Jake A. Leahy

Jake A. Leahy is a tax attorney at Airdo Werwas who advises businesses and their owners, nonprofit and tax-exempt organizations, and governmental entities on tax, transactional, and regulatory matters, as well as complex disputes.

Jake's practice includes counseling clients on issues arising in mergers and acquisitions, reorganizations, affiliations, and other business transactions. He also advises on tax-exempt organization matters, including exemptions, executive compensation, employee benefits, governance, unrelated business activities, and transactions involving charitable organizations. His work frequently requires addressing the corporate, contractual, fiduciary, and regulatory issues that accompany the underlying tax questions.

Jake advises local governments on tax and financial matters, property taxation, intergovernmental arrangements, and governance. He particularly enjoys helping local governments establish and work with nonprofit organizations, including township foundations, from formation and tax exemption through governance and ongoing operations. In that work, he helps public bodies and nonprofit organizations develop practical structures for working together and carrying out their respective governmental and charitable missions.

Jake's broader practice also includes Illinois state and local tax, trusts and estates, and commercial litigation. He advises on state tax disputes and administrative matters, estate planning and administration, charitable trust administration, and disputes involving fiduciaries and charitable or family assets. These matters often involve overlapping questions of taxation, ownership, succession, fiduciary responsibility, and the stewardship of assets.

Jake's experience with government spans nearly a decade, beginning with six years as an elected member of the Bannockburn School District 106 Board of Education and continuing through legal roles as an Assistant Illinois Attorney General and a Judicial Law Clerk in the Circuit Court of Cook County. At the Attorney General's Office, he served in the Revenue Litigation Bureau and Estate Tax Section, representing state agencies in matters ranging from audit disputes through litigation and collections. Before entering legal practice, Jake gained experience with business and financial matters through work in a family office, a Big Four accounting firm, and as a licensed real estate broker.

Jake regularly writes and speaks on federal, state, and local tax matters, tax-exempt organizations, trusts and estates, business issues, and local government. He is active in several professional and bar organizations and is a past Chair of the Chicago Bar Association State and Local Tax Committee. Jake holds a Master of Laws (LL.M.) in Taxation and a Certificate in State and Local Taxation from Georgetown University Law Center.

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

• U.S. District Court for the 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

Presentations

• "Advanced Topics in Township Foundations: Understanding the Role of the 501(c)(3) Organization," the Illinois Association of Township Administrators (IATA) Meeting, Lake Zurich, Illinois, July 8, 2026. 
• “What the IRS Already Knows: Information Reporting, Automated Enforcement, and Modern Tax Compliance,” Chicago Bar Association, May 22, 2026.
• “Demystifying Property Tax Objections: What Township Officials Need to Know,” Illinois Township Attorneys Association Annual Educational Seminar, Bartlett, Illinois, May 15, 2026.
• “Foundations, 501(c)(3) & Intergovernmental Agreements – Ask the Attorney,” Illinois Township Association of General Assistance Caseworkers Annual Educational Conference, Peoria, Illinois, April 23, 2026.

Publications

• "Is It a Gift? Charitable Deductions Under IRC § 2055,” Illinois State Bar Association Trusts & Estates, August 2026.
• “Form 990: Classifying a School That Hasn’t Opened Yet: Obtaining IRS Approval and What Happens If the IRS Disagrees,” CPA Practice Advisor, August 4, 2026.
• “Who Decides? Home Rule Authority and the Illinois Constitution,” DCBA Brief, Vol. 39, Issue 1, July/August 2026.
• “Illinois’ Digital Asset Tax Creates a New Compliance Regime for 2027,” CPA Practice Advisor, July 24, 2026.
• “Seven Form 990 Red Flags CPAs Should Not Ignore,” CPA Practice Advisor, July 22, 2026.
• “What’s Said to AI May Not Stay in AI,” Illinois Bar Journal, May 2026.
• “Diversity Jurisdiction and a History of How We Came to the ‘Nerve Center Test’ for Corporate Citizenship,” Illinois State Bar Association, March 2026.
• “When the Text Isn’t Clear: What Lawyers Should Know About the Canons of Construction,” Illinois State Bar Association, February 2026.
• “What Elegant Legal Writing Gets Right About Legal Writing,” Illinois State Bar Association, January 2026.