken that same regulatory action for a perfectly legitimate reason. mr. katyal: there the government's conduct would be objectively unreasonable and it would flunk our test. we are not seeking to change the law. we are just pointing out when you're in a situation like this of conceding illegality there is

an obvious alternative explanation for what ms. vullo was doing, which was enforcing the law. this is the worst case for you to say this should go past 12 v. 6, that i think any plaintiff would be able to do this. >> what was the conceited illegality? mr. katyal: in the complaint it attaches the three consent orders by the insurers. >> those are those three. mr. katyal: what they said was illegal, the insurance products with the nra. justice sotomayor: what made it illegal that the nra did not

have to offer its products to someone else? that is where i am confused. mr. katyal: once the nra was acting this way ms. vullo entered into contract them for a broader set of sanctions. that happens all the time. justice sotomayor: why are the other insurance carriers that have these similar policies -- the new york state bar association, all of the other people who have similar policies, why are they different? mr. katyal: because they did not do what the nra did, which is not just act unlicensed but offer these insurance policies that seriously violate public policies called murder insurance that cover intentional criminal acts. when you have those things together -- justice sotomayor: i can check

the record. ok. mr. katyal: our position is the short -- is the court should look at both of these. all of the different conduct together. we think anyone individually does not add up to something coercive and together they did not add up to something coercive. the other point i would like to make, and this goes back to justice alito, dear points about the standard at the pleading stage. it is relevant to note there were two alternative explanations for what was going on with these big behemoth companies. one was they were conspiring and illegally agreeing to divvy up the market. the other is they made individual determinations to do that. >> you are right. it says you have to look at the whole of the allegations to

determine whether it is plausible or not. here, doesn't that mean we have to look at all the allegations and complaints? mr. katyal: correct. the one we have not talked about is this reputational risk, these industry guidance letters. we think the industry guidance letters are so far removed from bantam books, we would encourage you to look at footnote five in bantam books. in those letters it does not say anything like we are going to sue you or regulate, unlike what the threat was in bantam books bringing in the attorney general or the chief of police. they do not say she is investigating the companies for anything. there is no reference to an investigative body. it does not say there is any reputational risk with the banks and insurers maintaining their

ties. it says if any reputational risk . i think the most important point, and this goes to something justice kagan said earlier, these are not the only industry letters they send. they send them all the time, including -- if you want a good example take a look at the one they cite about cryptocurrency. that says companies have legally uncertain practices and make inaccurate disclosures and agencies are evaluating the legal permissibility and compliance with applicable laws and regulation. if you're going to issue something like that you will have a disclaimer like the one they point out in their reply brief. this letter is the opposite. the concern we have is if you point to that as part of a

bantam books claim you will just incentivize people to issue reputation risk letters which are obviously important. >> you are not suggesting that if after the initial conduct by ms. vullo and the reaction of the nra that she instructed her staff to go through these policies and find something that violates some regulation in there that she could then send against the basis of terminating all of that and the basis of the newly discovered violations? mr. katyal: there would be objectively unreasonable. that is like going through to target one person. that will be impermissible. the difference with this case is they did not point to a comparator. what they are asking is this an

outlier prosecution or not? there only claim, as justice sotomayor was saying, the optometrists association, those folks were not doing the same thing at all. at most they were offering an unlicensed product. they were not offering something as dramatically dangerous to public policy as so called murder insurance. that is why what ms. vullo was doing was explainable. there is an obvious alternative explanation. that is why if you let this complaint go forward you will be saying to government regulators everywhere that you have to be careful about the speech you say. last week some of you heard the president say we beat the nra, we will beat the nra again. a in which the government criticizes that. all of those statements will be

used as an example in affirmative litigation to issue stripe suit to stop enforcement actions by the ftc and the justice department and by states and the like. i am troubled by the fact the solicitor general is not embracing that. i think it is important to point out many states are. we have a brief from 10 different individuals. i take with the solicitor general has done. to read paragraph five so broadly it becomes coercive. we do not think that opinion is right. if you try to do that, you would be opening the door to something very dangerous and destructive down the road, which is this case will be cited. they already had a track record of using a bantam books situation to stop other enforcement action, not just this one. it is not just the nra today, it is every regulated party from tiktok on. justice alito: you say in your

brief this case is not even close. you stand by that? mr. katyal: i do. under the existing law. chief justice roberts: thank you, counsel. rebuttal? >> i agree with my friend on one point. this case is not close. [laughter] with respect, he is taking a particular standard this court adopted in a particular context. tens of thousands occur every day and adopt a particular rule with respect to the 1983 damage actions. this is a first amendment question. it is not a 1983 question. this is not a retaliatory case.

this is a case that arises very rarely. i looked at bantam books and in 60 years there been 20 to 40 cases in the court of appeals over 60 years involving attempts by the government to coerce a third-party party to punish someone else's speech. that is very different from the situation. you have to change the law substantially to adopt that. with respect to the tweets, they were issued after the first complaint but they were issued before the second amendment complaint, which is the operative complaint. they are perfectly appropriate to consider. nobody disputes exactly what he said. they want them out of the case because they demonstrate the permissible motive. carry guard is a red handing.

it was suspended by the nra in 2017. everything we are talking about happened after november, 2017. lloyd did not underwrite carry guard. it says cut your ties with gun groups, especially the nra, because i'm trying to weakened them. gun groups do not have carry guard, only the nra did. the guidance letters say nothing about carry guard. this is not a guidance letter about infractions, this is a guidance letter about the nra and albert -- and other gun promotion organizations. the insurance was not all illegal. the nra did not have insurance license. it was not an insurance company. it was the american optimal adjusts organization -- up to molly just organization -- there

were some infractions in terms of how it was marketed, how the compensation structures that were quite commonplace in the industry and she enforced them against them and not against others. finally, the notion that this is business as usual. business as usual for a government official to speak with a private party and say we will go easy on you if you ate my campaign. that is not an ordinary plea negotiation.