PUBLISH 

UNITED STATES COURT OF APPEALS 

FOR THE TENTH CIRCUIT 

_________________________________ 

UNITED STATES OF AMERICA, 

 Plaintiff - Appellee, 

v. 

JOSEPH C. KUPFER, 

 Defendant - Appellant. 

No. 13-2189 

_________________________________ 

Appeal from the United States District Court 

for the District of New Mexico 

(D.C. No. 1:10-CR-03383-WJ-1)

_________________________________ 

O. Dean Sanderford, Assistant Federal Public Defender (Virginia L. 

Grady, Federal Public Defender, with him on the briefs) Office of the 

Federal Public Defender, Denver, Colorado, for Defendant-Appellant. 

Jeremy Pena, Assistant United States Attorney (Damon P. Martinez, 

United States Attorney, with him on the brief) Office of the United 

States Attorney, Albuquerque, New Mexico, for Plaintiff-Appellee. 

_________________________________ 

Before BRISCOE, Chief Judge, BALDOCK, and BACHARACH, 

Circuit Judges. 

_________________________________ 

BACHARACH, Circuit Judge. 

_________________________________ 

FILED 

United States Court of 

Appeals 

Tenth Circuit 

August 19, 2015

Elisabeth A. Shumaker 

Clerk of Court

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 1 
-2- 

According to the government, Mr. Joseph Kupfer and his wife 

conspired to enable Dr. Armando Gutierrez (a media consultant) to 

increase his compensation under a State contract without any 

additional work. In exchange for the increase, Dr. Gutierrez allegedly 

gave kickbacks to Mr. Kupfer through Mr. Kupfer’s consulting 

company. The government alleged that Dr. Gutierrez had disguised 

the kickbacks as payments for Mr. Kupfer’s work on a separate media 

campaign involving voter awareness. 

The government successfully prosecuted Mr. Kupfer in two 

trials. In the first, the jury found Mr. Kupfer and his wife guilty of 

tax evasion. In the second, the jury found Mr. Kupfer guilty of 

stealing and participating in a conspiracy to steal federal government 

property with a co-defendant, Dr. Gutierrez. The district court 

entered a judgment of conviction for these crimes and sentenced 

Mr. Kupfer to ten years in prison. Mr. Kupfer appeals the conviction 

and sentence on all counts. 

On appeal, we affirm the conviction and reverse and remand to 

the district court for resentencing. 

I. Issues Involving the Conviction 

 We start with Mr. Kupfer’s challenges to the conviction. 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 2 
-3- 

 A. Tax Evasion Trial 

 Mr. Kupfer and his wife jointly filed federal income taxes from 

2004 to 2006, but failed to report over $790,000 in gross income. The 

government charged Mr. Kupfer with three counts of tax evasion and 

aiding and abetting, one count for each year. See 26 U.S.C. § 7201; 

18 U.S.C. § 2. Mr. Kupfer admitted that he had failed to report a 

substantial amount of gross income, but denied that his underreporting was willful. The jury disagreed and found Mr. Kupfer 

guilty on each count. On appeal, he challenges the adequacy of the 

jury instructions and the district court’s response to an allegation of 

jury misconduct.1

 On both issues, we conclude that the district court 

acted within its discretion. 

 1. Jury Instructions 

The district court instructed the jury that it could find guilt 

only if Mr. Kupfer’s under-reporting of income had been willful. 

According to Mr. Kupfer, the court should have gone further, 

instructing the jury that the under-reporting would not have been 

considered “willful” if it had been merely negligent, inadvertent, 

accidental, mistaken, or reckless. We rejected this contention in 

 

1

 Ms. Elizabeth Kupfer filed her own appeal in the tax evasion 

case, and Mr. Kupfer joins in her arguments. See Fed. R. App. P. 

28(i). We more fully addressed the issues on the tax counts in United 

States v. Kupfer (Elizabeth), No. 13-2138, __ F.3d __, 2015 WL 

4081108, at *1-3 (10th Cir. July 7, 2015).

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 3 
-4- 

deciding Ms. Kupfer’s appeal. United States v. Kupfer (Elizabeth), 

No. 13-2138, __ F.3d __, 2015 WL 4081108, at *1–3 (10th Cir. July 7, 

2015). Based on our opinion in that appeal, we conclude that the 

district court acted within its discretion in declining to include Mr. 

Kupfer’s proposed language. 

2. Juror Misconduct 

After the trial ended, Ms. Kupfer submitted an affidavit from a 

juror stating that a fellow juror had commented about other charges 

during jury deliberations. Based on this affidavit, Mr. Kupfer 

requested a new trial on the ground of juror misconduct. The district 

court declined to conduct a hearing or grant a mistrial. We conclude 

that these rulings fell within the district court’s discretion because 

the court could reasonably determine on the record it had that (1) a 

hearing was unnecessary and (2) the improper remarks were 

harmless. 

