United States v. Chube, Charles R. ( 2008 )


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  •                              In the
    United States Court of Appeals
    For the Seventh Circuit
    ____________
    Nos. 06-3674 & 06-3675
    UNITED STATES OF AMERICA,
    Plaintiff-Appellee,
    v.
    DAVID DEMARET CHUBE II and
    CHARLES RANDALL CHUBE,
    Defendants-Appellants.
    ____________
    Appeals from the United States District Court for the
    Northern District of Indiana, Hammond Division.
    No. 2:04-CR-00096—Rudy Lozano, Judge.
    ____________
    ARGUED SEPTEMBER 28, 2007—DECIDED AUGUST 15, 2008
    ____________
    Before ROVNER, WOOD, and EVANS, Circuit Judges.
    WOOD, Circuit Judge. Responding to growing concerns
    about widespread abuse of OxyContin, a Schedule II
    narcotic opioid often prescribed to treat chronic pain, the
    federal Drug Enforcement Administration (“DEA”) in 2001
    launched a public campaign called the “OxyContin
    Action Plan” to ferret out unlawful uses of the drug. Dr.
    David Demaret Chube II and his brother Dr. Charles
    Randall Chube (“Dr. David” and “Dr. Randy,” respec-
    tively, or, collectively, “the Doctors”) were two of the
    2                                   Nos. 06-3674 & 06-3675
    hundreds of physicians investigated by the DEA for
    possible illegitimate prescribing of the drug. On February
    2, 2005, the Doctors were charged in a 33-count indict-
    ment with unlawful distribution of controlled substances,
    health care fraud, and conspiracy to commit each of those
    offenses. After a two-week jury trial, the jury acquitted
    Dr. Randy of 32 out of 33 charges, and acquitted Dr.
    David of 27 out of 33 charges, rejecting both the conspiracy
    charges and many distribution charges. It found Dr. Randy
    guilty of one count of unlawful distribution and Dr. David
    guilty of four counts of unlawful distribution and two
    counts of defrauding a health benefit program.
    After the sentencing hearing, at which relevant conduct
    findings played a critical role in enhancing each brother’s
    advisory Guidelines range, the district court sentenced
    Dr. Randy to five years’ imprisonment and Dr. David to 15
    years. Both men appeal. We affirm their convictions, but
    we vacate both sentences and remand for resentencing.
    I
    The Doctors jointly owned a clinic, Great Lakes Family
    Health Center, which opened its doors in 1998 in Gary,
    Indiana; they opened a second office two years later in
    nearby Munster, Indiana. Prior to starting the Great Lakes
    clinic, the two had practiced medicine with their father
    in Gary. During the years that the Doctors operated
    their clinics, many patients came to them seeking relief
    from severe chronic pain. Like many practitioners, the
    Doctors treated some of these complaints with OxyContin,
    a drug that has received praise from pain-management
    organizations and specialists for its ability to alleviate
    debilitating pain. From 1995 to 2001, the drug’s maker,
    Nos. 06-3674 & 06-3675                                       3
    Purdue Pharma, openly (and, we now know, falsely)
    marketed OxyContin to physicians as a less-addictive
    alternative to other pain-relieving drugs. Because of an
    emerging realization that OxyContin was addictive and
    thus prone to abuse, the drug eventually attracted the
    DEA’s attention.
    The DEA was led to the Doctors by one of their patients,
    William Perry Mitchell, who lived in Benton Harbor,
    Michigan, about 70 miles from the Great Lakes clinic in
    Gary. He was one of several patients from that area.
    Although the Doctors had several legitimate patients, the
    proof at trial showed that others had no real medical
    complaints and went to the Doctors’ clinic solely to obtain
    OxyContin. Mitchell was arrested on September 17, 2001,
    and charged in the U.S. District Court for the Western
    District of Michigan with knowingly and intentionally
    distributing OxyContin pills. Mitchell and his girlfriend
    had obtained the pills in question using prescriptions
    written by either Dr. David or Dr. Randy. In exchange
    for a provision in his plea agreement offering a possible
    reduction in his sentence, Mitchell agreed to name his
    “suppliers,” to testify against them, and to bring more
    witnesses to the Government who would do the same.
    Mitchell fulfilled all parts of his bargain, as did the Govern-
    ment.
