United States v. Jason Rosales

RECOMMENDED FOR PUBLICATION
Pursuant to Sixth Circuit I.O.P. 32.1(b)
File Name: 21a0062p.06

UNITED STATES COURT OF APPEALS
FOR THE SIXTH CIRCUIT

UNITED STATES OF AMERICA, ┐
Plaintiff-Appellee, │
│
> No. 19-3749
v. │
│
│
JASON ROSALES, │
Defendant-Appellant. │
┘

Appeal from the United States District Court
for the Southern District of Ohio at Dayton.
No. 3:17-cr-00024-1—Walter H. Rice, District Judge.

Argued: January 14, 2021

Decided and Filed: March 12, 2021

Before: SUHRHEINRICH, CLAY, and DONALD, Circuit Judges.

_________________

COUNSEL

ARGUED: Kathleen Basalla, Trane Robinson, UNIVERSITY OF CINCINNATI COLLEGE
OF LAW, Cincinnati, Ohio, for Appellant. Kevin Koller, UNITED STATES ATTORNEY’S
OFFICE, Cincinnati, Ohio, for Appellee. ON BRIEF: Colter L. Paulson, SQUIRE PATTON
BOGGS (US) LLP, Cincinnati, Ohio, Nathan L. Colvin, UNIVERSITY OF CINCINNATI
COLLEGE OF LAW, Cincinnati, Ohio, for Appellant. Kevin Koller, UNITED STATES
ATTORNEY’S OFFICE, Cincinnati, Ohio, for Appellee.
 No. 19-3749 United States v. Rosales Page 2

_________________

OPINION
_________________

SUHRHEINRICH, Circuit Judge.

I. INTRODUCTION

Following a jury trial, Jason Rosales appeals his convictions for conspiracy to possess
with intent to distribute and attempt to possess with intent to distribute 500 grams or more of
methamphetamine under 21 U.S.C. §§ 846, 841(a)(1), and 841(b)(1)(A)(viii), and his sentence of
240 months’ imprisonment.

For the following reasons, we affirm the convictions and remand to the district court for
resentencing.
II. BACKGROUND

In February 2017, Monica Duran agreed to transport drugs for her boyfriend “Christian”
from Santa Ana, California to Springfield, Ohio on a Greyhound bus. Duran hid ten packages of
methamphetamine, weighing a total of 4,427 grams, in a black duffel bag.

Christian arranged for money to be transferred to Duran to cover the expenses of the
transport. On February 10, Christian texted Duran a reference number for a money wire to
Walmart along with “send[er] Terry Tolle.” Subsequent investigation identified Tolle as the
father of Rosales’ then-girlfriend Tinisha Delong.

On February 13, the Drug Enforcement Agency (“DEA”) intercepted Duran while she
was en route to Ohio. Duran agreed to cooperate in exchange for leniency and allowed the
government to copy all calls, texts, and data from her cellphone.

That same day, under the direction of law enforcement, Duran texted Christian to inquire
whether the drug delivery would occur that night and whether he would send her the number of
the local contact. Christian sent Duran the address of a local Comfort Inn, indicating that a prior
drug delivery had taken place there. At 1:12 a.m. on February 14, Christian texted Duran the
number for the local contact, which ended in 0163, along with the words, “on the part of the
 No. 19-3749 United States v. Rosales Page 3

cousin.” Duran testified that she understood from the text that this was the person to whom she
was supposed to deliver the drugs, and that she should tell the contact she was calling on behalf
of the cousin.

At around 10:42 a.m. on February 14, Duran told Christian she would call the contact.
Christian texted Duran, “they are ready for you to speak to them. Okay. First someone will
come by for you to give them that, [and] then another person will come by for them to give you
papers, okay.” Duran then called the number Christian had texted her the night before, and
Rosales answered. She told him that she was calling “on behalf of cousin,” to which Rosales
replied, “Yes, he wasn’t calling me. Well, I’m going to call him.” A short time later in a
subsequent conversation Rosales expressed confusion about where he was supposed to go to
meet her. When Duran texted Christian about this confusion Christian responded, “He doesn’t
know where the hotel is. Well, they met up there last time unless it’s someone else who is
coming to pick up. Give him the address then.”

