Waskow received his commission upon graduation from the U.S. Air Force Academy in 1970, and he served as a forward air controller and instructor pilot early in his career.

Selected to fly the F-15 Eagle early in its operational deployment, he has flown all models and variants of the air-to-air F-15.

He has held command at all levels—fighter squadron, wing and numbered air force.

In addition to significant combat experience in Vietnam, Waskow commanded the 42nd Air Base Wing at Maxwell Air Force Base.

[1] Waskow contributed extensively to contingency operations Deny Flight and Silver Wake in the Balkans, Noble Eagle in Hawaii in 2001, and Unified Assistance in Japan in 2005.