LOUIS McINTOSH, AKA LOU D, Petitioner, v. UNITED STATES, Respondent
Interviewer(s): Samuel A. Alito, Jr., Elena Kagan, John G. Roberts, Jr., Ketanji Brown Jackson, Neil Gorsuch, Brett M. Kavanaugh, Sonia Sotomayor, Clarence Thomas
Interviewee(s): Matthew Guarnieri, Steven Y. Yurowitz

John G. Roberts, Jr.: We'll hear argument first this morning in Case 22-7386, McIntosh versus United States.

Steven Y. Yurowitz: Mr. Chief  --

John G. Roberts, Jr.: Mr. Yurowitz.

Steven Y. Yurowitz: Mr. Chief Justice, and may it please the Court:  Rule 32.2(b) states in unequivocal terms that a district court must enter a preliminary order of forfeiture prior to sentencing.

In this case, no one disputes no such order was entered, and there's also no dispute why not, as the Second Circuit found, because the government did not submit one. Indeed, none was entered until three years after sentencing.

Petitioner contends that Rule 32.2(b) is a mandatory claims-processing rule and the failure to enter the preliminary order of forfeiture is fatal to the government's ability to seek forfeiture. Such a reading  is consistent with the plain language of the rule, its structure and purpose.

The plain language requires entry of a preliminary order prior to sentencing.

This Court has never interpreted the term "must" to  mean a mere time -related directive. Such an interpretation is also consistent with the rule's comprehensive  structure pursuant to which forfeiture must be addressed.

Those directives start from the beginning of the case, continue through verdict, then prior to sentencing, at sentencing, and after sentencing.

This highly calibrated structure confirms the mandatory nature of the need to enter the preliminary order of forfeiture.

The purpose of Rule 32.2(b)'s requirement to enter the preliminary order prior to sentencing also reflects the goal of procedural due process and finality, all of which are indicative of a prophylactic mandatory claim-processing rule. Finally, Rule 32.2(b)'s requirement to enter a preliminary order of forfeiture is nothing like those rules which this Court has held were mere time-related directives.

Those cases involved either administrative rules and  the concern of imposing mandatory conditions on bureaucratic agencies or rules designed to protect third parties, not before the court, such as the victims in Dolan and the public in Montalvo-Murillo. This Court should conclude that Rule 32.2(b) is a mandatory claim-processing rule. I invite the Court's questions.

Clarence Thomas: But didn't your client -- didn't Petitioner have actual notice that the government was going to seek forfeiture?

Steven Y. Yurowitz: He had notice in the  -- in the indictment in the bill of particulars from  --but, from that point on, the government was silent.

There was no notice -- the government provided no indication after verdict that it was going to be seeking forfeiture until literally the 11th hour, 59th minute, when the court said it was about to impose sentencing.

Clarence Thomas: So how exactly was he prejudiced by what the government did here?

Steven Y. Yurowitz: He was prejudiced by a loss of value on the car, and there were third-party rights, third-party claimants that are also prejudiced because, until a preliminary order of forfeiture is entered , third-party claimants cannot litigate their rights.

Clarence Thomas: Were there any third-party claimants, though?

Steven Y. Yurowitz: The car was titled in his mother's name.

She presumably would have been a third-party claimant.

And she  -- she didn't get -- my understanding is she didn't even get notice.

Neil Gorsuch: How does the harmless error rule apply here?  I understand you just indicated to Justice Thomas that your client is prejudiced, but does a court have an obligation to assess the harmlessness of -- of this rule violation?  Rule 52 would normally require that.

Steven Y. Yurowitz: So Dolan set  -- set forth three potential rules for  --three potential buckets, a jurisdictional rule, a -- a mandatory claim-processing rule, and a time-related directive.

None of them  --

Neil Gorsuch: I -- I'm sorry, just to orient the discussion a little more precisely, we're dealing here with the Federal  Rules of Criminal Procedure, which have a harmless error rule built into them and say that they apply with respect to all of the other rules.

So what about that?

Steven Y. Yurowitz: So this -- even -- in this Court in Eberhart, when it was construing Rule 33, it didn't look to a harmless error rule because it held that it was a mandatory claim-processing rule.

This Court has never really looked to harmless error when  --in the context of a mandatory claim-processing rule even when they're rules, federal rules.

Neil Gorsuch: So even though the federal rules themselves say all of these rules are subject to a harmless error analysis, you would have us effectively carve out Rule 32?

Steven Y. Yurowitz: It's not just -- I would carve  -- I think this Court could carve out all mandatory claim-processing rules.

Neil Gorsuch: Okay.

Thank you.

Ketanji Brown Jackson: So I have a question.

I understand the merits of your argument, and I -- I want to know, if we agree  with you that what we have here is a claims -processing rule, you say that the result of that is that the Petitioner is entitled to enforce  -- enforce it.

And so what I'm trying to understand is, what does enforcement look like in this context?  What does it mean to enforce a deadline regarding this kind of  preliminary rule of forfeiture?

Steven Y. Yurowitz: When -- when  --when a preliminary order of forfeiture is not entered as it should be prior to sentencing, then the government loses its right to forfeiture.

Ketanji Brown Jackson: But  --but I thought -- I thought the order  -- the --the response was going to be that you just get a do-over. In other words, I mean, it's a  -- it's a procedural rule that occurs prior to the sentencing. That's what you've argued, right?  You have to issue this preliminary order of forfeiture.

