PUBLISH 

UNITED STATES COURT OF APPEALS 

FOR THE TENTH CIRCUIT 

_________________________________ 

UNITED STATES OF AMERICA, 

 Plaintiff - Appellee, 

v. 

JESUS ARELLANES-PORTILLO, 

 Defendant - Appellant. 

No. 20-3165 

_________________________________ 

Appeal from the United States District Court 

for the District of Kansas 

(D.C. No. 2:17-CR-20074-JAR-11)

_________________________________ 

Jacob Rasch-Chabot, Assistant Federal Public Defender (Virginia L. Grady, Federal 

Public Defender, with him on the briefs), Denver, Colorado, for Defendant-Appellant. 

Bryan C. Clark, Assistant United States Attorney (Duston J. Slinkard, Acting United 

States Attorney, and James A. Brown, Assistant United States Attorney, with him on the 

brief), Kansas City, Kansas, for Plaintiff-Appellee. 

_________________________________ 

Before BACHARACH, SEYMOUR, and PHILLIPS, Circuit Judges. 

_________________________________ 

PHILLIPS, Circuit Judge. 

_________________________________ 

 Jesus Arellanes-Portillo pleaded guilty to a collection of federal drug-trafficking, 

money-laundering, and immigration crimes. He now challenges the procedural 

reasonableness of his sentence. Arellanes-Portillo argues that the district court misapplied 

FILED 

United States Court of Appeals 

Tenth Circuit 

May 27, 2022

Christopher M. Wolpert 

Clerk of Court

Appellate Case: 20-3165 Document: 010110690171 Date Filed: 05/27/2022 Page: 1
2 

a three-level aggravating-role adjustment in calculating his advisory guideline range for 

his money-laundering offenses. We hold that the district court plainly erred by basing the 

aggravating-role adjustment on relevant conduct for his drug offenses and not exclusively 

for his money-laundering offenses. That violated U.S. Sentencing Guidelines Manual 

§ 2S1.1 Application Note 2(C) (U.S. Sentencing Comm’n 2018).1

 So exercising 

jurisdiction under 28 U.S.C. § 1291 and 18 U.S.C. § 3742(a), we vacate and remand for 

resentencing. 

BACKGROUND

I. The Indictment 

 A federal grand jury sitting in the District of Kansas indicted multiple defendants 

for crimes committed on behalf of a Mexican drug-trafficking organization operating in 

Kansas City. The indictment charged Arellanes-Portillo with twelve crimes: one count of 

conspiracy to distribute and to possess with intent to distribute more than five kilograms 

of cocaine, in violation of 21 U.S.C. §§ 846, 841(a)(1), 841(b)(1)(A)(ii), 18 U.S.C. § 2, 

and of conspiracy to distribute and to possess more than 100 kilograms of marijuana, in 

violation of §§ 846, 841(b)(1)(B)(vii), 18 U.S.C. § 2; three counts of possessing cocaine 

with intent to distribute, in violation of 21 U.S.C. § 841(a)(1), 841(b)(1)(B)(ii), 18 U.S.C. 

§ 2; one count of possessing cocaine with intent to distribute, in violation of § 841(a)(1) 

(without designating a subsection (b) penalty provision), 18 U.S.C. § 2; three counts of 

using a telephone to facilitate the conspiracy, in violation of 21 U.S.C. § 843(b); two 

1

 Having identified the governing guideline manual, we simply cite the 

applicable guidelines sections throughout the opinion. 

Appellate Case: 20-3165 Document: 010110690171 Date Filed: 05/27/2022 Page: 2
3 

counts of money laundering for attempting to transport funds from Kansas to Mexico to 

promote the conspiracy, in violation of 18 U.S.C. §§ 1956(a)(2)(A), 2; and two counts of 

knowingly possessing false immigration documents, in violation of 18 U.S.C. § 1546(a).2

II. The Presentence Report 

Arellanes-Portillo pleaded guilty to all counts without a plea agreement. In a 

written plea petition preceding his guilty pleas, he provided a factual basis for each of the 

charged offenses. 