    The parties’ briefs present starkly different portraits of
    the defendants and their conduct. (We note, however, that
    at this stage we must view the facts in the light most
    favorable to the jury’s verdict. See Jackson v. Virginia, 
    443 U.S. 307
    , 319 (1979); United States v. Thompson, 
    523 F.3d 806
    ,
    809-10 (7th Cir. 2008).) According to the Doctors, the
    evidence demonstrated that they believed, in good faith
    and with good reason, that their patients were seeking
    4                                   Nos. 06-3674 & 06-3675
    treatment for true medical complaints. The problem they
    face is that the jury did not have to accept their protesta-
    tions. But the Doctors also raise a legal argument: their
    convictions, they argue, assess their actions by reference
    to the standard of care applicable in a civil malpractice
    suit, but the proper standard is the one found in the
    Controlled Substances Act (“CSA”), which authorizes the
    conviction of a registered practitioner only if the prescrip-
    tion was written without a legitimate medical purpose
    and outside the scope of professional practice. The Govern-
    ment urges us to conclude that the evidence supports a
    finding that the Doctors were not using their medical
    licenses to treat patients with true complaints, but were
    acting as common drug dealers, earning substantial
    amounts of money by prescribing drugs to addicts whom
    they knew had no legitimate medical complaints and
    without conducting sufficient physical examinations,
    diagnostic tests, or other appropriate inquiries or proce-
    dures to determine that the prescriptions were war-
    ranted. The jury found, the Government continues, that
    this conduct violated the CSA and thus went beyond
    simple malpractice. In other words, it found that the
    Doctors were acting not as physicians, but as profiteering
    pill-pushers.
    The jury drew careful lines in its verdict. It exonerated
    the Doctors on the great majority of the charges, but it did
    convict Dr. Randy on one count of unlawful distribution,
    and Dr. David on four counts of unlawful distribution
    and two counts of health care fraud. On appeal, the
    Doctors support their argument about the erroneous use
    of the malpractice standard with an attack on two of the
    Government’s expert witnesses, Dr. Theodore Parran and
    Dr. Robert Barkin. Their testimony allegedly conflated the
    Nos. 06-3674 & 06-3675                                     5
    civil and criminal standards of care and thus created a
    risk that the jury found liability not because it concluded
    that the Doctors’ acts of prescribing medications fell
    outside the scope of legitimate medical practice, but instead
    because it thought they had been careless. The Doctors also
    argue that the experts’ testimony should not have been
    admitted because each impermissibly testified to legal
    conclusions.
    The Government’s case was not limited to these two
    experts. The jury also heard from 15 patients, 11 of whom
    testified that they were suffering from true medical prob-
    lems when they consulted the Doctors; the other four
    confessed that they fabricated their complaints solely to
    obtain painkillers. All said that they reported severe
    pain to the Doctors. Those who fabricated their com-
    plaints said they did not tell the Doctors that they were
    lying or that they were addicted to the drugs, for doing
    so would have thwarted their efforts to obtain the pills. The
    battleground of the litigation, then, was whether the
    Doctors knew that no legitimate medical reason existed
    for prescribing painkillers to these patients.
    At sentencing, the district court’s relevant conduct
    findings dramatically enhanced each defendant’s ad-
    visory Guidelines range. Before adding the relevant
    conduct, Dr. Randy was facing an advisory Guidelines
    range of 0 to 6 months’ imprisonment; because this fell
    within Zone A of the Guidelines grid, probation alone
    would have been permissible. Dr. David was looking at
    an advisory Guidelines range of 21 to 27 months in prison.
    Relying primarily on spreadsheets of alleged unlawful
    prescriptions compiled by the Government, which in-
    cluded any prescription for a controlled substance found
    in any of the 98 patient files seized in the Government’s
    6                                  Nos. 06-3674 & 06-3675
    searches of the defendants’ clinics, and on the expert
    testimony of Dr. Parran, the district court found that each
    defendant was responsible for all controlled sub-
    stances—including (among others) OxyContin, Vicodin,
    and Xanax—that either doctor had prescribed to the
    patients whose charts had been admitted into evidence at
    trial. The court then sentenced Dr. Randy to 60 months’
    imprisonment, and Dr. David to 180 months. We discuss
    below additional details of the sentencing proceedings,
    where relevant.
    II
    We first address the arguments that the Doctors raise
    against their convictions. They focus on the expert testi-
    mony of two Government witnesses, Dr. Theodore Parran
    and Dr. Robert Barkin. Dr. Parran, who specializes in
    internal medicine and addiction medicine, evaluated all 98
    patient files in the record. Based on that review, he con-
    cluded that the prescribing “was not done consistent
    with the usual standards of medical practice” and thus
    was not done with a “legitimate medical purpose.” Dr.
    Barkin was called as an expert on pharmacology. Though
    not a medical doctor, Dr. Barkin received his doctorate
    in clinical pharmacy in 1985 and is board-certified by
    various associations for pain management and forensic
    medicine. Like Dr. Parran, Dr. Barkin testified solely on
    the basis of the patient charts, although he reviewed only
    a selection. He, too, concluded that the prescriptions in
    the charts that he reviewed were issued “[o]utside the
    scope of medical practice, not for legitimate purposes.”
