Seat 4: Tony Gregg, USA (5,680,000)
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Tony Gregg's run to the final table has been nothing short of impressive, as the Maryland native, commonly referred to as poker's "end boss," has now reached the PokerStars Caribbean Adventure final table for a third time.
Back in 2009, Gregg showed up at the PCA with one recorded live cash for $8,625 under his belt, though he was an experienced and respected online player under the moniker "wwwBTHEREcom." He promptly booked a second-place finish for $1.7 million, falling heads up to online qualifier Poorya Nazari, who won the largest first-place prize in PCA Main Event history at $3 million.
Three years later, Gregg found himself at the final table once again. This time, he finished sixth for $364,000 in a tournament eventually won by John Dibella.
Gregg is now guaranteed at least $153,920 for this run, but our guess is that that's going to turn into a bit more. As it stands right now, Gregg has pocketed over $2.2 million in winnings from this event alone. The result has also already pushed him over $10 million in career live tournament earnings.
While Gregg has had an insanely successful career at PCA, his awards extend further. In 2012, Gregg won the World Poker Tour Parx Open Poker Classic for $416,127. Less than a year later, he took second to Steven Silverman in the European Poker Tour Monte Carlo Grand Final €25,500 High Roller for €760,000 ($996,551). Then, just over a month after his runner-up finish in Monaco, Gregg scored $4.83 million when he won the 2013 World Series of Poker $111,111 One Drop High Roller.
Thanks to a late charge on Day 5, Gregg will enter the final day of play with 5.68 million in chips. That's good enough for second place overall, and we'll see if the third time is a charm for Gregg.