16 Unbelievable Poker Events You Didn’t Know

13 Jan 2025

The game of poker was really booming in the early 2000s and you won't believe the excessive, ridiculous, greedy, and cringeworthy things that poker fans had to witness during those days. From monkeys supposed to be playing in the WSOP Main Event, to million-dollar freerolls, ridiculous poker ads on TV, here are 17 top poker events you probably did not know. Let’s start!

In the 2006 WSOP, the now-defunct poker company, PokerShare, tried to buy in a monkey into the Main Event. People at PokerShare actually taught a chimp named Mikey rudimentary poker skills such as moving chips all-in and sitting at a table.

Unexpectedly, there was a lot of protest from the players who did not want to get knocked out of the Main Event by the monkey. The fact that the monkey wasn't even permitted to play may be the story's funniest element.

Caesars decided to start the 2014 WSOP by literally firing $10,000 into the Amazon room. The majority of players remained cool and maybe scooped up a dollar or two, while a few players dived to the floor to scoop up as much money as they could.

The money drop, according to WSOP executive director Ty Stewart, was intended to kick off the series by bringing a positive energy to the Rio.

In the mid-2000s, the popularity of poker had been used by advertisers to sell everything from deodorants to beer, and then Mayor Labs put another notch on, or more appropriately, below the belt.

A contraceptive company called Kimono aired a series of TV ads called «When One-Eyed Jacks Are Wild» that consisted of using contraceptives instead of chips. Mayor Labs wanted to use a poker theme to sell its product. No doubt, some women will resent or at least regret this ad's innuendo. Others will smile, or maybe blush.

Unlike other poker games, the short-lived Bomb Shell Poker offered the chance to win a date with a model in addition to monetary prizes. Bomb Shell Poker offered a roster of models that would actually play poker on the site, but you could also win the chance to email them personally or win a date.

It's also kind of funny that Bomb Shell Poker immediately assumed its players did not have the ability to get their own dates. In the end, Bomb Shell Poker was but a blip in the online poker world and never really made much of an impact

Many Poker websites offered celebrities money in exchange for Sponsorships. During the poker boom, after learning the game from Ellen DeGeneres, actress Cameron Diaz declared her love for poker in 2005.

Cameron was given the opportunity to promote BetChris.com for $1.5 million, but she declined the offer. It is uncertain if Cameron Diaz participates in poker now, but once the UIGA was approved in 2006, a number of famous people stopped sponsoring the game.

Midway through the 2000s, Paris Hilton was breaking out and garnering a lot of media attention. She also enjoyed playing a bit of poker, and it was widely said that one time she lost a $200,000 Bentley in a poker game. PartyPoker gave Hilton a freeroll ticket, where she could win the Bentley back if she defeated Mike Sexton in a head-to-head match.

Most probably, the match never took place. Apparently, the poker world could not get enough of Hilton, as Cloney Gowen would later challenge the heiress to a $100,000 heads-up challenge. Paris Hilton did not accept, although she did play the WPT Invitational and a few other invite-only live tournaments.

In 2004, self-made English multimillionaire Dominic Morocco paid $4 million for Mike Tyson's home, but then he decided to offer everyone the chance to win it for free, including Mike Tyson. His idea was to have a huge poker tournament with hundreds of competitors playing to earn their spot at the six-player final table. Four of the finalists would be top finishers from the qualifying tournament.

The fifth and sixth will be Morocco and Mike Tyson themselves, thus giving Tyson the chance to win his house back. People might think that Dominic, maybe some kind of crazy English eccentric, giving away Tyson's house, but contestants pay thousands of dollars each to enter high-stake poker tournaments, plus there are also rights to a reality TV show based on this. There has been no word since as to whether the show ever came to fruition, and there had been no evidence of it.

Even religious groups were trying to get into poker in the mid-2000s. Caruso, an Arkansas-based Christian apparel and gift company, was cashing in on the nationwide poker craze, spreading the gospel with poker chips that had inspirational messages on them like Jesus Went All In For You and Call On The Name Of The Lord.

Bodog was well-known for its extravagant poker promotions, but the iconic, wild-card poker reality show was the cherry on top. Calvin Ayer, the creator of Bodog, served as the tournament's host on the program, which included both pros and qualifiers. The qualifiers were sent to Antigua for a week of partying while the show was being filmed.

