Court Opinion

ID: 6335605
Source: CourtListenerOpinion
Date Created: 2022-04-27 21:00:33.103591+00
Date Added: 2024-06-11T09:23:58.923222
License: Public Domain

In the

    United States Court of Appeals
                 For the Seventh Circuit
                     ____________________
No. 20-2829
UNITED STATES OF AMERICA,
                                                   Plaintiff-Appellee,
                                 v.

DAVID D. MAJOR,
                                               Defendant-Appellant.
                     ____________________

         Appeal from the United States District Court for the
                    Central District of Illinois.
            No. 19-cr-10014 — James E. Shadid, Judge.
                     ____________________

    ARGUED NOVEMBER 2, 2021 — DECIDED APRIL 27, 2022
               ____________________

   Before SYKES, Chief Judge, and FLAUM and JACKSON-
AKIWUMI, Circuit Judges.
   FLAUM, Circuit Judge. David Major pleaded guilty without
the beneﬁt of a plea agreement to three charges stemming
from his activities dealing heroin and fentanyl. Major was
sentenced to twenty years’ imprisonment. He now challenges
the basis of his sentence, arguing that the district court’s fac-
tual ﬁndings were erroneous and caused it to calculate an in-
correct Sentencing Guidelines range. He also argues that his
2                                                 No. 20-2829

designation as a “career oﬀender” overstated his past crimi-
nal conduct, so that his sentencing under the career oﬀender
Guidelines range was therefore unreasonable.
    Because the district court made no clear errors in its ﬁnd-
ings of fact and did not abuse its discretion in deciding Ma-
jor’s sentence, we aﬃrm.

                     I.   Background

    A. A.K.’s Overdose Death and the Government’s Subse-
       quent Investigation
    In December 2018, a twenty-six-year-old woman, A.K.,
was found dead in her bedroom in Pekin, Illinois, with fresh
needle marks on her arm consistent with heroin use. An au-
topsy later determined that her cause of death was the “com-
bined toxic effects of acetyl fentanyl, fentanyl, and Mitragyn-
ine,” though officers did not find any drugs in the home.
    Officers began investigating A.K.’s death and learned that
the night before she died, she had taken an Uber home from
an address where a person named Dawn Bukowski lived with
her boyfriend. When the officers interviewed Bukowski, she
admitted that she used heroin and had provided some to A.K.
around 6:30 PM the night before she was found dead. Bukow-
ski explained that A.K. had reached out to Bukowski’s boy-
friend through the “dark web,” looking for heroin because
she was afraid she was about to start experiencing with-
drawal symptoms. A.K. did not know where else to obtain the
drugs since she had only recently moved to the area. Bukow-
ski’s account was confirmed by text messages recovered from
her phone. Bukowski’s texts also revealed that she told her
boyfriend A.K. was “really fucked up” after she injected the
No. 20-2829                                                  3

drugs at Bukowski’s home immediately after purchasing
them. Bukowski later testified that she “could tell that [A.K.]
was really, really messed up” shortly after taking the drugs,
though she appeared to “snap[] out of it” by the time she left
Bukowski’s house, around 7:30 PM.
    A.K. took the rest of her unused drugs with her when she
left Bukowski and got in her Uber. The driver later told offic-
ers that A.K. seemed “intoxicated but not overly intoxicated”
during the ride to her home. When A.K. arrived home, she
greeted her parents, who said that she appeared normal, be-
fore heading to her room for the night. Her mother discovered
her unresponsive in her bedroom around 5:30 AM the next
morning.
    Bukowski told the investigating officers that she had pur-
chased the drugs she resold to A.K. from someone named
“Don,” whom the officers soon determined to be the Defend-
ant, David Major. In February and March 2019, police set up
a series of controlled drug buys from Major. Often, these buys
resulted in the source receiving drugs directly from Major,
but sometimes, Major would direct the source to contact “the
girls,” his associates Stephanie Lobb and Natalia Menchaca.
    After the controlled buys, police arrested Lobb and
Menchaca as they were returning to the Peoria area from Chi-
cago. In their possession, the women had 9.4 grams of heroin
and fentanyl. Both provided cooperative statements to law
enforcement. Menchaca stated that she had been acquiring
heroin from Major for about eight months and had worked
for him for the last three months. She further stated that she
and Lobb traveled to Chicago about once a week to purchase
between a half-ounce and an ounce of heroin for Major. Lobb
provided similar information and estimated that the pair had
4                                                   No. 20-2829

