More than 20 years in the Marine Corps, Winklosky served as prosecutor, defense counsel, trial judge, staff judge advocate, executive officer and professor of law. After retiring from active duty, he entered private law practice. He later continued his public service as a federal administrative judge at the U.S. Department of Agriculture. He now practices as a counsel in Pittsburgh, PA, representing clients in complex federal and state litigation across numerous industries.
Winklosky is equally committed to serving the Academy and the broader community. He is vice president of the Greater Pittsburgh Chapter of the USNA Alumni Association and a longtime Blue & Gold Officer, mentoring prospective midshipmen. His extensive volunteer service includes his role as a knight of magistral grace in the Order of Malta, board member of The Hear Foundation, community advisory committee member for the Eradicate Hate Global Summit, board member of Neighborhood Legal Services (2015–2021), Leadership Pittsburgh Cohort XXXVI, longtime contributor to the Allegheny County Bar Association Veterans Legal Clinic and service on the Marine Corps Scholarship Foundation’s Steel City Scarlet & Gold Committee. He has provided hundreds of hours of pro bono legal support to veterans, asylum seekers and low-income individuals.
Family and service have always been central to his life. He and his wife, Tricia, have been married for more than 31 years. Tricia is the head of Well-Being Programs and Services at Hope for The Warriors, a nonprofit organization that supports military members, veterans and their families. They have three children: Drew, a U.S. Marine Corps captain and CH-53 pilot; Alex, an economist; and Annaliese, a lieutenant in the U.S. Space Force.
Anchored in the Naval Academy’s values of honor, integrity, service and leadership, Devin seeks to serve on the Board of Trustees to strengthen the alumni community, advance the mission of the Academy, uphold its traditions and support the next generation of Naval leaders.