Several hours later when Duran called Rosales, he told her that he “shouldn’t be that
long” and again clarified which hotel he was supposed to meet her at. He then texted, “[s]o its
outside.” Duran testified that she understood this to be a reference to the drugs and responded
affirmatively. A few minutes later Rosales texted that he was outside in a burgundy minivan, but
law enforcement officers saw no such vehicle. Duran then called Christian and told him that the
contact was not outside. Christian said he would call the local contact. Christian called her back
a few moments later and said he had spoken with the contact and that this was a tactic to make
sure she had not been followed.

Shortly thereafter Christian texted her that the new plan was for her to take a taxi to a
house in Springfield, Ohio. Law enforcement identified the house as the residence of Rosales
and his father Stephen Rosales. Following instructions from law enforcement, Duran insisted
that the delivery take place at the hotel.

Around 4:30 p.m. Christian called Duran. Though the DEA inadvertently did not record
that call, DEA task force officer Sean Zint, while listening to the call between Christian and
Duran wrote down, “elevated Ram P.U. $5,000.” A short time after that call Rosales texted
 No. 19-3749 United States v. Rosales Page 4

Duran that he was “outside in a big truck.” Christian then called Duran and said, “they are
around there now.” After realizing that he was at the wrong hotel, Duran texted Rosales the
address of the Comfort Inn in Dayton, Ohio and confirmed with Christian that Rosales was on
his way to the correct location.

At 5:19 p.m. Rosales texted Duran that he was on his way to meet her and also said,
“You’re going with me. My brother said you don’t want to be there. You can stay—no
problem. No one is going to mess with you. You can stay as long as you like. Pops will be
there.” Duran testified that she was confused about this message because she had not agreed to
stay at anyone’s house.

At 6:13 p.m. Rosales texted Duran that he had arrived. Duran told him, “Go to the
Nissan truck that has the Wisconsin plates. I put the bag there underneath.” Rosales then texted,
“are you ready?” Rosales parked his truck next to the minivan and, without waiting for Duran,
picked up the large duffel bag containing the drugs and placed it in his car.

At that point, a group of armed officers surrounded Rosales. Rosales then threw his
phone to ground, causing it to break apart, and said, “fuck it.” As he was being searched incident
to arrest Rosales told the arresting officer, “I bet you had fun today.” That evening, officers
searched for the cellphone, but recovered only the battery and cover of Rosales’ phone. An
officer returned the next day to continue the search but was unable to locate any other parts of
the phone.

Officers found a bundle of cash totaling $6,962 in Rosales’ front pocket, $5,000 of which
was in large bills. Officers also searched the pickup truck and found two money orders from a
Walmart in Springfield, Ohio. Both money orders were sent around 4:00 p.m. on February 10,
approximately one hour before Christian had texted Duran the details of the money order that
had been sent in her name to fund the transport. The officers also searched Rosales’ home,
where they found $9,500 in cash and a knife. No controlled substances, drug paraphernalia, or
drug ledgers were found.

The DEA issued an administrative subpoena for the subscriber information and toll
records of the 0163 phone number. The service provider was not able to provide subscriber
 No. 19-3749 United States v. Rosales Page 5

information, but the toll data for the phone number listed the contacts with Duran’s phone along
with nine contacts on February 13 and seven text messages exchanged on February 14 between
the 0163 number and a Mexican phone number used by Christian. The toll records indicated that
the last outgoing communication was at 6:31 p.m. on February 14, which was about the time that
Rosales was arrested and spiked his cellphone. Several incoming calls came after that time, but
none were connected, suggesting the phone was no longer in use.

At trial, over the objection of both parties, the court instructed the jury to find the
quantity of drugs involved in the conspiracy as a whole, rather than just the amount that was
foreseeable to Rosales.

The jury convicted Rosales on both the conspiracy and attempt to possess counts. The
jury found that the conspiracy involved 4,427 grams of methamphetamine. It also found the
same quantity for the attempt to possess count.

At sentencing, over Rosales’ objection, the district court gave a two-point enhancement
for obstruction of justice because Rosales had thrown his cellphone to the ground during his
arrest. The court departed down from the Guidelines range and imposed a sentence of 240
months’ imprisonment for each count, to be served concurrently.