made about fifteen trips to Chicago over the last few months
for this purpose. Police subsequently arrested Major, who
waived his Miranda rights and admitted that he sold drugs
and had purchased them from a contact in Chicago. Text mes-
sages between Major and Bukowski confirmed that he sold
her drugs and that his heroin was laced with fentanyl. For in-
stance, he sent her a picture of a white, rock-like substance,
with a caption referring to “that fintnal.”
    In April 2019, a grand jury indicted Major, Menchaca, and
Lobb with drug-trafficking and conspiracy offenses (none of
which directly pertained to the December 2018 drug transac-
tion that led to A.K.’s death). Major eventually pleaded guilty
to three charges: one count of conspiring between December
2018 and March 2019 to distribute and possess with intent to
distribute heroin and fentanyl, see 21 U.S.C. § 846, and two
counts of distributing heroin and fentanyl in February 2019,
see 21 U.S.C. § 841(a)(1), (b)(1)(C). At the change-of-plea hear-
ing, he specifically admitted under oath that he “actually dis-
tribute[d] heroin and fentanyl.”
    B. Incident Involving Major’s Co-Defendant
   After Major entered his guilty plea, the Probation Office
prepared a presentence investigation report (“PSR”), which,
among other things, described the statements Lobb and
Menchaca made to the police. Based on Menchaca’s state-
ments, the PSR indicated that the conspiracy involved over
100 grams of heroin and 0.4 grams of fentanyl.
    A few months after the Probation Office filed its first PSR
and while Lobb was on bail, she called her attorney to de-
scribe a disturbing incident, which her attorney then relayed
to the police. Lobb stated that on the afternoon of April 28,
No. 20-2829                                                    5

2020, she was approached at her place of work (Burger King)
by someone she knew as “Ray Ray.” She had met Ray Ray
before and knew him as Major’s close friend (at the time, she
thought they were brothers) and his “enforcer.” Ray Ray en-
tered the drive-through lane going the opposite direction and
pulled up to Lobb. He held up his phone and told her that
Major wanted to talk to her. She responded that she could not
talk to him, and Ray Ray then stated that he thought he had
seen her walking a few days earlier. Ray Ray then drove off.
    Lobb later testified that she felt “threatened and intimi-
dated” by the incident, specifically because she had heard sto-
ries about Ray Ray’s violent past and knew that Major relied
on Ray Ray to “tak[e] care of things for him.” In fact, Lobb
testified, she had received a letter from Major from jail regard-
ing the instant criminal conspiracy, instructing her to “stand
tall or stay strong,” because Major “kn[ew] who set [them]
up” and “Ray Ray’s gonna handle it.” Lobb was sufficiently
spooked by the incident that two days later she arranged with
Pretrial Services to move out of the area.
    To investigate this incident, officers obtained recordings
of Major’s phone calls from jail. From these calls, officers
learned that Major told a variety of people that it was “very
important” that he speak with Lobb. On April 27, Major
placed one such call to his daughter, in which he asked if she
remembered the “girl that people was talking about that you
was supposed to be looking for?” His daughter responded
that she did not remember her name, and Major explained
that it was Lobb and further advised his daughter to call the
Burger King where Lobb worked immediately after hanging
up with him. He told his daughter to tell Lobb that Major was
not mad at her and that nothing was going to happen to her.
6                                                   No. 20-2829

Later that day, Major made a similar call to another woman.
He told this woman to tell Lobb that Major was “not mad at
her and ain’t nobody going do shit to her. I need to talk to her,
it’s very important.”
    The next day, Major made a call and spoke to Ray Ray,
whose real name is Kimmit Smith. Ray Ray told Major, “That
bitch is scared as hell,” to which Major replied that he knew
it and that he hoped Ray Ray did not scare her. Major then
laughed and said, “I hope you don’t try and tell the people
I’m trying to do anything … what they say?” Ray Ray told
Major that the woman had asked what Major wanted her to
say. Ray Ray then said, “Some things a mother fucker can’t
say over these lines.” Major replied, “I know, that’s the truth
… that’s why I needed the number.” When Ray Ray told Ma-
jor that he didn’t ask for the woman’s phone number because
“she got scared and I [Ray Ray] got scared,” Major began
laughing again.
    Major then told Ray Ray that Menchaca had said that Ma-
jor was buying an ounce of heroin per week, which he said
was “bullshit” and was why he needed to speak to Lobb. Ray
Ray replied that Lobb had told him that she could not talk to
Major. Major then said that he did not want Ray Ray to scare
her and that he needed to “clean it up.” Major told him to “get
on it today.” A few minutes later, Major called Ray Ray back
and told him that he didn’t need anybody saying, “These peo-
ple came up here and blew on me[,] so you got to calm a
mother fucker down today.” Major said that he was upset be-
cause Menchaca had lied about the amount of drugs they had
dealt and that he needed Lobb to tell the truth that it was a
lesser amount than what Menchaca had claimed. Major gave
Ray Ray the phone number for Burger King and told him he
No. 20-2829                                                    7

