Caffey played high school basketball at Centennial.[1]
College career
As a true freshman, Caffey played in all 34 games, starting two, averaging 5.9 points, 2.8 rebounds, 2.2 assists and 0.7 steals per game.[1] As a sophomore, he started all 33 games for LBSU, averaging 32.8 minutes, 12.0 points, 4.0 rebounds, 1.4 steals and 3.8 assists per game, improving his numbers a lot. Due to his performances, he Earned a First-Team All-Big West honor.[1] During the next two years, his numbers became better and Caffey managed to gain First-Team All-Big West honors another two times, and was a three-time first-team All-Conference pick.[1]
Professional career
After going undrafted in the 2015 NBA draft, Caffey joined Jászberényi KSE of the Hungarian League.[2] During his rookie professional year, Caffey averaged 15 points, 4.5 rebounds and 3.4 assists per game, and was also included to the Hungarian All-Star Game.
On September 20, 2016, he signed with Aries Trikala of the Greek Basket League.[3] He went on to average 8.4 points, 3.2 rebounds and 3.1 assists per game.