    The Doctors offer two reasons why both experts’ testi-
    mony should have been excluded in response to their
    Nos. 06-3674 & 06-3675                                       7
    motion in limine. They have an uphill battle, because our
    review is only for abuse of discretion. United States v. Watts,
    
    95 F.3d 617
    , 619 (7th Cir. 1996). The scope of their
    motion was the subject of some dispute. The Government
    describes it as a “breathtakingly broad” motion that
    sought to rule out all expert testimony that would sug-
    gest a violation of the standard of care applicable in civil
    medical malpractice cases. This, the Government argued,
    went too far. While it conceded that the expert testimony
    would not be conclusive on the question of the Doctors’
    criminal liability, it argued that “such evidence was
    relevant to circumstantially establishing that the defen-
    dants had knowingly and intentionally distributed drugs
    as mere pill-pushers rather than in the course of a profes-
    sional medical practice.” For their part, the Doctors pro-
    test that they have at all times recognized that the experts’
    testimony had some relevance. The goal of their motion
    was only somehow to limit the admissibility of such
    evidence when it tended to conflate the civil and criminal
    standards, not to exclude it entirely. But the memorandum
    supporting the defendants’ motion offers more support
    for the Government’s position:
    [t]he purpose of this Motion in Limine is to request that
    this Court enter a preliminary ruling prohibiting the
    Government from introducing any evidence at trial
    that the Chubes’ treatment of patients did not conform
    to the “standards of medical practice”, or any other
    evidence that would be suggestive of a violation of
    the civil standard of care applicable in medical mal-
    practice cases.
    The district court was entitled to take the Doctors at their
    word. On that understanding it did not abuse its discre-
    tion in denying the motion in limine.
    8                                    Nos. 06-3674 & 06-3675
    The Doctors also argue that the district court committed
    reversible error when it failed to exclude or strike the
    evidence during the trial, once it became clear that the
    testimony was creating precisely the type of confusion that
    the motion in limine sought to prevent. The net result,
    they assert, was effectively to reduce the Government’s
    burden from the standard of criminal intent to the negli-
    gence requirement that applies to civil malpractice. Fur-
    thermore, they argue, the experts provided what amounted
    to impermissible legal conclusions on the ultimate question
    of the Doctors’ intent. We address these two points in turn.
    A
    In order to support a violation of the CSA, the jury had
    to find that the Doctors knowingly and intentionally
    acted “outside the course of professional practice” and
    without “a legitimate medical purpose.” An implementing
    regulation issued under the CSA, 21 C.F.R. § 1306.04,
    reiterates this standard: “A prescription for a con-
    trolled substance[,] to be effective[,] must be issued for a
    legitimate medical purpose by an individual practitioner
    acting in the usual course of his professional practice.” See,
    e.g., United States v. Bek, 
    493 F.3d 790
    , 798 (7th Cir. 2007)
    (“[T]o convict . . . a practitioner registered to distribute
    controlled substances[] of violating § 841(a)(1), the gov-
    ernment must show that he prescribed controlled sub-
    stances outside ‘the course of professional practice.’”); see
    also United States v. Moore, 
    423 U.S. 122
    , 138-43 (1975). As
    one court summarized it:
    [T]o convict a practitioner under § 841(a), the gov-
    ernment must prove (1) that the practitioner distrib-
    uted controlled substances, (2) that the distribution of
    Nos. 06-3674 & 06-3675                                           9
    those controlled substances was outside the usual
    course of professional practice and without a legitimate
    medical purpose, and (3) that the practitioner acted
    with intent to distribute the drugs and with intent to
    distribute them outside the course of professional practice. In
    other words, the jury must make a finding of intent not
    merely with respect to distribution, but also with
    respect to the doctor’s intent to act as a pusher rather
    than a medical professional.
    United States v. Feingold, 
    454 F.3d 1001
    , 1008 (9th Cir. 2006)
    (emphasis in original).
    When all is said and done, we agree with the Govern-
    ment that it is impossible sensibly to discuss the question
    whether a physician was acting outside the usual course of
    professional practice and without a legitimate medical
    purpose without mentioning the usual standard of care. It
    is true that the experts did not, every time, spell out the fact
    that something more than conduct below the usual stan-
    dard of care was needed to show an absence of a
    valid medical purpose. Even the district court was not
    always as clear as it might have been (although as far as
    we can tell it never misspoke within the hearing of the
    jury). During a pretrial motions hearing, for example, the
    district court indicated its belief that reliance on the civil
    standard of care could be a permissible theory of the
    case for the Government:
    [B]oth sides are entitled to put in their theory of the
    case. And if [the prosecution’s] theory of the case is
    that these doctors have dispensed drugs improperly
    because they didn’t do the proper work-up, that may
    be a question of fact for the jury. You may not like
    the way they do it, but I don’t know that the gov-
    ernment can’t do that.
    10                                     Nos. 06-3674 & 06-3675
    The following exchange at the trial, however, was more
    typical:
    Q. [by the prosecution]: Doctor, would you like me to
    repeat the question?
    THE WITNESS: I believe I recall it pretty well. . . . It
    is never appropriate to write a prescription for the
    spouse of a patient when that prescription is intended
    for the patient; even more so when it’s a Schedule II
    narcotic. . . . It’s not consistent with the usual course of
    medical practice.
    Q. And that would not be for a legitimate medical
    purpose, correct?
    A. Correct.
    THE COURT: Counsel, this is being asked regarding
    standard of care, not legality?
    [PROSECUTION]: Absolutely, your Honor.