And so let's say the court doesn't do that.

You say that the individual should be entitled to enforce it.

And I guess what I'm asking is, isn't the scope of the enforcement the argument that they need  -- that the district court needs to do it over?

Steven Y. Yurowitz: The -- when you are construing a mandatory claim-processing rule, the effect of it is that if you don't stick to it  -- if you don't -- if you don't carry out the duty, you lose the right.

Ketanji Brown Jackson: But that's -- but you say that's a jurisdictional rule.

On page 2 of your brief, you say most deadlines have consequences.

A missed jurisdictional deadline prevents the court from permitting or taking the action to which the statute attached the deadline.

So, if the same consequence applies to the claims -processing rule, I guess I'm confused.

Steven Y. Yurowitz: But the difference between a jurisdictional rule and a claims -processing rule is a jurisdictional can never be waived.

A mandatory claim-processing rule could be waived or forfeited.

Elena Kagan: But -- but that can --

John G. Roberts, Jr.: Well, it's not -- I was just going to say the  -- the --in terms of the benefit of the rule, I would assume what they would do is just, okay, here's  -- now we're giving you notice, here's the preliminary order, and it'll be -- you know, sentencing will be in another week as opposed to that.

If you think that what the rule is about is  --is allowing notice to the defendant, so it's prepared for whatever the final order is going to say, it seems to me that that's  -- even if it's jurisdictional, as you say, that means you can't rely on the existing order to give notice, but it doesn't mean you can't just give notice, you know, a week later, give him the same benefit that he would get if the rule were complied with?

Steven Y. Yurowitz: If  --if the notice came before sentencing and it was entered before sentencing, then there's not a problem.

The problem is, in this case, there was no order entered until three years after, at which point you're disrupting the finality of the sentence. This is  -- forfeiture is an element of sentencing.

And there's -- there's an element of finality to it, and that's one of the objectives that the rule is designed to  --to foster.

It also is designed to benefit third -party claimants because, until you have -- until you have entry of an order, third-party claimants can't even be litigated, which, in this case, there was no  --there was no notice served until 12 years after.

Elena Kagan: But the -- a mandatory claims -processing rule is subject to waiver, unlike a jurisdictional rule.

So a person would  have to object to the failure of the court.

And once the person objects, won't the court just do what the court does, and what would be the difference?

Steven Y. Yurowitz: It  --it's our position that the  --the time to object is when the -- when the preliminary order of forfeiture is entered.

The government is equivocal as to what precise time, but if -- it's not too much to ask the government to, if they're seeking to deprive someone of property, to dot their I's, cross their T's, raise this issue before sentencing and  -- and have the court address it.

Elena Kagan: I  --I -- I guess I'm not understanding.

If the person objects at the time of sentencing, and then the court says, you know, you're right, I should enter a preliminary order and enters a preliminary order, then you have no complaint?

Steven Y. Yurowitz: Right.

Elena Kagan: So isn't that just what's going to happen even if the court fails to enter a preliminary order prior to sentencing?  A person in your client's position  will have to object.

Then the court will enter a preliminary order.

And I  --I guess what I'm saying is that the rule you're asking  for will make no difference in the end in 99 percent of the cases.

Steven Y. Yurowitz: We would take the position that the time to object is at the time a preliminary order of forfeiture.

Rule 32.2 places no obligations on the  --on the defendant.

What the government is seeking to do here is to shift the burden to the defe ndant. It's the government's obligation.

They're the ones who are seeking to deprive a defendant of property.

They're the ones who should be moving.

If at the time a -- when -- if it came back to the district court in this case and the government submitted their preliminary order  of forfeiture and the defendant had kept quiet, yes, he waived it.

But, up until then, there was no waiver.

Samuel A. Alito, Jr.: The -- and the typical mandatory claims -processing rule tells one of the parties to the case that if you want to assert a particular claim, you have to raise it.

It puts the -- it imposes a duty on one of the parties, but Rule 32.2 places a burden -- places a duty on the judge.

Do you have any examples of cases in which we have held that something is a mandatory claims-processing rule where the duty is placed on the court and not on one of the parties?

Steven Y. Yurowitz: Gonzalez versus Thaler and Santos -Zacaria are both obligations that are placed on the court.

A  --a -- a preliminary order -- it's an order.

It's an order of the court.

It could only be entered on the -- by the court, but at the end of the day, it's the government that's seeking the deprivation of the property, so they're going to have to provide the court with the  -- the information to enter that order.

Ketanji Brown Jackson: So I asked you about remedy because I guess I'm -- I think there's actually a deeper kind of procedural concern  here that is making me wonder whether we can actually reach the merits of the question that you're asking in this case, and it comes from the fact that as I look at the procedural history of this case, your client actually was  resentenced and procedurally resentenced properly.

So this is what I mean, that you -- you are raising concerns right now about the process that the district court undertook to issue the first forfeiture order in this case.

And you say the district court failed to issue the preliminary order of forfeiture before that sentence and two years later, when it did issue a preliminary order of forfeiture with respect to that sentence, that was too late, that the first forfeiture order was invalid.

But it looks from the procedural history as though the court of appeals vacated that forfeiture order and that you're actually here today pursuant to your client's case that is now relevant to the second forfeiture order.

Do you understand what I'm saying?

Steven Y. Yurowitz: Yes.