On appeal Rosales argues that (1) there was insufficient evidence to convict on
conspiracy to possess with intent to distribute and attempt to possess with intent to distribute;
(2) the district court erred by not instructing the jury to find only the quantity of drugs in the
conspiracy that was reasonably foreseeable to the defendant; and (3) the district court erred in
applying a two-level sentencing enhancement for obstruction of justice.

III. ANALYSIS

A. SUFFICIENCY OF THE EVIDENCE

We review de novo a challenge to the sufficiency of the evidence. United States v.
Farrad, 895 F.3d 859, 871 (6th Cir. 2018). We consider “whether, after viewing the evidence in
the light most favorable to the prosecution, any rational trier of fact could have found the
essential elements of the crime beyond a reasonable doubt.” United States v. Tocco, 200 F.3d
 No. 19-3749 United States v. Rosales Page 6

401, 424 (6th Cir. 2000) (quoting Jackson v. Virginia, 443 U.S. 307, 319 (1979)). “We do not
weigh the evidence, assess the credibility of witnesses, or substitute our judgment for that of the
jury.” United States v. Smith, 749 F.3d 465, 477 (6th Cir. 2014) (cleaned up). Circumstantial
evidence alone can be sufficient to sustain a conviction, even if it does not remove every
possibility besides that of guilt. United States v. Hendricks, 950 F.3d 348, 352 (6th Cir. 2020)
(cleaned up).

To sustain a conviction for conspiracy under 21 U.S.C. § 846, the government must have
demonstrated: (1) an agreement to violate drug laws; (2) knowledge and intent to join the
conspiracy; and (3) participation in that conspiracy. United States v. Deitz, 577 F.3d 672, 677
(6th Cir. 2009).

Rosales argues that the government failed to prove beyond a reasonable doubt that he had
the requisite intent for either conviction. He argues that his conduct was at least as consistent
with the defense’s theory that he was merely picking up a guest and had no knowledge that she
was a drug courier. Rosales also suggests that there was no evidence that he was a drug dealer
beyond the cash found on his person and in his home. He further argues that, without more
direct evidence demonstrating his knowledge that the bag contained drugs and that he was a part
of the conspiracy, no reasonable jury could have found him guilty.

But a conviction can be sustained “even if [the evidence] ‘does not remove every
reasonable hypothesis except that of guilt[.]’” Hendricks, 950 F.3d at 352 (quoting United States
v. Spearman, 183 F.3d 743, 746 (6th Cir. 1999)). Here, Rosales suggested that he was merely
picking up a friend of a friend from out of town. He supported this theory by pointing out,
amongst other things, that the government had not found any overt references to drugs in any of
his conversations with Duran. He also suggested that his alleged initial confusion about to where
to pick her up was incompatible with Christian’s statement that “they met up there last time.”
While these are plausible arguments to make at trial, they were clearly rejected by the jury when
it found Rosales guilty on both counts.

Rosales argues that the single transaction that took place is insufficient to demonstrate
that there was a conspiracy to violate drug laws. It is true that “[t]he buy-sell transaction is
 No. 19-3749 United States v. Rosales Page 7

simply not probative of an agreement to join together to accomplish a criminal objective beyond
that already being accomplished by the transaction.” United States v. Hamm, 952 F.3d 728, 736
(6th Cir. 2020) (quoting United States v. Townsend, 924 F.2d 1385, 1394 (7th Cir. 1991)). To
establish that a single transaction is part of a larger conspiracy we have considered several
factors, including: “(1) the length of the relationship; (2) the established method of payment;
(3) the extent to which transactions are standardized; and (4) the level of mutual trust between
the buyer and the seller.” Deitz, 577 F.3d at 681 (citation omitted).

Here, a reasonable jury could have found that there was a previous relationship between
Rosales and Christian. Christian indicated to Duran that someone whose phone number ended in
0163 would be coming to retrieve the drugs. When Duran called that phone number Rosales
answered. Rosales never identified himself, nor asked Duran to identify herself. The only
identifying information was Duran’s initial statement that she was calling on behalf of the
cousin. Rosales seems to have understood this to mean Christian, as he did not question who the
cousin was and instead said, “Yes, he wasn’t calling me. Well, I’m going to call him.” A
reasonable jury could have inferred from this interaction that there was a previous relationship
between Rosales and Christian.

