Jefferson County v. M.D. Dannie E. Williams

United States Court of Appeals
For the Eighth Circuit
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No. 24-1550
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Jefferson County
Plaintiff - Appellee
v.
M.D. Dannie E. Williams; Delmar Primary Care Associates, LLC; Gurpreet S.
Padda; Comprehensive Pain Associates, LLC; Interventional Center for Pain
Management, P.C., doing business as Padda Institute Center for Interventional Pain
Management; Teva Pharmaceuticals USA, Inc.; Teva Pharmaceuticals, Ltd.;
Cephalon, Inc.; Watson Laboratories, Inc.; Actavis, LLC; Johnson & Johnson;
Janssen Pharmaceuticals, Inc.; Noramco, Inc.; Endo Health Solutions, Inc.; Endo
Pharmaceuticals, Inc.; Allergan PLC; Actavis Pharma, Inc.; Mallinckrodt plc;
Mallinckrodt LLC; SpecGx, LLC; McKesson Corporation; Cardinal Health, Inc.;
Amerisourcebergen Corporation; AmerisourceBergen Drug Corp.; Hunt Fitz Drug,
Inc., doing business as Keller Apothecary; Express Scripts Holding Company;
Express Scripts Pharmacy, Inc.
Defendants
Express Scripts, Inc.
Defendant - Appellant
Wal-Mart, Inc.; Target Corporation; Walgreen Company; CVS Health
Corporation; CVS Pharmacy, Inc.; Caremark Rx, LLC; Caremark PCS Health,
LLC; Caremark, LLC; Missouri CVS, LLC; Depomed, Inc.; United Health Group,
Inc.; Optum, Inc.
Defendants

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OptumRx, Inc.
Defendant - Appellant
Mylan Pharmaceuticals, Inc.; Mylan N.V.; Richard S. Sackler, M.D.
Defendants
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Appeal from United States District Court
for the Eastern District of Missouri - St. Louis
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Submitted: April 16, 2025
Filed: July 28, 2025
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Before SMITH, SHEPHERD, and KOBES, Circuit Judges.
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SMITH, Circuit Judge.
Express Scripts and OptumRX appeal the district court’s1 order remanding
the case to state court based on their untimely removal. We affirm.
I. Background
Express Scripts and OptumRX, pharmacy benefit managers (collectively,
“PBMs”), administer drug plans for clients, including federal agencies such as the
Department of Defense (DoD) and the Veterans Health Administration. Jefferson
County, Missouri (County) brought this suit seeking relief under Missouri public
nuisance law alleging that the PBMs harmed the public by facilitating prescription
opioid abuse. Specifically, they alleged that the PBMs’ preference to distribute these
opioids led to 324 deaths and 1,941 emergency room visits, among other alleged
1 The Honorable Matthew T. Schelp, United States District Judge for the
Eastern District of Missouri.

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costs to law enforcement, prosecution, prisons, and addiction treatment. Allegedly,
the PBMs do this through formularies and pricing strategies, which “control[] which
pain medications reach the marketplace.” R. Doc. 13.
The County filed its initial Petition in the Twenty-Second Judicial Circuit
Court of Missouri in the City of St. Louis. It then filed several amended petitions,
including a second amended petition on June 15, 2020. On December 1, 2023, the
PBMs filed a notice of removal seeking removal pursuant to 28 U.S.C. §§ 1442(a),
the federal officer removal statute, and 1446(b)(3). The County then sought remand
to state court, which the district court here granted. The PBMs appeal the grant of
the remand motion.
This case, at one point, was part of the federal Opioid Multidistrict Litigation
(MDL). It had been removed by then-defendant CVS to In re National Prescription
Opiate Litigation, 1:17-md-2804-DAP, R. Doc. 1987 (N.D. Ohio July 22, 2019). But
on July 24, 2019, the district court in that case severed and remanded this case to a
Missouri state court. The PBMs had objected to the severance and remand while the
MDL had the case. See id. at R. Doc. No. 1931.
After severance and during discovery, the PBMs requested the County to
identify whether the claims that it alleged were related to the PBMs’ contractual
services with federal health plans. In response, the County provided a “Red Flag
Analysis.” The Red Flag Analysis identified the prescription claims that the County
was relying on in its case. The County continually updated this Red Flag Analysis,
including the Sixth Red Flag Analysis served on February 3, 2022. The Sixth Red
Flag Analysis contained claims made by Express Scripts related to the DoD. On the
same day, the County sent an email and letter to the PBMs claiming that it was
withdrawing the analysis based on an error. On February 14, 2022, the County sent
a new Red Flag Analysis, which still contained federal claims.
On March 10, 2022, the PBMs sent a letter to the County saying that they
intended to remove the action to federal court unless the County