Ketanji Brown Jackson: So we now have a new forfeiture order.

And with respect to that forfeiture order, before resentencing, the  district court filed a preliminary order of forfeiture and you didn't object, sentenced your client.

You, I think, agreed to the forfeiture order at that point, so I guess I don't understand how we have the ability now to say anything about potential defects with respect to the first forfeiture order.

Can you help me with that?

Steven Y. Yurowitz: Yeah.

So I  -- I didn't represent the Petitioner at that sentence becaus e of a quirk of CJA rules, but the -- that -- that forfeiture -- entry of the preliminary forfeiture at the subsequent resentencing was always subject to the appeal that was pending then through the appellate process, his direct appeal, which is that the government waived their right to -- lost their right to forfeiture.

Ketanji Brown Jackson: No, I understand. But  --but that order doesn't exist anymore.

So how  -- how do -- how do we give you a remedy -- even if you're right about what you're saying in this case, I guess I don't understand how we're in a position to give you any remedy today.

That order has been vacated.

And what you're arguing is that order was defective because there was no preliminary order of  forfeiture.

So, fine.

That order doesn't exist anymore.

What  --so what -- what can we do about that now?

Steven Y. Yurowitz: It  -- it -- it's  -- it's the same -- it's the same defendant who's subject to sentencing.

It's what -- the Petition  --the Petitioner's position is that the government has lost that right, whether it's this particular order or a later order, if they've lost their right to sentencing, the y've lost  --

Ketanji Brown Jackson: Did he object to the new forfeiture order, the second one, on this basis?

Steven Y. Yurowitz: He was continuing -- he was still -- his appeal was still in -- in the appellate process.

Obviously, because the  Second Circuit had held at that point that the for  -- the government's ability to collect forfeiture was still pending, he was going to negotiate -- work with them on a number which  was substantially lower, but at the same time, his  --the appeal process was still  --was still going.

And, matter of fact, we filed this cert petition objecting to the government's ability  to collect on forfeiture.

Ketanji Brown Jackson: So what remedy can we give you today?

Steven Y. Yurowitz: That the government is prohibited from imposing  --seeking forfeiture.

Ketanji Brown Jackson: With respect to the second order?

Steven Y. Yurowitz: With -- with respect to -- with respect to this case.

Samuel A. Alito, Jr.: Can I go back to your -- your prior answer when you spoke about Santos -Zacaria and Gonzalez versus Thaler? In  -- in the latter case, Gonzalez versus Thaler, the provision said a certificate of appealability may issue only if the applicant has made a substantial showing of the denial of a constitutional right.

So that put a duty on the applicant, not the court. Santos-Zacaria, the statute said a court may review a final order of removal only if the alien has exhausted all administrative remedies available to the alien as a right.

It  put a duty on the alien, not on the court.

So do you have any other examples of cases where we have said that something is a  mandatory claims -processing order, provision, I'm sorry, a mandatory claims-processing provision where the duty is on the court and  not on one of the parties who wants to process the claim?

Steven Y. Yurowitz: I  -- I --I don't, but, Justice Alito, even in those cases, the ultimate responsibility, for example, in Gonzalez, it was the Court that had to issue the court  --the -- the  --the COA.

So it was the court  --it was the court's action.

It was based on a litigant's conduct, but it's the same thing in this  --in this instance. The  -- the court's ability to enter a preliminary order of forfeiture is based on the government's request indicating that they're going to be seeking forfeiture and they're providing the court with the information.

Brett M. Kavanaugh: What do you do about the different language of 32.2(A), which  does say a court must not enter a judgment of forfeiture in a criminal proceeding unless the  indictment contains notice?  In other words, the specific consequence is set forth in the rule there, but it's not in the rule at issue here?

Steven Y. Yurowitz: I  -- I think there's a specific reason why in A it had to specify the consequence, because it's based on the underlying statute.

And in the underlying statute, it talks in permissive terms.

Th e word used is the government may, may file a bill of particulars.

And the rules wanted to take it further.

So, therefore, they wanted to make it mandatory, so they indicated a consequence.

When it comes to (b)(1)(A), that -- that concern doesn't apply.

Sonia Sotomayor: Justice Alito was asking you that -- about what other example you had of a mandatory jurisdictional rule.

And as you pointed out, there really aren't.

But I'm wondering how I can view this rule as a mandatory jurisdictional view when it has the  biggest carveout I've ever seen.

It says you have to  -- the court has to file a preliminary order before sentencing "unless doing so is impractical."  So why can't it do it an hour before the sentencing?

Steven Y. Yurowitz: So, Justice Sotomayor, impractical does not mean inconvenient.

It  -- it  --dictionaries define it as incapable.

It -- that exception doesn't give the court the ability to -- to impose an order at any --

Sonia Sotomayor: Well, having been a district court judge and having hundreds of sentences on my docket at one point,  sometimes it's not really inconvenient.

It's almost impossible to keep up with those things, and you do  -- you do do it a little bit later. But my point is, who decides that? Meaning you go up on appeal, the court of appeals now has to hold a hearing to see why the district court judge didn't issue the order a month before, two months before, three months before?  I guess my point is generally, when we think of mandatory rules, they set a fixed goal, a fixed deadline, something that you can know and meet without discretion being involved.

Steven Y. Yurowitz: So Rule 32.2(b) imposes that same firm deadline.

