Cliff is a retired USAF JAG. He was commissioned in 1983 and began his active career at Luke AFB, AZ in 1983. Subsequent assignments include Kusan AB, ROK (1984-85), Langley AFB, VA (1985-88), Barksdale AFB, LA (Eighth Air Force, 1988-91), George Washington University (1991-92), Langley AFB, VA (HQ ACC (1992-95), Scott AFB, Il (HQ AMC, 1995-98), McChord AFB, WA (1998-2001), and Offutt AFB, NE (2001-04).  Cliff was the installation Staff Judge Advocate at McChord AFB and Offutt AFB. He retired from active duty in October 2004 as a Colonel and accepted a civil service position in July 2004 at HQ AMX/JA as the principal environmental law attorney.  Cliff retired from civil service HQ AMC/JA in January 2020.

Cliff and his wife Carole, have three children all residing in the St Louis, MO area. Carole was an active-duty AF nurse for approximately ten years, leaving active duty in 1992 after the birth of their twin boys. They have owned their condo in Hampton for some time and decided to make the Tidewater area their permanent home in June 2020 after his retirement from civil service.