Winklosky is a 1993 Naval Academy graduate, retired Marine Corps lieutenant colonel, former federal administrative judge, and accomplished litigator whose life reflects a deep commitment to public service, leadership and the Academy’s core values. He began his Marine Corps career with 2nd Battalion, 5th Marines, serving in key leadership and administrative roles before being selected for the highly competitive Marine Corps Funded Legal Education Program, through which he transitioned to the judge advocate community.
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.