A native of Massachusetts, Jonathan “iftarii” Jaffe now makes his living playing poker in Montreal. Jaffe has had amazing success playing online, specializing in heads-up sit and gos. His prowess has become so respected that he is one of the resident pros on IveyPoker.

Though heads-up sit and gos are totally different than large multi-table tournaments, Jaffe’s skills have translated very well to the live poker world. Before the 2013 Main Event, Jaffe had cashed 14 times at the World Series of Poker, though just once in 2013. He has yet to win a bracelet; his best finish in a WSOP event was fourth back in 2008 in, fittingly, the $10,000 No Limit Hold’em Heads-Up Championship.

Jaffe’s greatest live poker tournament accomplishment also occurred in 2008, when he came agonizingly close to a major tournament title, placing second in the World Poker Tour World Poker Finals at Foxwoods. The $670,636 he received for his efforts was likely a nice consolation.

All told, Jaffe has won almost $1.2 million on the live tournament circuit. To put that in perspective, his bio at IveyPoker states he has made over $800,000 in profit from online heads-up sit and gos alone. In 2009, he further planted his flag in the online world by winning the $25,000 No Limit Heads-Up Event of the PokerStars World Championship of Online Poker for $315,000.

Jaffe had a great run throughout most of Day 5 of the 2013 WSOP Main Event, going into the dinner break as one of the chip leaders. He took a large step back just as the night was about to end, when he perhaps got caught trying to be a little too aggressive.

Marc McLaughlinhad raised to 80,000 pre-flop, J.C. Tran called, and Jaffe three-bet to 240,000. McLaughlin called and Tran folded to bring on a flop of 9h-Qc-Kd. Jaffe checked, McLaughlin bet 250,000, and Jaffe once again three-bet to 600,000. McLaughlin called. They both checked the 4c on the turn and once more when the river brought on the Qd. Jaffe turned over Tc-9c for two pair, but McLaughlin had As-Kh for a better two pair, causing Jaffe to lose a healthy chunk of chips.

Jaffe ended up exiting the Main Event in 42nd place for $185,000.