This year Shulman enters the finale fourth in chips but back in the year 2000 he held a commanding lead over the rest of the table, which included one Chris "Jesus" Ferguson.
One bad beat set the stage for Shulman's elimination in seventh and paved the way for Jesus to become a world champion.
Now, just nine years later, Shulman has another chance at winning the biggest tournament in poker.
Shulman compares his poker game to the boxing style of Floyd Mayweather, lots of jabs without throwing any wild knockout punches. He would rather wear his opponents down than go for broke.
He's realistic about the state of his game, however, saying it's nowhere near the level it was in 2000.
He also has a healthy level of respect for his opponents. After watching previously unknown players like Kevin Schaffel and Steven Begleiter succeed in other big-buy in events since making the final table, Shulman know it's not going to be an easy road to the bracelet for anyone.
Unlike the rest of the November Nine Shulman opted to lay low in the last four months, choosing his wife and two children over the tournament circuit.
Shulman also has a chance to set an interesting record, should he take down the title. Just a month ago his father Barry Shulman won the WSOP Europe Main Event, which means both titles could be held by a father and son in the same year.
Jeff Shulman has been a fixture in the poker world over the last few decades, making over $1.3 million not including this year's main event. He has the skills and he has the experience. Only time will tell if it will be enough.
Check out the video we shot with him back in Las Vegas below, and tune into our Live 2009 WSOP Coverageon November 7th to see how it all shakes out.
More 2009 WSOP Main Event final table profiles