Rosales asserts that there was no evidence of an established method of payment. But
Christian had told Duran that someone in a Ram pick-up truck would give her $5,000. DEA task
force officer Zint testified that his note from the phone call between Christian and Duran in
which he had written down “elevated Ram P.U. $5,000,” referred to a description of the
contact’s vehicle and that Duran was supposed to pick up $5,000. At the time of his arrest,
Rosales had $5,000 cash in large bills in his pocket. Furthermore, a money order receipt found
in Rosales’ car listed Terry Tolle as the sender, the same individual Christian had told Duran
would be transferring money to her for the transport on February 10.

The third Deitz factor, which looks at the standardization of transactions, also supports
the conviction. Christian texted Duran the address and telephone number of a Comfort Inn,
indicating that a previous drug transaction had taken place there and that the local contact
“already know[s] which one it is.”
 No. 19-3749 United States v. Rosales Page 8

Finally, the evidence arguably demonstrated that there was some level of trust involved in
this transaction. The government estimated that the street value of methamphetamine is
$60,000-$80,000 per kilogram and presented testimony that drug dealers often enter into fronting
arrangements to accept drugs without any upfront payments. If Rosales was only going to pay
$5,000 up front for drugs that were worth over $200,000, the jury could have interpreted that as a
sign of the trust between him and Christian, lending further credibility to the conspiracy charge
under the fourth Deitz factor.

Furthermore, this court has also found that “large quantities of drugs, such as a kilogram
or more, support an inference of a conspiracy.” United States v. Lopez-Medina, 461 F.3d 724,
748 (6th Cir. 2006). This case involves 4,427 grams of methamphetamine, which far exceeds the
quantity a simple drug user would typically possess. The drug quantity therefore supports an
inference of a conspiracy despite there only being a single transaction.

Rosales also argues that there was no evidence that he knew he was agreeing to violate
drug laws. He suggests that while the evidence indicates he agreed to work with Duran and
Christian, it does not demonstrate that he knew what he was agreeing to do involved a violation
of drug laws. He relies on United States v. Sliwo, where this court overturned a conspiracy
conviction where the defendant had assisted in moving a van before it contained drugs and had
acted as a lookout. 620 F.3d 630, 633 (6th Cir. 2010). There, we found that the evidence “may
be sufficient to show that Defendant had knowingly decided to work with his alleged co-
conspirators, but it says nothing about whether Defendant knew that the ultimate purpose of the
conspiracy was possession of marijuana.” Id at 634.

Unlike in Sliwo, the facts of this case demonstrate Rosales’ direct involvement with the
drugs. First, when Duran spoke with Rosales, he attempted to confirm that “it’s outside,” which
Duran testified she understood to be referring to the drugs. Rosales then proceeded to pick up
the bag without waiting for Duran. Though Rosales claims that he had no knowledge of the
drugs and was just trying to pick up Duran, a jury could reasonably conclude that his statements
and conduct demonstrate that he was there primarily to pick up the bag rather than Duran.
Furthermore, money order receipts that matched the name of the individual who had initially
 No. 19-3749 United States v. Rosales Page 9

wired money to Duran to facilitate the transport were found in the car Rosales was driving,
further linking him to the conspiracy.

Rosales suggests that the fact that he had only a small amount of cash on him and in his
house is evidence that he was unaware of the large quantity of drugs in the bag. This argument is
also unavailing. As explained above, the government presented evidence to the jury that fronting
arrangements are common in drug conspiracies. That no typical evidence of drug dealing was
found at Rosales’ house does not undermine the jury verdict because the government also
provided testimony that drug dealers often use stash houses to conceal their activity.

Granted, there is no smoking gun evidence that confirms Rosales had knowledge that the
duffel bag contained 4, 427 grams of methamphetamine, but such evidence is not needed to
sustain a conviction. The circumstantial evidence presented at trial, especially when considered
as a whole, would allow a reasonable jury to conclude that Rosales conspired and attempted to
possess with intent to distribute the drugs. Rosales asserts that this evidence is insufficient
because his defense theory that he was merely picking up an out of town visitor was just as likely
to be true. However, suggesting an alternative explanation for the facts does not satisfy the “very
heavy burden” of showing that even when “[a]ll reasonable inferences and resolutions of
credibility are made in the jury’s favor” the government’s evidence was still insufficient. United
States v. Cox, 871 F.3d 479, 490 (6th Cir. 2017) (citations omitted). It is not enough that Rosales
proffered another theory to explain his conduct. A jury found him guilty beyond a reasonable
doubt, and making all reasonable inferences in its favor, we do not second-guess its conclusion.

