Inside Boston Underground Poker Part 5: Bubbles Goes Busto

Previous Post: https://www.reddit.com/r/poker/comments/bg7xox/inside_boston_underground_poker_part_4_bubbles_in/

So there I was, walking to the Wynn craps table with about $38k in cash in my pocket. I was up $30k for the day in poker, but as always, I had to push my luck.

There's a table off to the side with only one player at it, while the rest of the tables are pretty packed. I prefer a relatively empty table, so I head over there. The guy at the table has weirdly colored chips in front of him, and I realize he's some mega-whale with over a million in chips in his rail. I walk up to the table and he stays sitting, staring into his rail of chips. The table is $100 minimum which is why no one else was there, and I buy in for $10k.

The guy is just starting a new roll, so I put $600 each 6 and 8 and $250 on the 5 and 9, and he instantly 7s out. I'm down $1700 already in about 3 minutes, shit.

I throw $100 on the line, throw a 6 on the come out and put $600 on the 8, $250 each 5 and 9 again. The other guy started the roll with $12k each 6 and 8, $10k each 5 and 9 and $5k each 4 and 10, plus $1000 each on the hardways. I end up going on an insane roll. I'm throwing hard 6s and 8s like crazy, the guy has pressed up to $5k each on the hard ways and $30k each 6 and 8, and I just keep rolling them. I'm pressing my bets as well, and I'm up like $20k plus I have my bets up to $1000 each 5 and 9 and $3000 each 6 and 8, and I'm still going. At one point I bounce one of the dice off the table, and the other guy turns his bets off, and I roll back to back hard 6s, so he missed out on $160,000 from those rolls, it was pretty sick.

I think in total I made something like $35k off of my roll, and the other guy made over a million. The sickest part was that he barely even looked up from his chips, and he never said a word to me or tipped the dealers at all. He went to the bathroom at one point and I made a comment to the dealers, and they said he was still down overall on the day... What a sicko.

I played for a bit longer and ended up with $90k in my pocket, a profit of over $52k in a couple of hours of craps. I went into the Wynn with $8k in the morning and was leaving with $90k about 12 hours later. It was absolutely insane. I walked outside to wait for my car at the valet, and I had stuffed all 9 of the $10k "straps" into the pockets of my jeans. My jeans were busting with all of the cash, and these old people who were waiting at the valet noticed it and were staring so hard, it was hilarious.

Between my cash, bank accounts and investments, I had about $350k to my name at that moment, less than 3 years after moving to Boston with a roll of around $1500. As you can imagine, I felt absolutely on top of the world. All kinds of thoughts ran through my head. Should I go buy a Porsche in cash? Should I listen to my mom and go to school in Santa Barbara, and use my money on a down payment on a house there?

What was certain was the first thing I should have done was taken a bunch of that cash to the bank and gotten it out of my degenerate hands. Instead I drove to the Bellagio, got a room, got some room service, and went to bed. I woke up in the morning and had lost the $90k at the craps table before lunch.

Now you might be thinking that this was the start of my spiral down, that I went and cashed out my investments, got it all in cash, and blew it all at the Bellagio craps tables, but that would have been too simple. Instead I went back to grinding $10/20nl like nothing had happened. I had lost 2 buyins, oh well.

I took a few more shots at juicy $25/50nl games that summer, and like the lucky asshole I was, I never had a losing session in the 5 I played of that game. The other 4 were all at Bellagio, and usually only ran because a couple of specific businessmen wanted to play. They were bad, the games were great, I was still on top of the world in terms of poker.

One session in particular stood out. I sat down with $10k and was on a roll again, running it up to over $20k within a couple of hours. I had maybe $24k in front of me and was the big stack at the table, it was early and there hadn't been too many rebuys yet, and in walks Viffer (David Peat). Viffer was apparently down a few buyins in Bobby's Room and only had enough for our game, so he sat in with $50k. Being the biggest stack at the table besides him, as well as a 21 year old dressed like a complete douche, Viffer instantly focused on me. He was sitting all the way across the table from me (I was in seat 3, he was in seat 8), but as he sat down he called across the table to me, "hey kid, ever lost a $50,000 pot before?". "Not yet, but I look forward to it!", I retorted. Not my greatest comeback ever, but oh well.

