Lt. Tom Winkler was born in London, England, and grew up in Washington, D.C., graduating from Gonzaga College High School in 1992. He attended the University of Virginia on a Naval Reserve Officer Training Corps scholarship, earning a B.A. degree in History, and was commissioned as an ensign in 1996.

Tom reported to NAS Pensacola, Fla., for aviation indoctrination in January 1997. He completed primary flight training in the T-34C Mentor at NAS Corpus Christi, Texas, and transferred to NAS Meridian, Miss., for intermediate flight training in the T-2C Buckeye, and NAS Kingsville, Texas, for advanced flight training in the T-45 Goshawk. He received his wings of gold in December 1999.

In January 2000 Tom reported to Strike Fighter Squadron 125 (VFA 125) in Lemoore, Calif., for training in the F/A-18 Hornet. In May 2001 he reported to the VFA 82 "Marauders," stationed at MCAS Beaufort, S.C. While with the "Marauders," Tom deployed aboard USS Theodore Roosevelt (CVN 71) in September 2001 and aboard USS Enterprise (CVN 65) in August 2003. During these two six-month deployments Tom flew 45 combat missions over Afghanistan and Iraq in support of Operations Enduring Freedom and Iraqi Freedom. While with the "Marauders," Tom served as the schedules officer, avionics/armament division officer, NATOPS officer, assistant operations officer and head landing signals officer.

In May 2004, Tom reported to the Marine Corps Strike Fighter Training Squadron 101 (VMFAT 101) "Sharpshooters," where he served as an F/A-18 instructor pilot, schedules officer, landing signals officer, flight officer and T-34C pilot.