needed to go up there that day. He said it would “help him
out a lot” if Lobb said they never went up there (presumably
Chicago) for ounces and “that’s the truth.” He later clarified
that Lobb’s testimony to this effect would undermine the
credibility of Menchaca’s statements during sentencing.
   C. Major’s Sentencing
     The Probation Office filed its final, revised PSR on Septem-
ber 10, 2020, a few days before sentencing. In addition to re-
counting the above facts (including Major’s phone calls from
jail), the PSR calculated a Sentencing Guidelines range based
on Major’s offenses, related conduct, and criminal history.
    It calculated his base offense level for the conspiracy
charge to be 24. Because he was “an organizer, leader, man-
ager, or supervisor” in the conspiracy, two levels were added.
See U.S.S.G. § 3B1.1(c). Two more levels were added for ob-
struction of justice, based on Major’s phone calls from jail and
Ray Ray’s approaching Lobb at work. See U.S.S.G. § 3C1.1.
This brought his adjusted offense level to 28. His total offense
level was increased to 32, however, because he qualified as a
“career offender” under U.S.S.G. § 4B1.1 (he had a previous
felony drug conviction and a conviction for aggravated kid-
napping). The PSR stated that a reduction for acceptance of
responsibility was inappropriate. Major’s criminal history
was calculated to be category III, but based on his qualifica-
tion as a career offender, it was increased to category VI. An
offense level of 32 and a criminal history category of VI re-
sulted in a Guidelines imprisonment range of 210–262 months
for each count. The statutory maximum for each of Major’s
offenses of conviction is 20 years, which altered the guideline
imprisonment range to 210–240 months. The PSR stated that
the probation officer had not identified any factors under 18
8                                                 No. 20-2829

U.S.C. § 3553(a) that warranted a sentence outside of this
range.
    At the sentencing hearing, Major’s counsel objected to cer-
tain factual findings in the PSR and argued that the career of-
fender status overstated Major’s criminal history because his
predicate conviction for aggravated kidnapping was over
twenty-five years old. As relevant to this appeal, the factual
findings Major challenged were: (1) that Major was the sup-
plier of the fentanyl-laced heroin that led to A.K.’s overdose
death, (2) that Major had obstructed justice by attempting to
influence Lobb’s testimony, and (3) that Major had not ac-
cepted responsibility for his conduct. Notably, despite Ma-
jor’s recorded phone calls disputing Menchaca’s account of
the drug quantity at issue, Major withdrew his objection to
the amount of heroin and fentanyl set forth in the final PSR—
even though the Probation Office increased the calculated
amount of fentanyl from .4 grams to 9.8 grams between the
first and final PSR and the heroin assessment had not
changed.
    To make its rulings on Major’s objections, the court heard
testimony from the officer who responded to the scene after
A.K.’s mother found her dead, Bukowski (the woman who
bought drugs from Major and then resold some of them to
A.K.), Lobb, and the officer who investigated Major’s phone
calls from jail. The testimony essentially conveyed the facts
recounted above. Based on this testimony, the district court
rejected all of Major’s arguments.
   The district court also heard a victim impact statement
from A.K.’s mother and a statement from Major himself.
A.K.’s mother addressed Major and stated:
No. 20-2829                                                    9

       This is a loss that I will never recover from, pain
       that time does not heal or even ease. Every day
       I relive the experience of finding my daughter. I
       see her unseeing eyes. I feel the unnatural cold-
       ness of her body.
       I see mothers interacting with daughters, and I
       don’t have that any longer. I see grandchildren
       that I will never have, milestones that will never
       be reached, dreams and plans unfulfilled, a life
       extinguished. And for this reason, I hope that
       the Court would see fit to give you the maxi-
       mum sentence so that the likelihood of your
       participation in this act again would not hap-
       pen.
    Major began his statement by giving his condolences to
A.K.’s mother, but quickly clarified, “I’m not even sure who’s
at fault, but I understand that me, being a heroin dealer, that
you would look at me as being at fault here…. I know that my
actions could possibly did [sic] play a role or possibly did, but
I just want you to know that I do send my condolences to you
and your family.” Major then expressed his remorse to the
court and stated that he only dealt drugs to feed his own ad-
diction and to treat a medical condition that made it difficult
for him to eat. Major then transitioned to minimizing his con-
duct. He described himself as “just a drug user who was get-
ting high, to have some few friends to direct that high, and
with their money I could get by with.” He also stated, “I never
meant to sell nobody no fentanyl. I can’t believe that I’m hon-
estly facing this much time when all I actually did was sell
Dawn two dime, three dime bags of dope for $50. That’s what
my conspiracy really consists of. Your Honor, I sold a friend
10                                                  No. 20-2829