    Thus, what the jury heard was (1) an opinion from the
    expert that no legitimate medical purpose existed for the
    prescription in question; and (2) a clarification from the
    court that the “standard of care” is an issue distinct from
    the question of “legality.” The former was just what
    defense counsel, during a sidebar immediately
    preceding this exchange, had argued that Dr. Parran could
    testify to, and the latter reflected the distinction that the
    Doctors now claim was not properly drawn during the
    trial. We are satisfied that the district court did not abuse
    its discretion in permitting this line of questioning and
    that a properly instructed jury could keep the relevant
    concepts straight. Given this finding, we need not address
    the Doctors’ failure at crucial points to object to this line
    of inquiry.
    Nos. 06-3674 & 06-3675                                     11
    The Doctors also argue that the district court’s charge
    to the jury was insufficient to cure the confusion created
    by the experts’ testimony. Given the practical reading
    we give to jury instructions, see United States v. Matthews,
    
    505 F.3d 698
    , 704 (7th Cir. 2007), we find no merit in this
    point either. The district court’s instructions to the jury
    contained no inaccurate statements of the law. Viewing
    the charge as a whole, we see several points at which
    the instructions make clear that unlawful-distribution
    liability cannot attach unless no legitimate medical pur-
    pose existed for the prescription. The charge elaborated
    on the meaning of the phrases “in the course of profes-
    sional practice” and “no legitimate medical purpose”:
    A controlled substance is prescribed by a physician
    in the course of his professional practice, and there-
    fore lawfully, if the substance is prescribed by him in
    good faith in medically treating a patient.
    Good faith means good intentions and the honest
    exercise of good professional judgment as to a
    patient’s medical needs. Good faith means an obser-
    vance of conduct in accordance with what the physi-
    cian should reasonably believe to be proper medical
    practice.
    In order to determine whether or not a prescription
    or prescriptions were issued in the course of a defen-
    dant physician’s professional practice, you may con-
    sider all of the evidence of circumstances sur-
    rounding the prescribing of the substance in question,
    the statements of the parties to the prescription transac-
    tions, any expert testimony as to what is the usual
    course of medical practice, and any other competent
    evidence bearing on the purpose for which the sub-
    stances in question were prescribed.
    12                                  Nos. 06-3674 & 06-3675
    Unless you find beyond a reasonable doubt that an
    act of prescribing charged in the Superceding Indict-
    ment was not done in the course of his professional
    practice, then you should find the defendant you are
    considering not guilty of the charge you are consider-
    ing.
    In addition, the court permitted defense counsel to draw
    out the distinctions between the civil and criminal burdens
    during opening statements, cross-examinations, and
    closing arguments.
    Though it is true that the jury instructions did not
    spell out the distinction between the civil and criminal
    burdens of proof as expressly as the court did in a case
    reviewed by the Fourth Circuit, see United States v. Alerre,
    
    430 F.3d 681
    , 687 & n.5 (4th Cir. 2005), there is no one
    right way to convey the governing standards. This is
    particularly true where, as here, the defense made no
    effort even to propose the desired instruction. If it were
    vital to the defense that the jury receive further clarifica-
    tion on this issue, then the defense should have sub-
    mitted a proposed instruction. In sum, the district court did
    not abuse its discretion in allowing this expert testimony.
    Its instructions to the jury accurately described the gov-
    erning standards, and the Doctors’ failure to make any
    contemporaneous objection or to propose an alternative
    or additional instruction was fatal to their claim on appeal
    for reversible error.
    B
    The Doctors’ second challenge to the Government’s
    expert witnesses is that their testimony invaded the
    province of the jury by giving opinions on the ultimate
    Nos. 06-3674 & 06-3675                                   13
    legal question whether they knowingly violated the law.
    After raising this objection in their motion in limine, the
    Doctors did not repeat it during the trial. If the ruling on
    the motion in limine was “definitive,” then this was enough
    to preserve the argument. See FED. R. EVID. 103(a). Here,
    the court did not signal any willingness to reconsider
    its ruling during the trial, and so we apply the usual abuse
    of discretion standard to this part of the case.
    The question whether the district court improperly
    allowed the prosecution’s experts to testify as to impermis-
    sible legal conclusions boils down to an inquiry into the
    court’s application of FED. R. EVID. 704, which permits an
    expert to testify about an “ultimate issue to be decided by
    the trier of fact,” Rule 704(a), but nonetheless prohibits
    the expert from stating “an opinion or inference about
    whether the defendant did or did not have the mental
    state or condition constituting an element of the crime
    charged or of a defense thereto,” Rule 704(b). We must
    decide whether, in opining that the Doctors wrote pre-
    scriptions with no legitimate medical purpose, the
    experts in this case crossed the line established by Rule
    704(b).
    The Government argues that neither Dr. Parran nor Dr.