In the presentence report (“PSR”), the United States Probation Office calculated 

the advisory guideline range using the money-laundering guideline, § 2S1.1. Under 

§ 2S1.1(a)(1), the PSR set the § 2S1.1 base offense level at 32. It did so by incorporating 

the offense level from the drug guideline, § 2D1.1(a)(5), (c)(4) for the drug weight 

involved in Arellanes-Portillo’s offense.3

 Next, the PSR added two levels under 

§ 2S1.1(b)(2)(B), based on Arellanes-Portillo’s convictions for money laundering under 

18 U.S.C. § 1956. After that, the PSR added three offense levels for his aggravated role 

in criminal activity involving five or more participants, based on § 3B1.1(b). Finally, the 

2

 Arellanes-Portillo’s immigration convictions aren’t at issue in this appeal. 

They don’t affect his final advisory guidelines sentencing range. See § 3D1.4(c) 

(explaining that any group of offenses “9 or more levels less serious” than the group 

with the highest total offense level don’t affect the ultimate total offense level). 

3

 As we discuss later, the district court at the sentencing hearing upped the 

incorporated § 2D1.1 “offense level” by another two offense levels to 34 after finding 

Arellanes-Portillo responsible for maintaining a drug premises under § 2D1.1(b)(12). 

Appellate Case: 20-3165 Document: 010110690171 Date Filed: 05/27/2022 Page: 3
4 

PSR subtracted three offense levels for Arellanes-Portillo’s timely acceptance of 

responsibility.

III. PSR Objections & Sentencing 

Before the sentencing hearing, Arellanes-Portillo objected to the three-level role 

adjustment. In an Addendum to the PSR, the probation office restated ArellanesPortillo’s objection in these words: “Mr. Arellanes-Portillo was not the manager, 

someone named Bolo was. We do not believe that the enhancement should apply.”4

 R. 

vol. 3 at 38. The government defended the PSR’s aggravating-role adjustment on grounds 

that “[t]he Tenth Circuit has consistently held that the ‘enhancement under § 3B1.1(b) 

applies to a defendant who exercised some degree of control or organizational authority 

over someone subordinate to him in the drug distribution scheme.’” R. vol. 3 at 38–39 

(quoting United States v. Cordoba, 71 F.3d 1543, 1547 (10th Cir. 1995)). The 

government also cited evidence of Arellanes-Portillo’s role in the drug organization. 

The probation office sided with the government and retained the aggravating-role 

adjustment in the PSR. It found that Arellanes-Portillo qualified as a manager under 

§ 3B1.1(b) because “[h]e was the known leader of the Kansas City cell and directed CI1 

and CI2 in their drug trafficking activities.” R. vol. 3 at 39. So we see that the probation 

4

 Neither the written objection nor the government’s written response are in the 

record on appeal, so we rely on the Addendum to the PSR for the parties’ positions. 

Appellate Case: 20-3165 Document: 010110690171 Date Filed: 05/27/2022 Page: 4
5 

office and the parties evaluated the aggravating-role adjustment based on ArellanesPortillo’s drug activity, not his money-laundering activity. 

At the sentencing hearing, Arellanes-Portillo renewed his objection to the threelevel adjustment for his aggravating role in the offense. He contended that he had merely 

served as a mouthpiece for his superior in the organization, Portillo-Uranga, and that he 

had lacked “any autonomy in directing the way the organization runs, the way money 

comes in and out of the country or when drugs come in and out of the country.” R. vol. 2 

at 205–06. So he argued that he shouldn’t qualify for an aggravated-role adjustment. In 

response, the government rested on its earlier written response to Arellanes-Portillo’s 

PSR objection. 

After hearing from the parties, the district court ruled that Arellanes-Portillo had 

acted as a manager or supervisor as provided in § 3B1.1(b). In support, the court cited 

testimony that Arellanes-Portillo had been Portillo-Uranga’s “right hand man” and been 

referred to as “the head of the Kansas City cell.” R. vol. 2 at 206. Among other things, 

the court noted that Portillo-Uranga had delegated some of his authority to ArellanesPortillo “to contact Mike for purposes of delivering money to him to get to the 

suppliers[.]” R. vol. 2 at 207. It also determined that Arellanes-Portillo had been higher in 

the organization than some others “in terms of finding stash houses, using them, dropping 

them when they thought there was law enforcement heat on them.” R. vol. 2 at 207. From 

recorded phone calls, the court found that Arellanes-Portillo “directed people to go pick 

up drugs or deliver money, again, at the behest of Mr. Portillo-Uranga but, nevertheless, 

Mr. Portillo-Uranga didn’t tell them directly necessarily. He used the defendant to do that 

Appellate Case: 20-3165 Document: 010110690171 Date Filed: 05/27/2022 Page: 5
6 

because the defendant operated as a manager or supervisor.” R. vol. 2 at 207–08. The 

court further pointed out that Arellanes-Portillo had the authority to cut (dilute) the drugs, 

that he knew the identity of customers, and that he could set the drug price for some 

customers. From this, we see that the district court also relied on Arellanes-Portillo’s 

drug activity in assessing the aggravated-role adjustment, though it also mentioned some 

of his associated involvement with transporting drug proceeds to Mexico. 

