Jeffrey is from New York, and was the inaugural winner of BreakDown by a vote of 4-3 against alliance partner Bridget.

Jeffrey was the most outspoken contestant during his time in BreakDown, causing several conflicts with Ron, Holden and Aaron - he became the sixth person to leave the game and in doing so earned a spot on the Jury, but was invited to gamble coming back into the game on the outcome of a challenge. He won and returned to the game to a mixed reception from the remaining players. He maintains the record for Most Challenges Won with 5 (Two BreakDown Challenges & Three ShakeUP's)