MAO-MSO Recovery II, LLC v. State Farm Mutual Automobile ( 2019 )


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  •                                In the
    United States Court of Appeals
    For the Seventh Circuit
    ____________________
    Nos. 18-2377 and 18-2463
    MAO-MSO RECOVERY II, LLC, et al.,
    Plaintiffs-Appellants,
    Cross-Appellees,
    v.
    STATE FARM MUTUAL AUTOMOBILE INSURANCE COMPANY,
    Defendant-Appellee,
    Cross-Appellant.
    APPEAL OF: CHRISTOPHER L. COFFIN, et al.
    ____________________
    Appeals from the United States District Court for the
    Central District of Illinois.
    No. 17-1541 — Joe Billy McDade, Judge.
    ____________________
    ARGUED JANUARY 14, 2019 — DECIDED AUGUST 15, 2019
    ____________________
    Before WOOD, Chief Judge, and BRENNAN and ST. EVE,
    Circuit Judges.
    WOOD, Chief Judge. When all the dust is cleared away, this
    case is relatively straightforward: we must review a dismissal
    for lack of Article III standing and the imposition of sanctions
    2                                     Nos. 18-2377 and 18-2463
    under Rule 11. Only the factual backdrop is complex, as it
    deals with one aspect of the federal Medicare program. The
    Plaintiffs assert that they are assignees of certain private
    insurers called Medicare Advantage Organizations, which
    provide Medicare benefits. They brought a putative class
    action against State Farm Mutual Automobile Insurance
    Company in an effort to recover payments State Farm
    allegedly should have made to them as reimbursement for
    certain medical costs. The district court dismissed the action
    with prejudice, although the basis for the dismissal was lack
    of standing. In addition, the court imposed sanctions under
    Rule 11 of the Federal Rules of Civil Procedure against one of
    the plaintiffs, MSP Recovery Claims, Series LLC, and its
    attorneys.
    Plaintiffs, MAO-MSO Recovery II, LLC; MSP Recovery,
    LLC; MSPA Claims 1, LLC; and MSP Recovery Claims, Series
    LLC MSP (“Recovery Claims”), appealed. They argue that the
    court erred in its standing analysis, and that in any event it
    should not have dismissed the case with prejudice. Recovery
    Claims and the attorneys (Christopher Coffin, David
    Hundley, and Courtney Stidham) appealed the sanctions
    order. Finally, State Farm cross-appealed in order to preserve
    its alternative argument in favor of affirmance—that the case
    should be dismissed on the merits because plaintiffs failed to
    state a claim upon which relief can be granted. See Matushkina
    v. Nielsen, 
    877 F.3d 289
    , 297 (7th Cir. 2017) (noting that “[a]s a
    general rule, where a defendant has won dismissal for lack of
    standing or some other jurisdictional ground, modifying the
    judgment to dismissal on the merits” requires a cross-appeal).
    We conclude that the district court erred insofar as it
    dismissed plaintiffs’ case with prejudice, when the problem
    Nos. 17-3636 and 18-2463                                      3
    was a fundamental lack of Article III standing. But this victory
    gets the plaintiffs only so far. The court acted well within its
    discretion when it denied plaintiffs a third opportunity to
    cure the defects in their pleadings. The court’s order, in
    substance, was a jurisdictional dismissal with denial of leave
    to amend. So understood, we affirm the judgment and correct
    the record to reflect that the dismissal is without prejudice.
    We also dismiss State Farm’s cross-appeal. Finally, we find
    that the district court exceeded the bounds of its discretion
    when it imposed Rule 11 sanctions on Recovery Claims and
    its attorneys.
    I
    Although the issues before us are ultimately procedural,
    some background on Medicare is helpful to place them in
    context. Medicare is “the federal health insurance program
    for people who are 65 or older,” as well as for certain other
    groups. See https://www.medicare.gov/what-medicare-
    covers/your-medicare-coverage-choices/whats-medicare.
    While many Americans receive benefits directly from the
    government through Medicare Parts A and B, others receive
    their benefits from private entities known as Medicare
    Advantage Organizations, pursuant to Medicare Part C.