    Barkin ever claimed to know the Doctors’ intent, and so
    the opinions that they offered were not barred by Rule
    704(b). Particularly since the defense raised no contempora-
    neous objection, we agree with this position, though
    we note that portions of Dr. Parran’s testimony come close
    to a statement about the Doctors’ mental state. For exam-
    ple, when testifying about various “red flags” that signal
    drug-seeking behavior, Dr. Parran stated that these flags
    result in a situation where a doctor is “knowingly,” rather
    than “inadvertently,” “doing harm to a patient.” He then
    14                                   Nos. 06-3674 & 06-3675
    said that when enough red flags have appeared, one can
    say that a doctor “knew or should have known that harm
    was being done with these prescriptions.” But these
    statements are phrased in general terms (“a” doctor in “x”
    situation) and do not refer directly to the defendants. The
    district court thus did not abuse its discretion when it
    did not, on its own motion, intervene and halt this line
    of inquiry.
    The Doctors’ case is strikingly similar to one from the
    Eighth Circuit, United States v. Katz, 
    445 F.3d 1023
    (8th Cir.
    2006). Notably, the expert whose testimony was at issue
    in Katz was none other than Dr. Theodore Parran. In Katz,
    the Eighth Circuit rejected the defendant’s argument that
    Dr. Parran had impermissibly testified about Dr. Katz’s
    criminal intent. Acknowledging that “Rule 704(b) ‘prohibits
    experts from stating an opinion as to whether the defen-
    dant had the requisite mental state for the crime charged,’”
    the court was nevertheless satisfied that “Dr. Parran did
    not testify regarding the subjective mental state of Dr. Katz
    upon writing the prescriptions charged in the indictment.”
    
    Id. at 1032.
    The same is true in this case, for while Dr.
    Parran stated his opinion that no legitimate medical
    purpose justified the prescriptions in the files he reviewed,
    he repeatedly cautioned that he was looking only at the
    files and that he had never had any contact with either the
    patients or the Doctors. The same applies to Dr. Barkin’s
    testimony.
    The defense urges us to reject Katz, but we see no reason
    to do so. Its reasoning is sound, and it is consistent with
    similar decisions from this court. In United States v. Glover,
    
    479 F.3d 511
    (7th Cir. 2007), for example, we confronted a
    challenge to testimony from a law enforcement official
    that stated an opinion about the criminal nature of a
    Nos. 06-3674 & 06-3675                                   15
    defendant’s activities. We noted that this court has held
    on multiple occasions that “ ‘such testimony should not
    be excluded under Rule 704(b) as long as it is made
    clear, either by the court expressly or in the nature of the
    examination, that the opinion is based on the expert’s
    knowledge of common criminal practices, and not
    on some special knowledge of defendant’s mental pro-
    cesses.’ ” 
    Id. at 516
    (quoting United States v. Lipscomb, 
    14 F.3d 1236
    , 1242 (7th Cir. 1994)). We also have upheld the
    admission of expert testimony “to the effect that financial
    transactions did not comply with regulations and appeared
    to be fraudulent.” United States v. Davis, 
    471 F.3d 783
    , 789
    (7th Cir. 2006) (citing United States v. Owens, 
    301 F.3d 521
    , 526-27 (7th Cir. 2002)).
    We conclude that the district court did not abuse its
    discretion in admitting the testimony of Drs. Parran and
    Barkin. The court repeatedly told the jury that only the
    court can instruct the jury on what is or is not legal, and
    the expert witnesses in this case did not go so far as to
    offer an opinion on the Doctors’ subjective intent.
    III
    We turn now to the Doctors’ challenge to their sen-
    tences. They raise a single, though central, argument: that
    the district court erred in its determination of relevant
    conduct for purposes of U.S. Sentencing Guideline
    (“U.S.S.G.”) § 1B1.3. At the sentencing hearing, the dis-
    trict court concluded that although the jury had acquitted
    the defendants on most of the charged offenses, the
    Government had established by “clear and convincing
    evidence” that the defendants were guilty of all of the
    conduct described in the Presentence Investigation
    16                                   Nos. 06-3674 & 06-3675
    Reports (“PSRs”). The district court noted that the less
    rigorous preponderance-of-the-evidence standard likely
    would have been sufficient, but in light of lingering
    doubt on this question at the time of the hearing, the
    court opted for the higher clear-and-convincing threshold.
    Since then, United States v. Reuter, 
    463 F.3d 792
    (7th Cir.
    2006), has made it clear that it is the preponderance
    standard that applies to findings by a judge during sen-
    tencing. But even when we apply the proper preponder-
    ance standard to this record, we cannot conclude that the
    Government’s evidence was sufficient to include as
    “relevant conduct” all of the activities described in the
    PSRs.