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inform[ed] the PBM Defendants in writing on or before March 14,
2022, that it is withdrawing all challenges to federal prescription claims
and [would] not seek recovery from the PBM Defendants based on the
federal prescription claims—including but not limited to claims under
the Federal Employee Health Benefit Act and claims adjudicated or
processed for a plan controlled or sponsored by a federal governmental
department or entity (for example, the Department of Defense). . . .
R. Doc. 38-1, at 4. In the letter, the PBMs contended that the County’s “February 14
Red Flag Analysis shows for the first time that the County contends that many
different federal prescription claims support its claims against the PBM Defendants.
Given that fact, the PBM Defendants are entitled to remove this case to federal
court.” Id.
Despite the inclusion of federal prescription claims in the Red Flag Analysis,
the County disclaimed any future reliance on these claims. In a March 11, 2022 letter
and a March 16, 2022 joint stipulation, the County agreed that it would “not now or
at any time in the future seek to establish liability against” the PBMs related to any
“Federal Plan.” R. Doc. 1, at 10.
Then, on November 15, 2023, the County produced three expert reports
discussing theories of liability. These reports did not differentiate between federal
and non-federal prescription claims. The PBMs interpreted the County’s filings as
indicating its intent to establish liability using the federal claims. In response, the
PBMs moved for removal of the action to federal court under 28 U.S.C. § 1442(a)(1),
the federal officer removal statute. The County, in turn, moved the district court to
remand the case to state court. The district court granted the County’s motion to
remand to state court.
The district court based its remand decision on two considerations. First,
citing 28 U.S.C. § 1446(c)(3), the district court found that the PBMs’ removal was
untimely. The PBMs were required to file a notice of removal within 30 days of

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February 14, 2022, but failed to do so. The district court relied on the PBMs’
acknowledgements in their stipulation with the County and the March 11, 2022 letter
sent to the County to establish the PBMs’ awareness of the deadline for seeking
removal. See R. Doc. 2-16, at 1 (“[O]n February 14, 2022, [the] County served the
PBM [d]efendants with [discovery]. . . . that . . . include[ed] federal prescription
claims adjudicated or processed by the PBM [d]efendants. . . .”); see also R. Doc.
38-1, at 4 (“The February 14 Red Flag Analysis shows for the first time that the
County contends that many different federal prescription claims support its claims
against the PBM [d]efendants. Given that fact, the PBM [d]efendants are entitled to
remove this case to federal court.”). The district court determined that the documents
established that the PBMs could have sought removal as of February 14, 2022.
Second, the district court found that even if the notice of removal was timely
filed, removal would still not be substantively proper under 28 U.S.C. § 1442, as the
County had disclaimed all potential liability on the part of the PBMs related to any
federal claims, both in the March 11, 2022 letter and the joint stipulation that
followed.
The PBMs appeal the district court’s order granting the County’s motion to
remand the case to state court. 2
2 The County filed a motion to dismiss this appeal and a petition for
mandamus. In its motion, the County argues that this court lacked jurisdiction to
hear the appeal because the district court had not yet entered an order remanding the
case to state court. This is despite the district court’s decision stating that it was
“[h]ereby ordered that Plaintiff’s Motion to Remand . . . [be] granted.” R. Doc. 58,
at 12 (capitalization and bold omitted). The County points to the following line in
the order, which stated that “[a] separate [o]rder of [r]emand will be entered after
12:00 p.m. on Friday, March 15, 2024, unless Defendants file a notice of appeal.”
Id. But we look to the “substance of the order,” and the district court’s order was an
order remanding the case back to the state court. Meierhenry Sargent LLP v.
Williams, 915 F.3d 507, 509 (8th Cir. 2019). The line mentioning a separate remand
order was effectively a stay of the remand pending appeal, which the PBMs had
requested. We thus have jurisdiction to hear the appeal under 28 U.S.C. § 1447(d),
and the County’s motion is denied. The petition for mandamus is likewise denied,

