United States Court of Appeals For the Seventh Circuit ____________________ No. 22-2691 W. JAMES MAC NAUGHTON, Plaintiff-Appellant, v. ASHER VENTURES, LLC, et al., Defendants-Appellees. ____________________

Appeal from the United States District Court for the Northern District of Illinois, Eastern Division. No. 1:17-cv-4050 — Martha M. Pacold, Judge. ____________________

ARGUED MAY 17, 2023 — DECIDED AUGUST 3, 2023 ____________________

Before RIPPLE, SCUDDER, and LEE, Circuit Judges. LEE, Circuit Judge. William James Mac Naughton, a New Jersey attorney, represented Shai Harmelech and his com- pany, USA Satellite & Cable, in a lawsuit filed by the Russian Media Group (“RMG”) against them in 2006 (the “RMG Ac- tion”). Mac Naughton stopped representing Harmelech and USA Satellite after they failed to pay his legal fees. The RMG Action eventually settled, and the settlement agreement was converted to a judgment (the “RMG Judgment”). 2 No. 22-2691

A few years later, Mac Naughton purchased from RMG the rights to the unpaid portion of the settlement judgment. He then filed a torrent of actions in the Northern District of Illinois against his former clients, seeking to collect the RMG Judgment. In one of those actions, Mac Naughton sought to set aside Harmelech’s conveyance of his Highland Park, Illi- nois home to his son Etan, claiming it was a fraudulent trans- fer under Illinois law. We will refer to this lawsuit as the “Sunnyside Action” because the home is located on a street called Sunnyside Avenue. The defendants in the Sunnyside Action moved to dis- qualify Mac Naughton pursuant to New Jersey Rule of Pro- fessional Conduct 1.9(a), which states that a lawyer who has represented a client in a matter “shall not thereafter represent another client in … a substantially related matter in which that client’s interests are materially adverse to the interests of the former client.” In 2015, Judge James Holderman granted the disqualification motion and entered an order barring Mac Naughton from acting as counsel in further efforts to col- lect the RMG Judgment (the “Holderman Order”). Undeterred by the Holderman Order, Mac Naughton con- tinued prosecuting the Sunnyside Action. What is more, he filed several similar actions before different judges in the Northern District of Illinois. While the named defendants and legal claims in those other actions varied, the actions all were further attempts on Mac Naughton’s part to collect the RMG Judgment, in direct contravention of the Holderman Order. After Judge Holderman retired, Judge Gary Feinerman took over the Sunnyside Action. He dismissed the action with prej- udice as a sanction for Mac Naughton’s continued defiance of the Holderman Order. Mac Naughton v. Harmelech, 338 F. No. 22-2691 3 Supp. 3d 722 (N.D. Ill. 2018). Other judges with cases filed by Mac Naughton imposed similar sanctions. These dismissals (four total) came before us on a consoli- dated appeal in 2019. Mac Naughton insisted that the Holder- man Order was wrong because Judge Holderman had misap- plied Rule 1.9(a). But as we told Mac Naughton then, he was not free to disobey the Holderman Order simply because he disagreed with it. Regardless of the Holderman Order’s legal correctness, Mac Naughton was bound to follow it “unless and until it was undone through proper channels, such as re- consideration by the district judge or vacatur by us.” Mac Naughton v. Harmelech, 932 F.3d 558, 565 (7th Cir. 2019). Because Mac Naughton had never properly appealed the Holderman Order or asked Judge Holderman (or Judge Feinerman) to reconsider it, we affirmed