When a defendant presents credible evidence of prejudicial 

information during jury deliberations, a presumption of prejudice 

arises and the trial court must investigate. United States v. Davis, 60 

F.3d 1479, 1484–85 (10th Cir. 1995). To carry out that duty, trial 

courts must ordinarily hold a hearing; but in rare exceptions, the 

court need not hold a hearing if it would not be useful. United States 

v. McVeigh, 153 F.3d 1166, 1186 (10th Cir. 1998). 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 4 
-5- 

As explained in our opinion addressing Ms. Kupfer’s appeal, 

the district court acted within its discretion in declining to conduct a 

hearing and in denying the motion for a mistrial. United States v. 

Kupfer (Elizabeth), No. 13-2138, __ F.3d __, 2015 WL 4081108, at 

*3–6 (10th Cir. July 7, 2015). 

B. Conspiracy Trial 

The conspiracy trial involved allegations of overpayment to 

Mr. Kupfer, ostensibly based on his subcontract to help on a media 

campaign. This media campaign grew out of a federal grant to the 

State of New Mexico to increase voter awareness. With this grant, 

the State paid millions to a consultant (Dr. Gutierrez), who in turn 

paid over $740,000 to Mr. Kupfer. 

Dr. Gutierrez also had two other State contracts. One involved 

an anti-smoking campaign; the other involved an elder-abuse 

campaign. 

No misconduct is alleged with the elder-abuse campaign. But 

the government argued at trial that Mr. Kupfer had influenced the 

State to amend the contract for the anti-smoking campaign, allowing 

Dr. Gutierrez to obtain more than $950,000 in extra compensation. 

According to the government, Mr. Kupfer earned only a small 

fraction of the $950,000+. The remainder, according to the 

government, was a kickback to Mr. Kupfer for his role in getting 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 5 
-6- 

Dr. Gutierrez the increased compensation on his anti-smoking 

contract. 

 Invoking this theory, the government charged Mr. Kupfer with 

one count of conspiracy and three counts of stealing federal money or 

assisting another in stealing federal money. The jury found Mr. 

Kupfer guilty on all counts, and he argues that the district court erred 

by admitting evidence of the anti-smoking and elder-abuse contracts. 

1. Evidence Involving the Anti-Smoking Contract 

At trial, the government presented evidence of Mr. Kupfer’s 

role in a contract between the New Mexico Attorney General’s Office 

and Dr. Gutierrez. This contract called for Dr. Gutierrez to produce 

commercials on smoking prevention and cessation. 

 Mr. Kupfer moved to preclude evidence of this contract, 

arguing that (1) the evidence was not relevant and (2) it constituted 

inadmissible evidence of uncharged misconduct under Federal Rule 

of Evidence 404(b). The court overruled the objection, holding that 

(1) the evidence was probative as intrinsic evidence and (2) the 

probative value was not substantially outweighed by the danger of 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 6 
-7- 

unfair prejudice.2

 We conclude that the district court acted within its 

discretion in admitting the evidence. 

a. Intrinsic Evidence 

Mr. Kupfer challenges the characterization of the anti-smoking 

contract as intrinsic evidence. We reject that challenge. The district 

court acted within its discretion in concluding that the evidence was 

inextricably intertwined with the charged conduct. 

When we apply Rule 404(b), we distinguish between evidence 

that is extrinsic or intrinsic to the charged crime. United States v. 

Pace, 981 F.2d 1123, 1135 (10th Cir. 1992), abrogated on other 

grounds as recognized in United States v. Bell, 154 F.3d 1205, 1209–

10 (10th Cir. 1998). Evidence of other acts may be inadmissible 

under Federal Rule of Evidence 404(b), but this rule does not cover 

evidence that is considered “intrinsic.” United States v. Irving, 665 

F.3d 1184, 1212 (10th Cir. 2011). 

Evidence is considered 

 “intrinsic” when it is “directly connected to the factual 

circumstances of the crime and provides contextual or 

background information to the jury,” and 

 “extrinsic” when it “is extraneous and is not intimately 

connected or blended with the factual circumstances of 

the charged offense.” 

 

2

 In the alterative, the district court held that the evidence would 

be admissible as extrinsic evidence. We need not address the 

alternative rationale. 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 7 
-8- 

United States v. Parker, 553 F.3d 1309, 1314 (10th Cir. 2009) 

(quoting Thomas M. DiBiagio, Intrinsic and Extrinsic Evidence in 

Federal Criminal Trials: Is the Admission of Collateral OtherCrimes Evidence Disconnected to the Fundamental Right to a Fair 

Trial, 47 Syracuse L. Rev. 1229, 1231 (1997)). 