That's sentencing. The impractical exception is only that --

Sonia Sotomayor: But, again, an hour is inconvenient, but how about a day?  How about two?  How about three?  My whole point is  that once you build in discretion, how can you call it mandatory in the  --in the sense of it being jurisdictional?

Steven Y. Yurowitz: At that point, if the defendant -- nothing  --none of this happens in a vacuum.

The government, had they done their jobs  --job properly, they would have c ome to the court saying we're seeking forfeiture in this case.

They would have provided the information.

Now it may be that the district court couldn't get to it because it was impractical, but there would be notice to the defendant that there was going to  --

Sonia Sotomayor: Thank you, counsel.

Ketanji Brown Jackson: So can I just  -- I'm sorry.

So are you asserting that there was something wrong with the preliminary order of  forfeiture that the district court issued on April 23, 2023, before the resentencing?

Steven Y. Yurowitz: The -- the -- what was wrong is that the government shouldn't have been entitled.

There's nothing -- there's no -- I wouldn't point to any errors in that order.

It -- it --

Ketanji Brown Jackson: All right.

Did you object at the time of that preliminary order? Did you say the government should not be entitled to get a forfeiture because 10 years ago when they sent  -- when I was previously sentenced, the  --the district court didn't issue a preliminary order of forfeiture?

Steven Y. Yurowitz: I  -- I don't believe that the  --the defense counsel at that time did, but this was still a case that was in a direct appeal.

Ketanji Brown Jackson: All right.

Final question from me at least.

If you win this case today  and you go back on remand, what is the remedy?

Steven Y. Yurowitz: That the -- the forfeiture order be vacated.

Ketanji Brown Jackson: Which forfeiture order?

Steven Y. Yurowitz: Right now, the only one that's pending is the -- the most recent one that was entered in April 2020.

Ketanji Brown Jackson: And that one doesn't have the defect that you've identified, correct?

Steven Y. Yurowitz: It  --it has the defect in that it was entered when -- in violation of a mandatory claim-processing rule.

Ketanji Brown Jackson: Okay.

John G. Roberts, Jr.: Thank you, counsel.

Just to follow up on Justice Sotomayor's questions about impractical, it's not only impractical, but the qualification requirement has to be sufficiently in advance. And that's sort of another layer of broad discretion.

I know yours is years, so that wouldn't be covered, but in the typical case, it not only has to be imp ractical, but all you have to do is sufficiently.

It seems that there's a lot of wiggle room throughout the rule that seems inconsistent with the general notion of mandatory requirements.

Steven Y. Yurowitz: Even this Court in Eberhart, when it was dealing with Rule 33, it has the same ability for a judge to extend the deadline.

Defense counsel could make a motion saying probably it's  --I can't do it sufficiently in time, and the rule permits a  court to extend it.

This Court held that it was a mandatory claim-processing rule.

So the notion that there's flexibility doesn't undermine the fact that it's a claim -processing rule. The point is it's a rule that's designed to provide a -- a litigant with protections because the government is seeking to deprive him of his property.

A hundred and fifty years ago, this Court already said in French versus Edwards, where there's a rule that's designed to govern protections for somebody whose property is going to be deprived and there's a potential for prejudice, that's a mandatory rule.

John G. Roberts, Jr.: Thank you. Justice Thomas, anything further? Justice Alito? Justice Sotomayor? Justice Jackson, anything further? Thank you, counsel.

Steven Y. Yurowitz: Thank you.

John G. Roberts, Jr.: Mr. Guarnieri.

Matthew Guarnieri: Mr. Chief Justice -- excuse me.

Mr. Chief Justice, and may it please the Court:  The timing requirement in Rule 32.2(b)(2)(B) is mandatory, not discretionary, but characterizing that requirement as mandatory doesn't answer the question pr esented in this case.

The question here is, what follows when a district court violates the rule?  What are the consequences?  Now our basic submission in this case is that a violation of Rule 32.2(b)(2)(B) should be treated like any other garden-variety procedural error in the sentencing process. When a court commits a procedural error at sentencing, the normal thing to do is to apply Rule 52, which is the provision in the Federal Rules that codifies principles of harmless error and plain error.

Under Rule 52(a), if an error does not affect the defendant's substantial rights, it must be disregarded as harmless.

Petitioner tries to avoid the application of harmless error principles by characterizing this particular  requirement as a mandatory claim-processing rule.

Rule 32.2(b)(2)(B) is not such a rule for all the reasons that this Court identified in Dolan with respect to the analogous timing requirement in the Mandatory Victims Restitution Act.

Let me just emphasize three of the considerations that the Court stressed in Dolan: text, context, and purpose.

Textually, the rule here imposes an obligation on the court, not the litigants, and it does not specify any sanction for the court's violation.

That text operates in the broader context of a statutory framework that  makes clear that criminal forfeiture is a mandatory consequence of conviction and that forfeiture is part of the sentence imposed for the offense.

The purpose of requiring the entry of a preliminary order before sentencing is to ensure that the forfeiture that is actually imposed at the sentencing itself is accurate and complete.

Accordingly, when a district court neglects to enter a preliminary order of forfeiture before sentencing, in violation of  Rule 32.2(b)(2)(B), the court may nonetheless proceed to order forfeiture at the sentencing itself as long as the court's violation was harmless.

And we think that's what occurred here.

