I first started playing online poker almost 10 years ago. It was very different then; there was no Poker Stars or Full Tilt Poker, and there were fewer players. After all this was before Chris Moneymaker turned a $40 punt into millions at the WSOP, and thereby starting the online poker boom – for which he is credited. Indeed, many of today’s online poker players fall into two camps “pre-Moneymaker” and “post-Moneymaker”. I’m in the pre-camp and I know I’m outnumbered – but that’s fine with me.

How has the online poker landscape changed in the last decade? Well for a start Planet Poker is no longer in business, and Paradise poker, once the biggest online poker site, is now a pathetic shadow of its former self – as a skin site on the Boss Poker Network. The whole concept of poker skins and networks is something that poker players are now very familiar with, but this is only a fairly recent change. I actually think there are some really excellent networks (and some really poor ones too), but the big boys are still independents – just like they used to be. It’s almost impossible now to launch a fully independent online poker room without being part of a network. There’s just too much competition.

Is online poker as much fun? This is something I’m not so sure about. I’m probably looking back through rose tinted glasses, and remembering the good stuff…like typing “doh” in the Planet Poker chat box made a sound similar to Homer Simpson (oh what laughter!). Nobody talks these days as there too busy multi-tabling. I’m forgetting the frequent crashes and software problems of course. Indeed, it was the software problems that led to the demise of planet poker. RIP Planet Poker – it was fun while it lasted.

There have been huge improvements in the gameplay, the software, and the security of online poker rooms over the past few years. And let’s not forget third party software is now in abundance too, and there’s widespread use of data mining software. I’m not a fan of this though – I preferred it how it was, but I’m resigned to the fact that data mining is here to stay, sadly.

Along with the quantity, the quality of players has definitely increased over the last few years, and I think it’s fair to credit sites like Cardrunners for this. The games are tougher, there’s no doubt about that. Of course I prefer softer games, but cannot complain – since the people who take the time to learn how to play poker and dedicate themselves to the game will always improve, compared with a lazy players who are unwilling to change and adapt to the new landscape.

Oh, and 10 years ago there was no UIGEA – but that’s too depressing to talk about. Another time!

When you’re winning hundreds of thousands of dollars (maybe even millions) a year and you are a gambler at heart like most successful pro poker players, you’re probably going to throw your money around a little bit.  Okay, maybe you’ll throw it around a lot like some of the players who have been involved in some of my personal favorite prop bets of all time.  Here’s my list:

1. Ted Forrest is the biggest prop better out of any players on this list and he proved it by throwing $7,000 on the table in order to accept a challenge that he couldn’t run a marathon.  Unfortunately for him, the marathon fell on a day where Las Vegas was hit with 115 degree weather.  Nevertheless, Forrest somehow managed to make it around the UNLV track 104 and a half times to win the bet.  But it was costly as he had to be taken to the hospital for dehydration and foot burns after the track melted his shoes.

2. Staying with Ted Forrest, he once told Mike Matusow that he would give him $100,000 if Matusow could drop from his current weight (at the time) of 241 pounds to his old college weight of 181.  Matusow made it to 196 with 7 days left and had to cut 15 pounds over the last week to make it.  Amazingly, he cut the 15 pounds in 7 days using drastic measures and won the bet.

3. Golf is already an expensive enough game as it is but Daniel Negreanu and Patrick Antonius decided to make things a little more pricey as they bet each other $20,000 a hole over the entire 18.  Negreanu battled back to end up 20K ahead of Antonius by the end.

4. Howard Lederer is a devout vegan but decided that the $10,000 David Grey offered him to eat a cheeseburger was enough to break his status for a moment as he downed the cow patty. 

5. Doing a standing back flip is not exactly the safest thing in the world to do.  But Huck Seed took the risk as he learned to do the back flip in less than two months to win $10,000.