a bag of dope for $50 on two different occasions.” When the
court clarified whether it was Major’s position that he never
knew the heroin he purchased and resold had fentanyl in it,
Major responded, “I mean, no, I didn’t. All I knew, I was get-
ting heroin.”
          Before handing down Major’s sentence, the court
stated:
          I’m glad you made a statement, Mr. Major, be-
          cause it confirms for me that I made the right
          decision on acceptance of responsibility … be-
          cause clearly the evidence is otherwise…. And I
          can only say after listening to you, Mr. Major,
          that I’m more comfortable with the decision—I
          think I was right anyway, but I’m way more
          comfortable with the decision I made now about
          acceptance. And I guess the only thing I can say
          is if you spend a lifetime of being untruthful,
          that you—there comes a point where you don’t
          even know where the truth would help you,
          okay?
    Given that Major had pushed fentanyl-laced heroin onto
the streets of the community, deposited large sums of money
in connection with his crimes, was a leader in the conspiracy,
had a history of violence, played a part in the overdose death
of A.K., and attempted to obstruct justice, the court decided
that the statutory maximum sentence of twenty years’ impris-
onment was appropriate.
     Major now appeals this sentence.
No. 20-2829                                                   11

                      II.   Discussion

    Major challenges his sentence on four grounds. Namely,
he argues: (1) the court erred by finding that he sold the drugs
that caused A.K.’s death, (2) the court erred by finding that he
had obstructed justice, (3) the court erred by finding he had
not accepted responsibility, and (4) the court abused its dis-
cretion by sentencing him as a career offender because that
label overstated the seriousness of his criminal history.
    We use a two-step process to review a district court’s sen-
tencing decisions. “First, we determine whether the district
court committed any procedural error, such as failing to cal-
culate (or improperly calculating) the Guidelines range, treat-
ing the Guidelines as mandatory, failing to consider the
§ 3553(a) factors, selecting a sentence based on clearly errone-
ous facts, or failing to adequately explain the chosen sen-
tence—including an explanation for any deviation from the
Guidelines range.” United States v. Faulkner, 885 F.3d 488, 498
(7th Cir. 2018) (internal quotation marks omitted) (quoting
United States v. Reyes-Hernandez, 624 F.3d 405, 409 (7th Cir.
2010)). “Whether the district court followed proper sentenc-
ing procedure is a legal question reviewed de novo.” United
States v. Pape, 601 F.3d 743, 746 (7th Cir. 2010). Although, as
noted, it is a procedural error to select a sentence based on
erroneous facts, Faulkner, 885 F.3d at 498, we review the dis-
trict court’s findings of fact underlying the selected sentence
only for clear error, United States v. Ranjel, 872 F.3d 815, 818
(7th Cir. 2017). Major’s first three arguments challenge the fac-
tual findings underpinning the district court’s sentence and
thus fall under this first step.
12                                                    No. 20-2829

    Second, “[i]f no procedural error is found, then the sen-
tence is reviewed for substantive reasonableness”; we review
the substantive reasonableness of a sentence for abuse of dis-
cretion. Faulkner, 885 F.3d at 498. “A sentence is substantively
reasonable ‘if the district court gives meaningful considera-
tion to the factors enumerated in 18 U.S.C. § 3553(a), includ-
ing the advisory Sentencing Guidelines, and arrives at a sen-
tence that is objectively reasonable in light of the statutory fac-
tors and the individual circumstances of the case.’” United
States v. Patel, 921 F.3d 663, 672 (7th Cir. 2019) (quoting United
States v. Rosen, 726 F.3d 1017, 1027 (7th Cir. 2013)). “[W]e pre-
sume that a within-Guidelines sentence is reasonable.” Id.
Major’s fourth and final argument—that the district court
should have used its discretion to ignore Major’s “career of-
fender” designation—amounts to a challenge to the reasona-
bleness of the court’s sentencing decision.
     A. The District Court’s Factual Findings
    “Generally, facts considered at sentencing must be proved
by a preponderance of the evidence.” United States v. Lucas,
670 F.3d 784, 792 (7th Cir. 2012). Such facts must be based on
“reliable evidence, rather than speculation or unfounded alle-
gations.” Id. “Evidence will satisfy this requirement if it bears
sufficient indicia of reliability to support its probable accu-
racy.” Id. (quoting United States v. Santiago, 495 F.3d 820, 824
(7th Cir. 2007)). Sentencing courts may also draw inferences
and conclusions based on testimony given and evidence in-
troduced at a sentencing hearing. Id.
   “We will not disturb a sentencing court’s factual findings
unless they are clearly erroneous.” Ranjel, 872 F.3d at 818. This
standard is deferential, and “we will reverse only if ‘after re-
viewing the entire record, we are left with the firm and
No. 20-2829                                                                13

definite conviction that a mistake has been made.’” Id. (quot-
ing United States v. Marty, 450 F.3d 687, 689–90 (7th Cir. 2006)).
“If two possible conclusions can be drawn from the evidence,
then the choice between them cannot be clearly erroneous.”
United States v. May, 748 F.3d 758, 760 (7th Cir. 2014).

