Biggest Poker Upsets and Cinderella Stories in History

March Madness has already tipped off and it has us wondering: what are the biggest Cinderella runs and poker upsets in history? There are stories of WSOP newbies who went on to win it all, and wonderkid savants who took the game by storm. To bridge the gap between college basketball and poker, here are the tales of some of the best unexpected poker champions in history.

Greatest Poker Comebacks and Underdog Stories: Legendary Poker Wins

Stu Ungar’s 1997 WSOP Main Event Victory

Stu Ungar is one of the greatest poker players ever to hold a deck of cards. His career had incredible highs, but also devastating lows. He won the World Series of Poker back-to-back in 1980 and 1981. But after that, personal struggles took him into a downward spiral. The poker world consigned him to the bin of history and viewed him as something of a cautionary tale. By the late 90s, he wasn’t really thought of much at all by the nascent poker fanbase.

Then, in 1997, everything changed.

He made one of the greatest poker comebacks of all time (while battling serious health issues). The field never knew what hit it.

He totally dominated the opposition, playing like a man possessed. His style was very aggressive and totally without fear, or so it seemed. Ungar won his third Main Event title that year playing at a table setup right on Fremont Street. He then delivered one of the hardest lines in a post-win interview ever: “[T]here’s nobody that ever beat me playing cards. The only one that ever beat me was myself.”

When you can back it up like Stu, you can say things like that.

Jack Straus Gets It Done with a Chip and a Chair

Back at another one of the early WSOP events in 1982, Jack “Treetop” Straus won the Main Event with an insane comeback. His play at that event may be the ultimate testament to poker resilience, actually.

At one point, Straus pushed all his chips into the middle, got called, and lost a huge hand. His tournament run was over, right? Well, actually, he found a single $500 chip under a napkin. He then resumed play. After that, he surged ahead in one of the most legendary poker wins in history, grinding all the way to the final table. There, he claimed the championship.

His incredible turnaround may in fact be the origin of the famous poker phrase: all you need to win is a “chip and a chair.”

Greatest Poker Cinderella Stories

Enough about the pros. What about the amateurs who won it all?

Chris Moneymaker’s 2003 WSOP Win Shakes the World

No poker Cinderella story is more famous than Chris Moneymaker’s. He went from being a humble accountant in Tennessee playing online poker to an overnight sensation who won the entire WSOP Main Event. His improbable journey mirrored that of the legendary UNLV Runnin’ Rebels basketball squad. He started with a win in a $39 online satellite tournament that got him a seat in the $10,000 Main Event.

At the tournament, he came face to face with a cavalcade of poker elites. He played lethal poker and even managed to eliminate the legendary Phil Ivey along the way. In the final heads-up battle, he faced seasoned pro Sammy Farha. With a bluff for the ages and lots of other well-timed moves, Moneymaker pulled off a stunning victory. He took home a $2.5 million payday and played an instrumental role in launching the online poker boom. Moneymaker inspired the dreams of millions of players by proving that any online amateur could have what it takes to win the biggest game on Earth.

Jamie Gold’s 2006 WSOP Main Event Domination

Jamie Gold’s 2006 WSOP victory was quite unexpected. Not only was the talent agent a poker amateur, but he dominated his opponents. So many Cinderella stories involve a player defying expectations by surviving tough spots, but Gold was different. He bulldozed the competition. With an unprecedented run of good cards and savage table talk, he accumulated a massive chip lead early on. He never looked back, stacking up towers of chips and executing opponents all along the way. Gold took home the biggest Main Event prize in history at the time: $12 million.

Unexpected Poker Champions

Robert Varkonyi’s Wins the 2002 WSOP and Shuts Up One of the Biggest Mouths in Poker

Before Chris Moneymaker stepped on the scene, there was a poker player named Robert Varkonyi. He was an MIT grad, so you wouldn’t be surprised to learn he was good at a game involving fast mathematical calculations.

In 2002, he entered the WSOP Main Event as an unknown player, then shocked the poker world by winning it all. Phil Hellmuth was famously unimpressed with his game along the way. He went so far as to say that he would shave his head if Varkonyi won. Varkonyi eventually took the top spot, and Phil Hellmuth (to his credit) was as good as his word. He shaved his head in public and ate a rare slice of humble pie.

Joe Cada Becomes the Youngest WSOP Main Event Champion in 2009

Joe Cada’s 2009 victory was a mix of skill, endurance, and luck. This is true of nearly every player, but no one did it as young as Cada. At just 21 years old, he became the youngest WSOP Main Event champion in history. Cada survived elimination multiple times at the final table, needing to make several improbable comebacks. Ultimately, he was heads up with logger and poker amateur Darvin Moon. He won the overall victory and proved that the new era of young players was bringing a whole new spirit and strategy to the game of poker.

One More Poker Underdog Story

Jerry Yang “Psychoanalyzes the Competition” on the Way to a 2007 WSOP Victory

Jerry Yang was a complete unknown before the 2007 WSOP Main Event. However, as a psychologist by trade, he had some relevant skills to the game of live poker. Yang entered the WSOP through a $225 satellite tournament. Once at the final table, he played a no mercy style of poker (notice the theme among all these players – passive won’t get it done!) He personally eliminated multiple players and secured an $8.25 million prize.