    A
    We begin by emphasizing that the burden in the sen-
    tencing proceedings was on the Government to show that
    a given prescription had no legitimate medical purpose
    and was not dispensed in the usual course of medical
    practice. To meet that burden, the Government produced
    spreadsheets that listed every prescription for a con-
    trolled substance contained in the 98 patient files in
    evidence. The spreadsheets listed the patient’s name, the
    date of the prescription, the type of pill prescribed, and
    the dose. The probation officer used the spreadsheets and
    the pill totals that they tallied for the PSRs’ relevant
    conduct calculations. Those totals were as follows:
    • Dr. David prescribed 30 (5 mg) Percocet pills; 50 (7.5
    mg) Percocet pills; 180 MS Contin (30 mg) pills; 1,624
    OxyContin (10 mg) pills; 3,930 OxyContin (20 mg)
    pills; 10,255 OxyContin (40 mg) pills; 2,543
    OxyContin (80 mg) pills; 3,408 Vicodin pills; 31
    Nos. 06-3674 & 06-3675                                     17
    Tussionex pills; 5,427 Xanax pills; 180 Adipex-P pills;
    and 3,280 Valium pills. Converting the weights of
    those pills to marijuana, as provided in U.S.S.G.
    § 2D1.1, resulted in a marijuana equivalent of
    4,756.59 kilograms of marijuana.
    • Dr. Randy prescribed 40 Percocet (5 mg) pills; 270 MS
    Contin (30 mg) pills; 231 OxyContin (10 mg) pills;
    1,697 OxyContin (20 mg) pills; 3,488 OxyContin (40
    mg) pills; 6,010 OxyContin (80 mg) pills; 5,033
    Vicodin pills; 24 Tussionex pills; 4,067 Xanax pills;
    1,305 Adipex-P pills; 5,285 Valium pills; and 148
    Triazolam pills. The marijuana equivalent of these
    pills was 4,409.6 kilograms of marijuana.
    After adding a two-point enhancement to each doctor’s
    offense level for the use of a special skill, see § 2D1.1 app.
    note 8, the probation officer assigned an offense level of
    36 for each defendant. Paired with each one’s criminal
    history category of I, both calculations resulted in an
    advisory Guidelines range of 188 to 235 months’ incarcera-
    tion. The district court adopted those calculations in full
    and explained that it found both doctors responsible for all
    of the prescriptions in all of the files “because the Court
    finds by clear and convincing evidence that a conspiracy
    existed in that the prescriptions were written in furtherance
    of that conspiracy, and that both of these doctors were
    members of the conspiracy.” The court found that the
    Doctors jointly owned and operated their practice,
    shared profits, and participated together in the treatment
    of more than half of the 98 patients whose files were
    examined. Each defendant therefore was held responsible
    not only for the prescriptions that he wrote, but also
    for those that his co-defendant wrote.
    Relying on those findings, the district court sentenced Dr.
    Randy to the statutory maximum, 60 months’ imprison-
    18                                    Nos. 06-3674 & 06-3675
    ment, for his single count of conviction (count 10). Dr.
    David received a sentence of 188 months’ imprisonment on
    count 5, a term of 60 months on each of counts 10-12, and
    120 months on the health fraud counts, 20-21, all to be
    served concurrently. Each doctor was also ordered to pay
    a special assessment and a fine: $100 and $40,000 for
    Dr. Randy; $600 and $60,000 for Dr. David. Without the
    relevant conduct enhancements, Dr. Randy’s base offense
    level would have been 6; the two-point enhancement for
    special skill would have increased it to 8, resulting in an
    advisory sentencing range of 0 to 6 months in prison. Dr.
    David’s offense level before relevant conduct was 14,
    which would become 16 with the special-skill enhance-
    ment, for an advisory sentencing range of 21 to 27 months
    in prison.
    B
    Section 1B1.3 defines as relevant conduct “all reasonably
    foreseeable acts and omissions of others in furtherance
    of the jointly undertaken criminal activity.” This includes
    conduct of which the defendant was acquitted, see United
    States v. Watts, 
    519 U.S. 148
    , 156 (1997), and conduct for
    which he was never charged, see United States v. Anderson,
    
    517 F.3d 953
    , 963 (7th Cir. 2008). Nevertheless, the relevant
    conduct must be unlawful. United States v. Frith, 
    461 F.3d 914
    , 917-18 (7th Cir. 2006); United States v. Schaefer, 
    291 F.3d 932
    , 937-40 (7th Cir. 2002) (holding that it is “not enough”
    to show that defendant’s conduct is “disreputable and
    unethical”; to qualify as relevant conduct under the
    Guidelines, the conduct must be unlawful). In calculating
    relevant conduct, the sentencing court must make its
    findings by a preponderance of the evidence. The sentenc-
    ing record before us, however, does not distinguish
    Nos. 06-3674 & 06-3675                                   19
    between conduct that is unlawful and conduct that is
    the result of mistake or inadvertence. Inattention or
    negligence could lead a doctor to prescribe medication that
    is “medically unnecessary”; there is nothing necessarily
    criminal about such behavior. The PSRs did not offer any
    explanation why the prescriptions in the 98 files were not
    merely unnecessary, but indicative of illegal drug-pushing.
    They simply take the data in the Government’s spread-
    sheets and duplicate the figures as the findings of the
    probation officer.