The district court orally ordered Petitioner to forfeit the proceeds of his Hobbs Act robberies and a car that he purchased with those proceeds, despite the absence of a preliminary order before sentencing.

That error was harmless.

I welcome the Court's questions.

Clarence Thomas: Counsel for Petitioner said that the government should be held to  -- when it takes a person's property, to cross its T's and dot its I's.

How do you respond to that?

Matthew Guarnieri: Well, Justice Thomas, we take our obligations to the court seriously in this context.

And, certainly, the government has an important role to play in ensuring that district courts comply with the strictures of Rule 32.2, including rule 32.2(b)(2)(B).

But  that specific provision imposes an obligation on the court, not -- not on the government. And to your broader point, Justice Thomas, I -- I --I think the -- the principal protection for defendants in criminal forfeiture is that the obligation is on the United States to prove beyond a reasonable doubt that the defendant committed the offenses for which Congress specified criminal forfeiture as a penalty.

So Petitioner here and defendants generally are entitled to all of the myriad protections in the criminal process.

We were required to meet the beyond a reasonable doubt standard.

There was a jury trial in this case. We presented nine days' worth of testimony establishing that Petitioner committed these robberies.

And forfeiture is a consequence of the defendant's violation of the Hobbs Act.

Neil Gorsuch: Counsel, you mentioned Rule 52 in your opening.

I was a  little surprised, though, in reading your brief, it didn't appear until page 42.

Can -- can you explain -- and I -- I  -- I'm not being critical.

I'm -- I'm just wondering, is there a nuance here I'm missing? But, you know, this Rule 32 is a rule.

It's not a statute.

It's a rule.

And all of the rules are subject to harmless error analysis.

And I would have thought that would have been like the straightest, narrowest shot through this case, but I'm wondering whether I'm missing something.

Matthew Guarnieri: Well, you  --you are not, Justice Gorsuch.

We are trying to triangulate from the Court's existing precedent. The Court has indicated in other cases that there are provisions in the Federal Rules of Criminal Procedure that are best characterized as mandatory claim processing rules.

And violations of those other rules are not subject to harmless error analysis.

And the key case there, I think, is Eberhart addressing Rule 33, which is the rule specifying the time limits for moving for a new trial after conviction.

I think the same analysis would apply to Rule 35, which is the provision that specifies the time limits for correcting a  sentence after it has been imposed.

Those are mandatory and inflexible deadlines.

And a district court generally cannot ignore those deadlines if a party seeks  strict adherence to them.

Rule 32.2(b)(2)(B) is not  --

Neil Gorsuch: The default is that all the rules are subject to harmless error?

Matthew Guarnieri: Yes, I think that's right.

Neil Gorsuch: Okay.

Matthew Guarnieri: It's  -- and I think that's a useful way to think about the case. And, indeed, that's the  -- the framing that I was trying to establish in my opening here.

Really, it's Petitioner who's seeking to avoid the application of what the default framework here would be by characterizing this as a mandatory claims-processing rule.

Neil Gorsuch: Just one more question.

So, if  -- if we agree with that, are you asking us to apply the harmless error standard ourselves in this case, or is a remand  appropriate for a court to assess that question?

Matthew Guarnieri: Well, I think the Second Circuit already determined that any error here was harmless, as did the district court.

Both of those courts considered what we think are the right factors in this context, and that  is did the defendant have notice of the forfeiture and was he given an opportunity to contest it before the court ordered the forfeiture as part of the sentencing proces s. And Petitioner had both of those things here.

He was on notice that the government was seeking this forfeiture both through the indictment, the bill of particulars.

Neil Gorsuch: So you're not asking us to do a harmless error analysis.

You're asking us to say that it's already been done. Is  -- is that the gist of it?

Matthew Guarnieri: Yes.

We are asking this Court to affirm the judgment below, which itself  -- in --in which the Second Circuit itself established that there was no prejudice to the defendant here.

Neil Gorsuch: Thank you.

Sonia Sotomayor: Counsel, you talked about this being a court obligation, and I agree, but the government has an important role.

Here, the government promised to or was asked to prepare orders and I think at least twice failed to do so.

A ruling in your favor that this is a time-related directive seems to me as an inducement to encourage the government not to respond to a district court order.

I have to say I read this and I thought to myself this is a very strange district court.

If a government lawyer had ever done that to me as a district court judge, I don't think I would have been very kind.

But what inducements are we creating by not calling this a -- if not mandatory, a claim processing rule as opposed to a time-related directive?

Matthew Guarnieri: Well, Justice Sotomayor, I don't think characterizing this provision as a time-related directive would encourage violations of the rule if  -- if that is Your Honor's concern.

There are going to be substantial incentives for the government to encourage the district court to comply with this rule.

Sonia Sotomayor: What are the incentives?

Matthew Guarnieri: Well, the entry of a preliminary order of forfeiture before sentencing can be a basis for seizing property. And so the government in many cases is going to have an interest in ensuring that it has legal authority to seize and maintain assets that should be subject to forfeiture or that will be subject to forfeiture at the conclusion of the case.

So I think that's one substantial incentive.

Another, we often have an incentive to ensure that the Court enters a preliminary order of forfeiture in compliance with Rule 32.2 because that can provide notice to third parties that some particular specific asset is going to be subject to forfeiture.

It helps us to  --

Sonia Sotomayor: That didn't happen here.

