Jim parlayed his youth wrestling into a stint at Division I Virginia Tech. With his college wrestling behind him however, Jim found himself looking for a new competitive outlet, and found it in 2005 when he and older-brother Dan took up jiu-jitsu. Jim proved to be a quick study, taking first place in his first grappling tournament, and soon found himself making his professional mixed martial arts debut.

Jim was dominant in his debut, and quickly ran off 5 wins against many of the Northeast’s top lightweights, including another dominant performance over Elite XC veteran Muhsin Corbbrey en-route to an arm-bar victory. The streak set-up a bout against fellow stand-out Frank Edgar for the Reality Fighting Lightweight Title.

Despite his gym closing just two weeks prior to the bout, and his brother being unable to help him train due to injury, Jim and Edgar put on a war which saw a head kick liberate a chunk of cauliflower ear from Edgar. Ultimately, Edgar earned the decision, and transitioned to the UFC for his next fight, but being so close to the big show only served to motivate Jim.

Jim returned to the cage to challenge for the Cage Fury Fighting Championships Lightweight Title, and earned it with a powerful slam and a rear naked choke victory, just as Dan had earned his CFFC strap, and defended it with a jiu-jitsu clinic against Anthony Morrison. Unfortunately, CFFC folded before Jim had the chance to defend his title again.

Next on the docket was a match-up with veteran Nuri Shakir, but when Shakir came in 13 pounds overweight it seemed the fight wouldn’t even come to pass. Jim however was ready to fight, and took on the near-welterweight opponent, securing the win with a flying rear naked choke, earning him another title and setting the stage for a pair of battles with former-UFC and future-Elite XC vet Chris Liguori, who stood undefeated at lightweight.

Jim took both contests, via a cut stoppage and a guillotine choke, bringing him his fifth title. With the all the top regional fighters behind him, Jim got the call to the national level. First the UFC came beckoning, looking for Jim to take on Marcus Aurellio, but the IFL denied the move. Instead, Jim took on Bart Palaszewski. While the IFL favorite showed tremendous heart in escaping submission attempts, Jim’s grappling was smothering as he chained submissions throughout and earned a clear-cut decision victory and, with the ensuing IFL fold, finally earned his much-deserved spot in the UFC.