        1. Finding Regarding A.K.’s Overdose Death

    First, Major argues that the district court clearly erred
when it determined that he supplied the drugs that contrib-
uted to A.K.’s death. Significantly, the government did not
seek a statutory enhancement to Major’s sentence because he
was not charged with the particular sale of drugs to Bukowski
that Bukowski resold to A.K. See 21 U.S.C. § 841(b)(1)(C) (re-
quiring a sentence of twenty years to life if “death or serious
bodily injury results from the use of [the distributed] sub-
stance”); U.S.S.G. § 2D1.1(a)(2) (increasing the base offense
level if “the offense of conviction establishes that death … re-
sulted from the use of the substance”(emphasis added)). 1 Ra-
ther, the district court considered its finding about the rela-
tionship between Major and A.K.’s death when it weighed the
sentencing factors set forth in 18 U.S.C. § 3553(a).
   Major’s argument on this point boils down to a contention
that A.K. must have acquired more drugs from a different
source after leaving Bukowski’s home. Major seems to believe

1 For this reason, the government did not have to prove that the heroin
and fentanyl Major distributed was the “but-for” cause of A.K.’s death,
under Burrage v. United States, 571 U.S. 204, 218–19 (2014). See United States
v. Lawler, 818 F.3d 281, 285 (7th Cir. 2016) (“Nothing … prevents a sentenc-
ing court, when determining a defendant’s ultimate sentence, from con-
sidering the fact that death resulted,” even if the government cannot prove
but-for causation beyond a reasonable doubt).
14                                                No. 20-2829

that, because A.K. did not overdose the first time she injected
the drugs Bukowski provided, A.K. could not have subse-
quently overdosed if she injected the remainder of the drugs
at home. But these inferences are not supported by the evi-
dence submitted at the sentencing hearing. Cf. Lucas, 670 F.3d
at 792 (noting that sentencing determinations cannot be based
on “speculation or unfounded allegations”).
     Bukowski testified that A.K. was “really, really messed
up” immediately after injecting the fentanyl-laced heroin that
Bukowski had received from Major. In fact, Bukowski testi-
fied that she had shot up heroin with a number of people but
had “never seen nobody act like that.” A.K.’s behavior was
strange enough that Bukowski contacted her boyfriend at the
time to share her concern. Evidence also reflected that A.K.
left Bukowski’s apartment in an Uber around 7:30 PM and that
she took the remaining drugs from Major with her when she
left. Her mother told officers that A.K. arrived home, briefly
greeted her, and then went to her room, where the mother
found her unresponsive the next morning. Bukowski also tes-
tified that A.K. had asked her and her boyfriend for heroin
because she was new in town, was concerned about soon ex-
periencing withdrawal symptoms, and had no other means of
acquiring the drugs. And, though A.K. left Bukowski’s apart-
ment with leftover heroin, no drugs were found in A.K.’s
home. Finally, the autopsy report concluded that the toxic ef-
fects of heroin and fentanyl contributed to A.K.’s death. This
evidence supports the district court’s finding.
   Furthermore, the district court specifically found that Bu-
kowski was credible. “[W]here a sentencing challenge boils
down to a credibility decision, … our review is especially def-
erential to the district judge’s assessment of the testimony.”
No. 20-2829                                                                15

United States v. Etchin, 614 F.3d 726, 738 (7th Cir. 2010). And
even though no corroboration is necessary for a court to ac-
cept witness testimony, see id. at 739, Bukowski’s statements,
the testimony of the investigating officer, the Uber receipts,
and text messages from the time all corroborate each other.
The district court’s finding was not clearly erroneous, and this
finding supported its weighing of the factors set forth in 18
U.S.C. § 3553(a).

        2. Obstruction of Justice Finding

    Second, Major challenges the district court’s finding that
he obstructed justice by attempting to influence Lobb’s testi-
mony. 2 An offense-level enhancement for obstruction of jus-
tice is appropriate if:
        (1) the defendant willfully obstructed or im-
        peded, or attempted to obstruct or impede, the
        administration of justice with respect to the