In the end, the district court accepted the PSR’s sentencing recommendations with 

one exception—it added two offense levels to § 2S1.1(a)(1)’s base offense level for 

Arellanes-Portillo’s maintenance of a drug premises under § 2D1.1(b)(12). Thus, the 

offense level for the money-laundering offenses rose to 39, minus three offense levels for 

the timely acceptance of responsibility, which left a total offense level of 36. That, 

combined with criminal-history category of I, resulted in an advisory guidelines range of 

188–235 months of imprisonment. From that, the court imposed a term of 188 months. 

Arellanes-Portillo appealed. He no longer argues that his drug activity failed to 

support an aggravated-role adjustment for his drug offenses. Instead, now alert to 

§ 2S1.1’s Application Note 2(C), he challenges the district court’s aggravated-role 

adjustment on a different basis—that it erred by basing the adjustment on relevant 

conduct for his drug offenses, and not exclusively on relevant conduct for his moneylaundering offenses. 

Appellate Case: 20-3165 Document: 010110690171 Date Filed: 05/27/2022 Page: 6
7 

DISCUSSION

I. Drugs and Money-Laundering Convictions 

In evaluating this appeal, it helps to review how the probation office should have 

structured the PSR and how its skipping steps has led to the need for a resentencing. 

First, as mentioned, the PSR didn’t separate the drug and money-laundering 

counts into two separate groups of closely related counts. Instead, citing § 3D1.2(d), the 

PSR immediately lumped the seven drug-related counts and the two money-launderingrelated counts into a single “Count Group 1.” Apparently, the probation office mistakenly 

believed that the drug and money-laundering offenses immediately grouped together 

because their separate guidelines—§§ 2S1.1 and 2D1.1—are listed in the table at 

§ 3D1.2(d) (though, importantly, in separate rows).5

 

Second, the PSR should have calculated a total offense level for each of the two 

groups of closely related counts. For the drug-conviction group, the PSR should have 

calculated a base offense level of 32, added two levels for maintaining a drug premises, 

and then added three more levels for an aggravating-role adjustment.6

 That minus three 

5

 If the Guidelines Manual contemplated this immediate grouping across the 

§ 3D1.2(d) table’s rows, it wouldn’t need to direct that the closely related groups of 

drug convictions and of money-laundering convictions later be grouped under 

§ 3D1.2(c). See § 2S1.1 cmt. n.6. In grouping under § 3D1.2(c), a court must 

calculate the total offense levels for each group so that it can apply the one with the 

highest total level. See § 3D1.3(a); see also § 3D1.3 cmt. n.2. 

6

 As we understand it, Arellanes-Portillo no longer contests that he would 

qualify for the three-level aggravating-role adjustment for his drug offenses. Even if 

he did, having reviewed the record, we see more than sufficient evidence to support 

it. 

Appellate Case: 20-3165 Document: 010110690171 Date Filed: 05/27/2022 Page: 7
8 

levels for timely acceptance of responsibility would leave a total offense level of 34. As 

for the money-laundering group, the PSR should have calculated a base offense level of 

34 (the Chapter Two calculation for the underlying drug offenses, as explained above); 

added two levels for the convictions under 18 U.S.C. § 1956; added zero, two, or three 

levels for an aggravating-role adjustment (after applying § 1B1.3 to isolate any acts and 

omissions qualifying as relevant conduct to the money-laundering offenses as then 

applied to § 3B1.1); and then subtracted three levels for acceptance of responsibility. 

