Caskey attended Texas A&M University where he played football from 1997 to 1998, and won the Big 12 Championship Game in 1998.

Following the 1998 season, he focused his athletic career in track and field from 1999 to 2002, where he competed in discus and earned All-Big 12 honors in 2000.

[3] On February 25, 2010, Caskey was named offensive quality control coach for the Cincinnati Bengals.

During Caskey's time in Detroit in 2019, the Lions had four running backs rush for at least 200 yards, which was the most in the NFL.

[6] On September 9, 2021, Caskey was named offensive quality control coach for the Jacksonville Jaguars.