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II. Discussion
On appeal, the PBMs argue that the district court applied the wrong legal
standard to determine that their removal was untimely. They suggest that the district
court applied an improper discretionary standard. They assert that the court
determined the County’s February 14 Red Flag Analysis triggered the 30-day clock
under § 1446(b)(3) because the PBMs could have removed the case at that time. The
PBMs argue in favor of a mandatory standard. They contend that § 1446(b)(3)
requires an unequivocal statement from which they could have unambiguously
ascertained that removal was available. The PBMs contend that the February 14 Red
Flag Analysis was not unambiguous and did not require them to remove based on its
contents or cause them to forfeit the ability to seek removal. “We review the district
court’s decision to remand de novo.” Minnesota v. Am. Petroleum Inst., 63 F.4th
703, 709 (8th Cir. 2023) (emphasis omitted).
The federal officer removal statute permits removal of a state lawsuit to
federal court when it is commenced against “[t]he United States or any agency
thereof or any officer (or any person acting under that officer) of the United States
or of any agency thereof, in an official or individual capacity.” 28 U.S.C.
§ 1442(a)(1). Notice of removal must be filed within 30 days. Id. § 1446(b).
The 30-day period becomes applicable when developments in the case record
permit ascertainment that the suit qualifies for removal. Subsection (b)(3) states that
if the case stated by the initial pleading is not removable, a notice of
removal may be filed within 30 days after receipt by the defendant,
through service or otherwise, of a copy of an amended pleading,
motion, order or other paper from which it may first be ascertained that
the case is one which is or has become removable.
as the County has not demonstrated that it has complied with the requirements for
the petition under Fed. R. App. P. 21(a).

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Id. § 1446(b)(3). This 30-day removal period does not begin “until the defendant
receives from the plaintiff an amended pleading, motion, order, or other paper ‘from
which the defendant can unambiguously ascertain’” that the case is removable under
§ 1446(b)(3). Gibson v. Clean Harbors Env’t. Servs., Inc., 840 F.3d 515, 520 (8th
Cir. 2016) (quoting Graiser v. Visionworks of Am., Inc., 819 F.3d 277, 285 (6th Cir.
2016));3 see also Dietrich v. Boeing Co., 14 F.4th 1089, 1093–95 (9th Cir. 2021)
(applying the “unequivocally clear and certain” standard); Par. of Plaquemines v.
Chevron USA, Inc., 7 F.4th 362, 372 (5th Cir. 2021) (same).
We conclude that the PBMs unambiguously and unequivocally ascertained
that the February 14, 2022 Red Flag Analysis allowed removal of the case. The
PBMs said as much in their March 10, 2022 letter.4
The PBMs argue that the County’s withdrawal and/or its disclaiming any
reliance on federal claims in its Red Flag Analysis prevented the February 14, 2022
Red Flag Analysis from qualifying as “unequivocal” or “unambiguous[]” statements
supporting federal officer jurisdictional requirements. Appellants’ Br. at 35
3 The County argues that Dahl v. R.J. Reynolds Tobacco Co. provides a less
stringent definition of “ascertain” to trigger the 30-day clock. 478 F.3d 965, 970 (8th
Cir. 2007). But Dahl is inapposite. There, we held that because the case was
removable at the time of the initial filing of the case, § 1446(b)(3)’s “order or other
paper” clause could not be triggered to allow a new 30-day clock for removal. Id.
4See R. Doc. 38-1 (“[T]he PBM Defendants intend to remove this case to
federal court. The basis for this letter is the County’s . . . February 14, 2022
[discovery,]” which “shows for the first time that the County contends that many
different federal prescription claims support its claims against the PBM
[d]efendants. Given that fact, the PBM [d]efendants are entitled to remove this case
to federal court.”); see also City of Martinsville v. Purdue Pharma, L.P., No. 4:24-
CV-00002, 2024 WL 4218847 (W.D. VA. Sep. 16, 2024) (finding removal untimely
and waived in situation nearly identical to the instant case when PBMs threatened
removal after discovery revealed grounds for removal, then entered stipulation with
city to limit federal claims), aff’d sub nom., City of Martinsville v. Express Scripts,
Inc., No. 24-1912, 2025 WL 1039624 (4th Cir. Apr. 8, 2025) (unpublished per
curiam) (upholding remand based only on waiver).