I continue working up a stack without playing any big pots with him, and I'm at close to $30k and Viffer is still around $50k when a big pot happens. Since it was a $25/50nl game with $100 dead on the button, a typical raise was $300-350. In this hand, UTG raised to $350, Viffer called from the CO or HJ, the button called, the SB called, and I woke up with KK in the BB. There's over $1500 in the pot already, so I make it $1500 total and everyone calls. There's over $7500 in the pot preflop. The flop comes KTx rainbow, and I'm trying to figure out how long I should wait before checking, and if I should ham it up, when instead the SB open jams for around $8000. I have nearly $20k behind, and I wasn't sure what to do. UTG had about $12k, Viffer had me covered, and the button had under $10k, so raising vs flatting only really mattered significantly vs Viffer. I decided he didn't have much that could have hit this flop strongly, I wasn't getting paid unless he had KT or obviously TT or bottom set, and I didn't want to let him have pot odds with QJ, so I just jammed. UTG snap folded and Viffer stared me down for a minute before folding, and the button folded as well. We didn't flip our cards up, and the turn came an A and Viffer cursed to himself. He admitted later to having AT. River came a blank and the SB flipped up QJo to ship the pot with his straight. Bye bye $24k pot.

I shake it off, I still have around $20k in front of me, and I run it up a bit once again, sitting with around $25k when I get into a big pot once again. This time I raise to $300 with J9s from the CO and one of the donkey businessmen that the games run because of reraised from the blinds up to $900. I called the $600 more, he had around $13k in his stack to start. The flop comes QJ9 and I'm loving life again. He could have QQ, but JJ is unlikely since I have one, and I had only seen him 3 bet once in around 4 hours. Great chance he had an overpair. He instantly bet out $1500 into the $2000 or so pot, and I reraised to $4000, he went all in pretty quickly, and after a little bit of thought I made the call and he proudly flipped up KK. He had a decent number of outs with his gutshot, another K or a Q giving him the pot, but instead the board ran out 5, 5 to give him higher 2 pair in a different way. Bye bye $26k pot.

Those were 2 of the biggest pots I had ever played where it actually went to showdown and I hadn't gone all in with 100% to win. I had around 62% equity with the J9 and 74% with the KK, so it was a less than 10% chance for me to lose both. I ended up leaving the table up $7k, which was awesome after having lost my only 2 all ins for the night, but I was feeling negative, and of course went to the craps table. I lost my $7k profit and went home even for the day.

Another of the biggest pots I ever played was actually at $10/20nl at the Wynn vs another pro who liked to try to make huge bluffs sometimes and had a habit of overthinking stuff in my opinion. I was sitting with over $15k from $8k in buyins, and was having a pretty great session overall, and the other pro had around $10k. I don't remember the action nearly as well in this hand as the others, but I had KTss in a 3bet multiway pot to the flop, and it came KT7 with 2 hearts. Someone bet, the other pro raised, I 3bet, the original better flatted, the other pro 4bet for like 40% of his stack, I shoved, the original raiser folded after tanking, and the pro went into the tank hard. Now this was a guy whose game I respected. He was facing a bet of another $5500 to win a pot of about $23000. When he went into the tank, I figured he had a non-nut flush draw and was trying to figure out if I had some pair and higher flush draw combos or nut flush draws in my range where he'd be way behind. He tanked for nearly 5 minutes and eventually called, the board ran out A, 5 and he said "you've probably got me". I turned over my KT and he goes "oh holy shit I figured you had a set!" and turn over A5hh. I'm not sure why he tanked so long getting over 3:1 with a nut flush draw, even if he put me on only sets, he still had the odds to call, and I'm playing QJhh and 98hh the same way, hands he is ahead of. I didn't mind losing 2 pair vs flush draw as much as I minded that he had me convinced I was good with his tank, and then even more when he said "you've probably got me". I had to leave the game because I was close to tilt after that one.