B. JURY INSTRUCTION’S EFFECT ON SENTENCING

We review jury instructions de novo. United States v. Burchard, 580 F.3d 341, 345 (6th
Cir. 2009).

Because the offenses Rosales was charged under included a mandatory minimum of ten
years if the drug quantity involved was 500 grams or more of methamphetamine, the parties
agreed to use special verdict forms for both counts to calculate the drug quantities for the
purposes of the statutory sentencing ranges under §§ 841(b)(1) and 846. See Alleyne v. United
States, 570 U.S. 99, 103 (2013) (holding that any fact that increases the mandatory minimum is
 No. 19-3749 United States v. Rosales Page 10

an element that must be submitted to the jury). Based on a recent change in the Sixth Circuit
pattern jury instructions, the government proposed that as to the conspiracy count, the jury be
given a defendant-specific instruction rather than an instruction based on a conspiracy-wide
Pinkerton1 theory of liability. The proposed instruction would have required the jury to
determine the amount of drugs that “resulted from the Defendant’s own conduct and the conduct
of other co-conspirators that was reasonably foreseeable to him.” The district court rejected the
proposed defendant-specific instruction and instead gave a conspiracy-wide instruction, stating
that no evidence had been presented at trial that would indicate Rosales possessed anything less
than 500 grams of methamphetamine. The district court acknowledged that its decision “may be
proven to be error” and had a “full realization that [it] may be making a prejudicial error at least
as far as sentencing is concerned.”

Rosales argues that the conspiracy-wide instruction may have caused the jury to attribute
a greater quantity of drugs to him. He suggests that if the jury had received the defendant-
specific instruction, it may have found that less than the full 4,427 grams of methamphetamine
was foreseeable to him.

In United States v. Swiney, we held that a district court must employ a defendant-specific
approach for determining the extent to which a defendant charged under § 846 is subject to the
penalties set forth in § 841(b) based on his co-conspirators’ conduct. 203 F.3d 397, 406 (6th Cir.
2000). The Swiney court looked to the sentencing guidelines, which provide in U.S.S.G.
§ 1B1.3(a)(1)(B) that a defendant is subject to sentencing liability based on his own conduct and
the conduct of his co-conspirators only to extent that the co-conspirator(s)’ conduct was
reasonably foreseeable to him. Id. at 402. Thus, in cases where the defendant could be
criminally liable for the conduct of other conspirators, rather than giving a conspiracy-wide
instruction, the court must use a defendant-specific instruction when instructing the jury to
determine sentencing liability based on the quantity of drugs attributable to the defendant. See
Hamm, 952 F.3d at 745–46.

1
See Pinkerton v. United States, 328 U.S. 640, 647–48 (1946) (holding that coconspirators can be liable for
the ramifications of the conspiracy as a whole that were reasonably foreseeable as consequences of the unlawful
agreement).
 No. 19-3749 United States v. Rosales Page 11

Swiney does not precisely apply to the case before us because it places limits on liability
for the conduct of co-conspirators. As the government points out, “[h]ere, the only drugs at issue
were the [4,427 grams] of methamphetamine that Duran was supposed to deliver.” The jury
found that Rosales attempted to possess with intent to distribute this same quantity of drugs. The
jury also found that Rosales had entered into the conspiracy. Rosales argues that had the jury
been given the defendant-specific instruction it could have found that Rosales was anticipating
picking up a smaller quantity of drugs. But even under a defendant-specific approach, Rosales is
responsible for all quantities with which he was directly involved. When the jury found Rosales
guilty of the attempt to possess charge, it found he attempted to possess 4,427 grams of
methamphetamine. This means that the jury found beyond a reasonable doubt that Rosales had
the mens rea that 4,427 grams of drugs were in the duffel bag, which does not require that he
personally knew, or reasonably foresaw, any specific quantity of methamphetamine. See United
States v. Dado, 759 F.3d 550, 570 (6th Cir. 2014) (finding that “the penalty provisions of
§ 841(b) . . . require only that the specified drug types and quantities be involved in an offense”
(citation omitted)); see also United States v. Mahaffey, 983 F.3d 238, 243 (6th Cir. 2020). Thus,
because the jury found Rosales had attempted to possess 4,427 grams of methamphetamine when
he picked up the duffel bag, it logically concluded that he was liable for that same amount under
the conspiracy charge since that is the drug quantity he was directly involved with.

