Before Tobias Loss-Eaton became a lawyer, he assumed his calling would be in academia. As it turns out, professorship wasn’t ultimately in the cards, but elements of that role have nevertheless come to shape his work at Sidley, where he is a partner in the Supreme Court, Appellate, and Litigation Strategies practice.
“I’ve always liked the teaching aspect of my job,” Loss-Eaton said, referencing, by way of example, his running of the appellate advocacy training for summer associates in the Washington, D.C. office. “Working with junior associates on legal writing and litigation skills is really fun.”
His proficiency in appellate matters only enhances his inclination to educate. He has written or co-authored over 200 briefs in state and federal appellate courts, including more than 100 Supreme Court briefs. And, as a co-director of the Carter G. Phillips/Sidley Austin LLP Supreme Court Clinic at Northwestern Pritzker School of Law, he supervises students in researching and drafting briefs at the petition stage and on the merits. “You feel like you’re making a difference, and it’s wonderful skill development.”
Leading the Clinic — alongside renowned Supreme Court litigator and Sidley partner Carter Phillips and Sidley alum Jeff Green, a former partner in the firm’s Supreme Court and Appellate practice — was a natural fit for Loss-Eaton. “I’ve always loved the pro bono Supreme Court work that Sidley does. It’s fascinating.”
Clinic students monitor lower court decisions to identify promising pro bono cases to take to the Court — such as Abouammo v. United States, a pending merits case on the constitutional standard for venue in criminal prosecutions. “One of the Clinic students spotted the Abouammo appellate decision when it first came out and thought the reasoning and the result were worth digging into,” Loss-Eaton said.
That discovery led to Loss-Eaton’s Supreme Court debut in March 2026, where he argued on behalf of pro bono client Ahmad Abouammo. At issue in the matter: Where can the federal government prosecute a crime? “The immediate question,” Loss-Eaton said, “is whether this kind of obstruction-type offense can be prosecuted where the conduct occurred or where the effects were felt.”
The broader question, he said, is “on what basis, if any, can the government ever prosecute you somewhere other than where you actually did something?”
Leading up to his argument, Loss-Eaton participated in multiple moot courts with Sidley colleagues, Clinic participants, and co-counsel with the Federal Public Defender’s Office for the Northern District of California, which had represented the client from the outset before teaming up with Sidley. “They were deeply passionate, enthusiastic, and engaged. They have incredible case knowledge and are true experts when it comes to federal criminal law,” he said.
The Court agreed to hear the case in December 2025, meaning Loss-Eaton had to put together the merits briefing and oral argument simultaneously to meet the March 30, 2026 argument date — a decidedly compressed timeline. “We got literally the last possible moment with no slack at all.”
Yet the pressure had an upside for Loss-Eaton: it kept the case fresh. “Everything was fully top of mind for me as I was shifting into thinking about oral argument prep.”
He drew upon his tried-and-tested approach to appellate arguments. “Even though this was my first time in the Supreme Court, I didn’t want to be psyched out such that I would change things from the way I normally do them.” By the time he stood before the justices, he was ready. “I think I had gone through every permutation of every question,” he said. “I felt nervous and excited, but well prepared.”
Constitutional venue questions have rarely been addressed at the Supreme Court, making a decision in Abouammo — expected sometime in June 2026 — one of the Court’s first opportunities in nearly 30 years to weigh in on the issue.
Loss-Eaton noted that some of the arguments and questions from the justices focused on the lack of boundaries inherent in the digital era. But, he pointed out, the Court grappled with these same issues in the past, albeit in different forms: from letters crossing state lines, to telegrams and telephone calls.
“There’s always been a technological development that makes it easier to connect with people and potentially commit crimes. The Court’s task here is to think about the way the Constitution has always worked and then figure out how it applies in a new context.”
For Loss-Eaton, who maintains a robust pro bono practice, the Abouammo case is a perfect confluence of Sidley’s support and celebration of pro bono work. “Everybody was so enthusiastic about it from start to finish. This was a real investment of time for Sidley lawyers.”
He added: “I have always felt like Sidley walks the walk when it comes to pro bono work, in terms of time and resources, and the way that the work is taken seriously and celebrated.” In a testament to his own personal pro bono commitment, Loss-Eaton has received the Washington, D.C. office’s Mark Herzog (formerly Vincent F. Prada) Pro Bono Award every year since joining the firm in 2013 — although he demurs that it is a common occurrence given Sidley’s collegial culture. “There are so many people, every year, who are recognized for the amount of time that they put into their pro bono matters, of all different kinds.”
To his students and other young lawyers who hope to one day argue before the Supreme Court, his advice is grounded in experience: “The competition for paid Supreme Court arguments is incredibly stiff. The best path is to embrace pro bono work.”
