TOBIAS LOSS-EATON represents clients in civil and criminal litigation dealing with a range of difficult regulatory, statutory, and constitutional issues. Chambers USA, which has ranked him for Transport: Rail (for Railroads) in USA – Nationwide (2023), notes his “impressive experience,” with clients reporting that he is “a fantastic lawyer” and “an excellent civil litigation advocate.”
As a member of Sidley’s Supreme Court & Appellate and Regulatory Litigation practices, Tobias has extensive experience challenging and defending state and federal agency actions and regulations, including in the energy, trade, securities, and healthcare sectors. He has significant experience in complex contractual and commercial disputes, including cases involving the Federal Arbitration Act and insurance and reinsurance disputes. He has also litigated important cases on criminal law and sentencing, including in the Supreme Court.
Tobias is also part of Sidley’s Transportation group, which U.S. News and Chambers USA recognize as one of the nation’s top-tier practices. Chambers USA highlights his strong experience advising and litigating on behalf of the nation’s largest freight railroads (2023). He has represented the railroads in many cases involving federal preemption of state law, contractual disputes, challenges to regulatory action, and the proper interpretation of the Federal Employers Liability Act. He also advises airline-industry clients on federal preemption and regulatory issues. In 2023 alone, Tobias argued four transportation-law appeals in federal and state appellate courts.
Tobias prides himself on clearly and persuasively explaining complex legal issues to busy generalist judges, at the trial level or on appeal. One prominent legal writing expert praised Tobias’s briefs as better than the typical work product of “elite” Supreme Court advocates. Tobias has written or coauthored over 130 briefs in state and federal appellate courts, including 56 briefs in the Supreme Court. He has presented oral argument in the D.C., Second, Fourth, Sixth, and Seventh Circuits, in state appellate court, and in state and federal trial courts. Tobias is a co-director of the Northwestern Supreme Court Clinic at Northwestern Pritzker School of Law, where he teaches Supreme Court advocacy and supervises students working with Sidley lawyers on cases at the Court.
Tobias’s recent Supreme Court cases include:
- Representing the petitioner in a pending merits case addressing the meaning of “serious drug offense” under the Armed Career Criminal Act.
- Representing the respondent in a significant merits case addressing whether a state can assert general personal jurisdiction over any foreign corporation registered to do business there.
- Representing the petitioner at the certiorari stage and on the merits in Kahler v. Kansas, 140 S. Ct. 1021 (2020), a landmark case addressing whether the Constitution requires an insanity defense.
- Representing a major equipment manufacturer in a merits case about the duty to warn in maritime tort cases.
- Representing the respondents at the merits stage in United States v. Davis, 139 S. Ct. 2319 (2019), a successful due process challenge to a federal gun-possession statute.
- Representing election-law experts as amici defending state laws against “faithless” presidential electors.
His other significant matters include:
- Securing in district court—and then successfully briefing and arguing a Fourth Circuit appeal to defend—a multi-million-dollar breach-of-contract judgment arising from a rent-determination process under a long-term fiber-duct lease.
- Securing in district court—and then successfully briefing and arguing a Second Circuit appeal to defend— dismissal of “fraud on the FDA” claims against a pharmaceutical manufacturer under the False Claims Act.
- Successfully briefing and arguing a Seventh Circuit challenge to a Surface Transportation Board decision construing common-carrier railroads’ interchange obligations.
- Representing a national industry association in successfully challenging a customs regulation restricting excise-tax exemptions in the Court of International Trade, one of Law360’s top five trade rulings of 2020, and successfully defending the decision on appeal in the Federal Circuit.
- Successfully briefing and arguing a motion for judgment on the pleadings to secure a ruling that federal law preempted a local government’s attempt to condemn part of an active rail yard.
- Briefing and arguing a D.C. Circuit challenge to a regulation requiring railroads to disclose information about hazardous materials movements without confidentiality protections.
- Representing a natural gas company in Second Circuit and New York appellate cases about environmental approvals and eminent domain proceedings, including a successful challenge to a state agency’s denial of a Clean Water Act certification, which earned Law360’s “Legal Lion of the Week” title, and a successful defense of FERC’s subsequent waiver ruling.
- Representing a major freight railroad in successfully obtaining an injunction barring enforcement of a state fee on trains carrying hazardous materials on preemption grounds, and securing affirmance in the Ninth Circuit.
- Representing a professional sports franchise in a dispute over telecast rights fees, including obtaining vacatur of an adverse arbitral award in the New York Supreme Court and affirmance on appeal.
- Representing a corporate executive in a due process challenge to a prison sentence under the “responsible corporate officer” doctrine in the Eighth Circuit and in seeking Supreme Court review.
Before joining Sidley’s D.C. office, Tobias served as a law clerk to Judge Norman H. Stahl of the U.S. Court of Appeals for the First Circuit and Judge Henry H. Kennedy, Jr. of the U.S. District Court for the District of Columbia. Between his clerkships, he was an associate in Sidley’s New York office, where he focused on commercial litigation and disputes.
Tobias earned his J.D., cum laude, from Harvard Law School, where he was a senior policy editor of the Harvard Law & Policy Review and notes editor of the Harvard Law Review.