We regard evidence as intrinsic when it 

 was “inextricably intertwined” with the charged conduct,3

 occurred within the same time frame as the activity in the 

conspiracy being charged,4

 was a necessary preliminary to the charged conspiracy,5

 provided direct proof of the defendant’s involvement with 

the charged crimes,6

 was “entirely germane background information, . . . 

‘directly connected to the factual circumstances of the 

crime,’”7

 or 

 

3 United States v. Lambert, 995 F.2d 1006, 1007 (10th Cir. 1993) 

(quoting United States v. Williams, 900 F.2d 823, 825 (5th Cir. 

1990)). 

4

 See United States v. Parker, 553 F.3d 1309, 1315 (10th Cir. 

2009) (“The three transactions within the charged conspiracy timeframe are intrinsic to the crime and substantiate the criminal 

conspiracy.”). 

5

 Lambert, 995 F.2d at 1007. 

6

 Parker, 553 F.3d at 1314–15. 

7

 United States v. Irving, 665 F.3d 1184, 1212–13 (10th Cir. 

2011) (quoting Parker, 553 F.3d at 1314). 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 8 
-9- 

 was necessary to provide the jury with background and 

context of the nature of the defendant’s relationship to 

his accomplice.8

The district court could reasonably conclude that evidence of the 

anti-smoking contract had satisfied these criteria: Dr. Gutierrez’s 

payments to Mr. Kupfer and the anti-smoking contract amendments 

occurred together within a short time-period and tended to show the 

conspiracy being charged and Mr. Kupfer’s involvement. See United 

States v. Parker, 553 F.3d 1309, 1315 (10th Cir. 2009). 

The district court regarded the anti-smoking contract as 

intrinsic because it (1) was intertwined with payments Dr. Gutierrez 

had made to Mr. Kupfer and (2) showed Elizabeth Kupfer’s 

involvement in issuing payments. R., vol. VIII, at 3081–82. The 

district court based its ruling on the government’s theory of the 

intertwined relationship between the federal grant and the antismoking contract amendments, which is reflected by the timing of the 

payments to Mr. Kupfer. 

Within five months of receiving a $250,000 increase in the 

anti-smoking contract, Dr. Gutierrez paid $140,000 to Mr. Kupfer’s 

consulting company even though it had not yet begun work on the 

project. Id. at 1866–67, 2620–21. The court could wonder why Dr. 

 

8

 United States v. Hall, 508 F. App’x 776, 779–80 (10th Cir. 

2013) (unpublished). 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 9 
-10- 

Gutierrez was willing to pay Mr. Kupfer’s consulting company in 

advance. See id. at 1808 (discussing the facts that “the contract 

became effective 9-9-04, and that invoice [for $2 million] came in 

the day after”). 

Then, within thirteen months of the largest price increase under 

the anti-smoking contract ($350,000), Dr. Gutierrez made three more 

monthly payments (totaling $200,000) to Mr. Kupfer’s consulting 

company. 

Based on this timing, the jury could infer a connection between 

(1) Dr. Gutierrez’s price increases under the anti-smoking contract 

and (2) his payments to Mr. Kupfer under the voter-awareness 

contract. 

Mr. Kupfer argues that the voter-awareness and anti-smoking 

contracts were distinct because the contracts involved different 

agencies, only one of the contracts involved federal funds, and the 

anti-smoking contract preceded the voter-awareness contract by four 

years. It is true that the contracts were distinct. But the government 

theorized that Dr. Gutierrez had used money from the voterawareness contract to pay Mr. Kupfer for increasing the payments 

under the anti-smoking contract. Under this theory, both contracts 

(the voter-awareness and the anti-smoking contracts) were integral to 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 10 
-11- 

the scheme. The differences between the contracts did not invalidate 

the government’s theory. 

According to Mr. Kupfer, the government changed its theory at 

trial, characterizing the payments to Mr. Kupfer as kickbacks on the 

voter-awareness contract (rather than for the price increases on the 

anti-smoking contract). This argument reflects Mr. Kupfer’s 

confusion over the government’s theory. 

The government never accused Mr. Kupfer of doing something 

illegal to get Dr. Gutierrez the voter-awareness contract; the 

government’s theory―before, during, and after the trial―was that 

Mr. Kupfer and his wife had worked to land Dr. Gutierrez over 

$950,000 in additional payments under the anti-smoking contract. 

