Calcutt v. FDIC (Administrative)

Listen to the Calcutt v. FDIC Decision Syllabus here.

A banker was suspended and fined by the FDIC for actions he took on one financially troubled account. The Supreme Court reversed the Sixth Circuit, reasoning that the Court of Appeals must reverse the administrative agency if it reaches the same outcome for a different reason. Once an administrative agency has made an error of law, the decision must be remanded back to the administrative agency.

Tyler v. Hennepin County (Takings Clause)

Listen to the Tyler v. Hennepin County Decision Syllabus here.

In Tyler v. Hennepin County, Chief Justice Roberts writes for the majority, reversing the Eighth Circuit. The District Court and Circuit Court rejected a taxpayer’s claim that Hennepin County’s practice to keep the surplus after a tax sale violated both the Takings Clause under the Fifth Amendment and the prohibition on excessive fines under the Eighth Amendment. Here, the County recovered the $25,000 surplus on Tyler’s property. The Court reversed, finding that the state is not entitled to recover the surplus after a property is sold after the owner’s failure to pay real estate taxes. 

Sackett v. EPA (Environmental)

Listen to the Sackett v. EPA Decision Syllabus here.

In Sackett v. Environmental Protection Agency, the Supreme Court examines the scope the terms “waters” under the Clean Water Act. The EPA ordered the Sacketts, who purchased property in Idaho, to restore the property after the family backfilled it with dirt. The EPA claimed that putting dirt on their property violated the Clean Water Act, and threatened the family with $40,000 in penalties daily. 

The Sacketts claimed that the Clean Water Act did not apply, since the regulation was based on “waters of the United states.” According to the Sackett family, this definition should refers only refer to streams, rivers, lakes, and adjacent wetlands that have a continuous surface connection to those bodies of water.  The EPA asked the Court for a broader interpretation of the statute. The Court ruled against the EPA, reasoning that there must be a clear connection between wetlands and traditionally navigable waters to obtain jurisdiction under the Clean Water Act.

Dupree v. Younger (Post-Conviction)

Listen to the Dupree v. Younger Decision Syllabus here.

In Dupree v. Younger, the Supreme Court addressed whether a post-trial motion of a purely legal issue that was resolved at summary judgment, requires a post-trial motion to be preserved on appeal. Kevin Younger sued Neil Dupree, a correctional officer, under Section 1983. Dupree moved for summary judgment alleging that Younger had failed to exhaust administrative remedies. The district court denied the motion. After Younger prevailed at trial by obtaining $700,000 in damages, Dupree appealed alleging the district court should have dismissed the suit. The Fourth Circuit, bound by its precedent, rejected Younger’s reasoning that he was required to file a Rule 50 post-trial motion to preserve the issue on appeal. The Supreme Court reversed, finding that pure questions of law resolved in summary judgment do not require a post-trial motion to preserve the issue for appeal. The Court writes in the syllabus: “And it makes sense: Factual development at trial will not change the district court’s pretrial answer to a purely legal question, so a post-trial motion requirement would amount to an empty exercise.”

Conclusion

After a historically slow start to the term, the Supreme Court is beginning to pickup the pace in releasing its decisions. For the most part, decisions released so far this term have either been unanimous or near unanimous. In cases with dissenting opinions, the splits have often broken the traditional ideological lenses. For example, the Andy Warhol decision saw a 7-2 decision, with Justice Kagan being joined by Chief Justice Roberts in her dissenting opinion. Time will tell to see if this changes as some of the more hot-button issues are still outstanding.

Jake Leahy

Jake A. Leahy

Attorney

Jake A. Leahy is a tax attorney at Airdo Werwas who counsels nonprofits, local governments, and businesses in tax, regulatory, and commercial matters.

He is a former Assistant Illinois Attorney General in the Revenue Litigation Bureau, where he handled…

Jake A. Leahy

Attorney

Jake A. Leahy is a tax attorney at Airdo Werwas who counsels nonprofits, local governments, and businesses in tax, regulatory, and commercial matters.

He is a former Assistant Illinois Attorney General in the Revenue Litigation Bureau, where he handled estate tax litigation, collections audits, and matters involving various state agencies. He previously served as a Judicial Law Clerk in the Circuit Court of Cook County, Law Division, Tax & Miscellaneous Remedies Section, working on administrative review actions, commercial disputes, and tax-related litigation.

Jake previously served on the Board of Education for Bannockburn School District 106 from 2017 to 2023, including as Vice President from 2020 to 2023. His experience in local government informs his work with public-sector clients, boards, and nonprofit organizations.

Jake is active in professional and bar organizations. He serves as an Assembly Member of the Illinois State Bar Association, Chair of the Chicago Bar Association’s State & Local Tax Committee and Young Lawyers Section Federal Tax Committee, and a member of the Editorial Board of the DuPage County Bar Association. He was recognized by the Illinois State Bar Association with its Law Student Public Service Award during law school, and by the Internal Revenue Service for his work with the Low-Income Tax Clinic at Holy Name Cathedral.

Jake earned his LL.M. in Taxation from Georgetown University Law Center, his J.D. from the University of Illinois Chicago School of Law, and his B.A. from the University of Illinois at Urbana-Champaign. He is admitted to practice in Illinois, the U.S. Tax Court, and the U.S. District Court for the Northern District of Illinois.

Outside of practice, Jake has completed three marathons, is a regular at Wrigley Field, and appreciates Chicago architecture.

Education

    • Georgetown University Law Center, LL.M. in Taxation, 2025

    • University of Illinois Chicago School of Law, J.D., 2023

    • University of Illinois at Urbana-Champaign, B.A. Political Science: Public Policy & Democratic Institutions, 2019

Admitted to Practice

    • Northern District of Illinois, 2025

    • U.S. Tax Court, 2024

    • Illinois, 2023

Associations

    • Illinois State Bar Association

    • Chicago Bar Association

    • American Bar Association, Tax Section

    • DuPage County Bar Association

    • Celtic Law Association