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(alteration in original) (quoting Gibson, 840 F.3d at 520). They argue that if they had
removed the case when the County’s February 14, 2022 Red Flag Analysis was
received, the district court would have taken into account the County’s
withdrawal/disclaimer and concluded that federal officer jurisdiction did not exist.
The PBMs assert that the district court must “apply a reasonable amount of
intelligence to its reading” of documents submitted by the plaintiff, and such a
reading would have required it to conclude that the February 14, 2022 Red Analysis
was equivocal or ambiguous. Id. at 34 (quoting Gibson, 840 F.3d at 519). But this
argument does not address whether the filing of the analysis triggered the 30-day
clock for removal under § 1446(b)(3). The County’s previous express stipulation
may have affected whether the County could meritoriously dispute removal but not
whether the PBMs could seek it in the first place.
The PBMs further argue that because of the allegedly ambiguous nature of the
withdrawal/disclaimer, removal was at most discretionary, not mandatory, and thus
the 30-day clock should not have begun to run. Cutrone v. Mortg. Elec. Registration
Sys., Inc., 749 F.3d 137, 146 (2d Cir. 2014) (“[E]ven if a defendant could remove …
because the case satisfies the requirements of federal subject matter jurisdiction, a
complaint or other document from the plaintiff that does not explicitly convey the
removability of a case does not trigger the removal clocks of 28 U.S.C. §§ 1446(b)(1)
and (b)(3).”). But Gibson and Cutrone did not deal with the situation here, as the
PBMs did “unambiguously ascertain” a right of removal, stated their knowledge of
that right to the plaintiff, but decided not to remove in reliance on a stipulation from
the County disclaiming federal liability. Gibson, Cutrone, and § 1446(b)(3) do not
provide any basis for a withdrawal or cancellation of an unambiguous statement.
In conclusion, the PBMs failed to timely remove after clearly ascertaining that
removal was available to them following the County’s service of its February 14,
2022 Red Flag Analysis. The PBMs were required to remove within 30 days of
receipt of that discovery because that discovery contained “federal . . . claims” that

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allowed “PBM [d]efendants . . . to remove this case to federal court.” R. Doc. 38-1,
at 4.5
III. Conclusion
Accordingly, we affirm the district court’s order to remand the case to the
state court.
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5 Because we hold that the PBMs failed to timely remove after service of the
February 14, 2022 Red Flag Analysis, we do not address (1) whether the initial
pleading was removable; (2) whether removal would have been substantively proper
given the County’s stipulation not to pursue federal claims; or (3) whether the PBMs
waived their right to remove after litigating in state court following that stipulation.

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