Matthew Guarnieri: -- defeat arguments later in  the proceeding that some third party comes in and claims that it was a bona fide purchaser of the assets if they were transferred during the course of the criminal case.

So, I mean, we -- we  -- there are good reasons here that it is Department of Justice policy to encourage district courts to enter preliminary orders of forfeiture before  sentencing, as Rule 32.2(b)(2)(B) requires.

Sonia Sotomayor: I have one last question.

Do you take a position on the Seventh Circuit's suggestion in U.S. versus Lee that you have to at least announce a forfeiture at sentencing, that you can't just not say anything and then later order one?  And they said that might be jurisdictional.

Matthew Guarnieri: Your Honor  --

Sonia Sotomayor: We don't have to address that here, but do you see a ruling here as permitting courts to do that as well?

Matthew Guarnieri: As I understand the Seventh  -- the Seventh Circuit's decision in Lee, the court suggested that although Rule 32.2(b)(2)(B), the provision that is at issue in the proceeding before this Court, is best characterized as a time-related directive, perhaps the timing requirements with respect to the entry of the final order of forfeiture at the sentencing hearing itself, perhaps those requirements should be treated as mandatory claim-processing rules. That was not directly at issue in Lee. We haven't briefed that issue here.

I don't  think anything that the Court says here about 32.2(b)(2)(B) would necessarily dictate an answer with respect to what is Rule 32.2(b)(4)(B).

And -- and so I don't think the Court needs to address it.

We haven't taken a position.

I -- I would say, in general, I think that's a harder case for us, and it's a harder case for some of the reasons that the dissenting Justices identified in Dolan.

And that is, in general, the rule here contemplates that the court will announce the forfeiture as part of imposing sentence on the defendant.

And if the court purports to act after sentencing, if it fails to address forfeiture at sentencing and it's acting after the sentencing proceeding, then we have a harder set of issues.

I mean, that's not just a Rule 32.2  problem.

It can also be a problem under the various statutes that specify that forfeiture shall be ordered at sentencing.

And as -- as I was alluding to earlier in my colloquy with Justice Gorsuch, there are constraints under, in particular, Rule 35 on a district court's authority to alter or correct a  sentence after it's been imposed.

So there are a lot of other extrinsic considerations that could come into play with respect to the final order at sentencing.

But those things don't support Petitioner's position here.

This case is limited to just the asserted error of failing to enter a preliminary order of forfeiture before the original sentencing proceeding.

Sonia Sotomayor: Thank you, counsel.

Ketanji Brown Jackson: So the government focuses right in on the merits, which, you know, is totally understandable, can I -- but can I get your thoughts on my concerns about the threshold, potential for a threshold procedural defect that actually inhibits our ability to reach the merits in this case?

Matthew Guarnieri: Justice Jackson, I  -- I think the way that would work under Article III, the question would be whether a judgment in Petitioner's favor is capable of granting him any kind of effectual relief.

Ketanji Brown Jackson: Yes.

Matthew Guarnieri: And I  --I think the answer is yes.

That's why we have not raised a  mootness argument in this case.

Ketanji Brown Jackson: Tell me how.

Matthew Guarnieri: I  --I -- well, it is true that there is now a new legally operative forfeiture order in this case as a result of the remand for unrelated reasons, but that order is currently pending appeal in the Second Circuit.

If this Court adopts Petitioner's view that this is a mandatory claim -processing rule, his position as I understand it is that violation of that rule is, I think he said this morning, fatal to the government's ability to obtain criminal forfeiture.

And so I think the case would go back to the Second Circuit.

And the Second Circuit could then entertain his argument that even the now operative new forfeiture order should be vacated  because it is the result of a series of proceedings that never should have occurred under his understanding of how the rule works.

Ketanji Brown Jackson: Right.

But, under his own argument, didn't he forfeit that claim? I mean, he says that if it's a claim pr ocessing rule, if you don't raise it, you lose it.

And  at the time of the second forfeiture order, he didn't raise it.

Matthew Guarnieri: I  --I think we would have reasonable arguments that, in fact, he has forfeited it even if it is a mandatory claim-processing rule, but I think those would go to the merits.

I don't think that those would deprive this Court of Article III authority to adjudicate the dispute that's before the Court today.

Neil Gorsuch: Do you think there are some  mandatory claim-processing rules that are directed to courts or executive agencies rather than to parties?

Matthew Guarnieri: Petitioner has yet to identify an example of such a rule.

I mean, there are rules, for example, the provision of the INA that was at issue in Santos-Zacaria, which my frien d mentioned this morning, that are phrased in terms of action by the court but clearly are designed to impose on the parties an obligation to take some step, such as exhausting administrative remedies.

We're not aware of and Petitioner has not identified another example of a rule like this where the obligation rests squarely on the judicial officer.

And  -- and that's one of the reasons that this case is similar to Dolan.

The -- the other case that I think is -- is directly on point here is Montalvo-Murillo, which is the case involving a provision of the Bail ReForm Act that imposed on the magistrate, on the judicial officer, an obligation to hold a pretrial detention hearing within a specified time, and the Court said that even if a -- if -- if the judicial officer violates that deadline, it doesn't mean that the defendant walks free.

You can have a later pretrial detention hearing because the error was harmless.

Neil Gorsuch: Is there something significant about that line that we might emphasize here?  The statute, after all, says that there shall be forfeiture, right?  I mean, that  --that's Congress's directive to us. And often government agencies and perhaps courts miss deadlines.

