United States v. Askins & Miller Orthopaedics, P.A., 924 F.3d 1348

Background

Askins & Miller Orthopaedics (a Sarasota medical practice run by brothers Philip and Roland Askins) repeatedly withheld employee federal income and FICA taxes but failed to remit them to the IRS from 2010 onward; the company admits the tax liabilities on returns but repeatedly did not pay.
IRS attempted collection for years: numerous in-person meetings, installment agreements (both defaulted), multiple levies on related entities, notices of federal tax liens, and trust fund recovery penalty assessments against the brothers; collection efforts were largely ineffective because funds were diverted among entities and hidden.
IRS sued in 2017 seeking (1) a permanent injunction requiring procedures to ensure future employment-tax deposits and (2) money damages for past-due taxes; it sought a preliminary injunction to preserve the IRS’s ability to collect going forward.
The district court denied the preliminary injunction, concluding the IRS had an adequate remedy at law (money damages) and that the proposed injunction was effectively an overbroad “obey-the-law” injunction; the IRS appealed.
On appeal the Eleventh Circuit held the case was not moot despite defendant claims the business had closed, and vacated/remanded the denial of the preliminary injunction, instructing the district court to consider collectability of future money judgments and Rule 65(d) specificity issues on remand.

Issues

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether the IRS lacks an adequate remedy at law so as to justify a preliminary injunction under 26 U.S.C. § 7402(a)	A damages suit is inadequate because Askins & Miller is judgment‑proof and will keep accruing unpaid employment taxes; injunctive relief is needed to stop ongoing losses.	Money damages are calculable; an action for damages is an adequate legal remedy, so equity should not issue an injunction.	The district court erred: collectability of a future judgment is relevant; where future harm is likely and judgment may be uncollectible, legal remedy may be inadequate—vacated and remanded.
Whether the case is moot given defendants’ alleged closure of Askins & Miller	N/A (plaintiff argues case remains live because conduct likely to recur and injunction addresses future liabilities).	Askins & Miller says it is no longer in business and has insufficient assets, so injunctive relief aimed at future operations is moot.	Not moot: voluntary cessation standard requires defendants to show it is ‘‘absolutely clear’’ conduct won’t recur; record shows long-standing pattern and ease of revival, so heavy burden not met.
Whether the proposed injunction is an impermissible "obey-the-law" injunction under Rule 65(d)	The injunction is specific: segregation of taxes, semiweekly deposits, restrictions on transfers, affidavits, and notifications—provides clear, objective duties beyond merely telling defendants to obey the law.	The injunction merely commands compliance with tax law and lacks specificity, raising enforceability and notice concerns.	The proposed injunction is sufficiently specific given statutory terms, defendants’ familiarity with obligations, and district court findings of proclivity for unlawful conduct; Rule 65(d) does not bar it here.
Whether Rosen v. Cascade bars equitable relief because plaintiffs ultimately seek money damages	N/A (IRS seeks prospective equitable relief in complaint; preliminary injunction aligns with permanent relief sought).	Rosen held courts generally cannot freeze unrelated assets to secure money damages; injunction inappropriate when only damages sought.	Rosen distinguished: Rosen involved damages-only litigation; here the complaint seeks permanent equitable relief under § 7402(a), so Rosen does not categorically bar the requested injunction.

Key Cases Cited

United States v. Ernst & Whinney, 735 F.2d 1296 (11th Cir.) (equitable powers under § 7402(a) are governed by traditional equitable factors)
Keeton v. Anderson-Wiley, 664 F.3d 865 (11th Cir. 2011) (four-factor preliminary injunction test)
Owner-Operator Indep. Drivers Ass’n, Inc. v. Landstar Sys., Inc., 622 F.3d 1307 (11th Cir. 2010) (standard of review for injunctions)
Sheely v. MRI Radiology Network, P.A., 505 F.3d 1173 (11th Cir. 2007) (voluntary cessation/mootness framework)
Friends of the Earth, Inc. v. Laidlaw Envtl. Servs., 528 U.S. 167 (2000) (‘‘absolutely clear’’ standard for voluntary cessation mootness)
Rosen v. Cascade Int’l, Inc., 21 F.3d 1520 (11th Cir. 1994) (limits on freezing assets in damages-only suits)
Grupo Mexicano de Desarrollo, S.A. v. Alliance Bond Fund, Inc., 527 U.S. 308 (1999) (limits on equitable relief in aid of future monetary recovery)
McComb v. Jacksonville Paper Co., 336 U.S. 187 (1949) (broad injunctions may be appropriate where proclivity for unlawful conduct shown)
Scott v. Roberts, 612 F.3d 1279 (11th Cir. 2010) (discussing irreparable injury vs. monetary remedies)
Levi Strauss & Co. v. Sunrise Int’l Trading Inc., 51 F.3d 982 (11th Cir. 1995) (irreparable harm doctrine in trademark context)