A native of Brawley, California, Skipper was an all-conference selection at Imperial Valley College, where he led the league in kickoff returns.
He then transferred to Whittier College, where he played defensive back and he paced the conference in punt returns during his career.
Skipper started his professional coaching career with the Philadelphia/Baltimore Stars of the United States Football League from 1983-1985.
He led the Demons to a 6-6 record and an appearance in the only Million Dollar Game would ever hold, won by Los Angeles Xtreme 38-6.
In 2009, Skipper helped make NFL history as two of his running backs, DeAngelo Williams and Jonathan Stewart, became the first set of teammates ever to rush for over 1,100 yards in the same season.