Under the government’s theory, Dr. Gutierrez had to pay 

Mr. Kupfer to secure the extra payments. Mr. Kupfer had no 

responsibilities under the anti-smoking contract, but he had a 

subcontract to help Dr. Gutierrez with the voter-awareness contract. 

That subcontract involved Mr. Kupfer’s production-related work on a 

short training video. For that work, Dr. Gutierrez paid Mr. Kupfer 

over $740,000. The government attributed those payments to 

kickbacks for the anti-smoking contract’s price increases. The 

kickbacks, however, were disguised as payments for Mr. Kupfer’s 

work on the voter-awareness contract. 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 11 
-12- 

 

Mr. Kupfer contends that the government dropped this theory at 

trial, but the government never wavered from this theory. At trial, 

for example, the government explained its conspiracy allegation in 

opening statements: 

 And you may ask why during the course of this 

trial, why the Defendant Gutierrez would pay $750,000 to 

Defendant Joseph Kupfer. The evidence, as I previously 

mentioned, is going to show that there were favors back 

and forth between these two men over the course of the 

years, political allies, friends. But $750,000? Here’s what 

you’re also going to learn, that in addition to the [voterawareness] contract that the defendant had with the 

Secretary of State’s office during this time frame, he also 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 12 
-13- 

had contracts with the Attorney General’s office where 

Elizabeth Kupfer was the chief financial officer. And 

these were lucrative contracts, you will learn. 

 

R., vol. VIII, at 1383–84. The government then discussed the 

amendments to Dr. Gutierrez’s anti-smoking contract, which 

increased his pay from $150,000 to over $1,100,000. Id. at 1384. The 

government repeated this theory in closing argument. Id. at 2931–33. 

In our view, the government’s theory has been consistent throughout 

the proceedings. 

 In these circumstances, the district court had the discretion to 

treat the evidence as intrinsic. 

b. Unfair Prejudice 

Mr. Kupfer also contends that the district court erred in 

applying Federal Rule of Evidence 403. Under this rule, the district 

court can exclude evidence if the probative value is substantially 

outweighed by the danger of unfair prejudice. Fed. R. Evid. 403. The 

district court concluded that the danger of unfair prejudice did not 

require exclusion.

In reviewing this conclusion, we apply the abuse-of-discretion 

standard. United States v. Archuleta, 737 F.3d 1287, 1292 (10th Cir. 

2013). Under this standard, the ruling was permissible. 

The court could reasonably view the evidence as highly 

probative. Mr. Kupfer acknowledges that the anti-smoking contract 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 13 
-14- 

was “highly suspicious” because it “ballooned Gutierrez’s pay by 

over $800,000.” Appellant’s Opening Br. at 31. 

The Increases in Dr. Gutierrez’s Anti-Smoking Contract 

The biggest jumps occurred in May 2004 and December 2004, 

with amendments that increased Dr. Gutierrez’s compensation by 

$250,000 and then $350,000. Between these two huge jumps, Dr. 

Gutierrez paid Mr. Kupfer’s company $140,000, before Mr. Kupfer 

had done any work on the anti-smoking campaign. 

And within thirteen months of obtaining the unexplained 

increase of $350,000 under the anti-smoking contract, Dr. Gutierrez 

paid Mr. Kupfer’s company another $200,000. Mr. Kupfer ultimately 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 14 
-15- 

collected a total of $746,375 for work on the voter-awareness 

contract. 

But even after being subpoenaed, Dr. Gutierrez never furnished 

a contract between himself and Mr. Kupfer (or Mr. Kupfer’s 

consulting company) and took two years to furnish invoices that had 

been subpoenaed. And in the invoices eventually furnished, Mr. 

Kupfer had provided only vague descriptions of his work (without 

any itemization). 

In these circumstances, the district court could view the 

$746,375 in payments to Mr. Kupfer’s company as compensation for 

the extraordinary increases in Dr. Gutierrez’s anti-smoking contract. 

As a result, the court could reasonably view evidence of the antismoking contract as highly probative. 

Under Rule 403, the court could still exclude the evidence if 

the probative value was substantially outweighed by the danger of 

unfair prejudice. But the court could reasonably view any prejudice 

as fair, rather than unfair. 

In urging unfair prejudice, Mr. Kupfer denies involvement in 

the numerous increases in Dr. Gutierrez’s anti-smoking contract. 

Mr. Kupfer says it was his wife, not himself, with the connections 

and position to engineer these price increases. According to Mr. 

Kupfer, the evidence was unfairly prejudicial because the jury could 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 15 
-16- 

impermissibly find him guilty by association because of his wife’s 

conduct, without finding any wrongdoing on the part of Mr. Kupfer. 