2 Although obstruction of justice typically increases a defendant’s offense
level under the Guidelines by two points, U.S.S.G. § 3C1.1, which would
have brought Major’s offense level up to a 28, Major’s qualification as a
“career offender” independently established a higher offense level of 32,
making this finding irrelevant for the purpose of increasing his offense
level, U.S.S.G. § 4B1.1(b)(3). This would ordinarily moot his challenge to
the obstruction-of-justice finding. See United States v. Collins, 352 F. App’x
96, 98 (7th Cir. 2009) (noting that where the defendant was sentenced
based on the higher offense level associated with a career offender desig-
nation, any challenge to a separate offense level adjustment would be
moot). The district court, however, also considered Major’s acts of obstruc-
tion when it determined that he did not adequately accept responsibility
for his conduct, and an acceptance-of-responsibility finding would have
decreased Major’s offense level after accounting for the career offender des-
ignation. Thus, his challenge to this factual finding is not moot.
16                                                 No. 20-2829

       investigation, prosecution, or sentencing of the
       instant offense of conviction, and (2) the ob-
       structive conduct related to (A) the defendant’s
       offense of conviction and any relevant conduct;
       or (B) a closely related offense ….
U.S.S.G. § 3C1.1. The commentary accompanying U.S.S.G.
§ 3C1.1 gives several examples of “the types of conduct to
which this adjustment applies,” including “threatening, in-
timidating, or otherwise unlawfully influencing a co-defend-
ant, … or attempting to do so[.]” Id. cmt. 4(A). The intimida-
tion of a co-defendant can be separate from “committing, sub-
orning, or attempting to suborn perjury.” Id. cmt. 4(B).
    Major protests that there was no “evidence that [he] had
ever threatened Lobb or … attempted to have her commit per-
jury.” He contends that he was simply trying to encourage
Lobb to tell the truth. Although he made some statements to
that effect during some of his phone calls, Major also knew
that those calls were being recorded—which he admitted dur-
ing his allocution, when he told the district court, “I know the
phones are recorded in jail.” Given this knowledge, it is un-
surprising and less than persuasive that—in court—Major de-
scribed his motive as merely encouraging Lobb to “tell the
truth.” Additionally, this assertion is undermined by the fact
that Major did not even object to the drug quantity set forth
in the PSR—the very issue on which he hoped Lobb would
contradict Menchaca.
    Moreover, even if Major did simply want Lobb to “tell the
truth,” this does not mean the district court clearly erred
when it held that Major’s attempts to pressure Lobb to “un-
dermine the credibility of Menchaca” were a “clear example[]
of trying to influence the testimony of a witness,” which
No. 20-2829                                                     17

constituted obstruction. We considered such a scenario in
United States v. Cheek, 740 F.3d 440 (7th Cir. 2014). In that case,
the defendant wrote a letter to the daughter of a witness
against him. Id. at 453–54. In the letter, the defendant told the
daughter that her mother (the witness) was lying to the gov-
ernment, and he implied that the daughter should influence
her mother to “tell the truth.” Id. at 453. The defendant wrote:
       To prove [the charge] why would they need
       your Mom to lie on me if they had something?…
       She couldn’t get more than 5 if she would’ve
       just plead guilty without lying on me.… The
       most she can get is 5 and me LIFE if she doesn’t
       tell the truth.… So I am praying that she don’t
       let them keep scaring her.… If God is willing
       you know who won’t tell that lie and I will be
       there to see yall in the near future.
Id. at 444 (errors in original). We held that the “district court
reasonably interpreted this effort as a willful attempt to per-
suade [the witness’s] daughter to try to sway her mother’s tes-
timony.” Id. at 454. “And an effort to influence a witness’s tes-
timony—albeit vicariously—is a prototypical example of ob-
struction of justice.” Id. (citing U.S.S.G. § 3C1.1 cmt. 4(A)).
    Following the reasoning in Cheek, even if Major was trying
to urge Lobb to “tell the truth” from his point of view, such
conduct may still constitute obstruction of justice if its pur-
pose is to persuade a witness or co-defendant to alter her tes-
timony. Here, the evidence clearly showed that Major made a
frenzy of phone calls to various associates and family mem-
bers in an attempt to affect Lobb’s testimony about the quan-
tity of drugs at issue. The context around these calls—in par-
ticular, the fact that Major asked his enforcer Ray Ray to get
18                                                   No. 20-2829

involved, the fact that Major was intentionally vague on the
recorded phone line about what he wanted his associates to
do, and the fact that Major and Ray Ray laughed about how
Lobb was “scared as hell”—was sufficient for the court to con-
clude that this attempt to influence Lobb’s testimony was un-
lawful.
    Thus, the district court did not err in finding that Major
attempted to influence his co-defendant’s testimony, and this
factual finding supported its determination—discussed fur-
ther below—that Major obstructed justice in a way that was
incompatible with accepting responsibility for his conduct.