    42 U.S.C. § 1395w-21(a). For each Medicare enrollee covered
    by a Medicare Advantage Organization, the Organization
    receives a per capita reimbursement from the federal
    government. The amount of that reimbursement may vary
    according to the characteristics of the individual enrollees and
    other factors. See In re Avandia Mktg., Sales Practices & Prods.
    Liab. Litig., 
    685 F.3d 353
    , 364–65 (3d Cir. 2012). The Medical
    Advantage Organizations assume the financial risk of
    insuring their enrollees. 
    Id. 4 Nos.
    18-2377 and 18-2463
    One other piece of Medicare vocabulary is important to
    this case: the difference between “primary” and “secondary”
    payments. When an enrollee is covered directly by the
    government (under Medicare Parts A and B), Medicare is
    statutorily barred from making payments for medical costs
    when an enrollee has benefited or is likely to benefit from
    some other insurance or worker’s compensation plan. The
    statute mentions such alternative sources of benefits as “a
    workmen’s compensation law … or … automobile or liability
    insurance policy or plan (including a self-insured plan) or …
    no fault insurance.” 42 U.S.C. § 1395y(b)(2)(A)(ii). In such
    situations, Medicare is a secondary form of coverage that
    applies only to costs not covered by the primary insurance.
    But if a primary insurer fails to pay, the government does not
    leave the enrollee and her medical providers in the lurch.
    Rather, it makes conditional payments to providers and then
    seeks reimbursement from the primary insurer. 
    Id. § 1395y(b)(2)(B)(i).
    An analogous provision in Medicare
    Part C makes the private Medicare Advantage Organizations
    secondary payers where enrollees have some form of primary
    coverage. 
    Id. § 1395w-22(a)(4).
    When the primary insurers fall
    down on their responsibilities, Medicare Advantage
    Organizations are authorized by statute to pay first and seek
    reimbursement later, just as the government may. 
    Id. Sometimes, however,
    the primary insurer never
    reimburses the secondary payer (be it the government or a
    Medicare Advantage Organization) for benefits it should have
    provided. In that case, the Medicare Secondary Payer
    provisions establish a private right of action that permits some
    private plaintiffs to sue for double damages. But the relevant
    section of the statute does not specify who may take
    advantage of that provision. All it says, without further
    Nos. 17-3636 and 18-2463                                         5
    elaboration, is that “[t]here is established a private cause of
    action for damages (which shall be in an amount double the
    amount otherwise provided) in the case of a primary plan
    which fails to provide for primary payment (or appropriate
    reimbursement) in accordance with paragraphs (1) and
    (2)(A).” 
    Id. § 1395y(b)(3)(A).
        The plaintiffs in this case are not themselves Medicare
    Advantage Organizations; they assert instead that they are
    assignees of claims that originally belonged to such entities.
    They argue that Medicare Advantage Organizations are
    among the proper plaintiffs that can exercise this private right
    of action, and that through the assignments, they stand in the
    shoes of those Organizations. The plaintiffs and related
    entities have pursued this theory not just in this litigation, but
    in several suits throughout the country. See, e.g., MAO-MSO
    Recovery II, LLC v. Gov't Employees Ins. Co., No. PWG-17-711,
    
    2018 WL 999920
    (D. Md. Feb. 21, 2018); MAO-MSO Recovery
    II, LLC v. Am. Family Mut. Ins. Co., No. 17-CV-175-JDP, 
    2018 WL 835160
    (W.D. Wis. Feb. 12, 2018). At the same time as it
    granted State Farm’s motion to dismiss the First Amended
    Complaint for lack of standing in this case, the district court
    agreed with the plaintiffs that the statute does support a
    private right of action for Medicare Advantage Organizations.
    In that respect, it relied on rulings from the Third and
    Eleventh Circuits. See Humana Med. Plan, Inc. v. W. Heritage
    Ins. Co., 
    832 F.3d 1229
    , 1238 (11th Cir. 2016); In re Avandia
    Mktg., Sales Practices & Prods. Liab. Litig., 
    685 F.3d 353
    , 355 (3d
    Cir. 2012). Although State Farm did not challenge this point
    in the district court, it has changed its tune on appeal and now
    argues that the private right of action does not extend to
    Medicare Advantage Organizations. Those entities, State
    Farm contends, must look to contract law for appropriate
    6                                    Nos. 18-2377 and 18-2463
    remedies. This dispute is at the heart of State Farm’s cross-
    appeal.