But Dolan kind of recognized what I'll call a better late than never rule in complying with congressional directives.

Thoughts?

Matthew Guarnieri: Justice Gorsuch, I think that's right, and  -- and to return to an exchange we had earlier, I mean, we have approa ched this case through the lens of Dolan. In Dolan, one of the considerations the Court emphasized in Dolan was that the statutory obligation in that case was placed on the court, not on the litigants, which is a sign that this might be something other than a mandatory claim-processing rule. Another consideration that the Court stressed in that case was that, as the name of that statute suggests, the -- the restitution was mandatory.

And so too here criminal forfeiture is mandatory.

Those are both important components of our argument.

If you think about this, when -- when you arrive at the sentencing proceeding, the district court who has failed to enter a  preliminary order of forfeiture faces a kind of dilemma because, on the one hand, you have a perceived violation of Rule 32.2(b)(2)(B),  assuming the impracticality exception doesn't apply, and on the other hand, you have numerous  interlocking statutes that direct the court, command the court to order forfeiture when the prerequisites are satisfied.

And so I think all of that, that surrounding mandatory framework, is another very important piece of the puzzle here.

And if the Court accepts that and accepts that those are two of the considerations that support treating this as a mandatory  --excuse me -- as a time-related directive rather than a mandatory claims -processing rule, that would suggest some outer limits if -- if that was the -- the  --

Neil Gorsuch: Yeah, I'm wondering what  --

Matthew Guarnieri: -- impetus of the question.

Neil Gorsuch: -- you know, how are we going to reconcile -- I mean, we now have three buckets, right, jurisdictional, mandatory  claims processing, and this Dolan thing.

And I'm wondering, what are the outer limits of the Dolan thing?  And that's what I'm trying to  explore with you, and is the government comfortable with a rule that it -- those are matters directed to the court by statute and have mandatory directives?

Matthew Guarnieri: I think that's right. I think those are the two key considerations here.

There are -- there are other considerations that I think also support treating this case the same way the Court treated  -- rather, treating this rule the same way the Court treated the statute in Dolan, but those are certainly the two principal ones that we emphasize in our brief.

Ketanji Brown Jackson: Is it the government's position that this is the kind of situation that if he's -- that he's right or wrong about his argument that if a court blows the deadline, there can never be another forfeiture in the case?

Matthew Guarnieri: Well, I think that's another significant way in which our approach differs from Petitioner's approach.

I think that, like other procedural errors, if there is a harmful violation of Rule 32.2(b)(2)(B) or a non-harmless violation, the remedy should be that the defendant in that case then gets the forfeiture proceedings that Rule 32.2 is supposed to provide.

So, if you arrive at sentencing or the case goes up on appeal and there's been a violation of the requirement to enter a preliminary order of forfeiture beforehand, the result should not simply be that the defendant in that case is absolved of what is supposed to be a mandatory part of the sentence for the defendant's offense.

The result should be a remand to the district court to  --to get it right.

Ketanji Brown Jackson: What have we said in other claims-processing scenarios?  And is that consistent with what normally happens if there is a claims-processing rule?

Matthew Guarnieri: I  am not aware of an example in which the Court has identified something as a mandatory claim -processing rule but, nonetheless, found that a violation of that mandatory rule could be remedied by a redo of  the proceedings in the district court. Ordinarily, mandatory claims -processing rules are -- and it's a category that is adjacent to jurisdictional  rules.

These are inflexible rules that impose on the parties some obligation that if they fail and the other party objects, the rule can be strictly enforced.

And Rule 32.2(b)(2)(B), like other requirements that attend the sentencing process, it doesn't rea lly make sense to treat the rule that way.

Ketanji Brown Jackson: And why is that?

Matthew Guarnieri: Well, because it would make Rule 32.2(b)(2)(B) a kind of aberrational part of sentencing.

If the district court fails to take the very steps that are identified in Rule 32 with respect to the sentencing process, the  -- the ordinary remedy for that is that you redo the sentencing.

Indeed, even with respect to errors that this Court has identified as structural, meaning they are not amenable to harmless error principles, the remedy for a structural err -- error is that you have a retrial or you have a resentencing.

It doesn't mean that the defendant is simply -- cannot be convicted of the offense or cannot be subject to a penalty that Congress has otherwise specified for that offense.

John G. Roberts, Jr.: Well, there are situations in which it does mean that.

So just  because it doesn't in this particular situation, there are others, like the situation in Dolan.

You're putting an awful lot of weight on a sharply divided opinion in Dolan.

Matthew Guarnieri: Well, Mr. Chief Justice, I -- I recognize that the dissenting Justices in Dolan had some very compelling and persuasive things to say.

One point I would make, and -- and we make this point in our brief, this case is one step removed from Dolan in the sense that here, the error is with respect to a part of the process that is antecedent to the sentencing itself.

And so, here, the district court failed to enter a preliminary order of sentencing beforehand, but it did orally order the forfeiture of the property and orally order a forfeiture money judgment at the sentencing itself.

And that's unlike the situation in Dolan, in which the  -- the sentencing court in that case left open the precise amount of restitution and then acted well after the 90-day deadline in the Mandatory Victims Restitution Act.

John G. Roberts, Jr.: Well, just because it doesn't have any serious consequences, if you're right that you just have a, you know, start over again a second time, I mean, there are situations where it would.

