In college, Craigwell played safety (and some wide receiver) with the Brown University football team.[2] He received All-Ivy League Football Honorable Mention for the 2008 season.[3] Craigwell graduated from Brown University in 2009 with a B.A. in Business Economics.[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.[6]
Rugby Union
Craigwell's journey to rugby began in June 2010. He was eating in a diner, and saw the Collegiate Rugby Championship on NBC. Craigwell admired the pace of the game and the athleticism of the players, and decided he wanted to play rugby.[7]
Craigwell began playing rugby in July 2010, having never played rugby a day in his life.[8] Craigwell was a fast learner, and by August 2010 Craigwell was playing in the USA Rugby Men's 7s All-Star Championships.[9] By the end of 2010, Craigwell was playing for the national team in the IRB Sevens World Series.
Former U.S. head coach Al Caravelli has remarked on Craigwell's abilities: "He is very powerful and his defensive ability is scary. He hits so hard, he is very explosive."[10]