    Plaintiffs’ efforts in the present case foundered, however,
    when the district court found that they did not have valid
    assignments from any Medicare Advantage Organization that
    made unreimbursed payments. Without the link to a proper
    Organization that possessed claims to reimbursement, the
    court concluded, plaintiffs had no injury for which they could
    seek redress on this or any other legal theory. Accordingly, it
    ruled, no matter the scope of the private right of action, these
    plaintiffs lacked standing to sue. We come to the same
    conclusion. We save for another day the question whether a
    Medicare Advantage Organization or a proper assignee of its
    rights may invoke the Medicare Secondary Payer private right
    of action for double damages against a primary insurer.
    II
    We now turn to the specific defects that the district court
    found to be fatal to the plaintiffs’ case. This appeal comes to
    us on a dismissal of the plaintiffs’ Second Amended
    Complaint. A brief review of the first two iterations of the
    complaint sheds some light on what went wrong and why
    plaintiffs are entitled to no further amendments.
    From the outset of this litigation, the question of standing
    has been hotly disputed. Plaintiffs acknowledge that they and
    similar organizations have filed a number of suits in which
    the initial complaints “did not name any exemplar
    beneficiaries or their corresponding assignor [Medicare
    Advantage] Plans.” Instead, they “generally alleged the
    assignments held by plaintiffs from multiple [Medicare
    Advantage Organizations], and alleged plaintiffs’ analysis of
    Nos. 17-3636 and 18-2463                                        7
    the data from multiple unreimbursed claims.” This led to
    successful defense motions to dismiss for lack of standing: as
    the plaintiffs put it, “[g]enerally, the district court rulings on
    these early motions were to dismiss the complaints, with
    leave to amend, directing some degree of greater specificity.”
    When State Farm in this case moved to dismiss the initial
    complaint for lack of Article III standing (among other
    grounds), the plaintiffs responded by filing an amended
    complaint to put more meat on the bone.
    The First Amended Complaint fell short, however. It
    identified an exemplar beneficiary by initials and a Medicare
    Advantage Organization (whose identity was redacted) that
    allegedly had made secondary payments, but it provided
    little additional information about the underlying claims or
    payments. Even after the district court issued a protective
    order, plaintiffs still failed to disclose the name of the assignor
    Medicare Advantage Organization to State Farm. This time,
    in response to State Farm’s motion, the district court
    dismissed the complaint for lack of Article III standing. It
    found that the plaintiffs could not demonstrate an “injury in
    fact” for purposes of Article III standing without more
    specificity as to the injuries sustained by the exemplar
    beneficiary and the assignor Medicare Advantage
    Organization that had allegedly paid the unreimbursed
    medical costs. The court gave the plaintiffs another chance to
    cure that defect by granting leave to amend.
    Plaintiffs took advantage of that opportunity and filed a
    Second Amended Complaint. In this iteration, the plaintiffs
    chose a new “exemplar beneficiary” (identified by the initials
    “R.Y.”) and named the Medicare Advantage Organization
    that had made the secondary payments as Health First
    8                                   Nos. 18-2377 and 18-2463
    Administrative Plans (“HFAP”). A chain of assignments
    transferred HFAP’s alleged right of recovery to Recovery
    Claims. The complaint alleged that R.Y. suffered specific
    injuries in an accident; that HFAP was the entity that paid
    medical costs for R.Y.; that State Farm entered into a
    settlement agreement with R.Y.; and that State Farm failed to
    reimburse HFAP for the costs HFAP had incurred.
    This time, however, there was a new problem: it was not
    clear that HFAP qualified as a Medicare Advantage
    Organization. After the defendants filed another motion to
    dismiss for lack of standing, but before the district court had
    arrived at a decision, a district court in Florida ruled in a
    related case that HFAP was not a Medicare Advantage
    Organization at all. MSP Recovery Claims, Series LLC v. Auto-
    Owners Ins. Co., No. 17-23841, 
    2018 WL 1953861
    *5 (S.D. Fla.