       3. Acceptance of Responsibility Finding

    Major next challenges the district court’s finding that he
had not accepted responsibility for his conduct and therefore
was not entitled to a reduction in his offense level under the
Guidelines. The Guidelines state that a two-level reduction is
appropriate if “the defendant clearly demonstrates ac-
ceptance of responsibility for his offense.” U.S.S.G. § 3E1.1(a).
The defendant bears the burden of proving his acceptance of
responsibility by a preponderance of the evidence. United
States v. Lister, 432 F.3d 754, 759 (7th Cir. 2005). “We review
the district court’s decision on this fact-based finding for clear
error.” Id. In doing so, we accord “[g]reat deference” to the
sentencing court, which is better equipped to “assess whether
a particular defendant is motivated by genuine acceptance of
responsibility or by a self-serving desire to minimize his own
punishment.” United States v. Cunningham, 103 F.3d 596, 598
(7th Cir. 1996) (citation and internal quotation marks omit-
ted).
No. 20-2829                                                     19

   When making this finding, “the sentencing judge is re-
quired to look beyond formalistic expressions of culpability
and to determine whether the defendant has manifested an
acceptance of personal responsibility for his offense in a moral
sense.” Id. (citation omitted). For this reason, simply pleading
guilty does not entitle a defendant to a reduction for ac-
ceptance of responsibility. United States v. Sellers, 595 F.3d 791,
793 (7th Cir. 2010). “A defendant who falsely denies, or frivo-
lously contests, relevant conduct that the court determines to
be true” generally will not qualify for the reduction. See
U.S.S.G. § 3E1.1 cmt. 1(A). “Attempt[ing] to minimize [one’s]
level of involvement in an offense” is sufficient to deny a re-
duction for acceptance of responsibility, even when the de-
fendant has pleaded guilty. United States v. Munoz, 610 F.3d
989, 993 (7th Cir. 2010).
    Once again, plenty of evidence supported the district
court’s factual finding. First, “[c]onduct resulting in an [ob-
struction-of-justice] enhancement … ordinarily indicates that
the defendant has not accepted responsibility for his criminal
conduct.” U.S.S.G. § 3E1.1 cmt. 4. It is only in “extraordinary
cases” that a defendant may receive an enhancement for ob-
struction of justice and also receive a reduction for acceptance
of responsibility. Id. It was not clearly erroneous for the dis-
trict court to conclude that this was not such an extraordinary
case.
   Moreover, Major objected to the presentence report’s con-
clusion that he sold the drugs that led to A.K.’s death, which
was a fact the court found to be both true and relevant. See
U.S.S.G. § 1B1.3 (defining “relevant conduct” for sentencing
purposes to include “harm that resulted from” acts that were
“part of the same course of conduct … as the offense of
20                                                   No. 20-2829

conviction”). On appeal, Major argues that his counsel—not
Major—contested whether heroin and fentanyl he sold con-
tributed to A.K.’s death. In support, he cites United States v.
Purchess, in which we held that “where the defendant remains
… silent as to relevant conduct but his lawyer challenges cer-
tain facts alleged in the PSR,” then the district court “should
attempt to ensure that the defendant understands and ap-
proves the argument before attributing the factual challenges
in the argument to the defendant for purposes of assessing
acceptance of responsibility.” 107 F.3d 1261, 1268 (7th Cir.
1997); see also Munoz, 610 F.3d at 994 (distinguishing between
factual challenges, which will jeopardize an acceptance-of-re-
sponsibility reduction, and legal arguments regarding undis-
puted facts, which will not).
    But Purchess is not relevant here, because Major personally
disputed whether his drugs caused A.K.’s death in his allocu-
tion at sentencing. For example, Major told A.K.’s mother,
“I’m not even sure who’s at fault [for A.K.’s death], but I un-
derstand that me, being a heroin dealer, that you would look
at me as being at fault here.” When the district court asked
directly whether Major was admitting to selling Bukowski the
heroin and fentanyl that she resold to A.K., Major responded,
“Sir, by what’s being said here today, I really don’t know be-
cause, you know, I, I—first, I really didn’t believe that I didn’t
[sic] sell them bags to [Bukowski] because I know what took
place that particular day…. I’m just saying I don’t know, and
I don’t believe the State [sic] proved to know it either. But it’s
a possibility that she did get them from me.” It is clear from
this exchange that Major himself contested this factual find-
ing.
No. 20-2829                                                   21