And I'm wondering if -- to what extent we should be concerned about the remedial aspect of it simply because it sort of could be a harmless foul in this case?

Matthew Guarnieri: Well, I mean, if you're thinking about this case in terms of, you know, what is the appropriate remedy for a violation of this rule, I do think we have the better argument on the equities there.

I mean, this is a mandatory component of the sentence.

It is in that sense akin to a min  -- a statutory minimum sentence.

If the district court commits an error in the process of imposing that mandatory sentence, it would be anomalous to conclude that the result is that the defendant is simply absolved of a  --of a consequence that Congress has made mandatory for that particular offense.

It would really  --I mean, it would, as I said, make Rule 32.2(b)(2)(B) stick out like a thumb in the sentencing process.

I think the other thing I would say is that our approach here, which has stressed harmless error, means that -- I mean, the delta between that approach and a mandatory claims -processing approach, you're talking about the small class of errors in which  -- excuse me, the -- the -- the -- the set of cases in which the error is harmless.

And we think, if the error is harmless, I mean, by definition, that means that any procedural error did not affect the defendant's substantial rights, there is no good reason if the error is harmless for the court to lack the authority to just proceed at the sentencing proceeding itself to order the forfeiture of the property that Congress has made subject to forfeiture.

John G. Roberts, Jr.: Thank you, counsel.

Anything further? Anything further?

Matthew Guarnieri: Thank you.

John G. Roberts, Jr.: Thank you. Rebuttal, Mr. Yurowitz?

Steven Y. Yurowitz: I  -- I'd just like to go back to Justice Gorsuch's question about harmless error.

The reason why there's no harmless error analysis is because this Court has never really applied harm -- harmless error in the context of either a mandatory claim-processing rule or  --or time-related directives.

Indeed, in Dolan, Chief Justice  -- Justice Roberts pointed out that it's a rule with no consequence because the majority said, even in unlikely instances where the delay does cause the defendant prejudice, the defendant remains free to ask the court to take that into account.

There's no obligation on the court to take that into account.

So this Court has never really applied harmless error analysis in this context.

And I think the reason why the  -- why these mandatory claim-processing rules are treated different and why Rule 32.2(b) should be within that bucket is because it's not simply  the defendant that's before the court whose rights are being affected.

There are third-party claimants' rights who are being affected who, at the time when the court is conducting any analysis, they're not even there before the court, and their rights are just being put to the side because they're not before the court.

Dolan's finding of a time-related directive was a very small slice.

It's just  -- it's  --it's a  --generally, it involves administrative action where, obviously, the court is reluctant and recognizes that administrative agencies, they're saddled with a lot of obligations, and they may not be able to keep their -- their obligations in a timely manner.

There are only really two exceptions, and that's in the bail context, where there's a public safety issue, and there's a pending case that's ongoing, unlike Rule 32.2(b), which is sentencing -- the final -- there's a finality  element to sentencing, and there's Dolan itself, which involved victims.

Victims are not the beneficiaries of Rule 32.2 (b). So I think that's why harmless error should not apply, because there is this category of a mandatory claim-processing rule.

My friend characterized it in terms that both  -- that there's no rule in terms of the  --where a mandatory claim processing is imposed on the  -- on the court.

He said -- but, you know, the - - I think the two cases, the Santos -Zacaria and Gonzalez versus Thaler, he said those were an obligation on the party.

It's the same thing here.

A district court coming in to impose forfeiture could do nothing without the government providing them the ammunition, and the first thing is the government coming in and saying post-verdict, pre-sentencing, we are going to seek forfeiture in this matter.

The government certainly has the right, even though they filed a bill of particulars, even though they put it in the indictment, they don't have to continue on that forfeiture.

They could  -- they could --they have the discretion.

They may have felt in the facts of this case is Defendant is getting  sentenced to 60 years, he is going to be the rest of his life in prison, we're not going to proceed with for the.

And certainly not an obligation on the Defendant to say:  Hey, what -- are you really -- you're -- are you letting me off the hook? It was the government's obligation to come in. There was not a word from the government in this case post-verdict, in the sentencing memorandum, when they got up to argue at sentencing, there was not a word about  --at sentencing. So in  -- in that terms, there --there -- it's the government  -- it's the government that really bore the burden.

And,  yes, the court -- it's an obligation on the court. The  -- the court needs the government to come forward with that.

So in that sense, it's -- it's both -- it's like -- it's -- it's -- it's the same situation as Gonzalez versus Thaler, where there's an obligation of the Court to indicate in the COA what -- what the constitutional basis is.

And if anything, in  --in that case it was more of an obligation on the Court because the Court had an independent basis to decide that there was a  -- a constitutional basis. And the other  -- the point about the  -- the fact that the forfeiture is mandatory and the  -- and the statute makes it mandatory, but it also in the same breath says it's going to be subject to the Federal Rules of Criminal Procedure, which is Rule 32.2.

As a matter of fact, even those forfeiture is mandatory.

If the government fails to allege it in the indictment, there's no -- even the government doesn't dispute that they cannot receive forfeiture.

So the --the rules could impose more obligations on the government -- on -- on the court than specified in the  -- in the --in the  --in the statute and it doesn't undermine the mandatory nature of  --of the obligation.

John G. Roberts, Jr.: Thank you, counsel.

The case is submitted.