But the district court could view the situation differently. There 

was evidence that both Kupfers (not just Ms. Kupfer) had strong ties 

to the Secretary of State. And sandwiched between two extraordinary 

compensation increases for Dr. Gutierrez were equally generous, 

unexplained payments from Dr. Gutierrez to the company owned by 

Mr. Kupfer, not his wife. In these circumstances, the district court 

could reasonably conclude that Mr. Kupfer was being held 

accountable for his own role―not his wife’s―in the huge increases 

paid to Dr. Gutierrez under the anti-smoking contract.9

 Thus, the 

district court did not abuse its discretion in applying Rule 403. 

2. Elder-Abuse Contract 

The district court allowed the government to use evidence of a 

contract between Dr. Gutierrez and the Attorney General’s office to 

create media materials raising awareness of elder abuse, dubbing the 

 

9

 Mr. Kupfer relies on United States v. Cardall, 885 F.2d 656, 

671 (10th Cir. 1989). Cardall does not support Mr. Kupfer’s 

argument. There we explained that the government must give a 

precise reason for introduction of evidence requiring a prior bad act, 

and the reason must involve the defendant’s participation in the bad 

act. 885 F.2d at 671. 

 Here, the government provided the precise reason for 

introduction of the evidence; that reason involved Mr. Kupfer’s own 

“bad act,” a scheme to obtain kickbacks for inflating Dr. Gutierrez’s 

payments from the State. 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 16 
-17- 

contract the “Elder-Abuse Contract.” The government alleged no 

wrongdoing with respect to that contract, offering it only as an 

example of a legitimate baseline to compare the cost of the antismoking campaign. Mr. Kupfer argues the district court erred in 

allowing use of the elder-abuse contract because there was no link 

between him and the evidence. We need not reach this argument for 

two reasons: 

1. The elder-abuse contract could have been admissible as 

probative evidence unrelated to character. 

2. Any error in admitting the evidence would have been 

harmless. 

a. The Admissibility of the Elder-Abuse Contract 

Under Federal Rule of Evidence 402, all relevant evidence is 

admissible unless otherwise stated by federal law or rule. Rule 

404(b) provides an example of a rule stating otherwise, for this rule 

precludes evidence of other acts. United States v. Commanche, 577 

F.3d 1261, 1267 (10th Cir. 2009). But this rule precludes the use of 

evidence only when it is offered to attack a witness’s character. Fed. 

R. Evid. 404(b); see United States v. Kendall, 766 F.2d 1426, 1436 

n.5 (10th Cir. 1985) (“To fall within the scope of 404(b), an act need 

not be criminal, so long as it tends to impugn a defendant’s 

character.”). 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 17 
-18- 

The evidence of an elder-abuse contract is not subject to Rule 

404(b) because it does not concern character. The government 

offered the evidence only to illustrate a legitimate contract between 

Dr. Gutierrez and the New Mexico Attorney General’s Office. Under 

the contract, Dr. Gutierrez received $63,418.92 (for which there was 

no allegation of wrongdoing). R., vol. VIII, at 1861–62. By 

comparison, Dr. Gutierrez received over $1.1 million for similar 

work under the suspect anti-smoking contract. Id. at 1867. 

Once the anti-smoking contract was admitted, the elder-abuse 

contract became relevant to show Dr. Gutierrez’s normal billing rate 

for a legitimate media contract. Because there was no suggestion of 

wrongdoing in connection with the elder-abuse contract, there was no 

danger involving use of the contract as character evidence. 

Minimal danger arose from this benign evidence and it had 

probative value; thus, the evidence was relevant and was not subject 

to exclusion under Rule 403 or Rule 404(b). 

b. Harmless Error 

Even if the district court had erred in admitting the elder-abuse 

contract evidence, it would have been harmless. 

We will not reverse a defendant’s conviction on the basis of a 

district court’s erroneous admission of evidence if the error was 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 18 
-19- 

harmless to the defendant. United States v. Blechman, 657 F.3d 1052, 

1067 (10th Cir. 2011). 

Under this standard, we ask if the error had a “substantial 

influence” on the trial’s outcome or generates “‘grave doubt’ as to 

whether it had such effect.” United States v. Rivera, 900 F.2d 1462, 

1470 (10th Cir. 1990) (en banc) (quoting Kotteakos v. United States, 

328 U.S. 750, 756 (1946)). To make this assessment, we review the 

entire record de novo, “examining the context, timing, and use of the 

erroneously admitted evidence at trial and how it compares to 

properly admitted evidence.” United States v. Hanzlicek, 187 F.3d 

1228, 1237 (10th Cir. 1999). 

