Thomas Michael O'Leary

The Honorable Thomas Michael O'Leary, United States Immigration Judge (Ret) passed away on October 4th, 2025 at Canyon Vista Medical Center in Sierra Vista, Arizona. Born in the Bronx, New York August 16, 1948, the Judge joins his parents James and Julia O'Leary, and his brothers, John, Jim and Joe in eternity. He will also reunite with that lovely special lady, Luise Ann O'Leary, who was his life for more than forty six years.

On the day he met Luise, Tommy realized two things: He had seen the most beautiful woman he would ever see and he would be in love for the rest of his life. Admittedly, Luise took a little longer to come around but, then again, she was a whole lot better looking.

The Judge is survived by his sister, Julia Rapp, his son, Richard, his daughter (in-law) Reyna, his beautiful granddaughters, Rhiannon, Camila and Mariann and his favorite grandson, Jordan.

A Visitation will be held at 12 pm on Monday, October 20th at the Hatfield Funeral Home, 830 AZ-92, Sierra Vista, Arizona 85635.

A funeral mass will be performed at Saint Andrew the Apostle Catholic Church, 800 Taylor Drive, Sierra Vista, Arizona 85635 at 10:30 am on Tuesday, October 21st, followed by a military burial ceremony at the Southern Arizona Veterans Memorial Cemetery, 1300 South Buffalo Soldier Trail, Sierra Vista, Arizona 85635 at 12 pm.

In lieu of flowers, the family requests your donations to Wounded Warriors, St. Jude Children's Research Hospital, Operation Smile or Tunnel to Towers.

Tommy graduated from Cardinal Spellman High School in 1966; became a Manhattan College Jasper; went to Wall Street; got drafted; went to war; became a Jasper again; returned to Wall Street; drove a taxi, and finally graduated from Herbert H. Lehman College in 1974. Still, he always will be a Jasper.

Upon graduation from Seattle University School of Law in 1977, Tommy embarked upon his legal career as a fledgling Deputy Prosecuting Attorney for Pierce County, Washington.

Commissioned as an Army Judge Advocate in 1978, his military career would span twenty six years of active and reserve service, which included deployment as a radio operator in Chu Lai, Vietnam, where he was awarded the Purple Heart and the Vietnam Cross of Gallantry.

His career as a Judge Advocate included billets as Senior Trial Attorney, Justice, Fort Polk; Chief Defense Counsel, Fort Polk; Chief Legal Advisor, Investigations, Office of Inspector General, Headquarters, United States Army Europe (USAREUR); Senior Defense Counsel, Giessen Military Community; Chief, Administrative Law and Chief, Legal Assistance, Office of the Staff Judge Advocate, Fort Knox.

CPT O'Leary served as a member of the Fort Knox School Board and was commissioned a Kentucky Colonel in 1986 by then Governor Martha Layne Collins.

In January, 1987, he left active duty to pursue dual careers as an Army Reserve Judge Advocate and the Department of Justice's Special Assistant United States Attorney/Sector Counsel, Tucson Sector, United States Border Patrol.

In September of 1996, Tommy retired from the Army Reserve and ascended to the bench as a United States Immigration Judge in which capacity he served for 24 years.

While adjudicating thousands of cases, his two favorite days as a judge were when he administered the Oath of Citizenship to his Irish cousins in Tucson, Arizona and when he administered that same oath to 600 new citizens at El Centro, California.

The pandemic cost him the opportunity to administer the oath to his daughter (in-law) Reyna but, it did not stop him from being incredibly proud of her the day she took it.

Tommy loved teaching; he instructed at the United States Army Armor Center, Fort Knox, the Border Patrol Academy and the Federal Law Enforcement Training Center (FLETC).

He joined the faculty of Embry-Riddle Aeronautical University as an Associate Adjunct Professor in 2002. Capitalizing on his Wall Street experience and his litigation before the MSPB, FLRA and NLRB, Professor O'Leary taught undergraduate and graduate courses in Business Law, Ethics and Aviation Industry Labor Relations.

Tommy valued family above all else. He was blessed with an extraordinary partner, Luise, to whom family always came first and who protected theirs with a fierce passion and an unyielding love.

God granted him and Luise an incredible son, Richard, a fantastic daughter (in-law), Reyna and four amazing grandchildren. He and Luise loved being Opa and Oma.

Road trips with Luise were the highlights of their life together and yearly reunions with the Bronx Boys cemented friendships which would last over sixty years.

The pinnacle of Tommy's life's journey was the family's visit to Ireland in 2023. During that trek, nine O'Leary sojourners created unbreakable bonds with the Emerald Isle clan and visited the farmhouse where James O'Leary (RIP) was born in 1899. Tommy always believed that Luise and Big Jim peered keenly from their perches in heaven on that day.

In December 2020, after forty five years of federal service and six in the private sector, Judge O'Leary retired to Sierra Vista to be with his family. The Judge lived a full and wonderful life. He will now rejoin Luise, through eternity, if she will have him (she still is a whole lot better looking).