That would leave a total offense level of 33, 35, or 36.7

 Third, under § 3D1.2(c), as directed by § 2S1.1’s Application Note 6, the PSR 

should have grouped the two separate drug and money-laundering groups. Under that 

grouping rule, the PSR would apply whichever group yielded the higher total offense 

level.8

 

II. Standard of Review

 Because Arellanes-Portillo contends that the district court misapplied the 

guidelines, we would ordinarily review de novo. See United States v. Ford, 613 F.3d 

1263, 1268 (10th Cir. 2010). But he concedes that in the district court he didn’t raise an 

objection based on § 2S1.1’s Application Note 2(C). So we review for plain error. See

7

 An offense level of 34 isn’t possible, because § 3B1.1 has a minimum twolevel adjustment. 

8

 Without this § 3D1.2(c) grouping, Arellanes-Portillo’s ultimate total offense 

level would have risen by two offense levels because his drug and money-laundering 

groups yielded total offense levels within four levels of each other. § 3D1.4(a). 

Appellate Case: 20-3165 Document: 010110690171 Date Filed: 05/27/2022 Page: 8
9 

United States v. Poe, 556 F.3d 1113, 1128 (10th Cir. 2009). Thus, Arellanes-Portillo must 

show: “(1) error, (2) that is plain, (3) which affects the party’s substantial rights, and (4) 

which seriously affects the fairness, integrity, or public reputation of judicial 

proceedings.” Id. (cleaned up). 

III. Analysis 

A. Error 

The district court erred by misapplying the Chapter Three aggravated-role 

adjustment to Arellanes-Portillo’s guidelines calculation for his money-laundering 

convictions. Tracking the probation office and the parties, the district court ran afoul of 

the guidelines’ precise rules for the application of Chapter Three adjustments. 

First, when Chapter Two sentencing calculations are self-contained in the 

guideline of the offense of conviction, §§ 1B1.1(a)(3) and 1B1.2(b) direct courts to 

calculate Chapter Three adjustments using the relevant conduct of the offense of 

conviction. Thus, for example, had the PSR calculated the total offense level for the 

group of closely related drug offenses, it would have used relevant conduct for the drug 

offenses in evaluating any Chapter Three adjustments. This is illustrated by ArellanesPortillo’s case, in which the Chapter Two offense-level calculation was self-contained in 

the drug guideline, § 2D1.1, and didn’t divert to a different Chapter Two offense 

guideline by cross reference or special instruction. 

Second, when sentencing calculations aren’t self-contained in the guideline of the 

offense of conviction, § 1B1.5(c) generally instructs courts to calculate the Chapter Three 

adjustments using relevant conduct from the offense associated with the incorporated 

Appellate Case: 20-3165 Document: 010110690171 Date Filed: 05/27/2022 Page: 9
10 

guideline.9

 But in the following terms, § 1B1.5(c) also alerts courts that exceptions may 

apply: “If the offense level is determined by a reference to another guideline under 

subsection (a) or (b)(1) above, the adjustments in Chapter Three (Adjustments) also are 

determined in respect to the referenced offense guideline, except as otherwise expressly 

provided.” § 1B1.5(c) (emphasis added).10

Here, the probation office, the parties, and the district court overlooked the 

exception found at § 2S1.1’s Application Note 2(C). That note instructs courts to 

calculate the Chapter Three adjustments for § 2S1.1 based on relevant conduct on the 

money-laundering offenses, and “not on the underlying offense from which the laundered 

funds were derived”: 

Application of Chapter Three Adjustments—Notwithstanding § 1B1.5(c), 

in cases in which subsection (a)(1) [of § 2S1.1] applies, application of any 

Chapter Three adjustments shall be determined based on the offense covered 

by the guideline (i.e., the laundering of criminally derived funds) and not on 

the underlying offense from which the laundered funds were derived. 

§ 2S1.1 cmt. n.2(C). 

As discussed earlier, the district court largely based its aggravating-role 

adjustment for the money-laundering offenses on relevant conduct from the drug 

9

 Section 2S1.1(a)(1) provides an example of this situation. That subsection 

uses the underlying offense’s offense level in setting its own base offense level. 

10 Subsections § 1B1.5(a) and (b)(1) pertain to cross references and 

instructions to apply another guideline. 

Appellate Case: 20-3165 Document: 010110690171 Date Filed: 05/27/2022 Page: 10
11 

offenses. In doing so, the court followed the lead of the probation office and the parties 

and proceeded as if the general rule found at § 1B1.5(c) applied. That was error.11 

Even so, the government argues that the district court didn’t err at all. It contends 

that “Arellanes-Portillo’s role in the drug-trafficking organization as a whole was 

relevant conduct with respect to his role in the money-laundering offenses, and the 

district court properly considered it in finding that Arellanes-Portillo qualified for the 

enhancement.”12 Appellee’s Br. at 15. This fundamentally misunderstands what relevant 

conduct is under § 1B1.3—and it contradicts § 2S1.1’s Application Note 2(C)’s 

command. 