    At several points in the proceedings, the district court
    made remarks suggesting it was confused or uncertain
    about the role that civil standard-of-care evidence
    should play in the relevant conduct determinations. For
    example, at the pretrial stage, the Government moved in
    limine to prohibit the defense from introducing testimony
    that other physicians had treated the Doctors’ patients in
    the same way as the defendants had treated them. The
    Government argued that the other doctors “are not
    capable of making that assessment whether or not these
    physicians were prescribing outside the scope of medical
    practice and procedure” because they, unlike Drs. Parran
    and Barkin, had not evaluated the patient charts. In
    response, the district court asked, “doesn’t any doctor have
    the right to say whether or not a patient that they’re
    treating within their field, whether the doctor beforehand
    was treating the patient within the standard of care?” (Em-
    phasis added.) The Doctors argue that while the district
    court may have been correct that any doctor is capable of
    opining about whether another physician met the standard
    of care when treating a particular patient, “the problem
    here is that the government was discussing the criminal
    standard (’outside the scope of medical practice’) and the
    20                                   Nos. 06-3674 & 06-3675
    district court responded with the civil standard (’the
    standards of care’).”
    During the sentencing hearing on September 6, 2006, the
    district court indicated that it may have relied on devia-
    tions from the civil standard of care in determining rele-
    vant conduct. The court stated, for instance: “My recollec-
    tion, and again, I want to take a look at the evidence, was
    that some of these patients came in and gave an excuse as
    to why they needed the drug, not that there was actual
    necessity.” As we have already said, an absence of med-
    ical necessity falls short of the criminal standard for
    prescribing outside the scope of medical practice alto-
    gether. We recognize the diligence of the district court in
    devoting substantial time to review all of the files and
    testimony from this long, complex trial. Even so, if the
    court evaluated the evidence with an eye for detecting
    failures to live up to the civil standard of care, then it
    clearly erred. On this record, we are not convinced that the
    district court properly distinguished between the prosecu-
    tion’s oft-repeated statements about “medically unneces-
    sary” or “careless” prescribing and the applicable crim-
    inal standard of prescribing without a legitimate medical
    purpose. The blurring of that line becomes even more
    apparent when we examine the transcript from September
    28, 2006, which was when the court articulated its
    findings and announced the defendants’ sentences.
    To support its relevant conduct findings, the district
    court relied almost exclusively on the testimony and
    conclusions of Dr. Parran. In effect, the court adopted the
    position of the Government that classified every prescrip-
    tion for the identified drugs in all 98 files as unlawful. The
    court discussed only 10 of those 98 files at the hearing,
    noting how, according to Dr. Parran’s testimony, those
    Nos. 06-3674 & 06-3675                                      21
    files offered evidence that the drugs dispensed to those
    patients were not prescribed for a legitimate medical
    purpose. This nearly-exclusive reliance on Dr. Parran’s
    testimony is troublesome, especially given his role as a
    “standard-of-care” expert.
    Summing up its findings, the district court stated:
    The Court has also taken the opportunity to review
    each of the 98 patient files in evidence. Numerous files
    contained evidence that the defendants were put on
    notice by pharmacies, organizations that monitor
    what prescriptions people get, and other entities
    regarding the patient’s drug seeking behavior. Trou-
    bling to the Court is that the records illustrate that the
    defendants turned a blind eye to these notices and
    continued to prescribe controlled substances to these
    patients without question. Moreover, there is evidence
    that nearly one-half of the 98 patients whose files were
    reviewed, came from the State of Michigan. There was
    evidence that sometimes two or more Michigan pa-
    tients would travel together to the defendant’s [sic]
    medical practice. Of these Michigan patients, most of
    them were prescribed controlled substances. This is
    more than coincidental and yet ignored and never
    acknowledged or considered by the defendants.
    This explanation is problematic for two reasons. First,
    stating that “[n]umerous files” contained evidence sug-
    gesting illicit prescribing is not sufficient to sweep every
    pill in all 98 files into the relevant conduct calculation. The
    same goes for the court’s account of Dr. Parran’s testimony,
    during which it made statements such as: “Dr. Parran
    found many files had red flags that were totally ignored by
    the defendants”; and “According to Dr. Parran, diagnostic
    work-ups were present in very few charts and he noticed
    22                                   Nos. 06-3674 & 06-3675
    that even when consultations were ordered, they were
    rarely ever followed up” (emphasis added). Such statements
    are too imprecise and indefinite to establish the illegality
    of all the prescriptions in all of the files.
    Similarly, the fact that “most” of the patients from
    Michigan were prescribed controlled drugs also provides
    no concrete foundation for including every pill dispensed
    to a Michigan patient as relevant conduct. The trial testi-
    mony revealed that many patients—from Michigan and
    Indiana alike—complained of and in fact experienced true
    medical problems. The court’s assumption of a lack of
    legitimate medical purpose for every prescription in 98 files
    after discussing only 10 files with any specificity was not
    enough to support its findings.