    Apr. 25, 2018) (“Auto-Owners”). The Florida court took judicial
    notice of the fact that HFAP does not appear on the list
    maintained by the Centers for Medicare & Medicaid Services
    of Medicare Advantage Organizations. 
    Id. Instead, HFAP
    is an
    entity that had contracted with a Medicare Advantage
    Organization—a closely linked entity by the name of Health
    First Health Plans—to provide a range of administrative,
    financial, and strategic-planning services. The two entities
    (Health First Administrative Plans and Health First Health
    Plans) shared very similar names, a holding company, and a
    Chief Operating Officer, Michael Keeler. But crucially, in the
    Florida court’s view, only Health First Health contracted
    directly with the government and qualified as a Medicare
    Advantage Organization for purposes of the private right of
    action that the plaintiffs were asserting. Accordingly, the
    Florida court found that HFAP did not have any recovery
    rights to assign, even assuming plaintiffs were correct about
    Nos. 17-3636 and 18-2463                                         9
    the private right of action: any such claims belonged only to
    Health First Health.
    Only one of the plaintiffs in this case—Recovery Claims—
    was a party to Auto-Owners. Nonetheless, the overlap was
    enough to matter. As in this case, the plaintiffs in Auto-Owners
    argued that whatever the proper characterization of HFAP
    might have been, its service contract with Health First Health
    meant that it could pursue Health First Health’s legal claims
    or assign them away. The Florida court rejected that
    contention, ruling that “a contract for services is not an
    assignment of rights,” and thus “HFAP [could] not assign
    rights to Plaintiff that were not assigned to it in the first place.”
    
    Id. This left
    the Florida plaintiffs without any rights to enforce.
    Similarly, in this litigation, the district court thought, the only
    purported assignment that could confer standing on any of
    the plaintiffs was one from HFAP to Recovery Claims.
    State Farm brought Auto-Owners to the attention of the
    district court the day after it was issued. The next day, the
    district court entered a Text Order directing the plaintiffs to
    explain why this litigation should not be dismissed on the
    same grounds.
    The plaintiffs complied with that order. Their response
    first argued that Auto-Owners was wrongly decided for two
    reasons: (1) HFAP does qualify as a Medicare Advantage
    Organization for purposes of the private right of action; and
    (2) the agreement between Health First Health and HFAP
    granted HFAP the power to enforce Health First Health’s
    legal rights as its agent, making the agreement the equivalent
    of an assignment. In a decision issued on May 25, 2018, the
    district court rejected both points.
    10                                    Nos. 18-2377 and 18-2463
    The court was particularly bothered by what it saw as a
    bombshell: the revelation in the plaintiffs’ response that
    Health First Health, which had never been mentioned in the
    Central Illinois case, not HFAP, was the entity that paid the
    unreimbursed medical costs. This fact contradicted earlier
    filings that identified HFAP as the payer with reimbursement
    rights. If that was true, the district court thought, then HFAP
    (whatever its status) never incurred any injury and so had no
    rights that it could assign. The court also reasoned that in light
    of this development, there was no need to decide, as the
    Florida court had, whether HFAP was a qualifying Medicare
    Advantage Organization. It was Health First Health that paid
    the unreimbursed bills, but the plaintiffs had an assignment
    only from HFAP. Only if Health First Health’s service contract
    with HFAP also assigned HFAP its legal rights could the case
    have a leg to stand on. And on this point, the district court
    agreed fully with its Florida counterpart: it emphasized,
    contrary to the plaintiffs’ arguments, that a document
    creating an agency relationship and one effecting an
    assignment of rights are two entirely different things.
    Accordingly, the district court dismissed the case on this
    ground alone. “Assuming HFAP is [a Medicare Advantage
    Organization], Plaintiffs still need to satisfy Article-III
    standing requirements, and this they cannot do.”
    Up to this point, we agree with the district court’s
    disposition of the case. Nothing in the agreement between
    Health First Health and HFAP suggests that Health First
    Health was assigning away any of its rights. Without such an
    assignment, HFAP’s own assignment to plaintiff Recovery
    Claims conveyed nothing, and thus the plaintiffs had no
    rights to enforce and no standing to sue. As we note when we
    reach the sanctions portion of this appeal, additional
    Nos. 17-3636 and 18-2463                                        11
    information later came to the district court’s attention, but
    that new information could not have affected the court’s order
    of May 25.