Section 1B1.3 doesn’t leave room for competing versions of what qualifies as 

“relevant conduct.” Section 1B1.3 sets precise boundaries. It declares whose and what 

11 Section 2S1.1 has a leakproof valve for admitting or excluding drug-related 

relevant conduct into the money-laundering sentencing calculation. First, by 

including the underlying drug offense’s “offense level” as its own base offense level, 

§ 2S1.1(a)(1) necessarily incorporates drug-related relevant conduct—here, relevant 

conduct in support of the drug-weight and the drug-premises enhancements under 

§ 2D1.1. Second, by instructing that any Chapter Three adjustments not be 

determined based on relevant conduct for the offenses underlying the moneylaundering offenses, § 2S1.1’s Application Note 2(C) seals off drug-offense relevant 

conduct from the money-laundering calculation for Chapter Three adjustments. 

12 On the other hand, Arellanes-Portillo contends that relevant conduct doesn’t 

even apply here. He says that § 2S1.1’s Application Note 2(C) activates the “[u]nless 

otherwise specified” preface to § 1B1.3. This is wrong. Section 1B1.1(a)(3) directs courts 

to use relevant conduct to assess specific offense characteristics, adjustments, cross 

references, and special instructions. Nothing in Application Note 2(C) says otherwise. 

Instead, that note concerns what relevant conduct applies in assessing Chapter Three 

adjustments. It opts for relevant conduct for the money-laundering offense, not relevant 

conduct for the underlying offense. 

Appellate Case: 20-3165 Document: 010110690171 Date Filed: 05/27/2022 Page: 11
12 

“acts and omissions” count as relevant conduct in assessing the applicability of base 

offense levels, specific offense characteristics, cross references, special instructions, and 

Chapter Three adjustments. See §§ 1B1.1(a)(1)–(3); 1B1.2; 1B1.3(a), (b). Those precise 

acts and omissions are the relevant conduct available for use in determining the 

applicability of Chapters Two and Three sentencing slots.13 In short, the government 

must justify an aggravating-role adjustment for money-laundering convictions with 

money-laundering relevant conduct. 

But in the district court, the government didn’t isolate § 1B1.3 “acts and 

omissions” from Arellanes-Portillo’s money-laundering offenses and explain how they 

would justify the role adjustment under § 3B1.1(b).14 And on appeal, the government 

goes far afield of § 1B1.3’s precise terms by morphing relevant conduct into something 

that supplants the needed “act or omission” with a legal determination instead—that 

13 For instance, if Arellanes-Portillo had used a minor in a drug transaction, 

that “act” would be relevant conduct to the application of § 3D1.4 (“Using a Minor to 

Commit a Crime”) in calculating the advisory range under § 2D1.1, but it wouldn’t 

be relevant conduct in calculating the advisory range under § 2S1.1. Conversely, if 

Arellanes-Portillo had gotten in a high-speed chase and recklessly endangered others 

while taking drug proceeds to Mexico, that act would be relevant conduct to the 

application of § 3C1.2 (“Reckless Endangerment During Flight) in calculating the 

advisory guideline range under § 2S1.1, but not under § 2D1.1. 

14 We agree that a § 1B1.3 “act or omission” for one offense could be an act or 

omission for another offense too. In United States v. Irvin, 682 F.3d 1254, 1277 (10th 

Cir. 2012), we stated that acts relevant to a bank-fraud conspiracy could also be 

relevant to money laundering. But such a dual “act or omission” could achieve that 

status only by independently charting through § 1B1.3 for each of the offenses. It 

may be much easier to do that for the two offenses in Irvin than for the drug and 

money laundering offenses in this case. 

Appellate Case: 20-3165 Document: 010110690171 Date Filed: 05/27/2022 Page: 12
13 

“Arellanes-Portillo’s role in the drug-trafficking organization as a whole” qualifies as 

“relevant conduct with respect to his role in the money-laundering offenses[.]” 

Appellant’s Br. at 15.15 We will stick with § 1B1.3 as written. 