    As for the scarcity in the files of results from diagnostic
    tests, such as MRIs and CAT scans, we need only repeat
    the district court’s own observation that, for many
    patients, such tests were ordered (sometimes repeatedly)
    and were not completed; for others, records of completed
    tests were in the patient’s file. Many patients testified that
    they failed to comply with testing requests from the
    Doctors because they could not afford the expensive tests
    like MRIs. See BlueCross BlueShield Ass’n, “How Much
    Things Actually Cost,” available at http://
    www.bcbs.com/coverage/basics/cost (stating the “average
    national cost of an MRI is nearly $2,000,” and for those
    insured by BlueCross BlueShield, “your cost for an MRI” is
    $378); Three Rivers Endoscopy Center, “Magnetic Reso-
    nance Imaging (MRI),” http://www.gihealth.com/
    html/education/mri.html (“The cost of an MRI study can
    range from $400 to more than $2,000, with a typical cost
    being about $800.”).
    We also note that while the 98 patient files at issue
    were part of the trial record, we initially did not receive
    Nos. 06-3674 & 06-3675                                      23
    them as part of the appellate record, because, it seems,
    the defendants did not have access to them. We ob-
    tained them (with some effort) from the Government,
    which sent us six boxes. Two boxes contained the 98
    files; one contained miscellaneous trial exhibits; three
    contained nothing but rubber-banded stacks of prescrip-
    tion forms. A prescription form contains only scanty
    information, usually no more than drug name, dose,
    date, doctor signature. Very little (if anything) about a
    prescription form indicates whether it was written “with-
    out any legitimate medical purpose.” To the extent that
    the Government’s spreadsheets and relevant conduct
    calculations relied on the prescription forms, a better
    explanation of why any reliable information could be
    gleaned from them and how it fit into the ultimate deci-
    sion about relevant conduct was necessary.
    The final troublesome part of the sentencing record is the
    district court’s failure to address evidence tending to
    suggest a legitimate medical purpose for several prescrip-
    tions in the 98 files. For example, the district court specifi-
    cally inquired during the first date of the sentencing
    hearing “whether there was any evidence in the trial of
    the Chubes’ lowering their patient’s [sic] dosages of
    OxyContin.” In response to that inquiry, the defendants
    produced excerpts from 19 patient charts showing reduc-
    tions in each patient’s dosage. Many of those decreases
    were accompanied by chart notes stating that the doctor
    was weaning the patient from OxyContin in an effort to
    avoid tolerance or addiction. These notes are reinforced
    by the testimony of several patients, who stated that the
    Doctors seemed concerned for the patients’ well-being
    and at times were working to wean the patient off of a
    strong drug being prescribed to avoid dependence. Any
    24                                   Nos. 06-3674 & 06-3675
    legitimate prescriptions must be deducted from the pill
    totals before a final determination of relevant conduct is
    possible.
    IV
    Thus, while we uphold the Doctors’ convictions, we
    must remand for resentencing. To establish relevant
    conduct, the Government bears the burden of showing
    that a particular prescription was dispensed with no
    legitimate medical purpose. Presenting only a spreadsheet
    or a prescription form filled out by one of the defendants is
    insufficient. This is not a situation, moreover, in which the
    district court may rely on sampling or extrapolation. Here,
    unlike other cases we have reviewed under § 841(a), the
    drug quantity used at sentencing was expressly based on
    the 98 patient files and the finite set of prescriptions
    contained within them. These are not defendants who,
    from a period of “y” to “z,” were dealing drugs on the
    street to an unclear number of people on an unknown
    number of occasions. Compare United States v. Noble, 
    299 F.3d 907
    , 911 (7th Cir. 2002) (“A judge has leeway to
    extrapolate quantities from witnesses’ [sic] statements of
    minimum sales over several occasions . . . .”); United States
    v. Durham, 
    211 F.3d 437
    , 444-45 (7th Cir. 2000) (“[I]t is also
    permissible for a court to take witness’ [sic] estimates of
    the amount of drugs they purchased and multiply that by
    the minimum quantity sold on each occasion, as well as
    extrapolate drug quantities from the amount of money
    used to purchase the drugs.”); United States v. Gaines,
    
    7 F.3d 101
    , 103-06 (7th Cir. 1993); United States v. Martz,
    
    964 F.2d 787
    , 790 (8th Cir. 1992).
    In this case, a defined set of concrete data formed the
    sole basis for determining the quantity of illegally pre-
    Nos. 06-3674 & 06-3675                                   25
    scribed drugs. For a prescription to be included in rele-
    vant conduct, the court must evaluate the facts surround-
    ing that particular prescription and explain why those facts
    render it unlawful. Generalizing from “numerous” files
    will not suffice. When the district court revisits relevant
    conduct on remand, it must explain its findings with
    respect to each patient and make a reasoned determination
    whether or not the Government has carried its burden of
    establishing that each prescription was dispensed outside
    the scope of medical practice and without a legitimate
    medical purpose.
    The convictions of David Demaret Chube II and Charles
    Randall Chube are AFFIRMED. Both sentences are VACATED,
    and we REMAND for resentencing each defendant in
    accordance with this opinion.
    8-15-08