One of the best things about poker is that anyone can win, regardless of who they are, where they come from, or how much money they’ve got. With the right mix of skill, patience, and a bit of luck, anyone can win big.
Online poker has really broken down barriers, allowing total strangers to compete with experienced pros on the world’s biggest stages. From $30 satellites to life-changing millions, the game has given us some of the most dramatic Cinderella stories in sports history.
And if you’re grinding the online tables yourself, the best way to maximize your edge is by securing one of the top poker rakeback deals. These give you more value back on every hand you play, which is great if you’re chasing that underdog dream.
10. Jack “Treetop” Straus and the ‘Chip and a Chair’ Miracle (WSOP 1982)
At the 1982 WSOP Main Event, Jack Straus shoved all-in, lost, and thought he was out until he found a single $500 chip hidden under a napkin at his seat.
That one chip was the foundation of the most iconic comeback in poker history. Straus fought his way back to win the championship.
The phrase “a chip and a chair” was coined here, reminding every player that as long as you have one chip, you still have a chance.
9. Stoyan Madanzhiev’s Record WSOP Online Triumph (2020)
Stoyan Madanzhiev from Bulgaria was known as a solid cash player, but few had him down as a WSOP Main Event champion. He entered the largest online tournament ever with 5,802 entries and shocked the poker world by winning $3.9 million, still the biggest online payout in history.
He even said he never thought he’d win so big, making him the ultimate online underdog.
8. Doulas12’s Sunday Million Shock (PokerStars 2008)
The PokerStars Sunday Million is the stuff of online grinders’ dreams, and in October 2008, “doulas12” pulled off one of the biggest upsets.
He started the final table with one of the smallest stacks, but then made an amazing comeback, beating “Crackpfeife” in a heads-up match to win an extra $30K, ending up with $125,478.
CardPlayer called it a “true underdog story”, showing that heart and grit can outshine chip stacks.
7. Sergey “CrazyLissy” Denisov’s WCOOP Main Event Comeback (2021)
The $5,200 WCOOP Main Event always attracts the best in the world, but few had “CrazyLissy” as champion.
He started Day 3 way behind chip leader Stevan Chew, but he kept doubling up and making his way back up. In heads-up, he turned a huge deficit against Pascal Lefrancois around, winning with some bold moves and good doubles to secure $1.5 million.
It was the kind of improbable, against-all-odds finish that feels like something you’d see on TV.
6. Marat “maratik” Sharafutdinov: 40 FPP to WCOOP Champion (2012)
This one’s a real legend. Russian micro-stakes grinder “maratik” only used 40 Frequent Player Points to qualify for the $5,200 WCOOP Main Event, which is pretty impressive.
When the pros were chatting about a deal at the final table, he famously typed: “I won’t go for a million.” He got exactly what he was looking for: beating Ryan Carter in a head-up match for 1,000,907 dollars.
This is the best in poker magic, from loyalty points to millionaire!
5. Grzegorz Glowny’s €530 Satellite to EPT Prague Title (2022)
Polish grinder Grzegorz Glowny wasn’t exactly a household name, with his biggest live cash prize just over $5K. But in 2022, after qualifying via a €530 satellite, he made a shock appearance in the EPT Prague Main Event.
After outlasting 1,190 players, negotiating a four-way deal, and winning €692,252 ($754,555), Glowny proved once again that online qualifiers can become European champions.
4. Sebastian Malec Turns $30 into Millions (EPT Barcelona 2016)
Sebastian Malec is a Polish-Irish student and former chess prodigy who got into the €5,300 EPT Barcelona Main Event by winning a $30 online satellite.
He made some bold calls and got pretty emotional when he won, which helped him defeat a final table full of stars and win €1.12 million.
His raw joy is exactly what makes him such an all-time favourite — it’s just the classic story of a micro-stakes grinder going on to become a live poker champion!
3. Jamie Gold’s Talent-Agent Blitz (WSOP 2006)
Jamie Gold wasn’t a professional poker player – he was a Hollywood talent agent who got his seat in the 2006 WSOP Main Event by bribing his way in.
He was a real powerhouse, with his bold table talk, aggressive play, and plenty of run-good, and he bulldozed the competition to win $12 million, the largest Main Event prize at the time.
Gold’s dominant run shocked the poker world and showed that charisma and guts could beat even the best pros.
2. Robert Varkonyi’s MIT-Geek Surprise (WSOP 2002)
Before Chris Moneymaker, there was Robert Varkonyi. The MIT grad entered the 2002 WSOP Main Event as a total unknown — and was openly mocked by pros, including Phil Hellmuth, who said he’d shave his head if Varkonyi won.
Varkonyi didn’t just win, he scooped $2 million and made Hellmuth keep his word.
His win, just before the online poker boom, was a sign of things to come. It was the start of a golden era for poker, with underdog champions taking the lead.
1. Chris Moneymaker’s $39 Satellite Miracle (WSOP 2003)
There’s no underdog story in poker bigger than Chris Moneymaker’s 2003 WSOP Main Event run.
The Tennessee accountant got in via an $86/$39 PokerStars satellite, knocked out Phil Ivey, and then bluffed Sammy Farha with K-7 in the legendary “bluff of the century.” He went on to win a cool $2.5 million.
Moneymaker’s win kicked off the poker boom, showing that even with a small bankroll and a dream, you can beat the best.