    We part ways with the district court only with respect to
    the bottom line. The decision that plaintiffs lacked Article III
    standing is one of jurisdictional significance: it means that the
    court had no authority to resolve the case. See, e.g., Spokeo, Inc.
    v. Robins, 
    136 S. Ct. 1540
    , 1547 (2016). And that is why the
    court erred by dismissing the case “with prejudice.” See, e.g.,
    T.W. and M.W. v. Brophy, 
    124 F.3d 893
    , 898 (7th Cir. 1997)
    (“[W]hen a suit is dismissed for want of subject-matter
    jurisdiction, that is, because the court has no power to resolve
    the case on the merits even if the parties are content to have it
    do so, it is error to make the dismissal with prejudice”).
    If a complaint fails to include enough allegations to
    support Article III standing for the plaintiffs, the court has
    only two options: it can either dismiss the complaint with
    leave to amend, or it can dismiss the case for want of
    jurisdiction and hence without prejudice. The Federal Rules
    of Civil Procedure allow for one amendment as of right and
    direct district courts “freely [to] give leave [for further
    amendments] when justice so requires.” FED. R. CIV. P. 15(a).
    But after the first round of amendments, the court has the
    discretion to deny leave to amend. If, after amendments, the
    jurisdictional problem persists, then the only option left is a
    dismissal without prejudice.
    A dismissal for lack of jurisdiction without leave to amend
    is not the same thing as a dismissal with prejudice. A
    dismissal with prejudice is a ruling on the merits, because it
    carries with it a preclusive effect that prevents the plaintiffs
    from relitigating—in any court, ever again—any claim
    12                                    Nos. 18-2377 and 18-2463
    encompassed by the suit. We have emphasized this
    distinction before. See, e.g., Murray v. Conseco, Inc., 
    467 F.3d 602
    , 605 (7th Cir. 2006) (“‘No jurisdiction’ and ‘with prejudice’
    are mutually exclusive.’ A court that lacks subject matter
    jurisdiction cannot dismiss a case with prejudice.”); Okoro v.
    Bohman, 
    164 F.3d 1059
    , 1063 (7th Cir. 1999) (“[A] judgment on
    the merits precludes relitigation of any ground within the
    compass of the suit, while a jurisdictional dismissal precludes
    only the relitigation of the ground of that dismissal.”).
    If plaintiffs believe they have satisfied the standing
    requirements of a proper state-court forum—requirements
    that may differ from those used by the federal courts—they
    may try their luck in state court. Or, if they later believe they
    can demonstrate that they have suffered an injury in fact after
    all, perhaps on the basis of a different assignment or exemplar
    claim, they can present these claims against the same
    defendant in a new federal suit (assuming of course that no
    independent barrier, such as the statute of limitations, exists).
    Indeed, in a case brought by these plaintiffs against the same
    defendant and before the same district judge—which the
    court called “a putative class action with slightly different
    facts, but consisting of virtually identical allegations under
    the law”—these plaintiffs did successfully demonstrate
    standing and survived a motion to dismiss. MAO-MSO
    Recovery II, LLC v. State Farm Mut. Auto. Ins. Co. (“State Farm
    I”), No. 17-cv-01537, 
    2018 WL 3420796
    at *1, *7 (C.D. Ill. July
    13, 2018).
    None of these later developments, however, means that
    the district court was required to let this lawsuit continue. The
    court did not abuse its discretion by saying “enough is
    enough.” It observed that “Plaintiffs have been given a few
    Nos. 17-3636 and 18-2463                                       13
    chances to demonstrate this Court has jurisdiction.” This suit,
    the judge thought, had run its course. Indeed, in a footnote
    explaining its dismissal “with prejudice,” the court cited
    Arreola v. Godinez, 
    546 F.3d 788
    , 796 (7th Cir. 2008) for the
    unassailable proposition that district courts “have broad
    discretion to deny leave to amend where there is undue delay,
    bad faith, dilatory motive, repeated failure to cure
    deficiencies, undue prejudice to the defendants, or where the
    amendment would be futile.” (Emphasis added). The only
    problem was thus the court’s use of the phrase “with
    prejudice” to signal that it would permit no more
    amendments.
