United States v. Jason Rosales ( 2021 )


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  •                               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.