In fact, Josh Aria took home $500,000 from the first season of the program. The tale, however, did not have a happy ending since reality TV show creator later sued Bodog on the grounds that it was a knockoff of a program she had created.

Players had the chance to earn 6% of Phil Ivey at the 2009 WSOP Main Event final table with this well-known promotion from Full Tilt Poker. It was actually two separate contests where one 9-player sit-and-go split a prize pool that was equal to 5% of Ivy's winnings. The winner of the other sit-and-go straight up received 1% of Ivy's overall winnings.

Instead, Ivy came in 7th place for $3.8 million, earning the fortunate player $38,000. It should be noted that Full Tilt did not actually give away Ivy's winnings. They just matched the value as he probably would've had something to say about that.

Before physicians objected to the high levels of sugar and caffeine in them, they were all in the rage in the mid-2000s, and poker is a game that benefits from energy boosts during prolonged sessions. None were bigger at that time than the Johnny Chan backed All in Energy Drink, which made a serious push for relevancy at the WSOP.

At the 2008 WSOP alone, players drank nearly 100,000 cans of All in Energy Drink and over 300,000 bottles of ultra-hydrating purified water. All in drinks ran a $500,000 freeroll during the 2008 WSOP for the top 1,200 loyal customers of its energy drink and bottled water. The tournament ran on July 1 with 26-year-old Miami player Michael Gadgians winning the first prize of $107,000 and a seat in the Main Event. The energy drink had lured some of the top names in poker to wearing its patches during the game, including Johnny Chan, David Williams, Patrick Antonius, Freddie Deeb, and Annie Duke.

PokerStars had partnered with London's foodie kings, Johns and Sons, to launch the All-in Kitchen, the world's first pay-by-poker restaurant. To celebrate the UK and Ireland poker tour kicking off in London, the All in Kitchen saw diners play poker to determine how much they pay for their meal. Their remaining chip count will determine whether they pay £10, £5 or come up trumps getting their meals for free on PokerStars.

For three days, diners had the opportunity to pay the full £50 per head menu fee or choose to play three hands to determine if their meal will be free or merely at a heavy discount. There really was no reason not to play the three hands since there is no risk and only gain possible.

Paradise Poker gave a $1.1 million freeroll. In 2005, poker sites were so desperate for players that Paradise Poker held a $1.1 million free tournament with $1 million going to the winner and $100,000 going to places 2-9.

It was a free roll but it did have some caveats. For months, the website offered three qualifying heats. There were up to 4,000 participants in each heat. You could enter the first heat for free but you had to use 100 million points or what are known as frequent player points to enter the subsequent heats.

In 2014, 888Poker offered a new kind of promotion and launched a new poker variant on its online platform called Snap Poker. Snap was a new fast full poker format that allowed players to play more hands at a faster speed. 

By playing Snap Poker on the website, participants could have won a trip to Prague on an L-39 Albatros fighter jet. They did not get to pilot it though which actually seems really smart.

Way back in the day, in February of 2007, Team PokerStars Pro Dario Minieri picked up the keys to a Porsche for free courtesy of his phenomenal play at PokerStars. He was the first of the players to drive off with a supercar just for playing on the world's most popular online poker site at that time.

Since then, a number of players have driven off with a Porsche purely from putting in some serious volume on PokerStars. At one point, PokerStars even offered an Aston Martin V8 for players who were able to earn a staggering 5 million frequent player points.

And lastly, Number 16, PokerStars was nearly featured in Casino Royale. The Bond franchise has established a wealth of partnerships with luxurious brands over the years. With Casino Royale's poker-driven plot, a number of big poker sites wanted their brand promoted in the movie. What people don't know is how close PokerStars came to being one of the official partners of the movie along with the mainstream sponsors Sony, Aston Martin, Omega, and various others.

According to Dan Goleman, one of the earliest marketers with PokerStars, there was a deal in place that would have seen a satellite on PokerStars end with a final table in the exact spot where James Bond and the villain Le Chiffre squared off in the Bahamas.

There was also a chance that PokerStars would have been featured in the movie as part of the deal. PokerStars even promoted a 007-themed poker merchandise. The brand would have been shown in numerous places throughout the casino scenes had the contract been approved. Despite the fact that the agreement with Casino Royale was cancelled, PokerStars did sign a contract with Aston Martin to support one of its racing teams. Due to this, a DB9 was in fact given away to a PokerStars participant in 2006.