Top-10 moments in my poker "career"

The other day, while describing how I first started playing poker to a new acquaintance, I realized that I've now been playing the game on a fairly regular basis for more than 10 years. That's longer than I've continually engaged in any other hobby other than running, and if I were to compare the number of hours I've spent running over the last 10 years to the number of hours I've spent playing poker, I have to say I think my old high school and college track coaches would be a little disappointed.

I started reflecting on all that time spent at the tables – most of it with good friends – and realized that I've had quite a few amazing moments in my poker "career." And here are the top-10.

10. Got invited to the "big" game in my home town
I'd played poker with friends a few times in high school and college, but it was never a regular thing. When I was a grad assistant in the athletic department at my alma mater, St. Lawrence, there was a group of guys that played poker just about every week. Most of the guys were a few years older than me, and half of them were good friends with my oldest brother. When I got the invitation to come to the game, I have to say I was pretty intimidated. I'd played cards with lots of these guys before, but never for money. And while none of them were rich, they all had real jobs and weren't grad assistants living off less than $200 a week.

I showed up with $40 in my wallet and a six-pack of Labatt Blue. I went home that night with six beers in my belly and $110 in my wallet, thanks to a great run in 4-card guts (I could write a whole column about the merits of that game). I remember sitting in the living room of the house I shared with two other grad assistants in the athletic department when I got home, counting the money four or five times just to be sure I had counted it correctly (the beer wasn't helping). Once I was certain on the profit, it didn't take me long to figure out that I'd won more in a few hours playing cards with friends than I made in two days of work.

I became a regular in the game, and while a $70 win was pretty atypical, it was the place where my poker hobby really began.

9. First casino tournament
I haven't played many casino poker tournaments, but I'm pretty sure I'll always remember the first one. It was a $120 no-limit Hold'em event at Foxwoods, and I didn't have a damn clue what I was doing. It was the beginning of the poker boom, probably the fall of 2003 or spring of 2004, and the event drew more than 300 people. I sat down at my table, and my heart was racing. The first hand of the tournament, I peeked at my cards, but I peeked in the wrong corner and only saw blank space. I turned them around and looked again and was shocked to see pocket aces.

My first casino tournament, I'm dealt pocket aces, and I'm convinced that Lady Luck is on my side and I'm going to take down the whole thing.

I was first to act, and with blinds at 25-25, I threw out a 100 chip, thinking that I was making a raise. A tournament veteran was quick to get clarification from the dealer, asking, "That's a call, right?"

"No, I meant that to be a raise," I protested.

"A single oversize chip without a verbal declaration of 'raise' is a call," said the dealer.

Needless to say, eight players called to get in a pot for cheap, knowing that I had a hand they could crack and that, since I had no idea what I was doing, they could take my whole stack. When the flop came out jack high, it was checked to me and I moved all in for 2,975 in a 200 pot. I'm lucky no one called, because if they did I certainly would have been behind.

Later in the tournament, I donked off all my chips with bottom two pair on a Q-10-9 board against a made straight. I was lucky to be in that event as long as I was. I walked out of Foxwoods pretty steamed that afternoon, but I got a good lesson in tournament poker, and I haven't made the mistake of throwing out a single oversize chip intended as a raise without declaring "raise" since.

8. First home game in South Boston
After leaving my home town, I spent a couple years in Maine, where I was able to organize a couple home poker games, but was never able to get the momentum to get a regular group together. I figured that would change when I moved to Boston, and soon after the move I got invited to play with a group of college hockey media folks that I was working with. But the game was at very low stakes (a $5 tournament buy-in, with the prize chopped between the top-two players), so it was difficult for me to focus and play my best (let alone win back the money I spent on beer!). My wife suggested I play with a group of guys she knew from ultimate Frisbee, including a few guys I'd met before. It was a little intimidating to play with a new group, but it helped that I knew the guy who was hosting and that one of his roommates was a good friend of mine from college.

Twenty minutes after I arrived, I'd already blown through my first $20 buy-in, and I was steaming. Despite the setback, I managed to claw my way back and post a small profit in the cash game portion of the night. Then we played a $20 no-limit Hold'em tournament, and I ended up chopping with another player to collect a $100 profit on the night. It was the first time I posted a triple-digit win. When I got home, my wife asked me how it went, and I pulled out five crisp $20 bills and said, "I won this many." I was pretty proud of myself, and I think she was a little worried about what she just got me into.

7. Playing the 24-hour poker game
It's hard for me to believe it, but yes, I've played in a 24-hour poker game three times. The first time was definitely the most memorable for me. We had one player show up with a dozen donuts at 4:30 a.m. We had a player drive six hours just to join us. And I was young enough to actually get through the whole game and recover from it in just a day or two. The third (and most likely last) was also memorable, but there's something special about your first time.

6. PokerRoom.com cruise/media tournament win
Just a month after I started working at Casino City, I got the opportunity to cover a poker tournament that was taking place during a Caribbean cruise, sponsored by PokerRoom.com. The night before the real tournament began, tournament organizers held an event for the players, their guests and the media. The winner of the 30-player tournament would get a set of 500 ChipCo ceramic chips with a PokerRoom.com "Meet Them and Beat Them" design. And 14 of us decided to throw in $50 for a last-longer. Well, not only did I last longest among those of us who were involved in the bet, I managed to win the whole thing (Warning – NSFW). I still have the chip set and use it regularly in my home game, and it was my first live tournament win.