The government showed that any error would have been 

harmless, for the elder-abuse contract had played only a minor role in 

the trial. On that contract, the government asked one witness five 

general questions. R., vol. VIII, at 1861–62. These questions 

pertained only to the amount of the fees ($63,418.92) and 

identification of Ms. Kupfer as the person overseeing the contract. 

Id. In these questions and answers, there was no suggestion of 

wrongdoing with respect to that contract. Id. And in closing 

argument, the prosecutor never even mentioned the elder-abuse 

contract. In these circumstances, we conclude that the evidence 

regarding the elder-abuse contract did not substantially influence the 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 19 
-20- 

trial or generate grave doubt about the outcome. Accordingly, any 

error would have been harmless. 

II. Issues Involving Procedural Reasonableness of the 

 Sentence 

 After entering a judgment of conviction, the district court 

sentenced Mr. Kupfer for all offenses. In deciding on the sentence, 

the court calculated the guideline range. According to Mr. Kupfer, 

the calculations were incorrect because the court had (1) selected the 

wrong guideline for the offense, and (2) improperly enhanced the 

sentence based on obstruction of justice. We agree with both of 

Mr. Kupfer’s arguments. 

A. Applicable Offense Guideline 

When calculating the appropriate guideline, the district court 

started by evaluating the trial evidence. R., vol. VIII, at 3253–61. 

Mr. Kupfer argues this approach constituted error because the court 

should have considered only the offense of conviction as charged and 

presented to the jury. We agree. 

 In reviewing the district court’s selection of the applicable 

offense guideline, we engage in de novo review. See United States v. 

Neilson, 721 F.3d 1185, 1187 (10th Cir. 2013).10 Applying de novo 

 

10 The government argues that the clear-error standard applies 

because the selection of the offense guideline turns on factual 

findings. As discussed below, we disagree. The district court 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 20 
-21- 

review, we conclude that the district court incorrectly chose the 

offense guideline. 

To determine the offense guideline in this case, the court had to 

engage in a three-step process11: 

1. identifying the charge from the indictment and jury 

instructions, 

2. finding the substantive offense in the guidelines’ 

statutory index, and 

3. finding the applicable guideline range. 

See U.S. Sentencing Guidelines Manual § 1B1.2 (U.S. Sentencing 

Comm’n 2012) (explaining the process for determining the applicable 

guideline). 

The district court should have begun by identifying the charge 

as one involving conspiracy to steal funds. In the superseding 

indictment, Mr. Kupfer was charged with two types of conspiracy 

under 18 U.S.C. § 371: (1) to steal federal money in violation of 18 

U.S.C. § 641, and (2) to defraud the federal government. R., vol. I, at 

11–20 (Count 1). But the court instructed the jury only on the first 

 

mistakenly relied on trial evidence to select the offense guideline. As 

we explain, selection of the offense guideline entails a three-step 

process involving legal determinations rather than factual findings. 

11 We do not necessarily prescribe this three-step process in every 

case. In our case, however, these three steps are necessary for the 

court to identify the offense guideline based on the indictment and 

jury instructions. 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 21 
-22- 

type of conspiracy: to steal federal money in violation of 18 U.S.C. 

§ 641. The jury was never instructed on the government’s fraud 

theory. Thus, we know that Mr. Kupfer was ultimately convicted 

under 18 U.S.C. § 641 for conspiracy to steal federal money. 

When assessing a conspiracy conviction, the sentencing 

guidelines instruct courts to choose the guideline provision that best 

fits the substantive offense underlying the conspiracy or use the 

general conspiracy guideline. U.S. Sentencing Guidelines Manual 

§§ 1B1.2, 2X1.1 (U.S. Sentencing Comm’n 2012). Here, the 

substantive offense involves a violation of 18 U.S.C. § 641. Thus, we 

turn to the statutory index to determine the guideline provision for 

§ 641. 

In the guidelines’ statutory index, § 641 is paired with two 

possible guidelines: (1) § 2B1.5 and (2) § 2B1.1. 

The first possibility (§ 2B1.5) involves stealing or damaging 

cultural heritage and paleontological resources. U.S. Sentencing 

Guidelines Manual § 2B1.5 (U.S. Sentencing Comm’n 2012). That 

provision is obviously inapplicable to our facts. 

The second option (§ 2B1.1) is a general provision covering 

theft, which fits the conspiracy to steal federal money. Thus, § 2B1.1 

provides the applicable offense guideline. 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 22 
-23- 

 The government disagrees, arguing that the applicable offense 

guideline is § 2C1.1. To get to § 2C1.1, the government points out 

that the conspiracy was charged under 18 U.S.C. § 371. Section 371 

appears in the statutory index and is paired with multiple guidelines. 