    On this understanding of the district court’s order, we find
    no abuse of discretion in its decision to dismiss on standing
    grounds and to refuse further amendments. While it is true
    that the plaintiffs had not previously had a chance to address
    the HFAP/Health First Health mix-up, they were on notice
    from the outset that the issue of standing would be front and
    center. If they were going to hang their hat on a single
    “exemplar” after two unsuccessful attempts, it was important
    to get it right on the third try. The district court’s frustration
    at their failure to do so was understandable. And the court
    was entitled to give little weight to their plea for another
    round of pleading, since their memorandum included
    nothing beyond a request for “leave to allege additional
    exemplar beneficiaries,” without naming them or providing
    any reason for the district court to believe that the fourth time
    would be the charm. Denying leave to amend under such
    circumstances was well within the district court’s discretion.
    See James Cape & Sons Co. v. PCC Const. Co., 
    453 F.3d 396
    , 400–
    01 (7th Cir. 2006) (finding that lack of specificity in proposed
    amendments justified denial of leave to amend).
    14                                  Nos. 18-2377 and 18-2463
    III
    In the same order that dismissed the Second Amended
    Complaint, the district court also ordered the plaintiffs to
    show cause why they should not be sanctioned for their
    earlier filings, which wrongly identified HFAP as the payer of
    the relevant medical costs. We address the substance of the
    sanctions issue below. Here we note that the plaintiffs’
    response to the order to show cause contained materials
    relevant to standing and the merits, including (1) a
    declaration attesting to many additional exemplars that could
    be alleged; (2) a purported “nunc pro tunc” or retroactive
    assignment from Health First Health to one of the plaintiffs,
    intended to cure the defect identified by the court; and (3) a
    declaration from Michael Keeler, the Chief Operating Officer
    of Health First Health and HFAP, explaining the relationship
    between the two entities and putting on the record that he had
    always intended to assign rights from Health First Health to
    the plaintiffs. On appeal, the plaintiffs argue that in light of
    this new evidence, the district court abused its discretion
    when it refused further amendments.
    We need not decide whether any of these documents
    might have been enough to call into question the district
    court’s dismissal without leave to amend, because the court
    did not have any of this evidence in front of it when it issued
    the dismissal order. The time to provide this information was
    in response to the defendants’ motion to dismiss or in the
    supplemental response to the district court’s Text Order
    regarding Auto-Owners. A post-dismissal filing in response to
    an order to show cause was too little, too late. And to make
    matters worse, the plaintiffs never filed a motion for
    reconsideration or relief from judgment. None of the
    Nos. 17-3636 and 18-2463                                       15
    information provided to the district court after the dismissal
    required it to revive the suit.
    Because we agree that the district court was without
    jurisdiction to address the merits of the case, that means we
    are, too. Accordingly, we also dismiss State Farm’s cross-
    appeal arguing for a dismissal on the merits.
    IV
    Finally, we must decide whether Rule 11 sanctions against
    plaintiff Recovery Claims and three of its attorneys were
    proper. We review the district court’s decision to impose
    sanctions for abuse of discretion. Cooter & Gell v. Hartmax
    Corporation, 
    496 U.S. 384
    , 405 (1990). When we apply that
    standard, however, we must bear in mind that “[a] district
    court would necessarily abuse its discretion if it based its
    ruling on an erroneous view of the law or on a clearly
    erroneous assessment of the evidence.” 
    Id. See also
    Equal
    Employment Opportunity Comm'n v. CVS Pharmacy, Inc., 
    907 F.3d 968
    , 973 (7th Cir. 2018) (explaining the Rule 11 abuse-of-
    discretion standard as clarified in Cooter & Gell).