B. Plain Error 

Error may be plain based on the text of statutes or Guidelines. See United States v. 

Powell, 767 F.3d 1026, 1035 (10th Cir. 2014). As mentioned, § 2S1.1’s Application Note 

2(C) requires that all Chapter Three adjustments “be determined based on the offense 

covered by [the money-laundering] guideline (i.e., the laundering of criminally derived 

funds) and not on the underlying offense from which the funds were derived.” 

§ 2S1.1(a)(1) cmt. n.2(C) (emphasis added). Failing to heed this instruction is error that is 

plain. See del Carpio Frescas, 932 F.3d at 332 (concluding the district court plainly erred 

by basing an aggravated-role adjustment “on del Carpio’s wire fraud conduct, not his 

money laundering conduct” contrary to § 2S1.1’s Application Note 2(C) (emphasis in 

original)); Capps, 977 F.3d at 257 (“[T]he District Court erred in applying the 2-level 

15 In support of its contrary view, the government cites United States v. Lopez, 

743 F. App’x 489 (3d Cir. 2018) and United States v. Ramirez, 555 Fed. App’x 315, 

322 (5th Cir. 2014). But even assuming these unpublished cases support the 

government’s view, they would succumb to published cases from the same circuits 

enforcing § 2S1.1’s Application Note (2)(C). See United States v. Capps, 977 F.3d 

250, 256–57 (3d Cir. 2020) (confining the § 2S1.1 aggravating-role analysis to 

money-laundering conduct and excluding all underlying mail-fraud conduct from that 

analysis); United States v. del Carpio Frescas, 932 F.3d 324, 332 (5th Cir. 2019) 

(reversing a district court’s abuse-of-trust adjustment for money laundering, because 

“the [district] court fixated on the wire fraud conduct, not the money laundering 

conduct”). 

Appellate Case: 20-3165 Document: 010110690171 Date Filed: 05/27/2022 Page: 13
14 

abuse of trust adjustment [based on mail fraud] to the money laundering offense 

calculation. Given the text of Commentary Note 2(c), we think the error is plain.”).

Moreover, our court has instructed that Chapter Three adjustments for moneylaundering offenses and their underlying offenses are independently calculated on their 

own relevant conduct. See, e.g., United States v. Keck, 643 F.3d 789, 800–01 (10th Cir. 

2009) (interpreting “Application Note 2(C) as governing only the applicability of 

adjustments on money-laundering convictions, as opposed to the offense calculations of 

other, related offenses”). And our fellow circuit courts uniformly abide by the direction 

given at § 2S1.1’s Application Note 2(C). See United States v. Salgado, 745 F.3d 1135, 

1138 (11th Cir. 2014) (“When the district court calculated Salgado’s offense level under 

§ 2S1.1(a)(1), it could base a role enhancement on his conduct in the money laundering 

conspiracy but not on his conduct in the underlying drug conspiracy.”); United States v. 

Rushton, 738 F.3d 854, 859 (7th Cir. 2013) (“The ranges would not have been the same 

had the 2–level enhancement for abuse of trust been permissible. It is permissible in a 

money laundering case—but only when the abuse of trust relates to the money laundering 

itself rather than to the underlying offense[.]”); United States v. Anderson, 526 F.3d 319, 

328–29 (6th Cir. 2008) (relying on § 2S1.1’s Application Note 2(C) to reverse the district 

court’s transporting a drug-offense-related Chapter Three mitigating-role adjustment to 

the sentencing calculation for the money-laundering crimes). 

C. Substantial Prejudice 

 Next, Arellanes-Portillo must establish that the error affected his substantial rights. 

To do so, he must show that “an error was prejudicial, meaning that there is a reasonable 

Appellate Case: 20-3165 Document: 010110690171 Date Filed: 05/27/2022 Page: 14
15 

probability that, but for the error claimed, the result of the proceeding would have been 

different.” United States v. Bustamante-Conchas, 850 F.3d 1130, 1138 (10th Cir. 2017) 

(en banc) (quotation omitted). “A reasonable probability is a probability sufficient to 

undermine confidence in the outcome.” United States v. Hasan, 526 F.3d 653, 665 (10th 

Cir. 2008) (quoting Sallahdin v. Gibson, 275 F.3d 1211, 1235 (10th Cir. 2002)). 