Two of these are § 2X1.1 and § 2C1.1. See U.S. Sentencing 

Guidelines Manual app. A, at 537 (U.S. Sentencing Comm’n 2012). 

The government insists that of these guidelines, § 2C1.1 presents the 

closest fit.12

When more than one guideline section is listed, the statutory 

index instructs the court to “use the guideline most appropriate for 

the offense conduct charged in the count of which the defendant was 

convicted.” Id., app. A, at 532. When the conviction involves a 

conspiracy, the court must “refer to § 2X1.1 (Attempt, Solicitation, 

or Conspiracy) as well as the guideline referenced in the Statutory 

Index for the substantive offense.” Id. § 1B1.2(a). Section 2X1.1 is a 

general catch-all provision that instructs courts to apply a more 

specific guideline section when a conspiracy is expressly covered by 

that section. Id. § 2X1.1(c)(1). 

According to the government, the conspiracy is expressly 

covered by § 2C1.1. We disagree. 

 

12 The government acknowledges that the other possible guideline 

provisions listed in the statutory index (under 18 U.S.C. § 371) do 

not apply. See Appellee’s Br. at 32. 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 23 
-24- 

To determine whether § 2C1.1 applies, we must determine how 

we go about selecting the applicable guideline section. Mr. Kupfer 

argues that we simply compare 

● the charge in the indictment that resulted in the 

conviction and 

● the corresponding provision in the guidelines’ statutory 

index. 

The government argues that we should also consider the facts elicited 

at the trial about the nature of the charged conspiracy. In our view, 

however, that argument is foreclosed by a 2000 amendment to the 

sentencing guidelines (Amendment 591). 

Prior to this amendment, the application notes suggested that 

the court could often select the offense of conviction based on the 

offender’s actual conduct. U.S. Sentencing Guidelines Manual 

§ 1B1.2 App. Note 3 (U.S. Sentencing Comm’n 1999). In 

Amendment 591, the Sentencing Commission deleted the application 

note to clarify that the defendant’s actual conduct bears on “relevant 

conduct,” which comes into play only after the court selects the 

offense of conviction. U.S. Sentencing Guidelines Manual, App. C 

(U.S. Sentencing Comm’n Supp. 2000); see United States v. Moreno, 

421 F.3d 1217, 1219 (11th Cir. 2005) (per curiam) (“Amendment 

591 requires that the initial selection of the offense guideline be 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 24 
-25- 

based only on the statute or offense of conviction rather than on 

judicial findings of actual conduct not made by the jury.”). 

The district court used the pre-2000 method when selecting the 

offense of conviction. Instead of focusing solely on the charged 

offense, as Amendment 591 requires, the district court relied on the 

trial evidence to identify the offense of conviction. In relying on the 

trial evidence, the court found that (1) the evidence had shown that 

the conspiracy involved fraud against the federal government and (2) 

the conspiracy included participation by New Mexico’s Secretary of 

State, an elected official. Based on these findings, the court 

characterized the conspiracy as one involving fraud and participation 

by a public official. With this characterization, the court concluded 

that the offense of conviction triggered § 2C1.1. 

Mr. Kupfer argues the court erred by considering these facts 

when selecting the applicable provision. We agree. 

Under Amendment 591, a district court may consider other 

relevant conduct later in the guideline calculation process, but not 

when selecting the offense of conviction. See United States v. Boney, 

769 F.3d 153, 161–62 (3d Cir. 2014) (“[T]he Guidelines Manual 

makes clear that the sentencing court must select the ‘most 

appropriate’ guideline based on the offense charged in the 

indictment, not the court’s perception of the facts of the case 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 25 
-26- 

presented at trial.”), cert. denied, __ U.S. __, 135 S. Ct. 1003 (2015); 

United States v. Almeida, 710 F.3d 437, 441 (1st Cir. 2013) (“[W]hen 

selecting the ‘most appropriate’ guideline, the sentencing court 

should look to the conduct alleged in the indictment, and not to 

uncharged conduct described in trial testimony.”); United States v. 

Aquino, 555 F.3d 124, 129 (3d Cir. 2009) (“[W]e may consider only 

offense of conviction conduct, not all relevant conduct, at Step 

One.”); see also Thomas W. Hutchison, et al., Fed. Sent. L. & Prac.

§ 1B1.3, Authors’ comment 2 (2015 ed.) (stating that the offense 

guideline is based on the offense of conviction, not relevant 

conduct). 

The district court determined that § 2C1.1 was appropriate only 

by examining the trial evidence in addition to the indictment and jury 

instructions. At trial, the government theorized that Mr. Kupfer and 

Dr. Gutierrez had conspired with the New Mexico Secretary of State. 