    A
    Rule 11 requires that attorneys certify “to the best of [their]
    knowledge, information, and belief, formed after an inquiry
    reasonable under the circumstances” that their filings have
    adequate foundation in fact and law and lack an “improper
    purpose.” FED. R. CIV. P. 11. Because the district court
    appeared to base its sanctions order on counsel’s lack of
    candor—i.e. filing documents with the court in bad faith —
    and a failure to undertake an objectively reasonable inquiry,
    we address both grounds. See Mars Steel Corp. v. Cont'l Bank
    16                                   Nos. 18-2377 and 18-2463
    N.A., 
    880 F.2d 928
    , 930 (7th Cir. 1989) (recognizing that Rule
    11 embodies both an objective and a subjective standard,
    prohibiting both “frivolousness on the objective side” and
    “bad faith on the subjective side.”)
    At this stage of the case, the district court had the benefit
    of the plaintiffs’ response to the order to show cause, in which
    they filed the additional materials mentioned above. Those
    submissions are relevant to the Rule 11 analysis.
    We begin with the finding of bad faith or “lack of candor.”
    We are hard-pressed to see any indication of intentional
    misrepresentation in this confused and confusing record.
    None of the counsel for Recovery Claims—the only party that
    was sanctioned—entered an appearance in the Florida Auto-
    Owners litigation. As far as the record shows, the first time
    these attorneys learned of the Auto-Owners decision was when
    State Farm brought the case to the attention of the district
    court here. We also agree with the plaintiffs that, contrary to
    the district court’s finding, there is no basis in the record for
    the conclusion that these attorneys knew anything about the
    HFAP/Health First Health distinction until they saw the Text
    Order. (The district court seemed to derive its conclusion
    from what it understood to be the plaintiffs’ “admis[sion] that
    [they] knew there were multiple ‘Health First’ entities and
    that HFAP did not actually pay R.Y.’s medical expenses … .”
    But the cited portion of plaintiffs’ response to the Text Order
    does not support that conclusion, and plaintiffs disclaim ever
    having made such an admission.) Without knowledge of the
    HFAP/Health First Health distinction, most of the supposed
    misrepresentations in the earlier filings regarding HFAP’s
    status as a Medicare Advantage Organization or as the payer
    of R.Y.’s medical bills look more like honest mistakes. The
    Nos. 17-3636 and 18-2463                                      17
    same goes for any misunderstanding about the nature of the
    assignment.
    The district court also appears to have found that
    counsel’s submissions after the Text Order was issued
    demonstrated a lack of candor inasmuch as they did not
    immediately admit (1) the inaccuracies in their earlier
    pleadings and (2) that fatal nature of the mix-up uncovered in
    Auto-Owners. This also goes too far. In light of the evidence
    the plaintiffs submitted to the district court on the Rule 11
    point, it is understandable why they had maintained that
    there was a colorable reading of the underlying assignment
    that would give effect to Keeler’s unquestioned intent, i.e., to
    assign Health First Health’s rights to plaintiff Recovery
    Claims. And as the district court eventually acknowledged in
    its order imposing sanctions, there was “some debate” on the
    question whether HFAP might qualify as a Medicare
    Advantage Organization (an issue that ultimately proved
    immaterial but that was relevant to the claimed accuracy of
    the earlier filings). True, the plaintiffs may have understated
    the scope of the problem in their response to the Text Order,
    and they may have erred by pursuing a legal argument that
    stretched agency theory too far. They also should have
    brought their supporting materials before the district judge at
    the same time as they filed their response to the Text Order.
    But in the absence of either affirmative representations or
    material omissions in the response to the Text Order, what we
    are left with is an aggressive litigation strategy with a
    colorable (if strained) basis in law and fact, rather than a lack
    of candor. That is not sanctionable conduct.
    The district court also had other grounds for imposing
    sanctions: carelessness and inattentiveness. As we have
    18                                    Nos. 18-2377 and 18-2463
    emphasized repeatedly, an ‘empty head but a pure heart is no
    defense.’” U.S. Bank Nat. Ass'n, N.D. v. Sullivan-Moore, 
    406 F.3d 465
    , 470 (7th Cir. 2005) (quoting Chambers v. Am. Trans
    Air, Inc., 
    17 F.3d 998
    , 1006 (7th Cir. 1994)). Because Rule 11
    imposes on attorneys a duty to conduct an “inquiry
    reasonable under the circumstances” before they attest to
    “knowledge, information, and belief” supporting their filings,
    even honest mistakes can be sanctionable. The district court
    found that the attorneys in this case failed to live up to that
    duty.
