In college, Craigwell played safety (and some wide receiver) with the Brown University football team.

[4] After college, Craigwell went on to the NFL, where he was signed as an undrafted free agent by the Miami Dolphins as a safety.

[5] However, he was relegated to the practice squad by the Miami Dolphins in May 2010, and was left to contemplate his future.

Craigwell admired the pace of the game and the athleticism of the players, and decided he wanted to play rugby.

[9] By the end of 2010, Craigwell was playing for the national team in the IRB Sevens World Series.