Because the Secretary of State was a public official, the court 

thought § 2C1.1 would apply. But Mr. Kupfer would have been guilty 

even if the Secretary of State had been blameless. See United States 

v. Huizar-Velazquez, 720 F.3d 1189, 1192 (9th Cir. 2013) (holding 

that § 2C1.1 did not provide the correct guideline because the crime 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 26 
-27- 

involved a scheme to trick the government out of its money rather 

than to corrupt government officials).13

Because § 2C1.1 does not expressly cover the offense as 

charged, § 2X1.1 would apply if we were to focus on the conspiracy 

charge under 18 U.S.C. § 371. Because § 2X1.1 is a general 

conspiracy guideline, the court calculates the base offense level by 

referring to the guideline for the underlying substantive offense that 

was the object of the conspiracy. U.S. Sentencing Guidelines Manual 

§ 2X1.1(a) (U.S. Sentencing Comm’n 2012). As discussed above, 

§ 2B1.1 appears in the statutory index and fits the substantive 

offense that was the objective of the conspiracy (violation of 18 

 

13 Mr. Kupfer relies on United States v. Neilson, 721 F.3d 1185 

(10th Cir. 2013). This reliance is misguided. As Mr. Kupfer points 

out, the Neilson panel did choose the offense guideline based in part 

on the defendant’s actual conduct. Neilson, 721 F.3d at 1188-89. But 

there the defendant pleaded guilty and admitted his conduct in 

connection with his guilty plea. Id. at 1186-87. 

 Even after adoption of Amendment 591, the guidelines have 

provided a narrow exception to the general rule that requires 

selection of the offense of conviction based on the offense that was 

charged in the indictment and that was the basis for the finding of 

guilt. U.S. Sentencing Guidelines Manual § 1B1.2(a) (U.S. 

Sentencing Comm’n 2012). This exception involves guilty pleas. 

When a defendant pleads guilty and stipulates to a “more serious 

offense than the offense of conviction,” the court must use the 

offense guideline applicable to the stipulated offense. Id. 

 This exception was applied in Neilson because there the 

defendant pleaded guilty. Neilson, 721 F.3d at 1186-87. Mr. Kupfer 

did not plead guilty, and this exception does not apply here. 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 27 
-28- 

U.S.C. § 641). See id., app. A., at 539. Thus, if we were to focus on 

the charge under 18 U.S.C. § 371, we would still need to apply 

§ 2B1.1 for the offense guideline. 

 

When we apply § 2B1.1, we obtain a guideline range of 78–97 

months. See R., vol. VIII, at 3254 (the district court’s 

acknowledgment that the base-offense level would have been 28 

under § 2X1.1). The district court mistakenly used § 2C1.1 as the 

offense of conviction, which led to a guideline range of 121–151 

months. See id. at 3258 (concluding that the base-offense level was 

32 based on § 2C1.1). That error requires reversal. 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 28 
-29- 

B. Obstruction of Justice Enhancement 

The district court made a second sentencing error, this one on 

the calculation of the total offense level for the tax evasion counts. 

In reaching that guideline, the court used an enhanced guideline on 

the ground that Mr. Kupfer had obstructed justice by failing to reveal 

his under-reporting of income. 

The parties agree that this enhancement constituted error. We 

too agree, for we have held that enhancement for obstruction of 

justice is improper based on a defendant’s failure to disclose his own 

crime. See United States v. Kupfer (Elizabeth), __ F.3d __, 2015 WL 

4081108, at *6 (10th Cir. July 7, 2015) (discussing the issue in 

connection with the obstruction of justice enhancement for Ms. 

Kupfer’s tax-evasion case). The parties also agree that this error 

became prejudicial once we concluded that Mr. Kupfer’s total offense 

level should have been 28 rather than 32. Oral Arg. at 18:57–19:49.14

Thus, the enhancement for obstruction of justice constitutes 

reversible error. 

 

14 The prejudice arises because of the corresponding adjustment 

to the offense guideline under the grouping rules. See U.S. 

Sentencing Guidelines Manual §§ 3D1.1–3D1.5 (U.S. Sentencing 

Comm’n 2012). 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 29 
-30- 

III. Conclusion 

We affirm the conviction. But we reverse and remand on the 

sentence with instructions to the district court to vacate the sentence 

and resentence Mr. Kupfer by (1) identifying the offense level under 

§ 2B1.1 rather than § 2C1.1, and (2) removing the enhancement for 

obstruction of justice. 

Appellate Case: 13-2189 Document: 01019477876 Date Filed: 08/19/2015 Page: 30