    It is one thing to lose on a point, however, and another to
    urge something so ill-founded that it is sanctionable.
    Although the standard for abuse of discretion is demanding,
    we conclude that the district court stepped over the
    boundaries of its discretion in imposing sanctions on the basis
    of carelessness or inattention. Again, the exhibits the plaintiffs
    filed in response to the order to show cause are instructive.
    The affidavit from Keeler demonstrates that Health First
    Administrative Plans (HFAP) and Health First Health Plans
    shared more than very similar names, a holding company,
    and a common COO; they were, for many purposes, almost
    indistinguishable to any external party dealing with them. As
    Keeler averred, “[Health First Health] acts through myself
    and its other corporate officers, but it has no employees …
    [Health First Health] takes no action except through HFAP’s
    agents and employees.” Affidavit of Michael Keeler, June 1,
    2018 at 1–2. To make matters more confusing, at least
    according to plaintiffs’ allegations, HFAP did business under
    the name “Health First Health Plans.” And even if Health
    First Health was the entity from whose assets the beneficiary
    was paid—meaning it possessed the reimbursement rights—
    plaintiffs point out that “the act of payment would not
    Nos. 17-3636 and 18-2463                                    19
    unreasonably or inaccurately be attributed to HFAP, which
    carried out all acts on behalf of [Health First Health].”
    Without getting further into the weeds, it suffices to say
    that this corporate arrangement was not just complex, but so
    freighted with overlapping names and functions that a mix-
    up was, at the end of the day, understandable. The district
    court did “not accept that Health First’s ‘corporate structure’
    was too confusing to warrant the misstatements in the Second
    Amended Complaint.” Respectfully, the district court
    reached its conclusion about the straightforward nature of the
    corporate arrangement while it was looking at it with the
    benefit of hindsight. The court did not give adequate weight
    to the plaintiffs’ additional evidence, nor did it consider
    carefully enough what the attorneys knew and when they
    knew it. (How could the details of this structure have been
    apparent at a time when the attorneys were unaware that
    there was a second “Health First” entity?) Sanctions against
    the attorneys for Recovery Claims were not warranted on this
    record.
    B
    The sanctions against plaintiff Recovery Claims must also
    be reversed. As discussed, we find that none of the actions or
    omissions of its counsel in this case amounted to sanctionable
    conduct. The district court did not point to any conduct by
    Recovery Claims itself, rather than its agents, that would
    independently allow us to sustain the imposition of sanctions.
    Unlike its counsel, Recovery Claims did have some
    knowledge of the Florida litigation. But we detect nothing
    improper in the two-day lapse between the Auto-Owners
    decision on April 25, 2018, and the district court’s Text Order
    on April 27, especially given the factual and legal arguments
    20                                   Nos. 18-2377 and 18-2463
    that plaintiffs might have wished to develop in response. It is
    true that there was a 14-day hiatus between Keeler’s affidavit
    in the Auto-Owners case, which explained the HFAP/Health
    First Health ownership structure, and the day the district
    court learned of the ruling that the Florida district judge made
    as a result. Nonetheless, we conclude that it is too much of a
    stretch to sanction plaintiff Recovery Claims for failing to
    recognize the implications of an affidavit filed in one case,
    without the benefit of any dispositive ruling on the issue, for
    a completely different case being litigated by a separate team
    of attorneys. As far as we can tell, the sanctions against
    Recovery Claims must rise or fall with the sanctions against
    its attorneys. And so they fall.
    Plaintiffs and their counsel have been punished for their
    missteps: the case was dismissed without leave to amend, and
    we affirm that dismissal today. But sanctions are a step too
    far.
    IV
    We AFFIRM the district court’s dismissal without leave to
    amend, but we modify it to be a dismissal without prejudice.
    We REVERSE the entry of sanctions against MSP Recovery
    Claims, Series LLC, and its counsel in this case. State Farm’s
    cross-appeal is DISMISSED. Each party will bear its own costs
    on appeal.