In other words, the jury found that Rosales was liable for the full quantity of drugs in the
conspiracy. It is for this reason any error stemming from the failure to give a defendant-specific
instruction was harmless. There was no possibility that the jury based the conspiracy quantity
determination on the conduct of others not reasonably foreseeable to Rosales because the jury
determined as part of the attempt charge that Rosales was responsible for 4,427 grams of
methamphetamine. Thus, it necessarily determined that his role in the conspiracy involved that
amount. “[A]n error is harmful as long as ‘there is a reasonable possibility’ that it ‘might have
contributed to the’ result.” Hamm, 952 F.3d at 748 (quoting Chapman v. California, 386 U.S.
18, 23 (1967)). For these reasons, while the district court erred in failing to provide
defendant-specific jury instructions, the error was harmless because it could not have contributed
to a different result.
 No. 19-3749 United States v. Rosales Page 12

C. OBSTRUCTION OF JUSTICE ENHANCEMENT

“We review the district court’s findings of fact for clear error but review de novo its
determination whether specific facts constitute an obstruction of justice under the sentencing
guidelines.” United States v. Williams, 709 F.3d 1183, 1185 (6th Cir. 2013).2

As noted, the statutory sentencing range for both counts was a mandatory minimum of
ten years to life. See 21 U.S.C. § 841(b)(1)(A)(viii). After applying the two-level enhancement
for obstruction of justice, Rosales was determined to have a Category III criminal history and an
adjusted offense level of 38. This resulted in a Guidelines range of 292 to 365 months’
imprisonment. The district court found that this range was “more than needed to carry out the
purposes of sentencing” and varied downwards to a sentence of 240 months’ imprisonment.
Without the obstruction of justice enhancement, the applicable Guidelines range would have
been 235 to 293 months’ imprisonment.

Under U.S.S.G. § 3C1.1, a two-level enhancement to the total offense level applies when
the defendant has “willfully obstructed or impeded, or attempted to instruct or impede, the
administration of justice with respect to the investigation, prosecution, or sentencing of the
instant offense of conviction.” Where the evidence is destroyed contemporaneously with arrest,
the enhancement does not apply unless it results in a “material hindrance” to the investigation or
the sentencing of the defendant. Id. at cmt. n.4. The obstructing conduct relied upon by the
district court was Rosales’ destruction of his cell phone, and neither party disputes that Rosales
spiked the phone on the ground contemporaneously with his arrest. Thus, for the enhancement
to apply the district court had to find both “willfulness” and “material hindrance.”

2
This court has “sent mixed messages” as to whether application of the Guidelines to the facts is reviewed
de novo or with “due deference” to the district court. See United States v. Thomas, 933 F.3d 605, 608 (6th Cir.
2019). For purposes of our case, it does not matter because the district court erred as a matter of law by failing to
make the necessary factual finding on the record.
 No. 19-3749 United States v. Rosales Page 13

The district court must “indicate with specificity what facts [it] considered in reaching its
offense level calculation.” United States v. Range, 982 F.2d 196, 198 (6th Cir. 1992). Rosales
asserts that the district court made conclusory findings untethered to specific facts. We disagree
in part. In addressing “willfulness” the court found that “Defendant was not trying to avoid
being shot but rather was trying to destroy the telephone, the cell phone, with which he and
Monica Duran had been communicating for many hours since she left the bus station.” The
court emphasized that the phone was “thrown to the ground with sufficient force so as to make
any information stored on the phone . . . impossible to retrieve.” These findings easily satisfy
the willfulness requirement of § 3C1.1.