5. Winning back-to-back $5 buy-in events online
A year after moving to Boston, I found myself out of work and looking for a job. I spent most of my mornings lounging around my wife's condo (she bought it before meeting me, so it was only in her name), browsing Monster.com looking for job opportunities and sending out resumes and cover letters.

I had an online poker account at the time, but vowed not to make another deposit until I got a job. That said, I did decide that it was worth taking a break every day to play in a tournament, so I jumped into a $5.00+$0.50 no-limit Hold'em event on PokerRoom.com every day at 10 a.m. Usually I'd last about an hour or two, and sometimes I'd eke out a cash, but finally after a few weeks I made a deep run. I got lucky quite a few times, but I managed to beat more than 180 people to pull off an improbable win and cash for more than $400.

I had no illusions that I was a great player, and I knew that I had gotten lucky, so I opted not to raise my stakes and instead committed to continuing to play one $5 tournament a day. So you can imagine my surprise when I sat down in the same tournament the next day and won the whole thing again.

With a profit of more than $850 in just two days, I decided to do the prudent thing and cash out almost all of it. I was unemployed at the time, so I needed the money. And in retrospect, maybe that was a good thing. Nothing would have been more devastating than winning that much money and losing it all in a matter of days, and if I'd had a steady job, that may have been exactly what would have happened.

4. Chopping the $80 noon tournament at the Rio
I don't get a chance to play much poker when I'm covering the World Series of Poker, and that's usually my only trip to Las Vegas each year. When I do, it's usually a $4/$8 Omaha Hi-Low game at the Venetian. Well I hadn't done very well at the Venetian in two brief trips one year, so I decided that on my final day in Vegas, I'd jump into one small tournament and take the red-eye home, licking my wounds.

Only I didn't have to lick my wounds.

There were about 20 people in total in the tournament, and had I been able to run good when I called an all-in bet with K-J vs. K-9, I probably would have won the whole thing, but after that hand, three of us had about the same amount in chips, so we decided to chop up the prize pool. It was about almost $400, which more than made up for my losses in the previous sessions.

The next year I decided to play the tournament again, this time as self-proclaimed "defending champion." I did end up with a great story to tell, but it really doesn't belong on a list of accomplishments in my poker "career." If you really want to know what happened, as Casino City Editor-in-Chief Vin Narayanan. He was highly amused.

3. Finishing 38th finish in the Daily Dollar at Full Tilt
Before Black Friday shut me out of the games at Full Tilt Poker, I occasionally jumped into the "Daily Dollar," a $1 no-limit Hold'em tournament with a $10,000 guaranteed prize pool that started at 8:00 p.m. ET. I loved the tournament because it offered a chance to play a rake-free event with a low buy-in with the prospect of a big payday. I believe the first-place prize was guaranteed to be at least $1,500.

I'd played the tournament about a dozen times before I managed to make a deep run. I played great poker the whole night. With more than 10,000 people in the event, I was pretty jazzed when we got down to the final 10 tables. And then we got the final five. I finally busted out in 38th place, cashing in for a grand total of $20. I looked at the clock and it read 2:30 a.m. I went to bed but didn't get to sleep until 4 a.m. It hardly seemed worth the time I'd spent – and the sleep deprivation I'd be facing the next day – for a mere $19 profit.

That night, I learned that I'm just not cut out to be an online multi-table tournament poker player. The amount of time needed to succeed in these event is just too much for the expected return.

2. Getting hired by Casino City
In early 2006, after more than five years working in athletic departments at institutions of higher education, I was looking for something new, but most of my applications were being sent to college admissions and fundraising departments. Then I saw an ad for a "poker reporter" position posted on Craigslist. It sounded like the perfect job for me, so I sent in an application. Two hours later, I got a phone call and conducted a quick phone interview, and I scheduled an interview for the next week.

Alarm bells went off in my head immediately. I was used to a higher education pace, where you might not hear about a job you applied for until three or four weeks later – so long you may have completely forgotten that you applied. The whole thing sounded like an identity theft scam to me, so with trepidation I told my wife about the interview. She seemed skeptical and I told her that I was going in fully prepared to walk out if anything seemed suspicious.

Imagine my surprise when I walked in and found a bustling office, full of cheery people who seemed quite busy. I met with several people during my interview, all of whom seemed genuinely excited about the future of the online gambling industry. I've spent five of the last eight years working in an industry that I find fascinating. Of course one of the biggest perks is my annual trip to Las Vegas to cover the World Series of Poker. Last year I got to see Antonio Esfandiari make history at the Big One for One Drop. I've also watched Chip Reese, Freddy Deeb, and Michael Mizrachi win the Poker Player's Championship (previously the $50,000 H.O.R.S.E. championship) and Phil Hellmuth finish second. I am glad that I replied to that ad, and unless this is the longest con ever, I'm grateful that Casino City took a chance on me.

1. Sending a player from our home game to the WSOP
It took a year to raise the cash, and the satellite took place over the course of about 11 hours, but we sent a player from our home game to play in a $1,500 no-limit Hold'em tournament at the World Series of Poker last year.

Jas beat half the field before busting out with J-J vs. A-A, and he had an experience that I hope he never forgets. The satellite itself was a highlight for me, despite the fact that I didn't last as long as I would have liked. While my own performance doesn't really merit an appearance on this list, the work that I put in to organize and sell the idea to the other nine players who participated is what gets this to the top spot on this list.

While the games have been harder to organize this year (more of us have kids, which makes it a little harder to get out), and we're far short of our target for revenue, we're still aiming to send someone back in 2014. Hopefully it will be me, I'll make a deep run, and there will be a new number one on this list.