“Confidence in the outcome can be undermined even if [his] showing would not satisfy 

the preponderance-of-the-evidence standard.” United States v. Yurek, 925 F.3d 423, 446 

(10th Cir. 2019). 

 The government contends that Arellanes-Portillo has failed to show substantial 

prejudice, relying partly on United States v. Gehrmann, 966 F.3d 1074 (10th Cir. 2020). 

In that case, we affirmed an aggravated-role adjustment after concluding that “[t]he 

district court’s findings as supplemented by undisputed facts show that Dr. Gehrmann 

acted as an organizer[.]” Id. at 1084. The government asks us to affirm based on 

undisputed evidence here too. 

But as Arellanes-Portillo notes, the government doesn’t have equally strong 

underlying district-court findings and undisputed facts here as compared to Gehrmann. 

For instance, here we lack critical district-court findings about the identity or number of 

“participants,” as needed to apply § 3B1.1(b). This means that the government is asking 

us to determine—in the first instance—what persons qualify as participants in the moneylaundering offenses. In doing so, we would have to determine what persons are 

“criminally responsible for the commission of the offense,” including those persons not 

even convicted. See § 3B1.1 cmt. n.1. That calls for determinations of witness credibility 

Appellate Case: 20-3165 Document: 010110690171 Date Filed: 05/27/2022 Page: 15
16 

and of offense elements including knowledge and intent. From a cold record, that is a tall 

order. We conclude that those determinations are best left to the district court on remand. 

 Alternatively, the government asks us to affirm on grounds that the criminal 

activity was “otherwise extensive.” See § 3B1.1(b). And it correctly notes that in 

Gehrmann, we acknowledged that we could reach this issue even if the district court 

hadn’t. 966 F.3d at 1082 (citing United States v. Belfrey, 928 F.3d 746, 751 (8th Cir. 

2019)). But we agree with Arellanes-Portillo that this isn’t an appropriate case to do so. 

As he points out, this issue first arises in the government’s appellate response brief. We 

again think it best to leave this to the district court to address on remand. 

With all this in mind, we return to whether Arellanes-Portillo has shown a 

“reasonable probability” that “but for the error,” “the result of the proceeding would have 

been different.” Bustamante-Conchas, 850 F.3d at 1138. We are satisfied that he has 

shown that reasonable probability. If, on remand, the district court were to determine only 

that the money-laundering offenses involved fewer than five participants, ArellanesPortillo’s aggravating-role adjustment would fall one offense level, leaving his advisory 

range at 168–210 months of imprisonment. And if the district court were to decline to 

apply an aggravating-role adjustment, his total offense level would fall two levels to 34 

(as the drug convictions would provide a higher total offense level then). That would 

leave an advisory guideline range of 151–188 months of imprisonment. For all reasons 

Appellate Case: 20-3165 Document: 010110690171 Date Filed: 05/27/2022 Page: 16
17 

given, our confidence in the outcome is undermined. So we conclude that ArellanesPortillo has shown substantial prejudice. 

D. Fairness, Integrity, or Public Reputation of Judicial Proceedings

 For the fourth prong of plain-error analysis, Arellanes-Portillo must show that the 

error “affects the fairness, integrity, or public reputation of judicial proceedings.” United 

States v. Sabillon-Umana, 772 F.3d 1328, 1333 (10th Cir. 2014). We conclude that he has 

met that burden here. Ordinarily, when an error affects the calculation of a defendant’s 

guideline range and the first three prongs are satisfied, the fourth prong is also met. See 

Yurek, 925 F.3d at 447. That is because reasonable citizens would “bear a rightly 

diminished view of the judicial process and its integrity if courts refused to correct 

obvious errors of their own devise that threaten to require individuals to linger longer in 

federal prison than the law demands[.]” Sabillon-Umana, 722 F.3d at 1333–34. Though 

Arellanes-Portillo may ultimately fail in lowering his advisory guideline range, we see a 

sufficient basis on which the district court might impose a lower advisory guideline 

range. In that circumstance, we conclude that he has met his needed showing on this final 

prong of plain-error review. 

CONCLUSION 

 In sum, Arellanes-Portillo has met his burden under the plain-error standard 

regarding the three-level aggravating-role adjustment. So we vacate his sentence and 

remand for resentencing consistent with this opinion. 

Appellate Case: 20-3165 Document: 010110690171 Date Filed: 05/27/2022 Page: 17