On the other hand, the district court did not make any factual findings as to the material
hindrance of the investigation.3 Although the court noted that the phone would have reflected
communication between Rosales and Duran, it did not discuss how not having the phone
materially impeded the government’s investigation.4 The government asserts that the phone may
have provided them with more information about the conspiracy and may have more concretely
tied Rosales to Christian and the conspiracy itself. This may be true, but without a specific
factual finding from the district court that Rosales’ spiking of the phone materially hindered the
investigation, the obstruction enhancement cannot be imposed. See United States v. Kaminski,
501 F.3d 655, 673 (6th Cir. 2007) (finding that a district court erred by applying an obstruction
of justice enhancement when it found only willfulness and not that the conduct had actually
significantly hindered the investigation); see also United States v. Williams, 952 F.2d 1504, 1516
(6th Cir. 1991) (“The focus of the guideline is on whether defendant . . . succeeded in
significantly impeding the investigation.”). Without this finding on the record, we cannot be
certain that the district court correctly applied the obstruction of justice enhancement.

3
This is somewhat understandable because Rosales did not specifically object to the enhancement on this
basis. Indeed, his argument before the district court focused entirely on the “willfulness” issue.
4
At trial, a law enforcement officer testified that he was not able to obtain information from the recovered
parts of the phone. However, some information was able to be recovered from the administrative subpoena of the
toll records. There was no testimony at trial regarding how the missing information materially hindered the
investigation. The district court did not refer to the missing information testimony at sentencing at all, let alone
indicate that it relied on it in applying the enhancement. Further, the PSR references that the destruction of the
phone impeded the investigation, but it does not indicate that the impediment was material.
 No. 19-3749 United States v. Rosales Page 14

The question thus becomes whether the error was harmless. Though the sentence
imposed was within the correct Guidelines range absent the obstruction enhancement, we cannot
be certain on this record that the district court would not have imposed a lower sentence had the
Guidelines range been properly calculated because the district court did not indicate that it would
have imposed a similar sentence absent the enhancement. See Molina-Martinez v. United States,
136 S. Ct. 1338, 1345 (2016) (finding that when a defendant is sentenced under an erroneously
calculated Guidelines range “the error itself can, and most often will, be sufficient to show a
reasonable probability of a different outcome absent the error”); United States v. Collins, 800 F.
App’x 361, 362 (6th Cir. 2020) (explaining that this court has generally only found sentences
based upon a miscalculated Guidelines range to be harmless error when a district court makes
clear that it would have given the same sentence even without the enhancement the defendant
seeks to challenge on appeal).

Our decision in United States v. Buchanan is instructive. 933 F.3d 501 (6th Cir. 2019).
There the district court erroneously applied an enhancement that resulted in a Guidelines range
of 63 to 78 months’ imprisonment. Id at 508. Without the enhancement the Guidelines range
would have been 51 to 63 months’ imprisonment. Id at 517. Despite the fact that the district
court varied downwards below the proper Guidelines range to 50 months, we still remanded for
resentencing because the district court had not clearly indicated that it would have imposed the
same sentence regardless of the applicable guideline range. Id. at 517–518.

The district court sentenced Rosales near the bottom of the Guidelines range that would
have been applicable without the enhancement because it felt that the higher range was “more
than [was] needed to carry out the purpose of sentencing.” But we cannot say with certainty that
it would have imposed the same sentence if it had started from that lower Guidelines range. See
Molina-Martinez, 136 S. Ct. at 1347 (finding that the Guidelines are a “starting point for the
sentencing” and serve as a “focal point” for the proceedings that follow). Though it seems likely
that the district court may reimpose the same sentence given its decision to depart downwards,
the burden of demonstrating certainty has not been met. See Collins, 800 F. App’x at 364
(remanding when the district court “might well still impose a similar sentence”).
 No. 19-3749 United States v. Rosales Page 15

For this reason, we remand to the district court for the limited purpose of reconsidering
whether the obstruction of justice enhancement applies after making the necessary factual
findings. In doing so, “we seek to provide the court with an opportunity to develop, on the
record, the precise reasons for its decision to apply the obstruction of justice enhancement.”
Range, 982 F.2d at 198.

IV. CONCLUSION

We AFFIRM as to the sufficiency of the evidence and the jury instructions, and
REMAND for resentencing as it pertains to the obstruction of justice enhancement.