    This, combined with the obstruction of justice finding, was
more than sufficient for the court to conclude that Major had
not accepted responsibility for his conduct. But any lingering
doubt is erased by other statements Major made during his
allocution. For instance, Major attempted to minimize his con-
duct, telling the district court, “I never meant to sell nobody
no fentanyl. I can’t believe that I’m honestly facing this much
time when all I actually did was sell [Bukowski] two dime,
three dime bags of dope for $50. That’s what my conspiracy
really consists of. Your Honor, I sold a friend a bag of dope
for $50 on two different occasions.” He also doubled down on
his claim that he did not know that the heroin he sold con-
tained fentanyl—despite his admissions to the contrary in text
messages (referring to “that fintnal”) and under oath at his
change-of-plea hearing. When directly asked by the district
court at sentencing, “So, you had no idea fentanyl was in
them?” Major replied, “I mean, no, I didn’t.” Immediately af-
ter this exchange, the district court concluded, “I’m glad you
made a statement, Mr. Major, because it confirms for me that
I made the right decision on acceptance of responsibility….”
   Ample evidence supported the district court’s conclusion
that Major had not accepted responsibility for his conduct by
the time he was sentenced; this finding was not clearly erro-
neous.
   B. The Substantive Reasonableness of Major’s Sentence
   Finally, Major argues that his sentence was substantively
unreasonable because—even though he technically qualifies
as a career offender under the Sentencing Guidelines—that
label overstates his criminal history. In essence, Major argues
that the district court abused its discretion when it did not ig-
nore the career offender enhancement when it sentenced him.
22                                                        No. 20-2829

     A defendant is classified as a career offender if:
        (1) the defendant was at least eighteen years old
        at the time the defendant committed the instant
        offense of conviction; (2) the instant offense of
        conviction is a felony that is either a crime of vi-
        olence or a controlled substance offense; and (3)
        the defendant has at least two prior felony con-
        victions of either a crime of violence or a con-
        trolled substance offense.
U.S.S.G. § 4B1.1(a). Such a designation sets the defendant’s
criminal history category to Category VI, and when the of-
fense of conviction’s statutory maximum sentence is between
twenty and twenty-five years (as is the case for Major), the
designation sets the offense level to 32. See id. § 4B1.1(b)(3).
For Major, this resulted in a Guidelines range of 210–262
months’ imprisonment, which was adjusted to 210–240 due to
the statutory maximum of twenty years’ imprisonment for his
convictions. 3 The district court sentenced Major to 240
months’ incarceration.
   As we have noted, Major was convicted of two prior of-
fenses that qualify him for the career offender designation: a
previous felony drug conviction and a conviction for aggra-
vated kidnapping. Major does not challenge these facts. But,
he complains, he was convicted of aggravated kidnapping in
1993, over twenty-five years prior to his sentencing in this
case. He also argues that the nature of that crime is unrelated

3Without the career offender designation, Major’s offense level would
have been 28, his criminal history would have been Category III, and his
Guidelines range would have been 97–121 months’ imprisonment. See
U.S.S.G. Ch. 5, Pt. A.
No. 20-2829                                                   23

to the instant conviction and that the aggravated kidnapping
conviction has “no bearing” on his propensity to commit
other offenses similar to the drug distribution charges at issue
in this case.
    For support, Major points to a Sentencing Guidelines pol-
icy statement, which says that “[i]f reliable information indi-
cates that the defendant’s criminal history category substan-
tially over-represents the seriousness of the defendant’s crim-
inal history or the likelihood that the defendant will commit
other crimes, a downward departure may be warranted.”
U.S.S.G. § 4A1.3(b)(1). Although the Supreme Court’s deci-
sion in United States v. Booker, 543 U.S. 220 (2005), rendered
the departure provisions “obsolete,” “district courts can still
take guidance from the departure provisions” and consider
them “when assessing the § 3553(a) factors.” United States v.
Bell, 887 F.3d 795, 798 (7th Cir. 2018) (citation and internal
quotation marks omitted).
    Notwithstanding Major’s arguments, the district court
handed down a sentence squarely within the concededly ap-
plicable career-offender Guidelines range. Such sentences are
presumed to be reasonable on appeal. See Rita v. United States,
551 U.S. 338, 347 (2007). Moreover, in “reviewing sentences
for substantive reasonableness, we do not substitute our judg-
ment for that of a district judge, who is better situated to make
individualized sentencing decisions.” United States v. Porraz,
943 F.3d 1099, 1104 (7th Cir. 2019). In fact, we will “uphold a
sentence so long as the judge offers an adequate statement of
his reasons consistent with the sentencing factors enumerated
in 18 U.S.C. § 3553(a).” Id.
   Here, the district court did just that. It thoroughly ex-
plained the reasons for its sentence, citing in particular the
24                                                  No. 20-2829

following facts: Major’s prior conviction for aggravated kid-
napping, his previous drug distribution conviction, the fact
that he “went right back to dealing drugs” after serving a
fourteen-year sentence for his drug conviction, his decision to
deal in the particularly dangerous combination of heroin
laced with fentanyl, his leadership role in the conspiracy, the
need to protect others from him, his attempt to obstruct jus-
tice, his minimization of his own wrongdoing, and his role in
the unfortunate death of A.K. Given these facts, the court did
not abuse its discretion by sentencing Major as a career of-
fender and imposing a Guidelines sentence of 240 months in
prison.

                    III.    Conclusion

    For the foregoing reasons, the decision of the district court
is AFFIRMED.