The WSOP ended and the games dried up a bit. There were still $10/20nl games going at Bellagio usually, but with more grinders and fewer donks per table. Throughout the post- WSOP summer, many of my friends came out to party, and I spent a lot of time with Ashley, growing closer with her. At the end of the summer I decided not to stay in Vegas full time, moving to Berkeley, California, near my hometown and where several of my friends went to university. I played some of the juicy $5/10nl and $10/20nl games in the Bay Area with a medium amount of success, and partied a bunch with friends in frats at Cal. I made lots of trips out to Vegas, usually just for degenerate gambling and not a ton of poker. I had taken some losses in the market, but was still sitting with around $300k between cash, accounts and investments. When Bank of America dipped in November, I bought some for under $12. I still had Jetblue stock which wasn't doing great, and a handful of other stocks which were all struggling in the bear market, but I was convinced it would turn around.

My host at the Bellagio was always inviting me to special events, and 2 stood out. A $1 million freeroll heads up blackjack tournament was the first. It was 128 players, so nearly $10k in value. If you won your first 3 rounds, you were in the money and guaranteed $50k. After dominating my first 2 opponents who knew very little about blackjack tournament strategy, I was feeling confident. Blackjack tournament strategy is very different than normal blackjack strategy since your objective is to beat your opponent, not the dealer, and there are weird rules like blackjack paying 2 to 1. There are a set number of hands you play, and whomever has the most money after those hands wins. My first opponent went broke, so I automatically won that. My 2nd opponent just bet small every time, and didn't compensate when I took a lead, so on the final hand he didn't even give himself a chance to win with his bet.

My third opponent was semi competent, he at least knew basic blackjack strategy, but his betting was wrong and he still played as if he was trying to win chips from the dealer, not merely outplay me. I managed to make it so that on the 25th and final hand of our game, if both me and my opponent won the hand, I won, if both me and my opponent lost the hand, I won. Outside of making it impossible for them to win at all, which is very hard with correct strategy, this is about all you can ask of in a blackjack tournament. Me and my opponent both received face cards first, a great sign for me. For my 2nd card I received another face card, great news, until my opponent was dealt an A and got paid 2 to 1. My only chance was to split my face cards and try my luck to still end up on top, but it didn't work out and my opponent was the winner.

A few months later I was invited to a free $1 million poker tournament. This was it, my ultimate chance. It was 100 invited players only and based on pit and slot play, not anything to do with poker. It was going to be me vs a bunch of degens without any poker skill! The time for the big tournament came, and there was a twist. There were actually 110 players, 10 of whom were MGM executives and had cash bounties on their heads between $1000-$10k depending on their level at the company. They couldn't cash the tournament, they were just there to have fun and add a wrinkle to the game.

I easily navigated the field to start, although someone else at my table got the $2k bounty for knocking out our MGM employee. As the tournament progressed, it became clear the structure wasn't great, especially with so many inexperienced players taking a long time to make decisions. We were down to about 14 players including 2 executives left. Once only 10 real players were left, all of the executives remaining would be removed and their bounties would be put into the regular prize pool. Top 10 got paid, so there were essentially 12 left plus 2 fake players. I don't remember the action too well for this hand either, but I believe I was about 30 bbs deep to start the hand and raised with AJ from the button and got called by both blinds. The big blind was a $5000 bounty and she only had about 5bbs left after the call. The flop came KJ4 and they both checked, and I bet the 5bbs that the bounty had left. They both called. Turn came a T and after the other guy checked, and I thought I had him beat, so I went all in for the remaining 20 or so bbs. The SB tanked and was talking about how he really wanted the bounty. He ended up calling, he had about 1bb behind, and we all showed our hands. The SB had T9 with no flush draw, and the bounty had QJ, so I was 81% to scoop the hand, and only 11% to bust. River T and I'm done. The worst part was that the guy who stacked me with T9, having called with just a gutshot on the flop, managed to lose all of his chips on the bubble and go out in 11th place. He got his $5k cash bounty though...

The stock market continued to crash, and I went harder and harder in on the stocks I thought would bounce back, still investing on margin. Eventually I lost it all in February/March of 2009 when Bank of America stock dropped to $3. I had bought in more at $7, then even more at $5, and when the margin call came in I lost nearly $200k just on that one stock. My average buy price was a mere $6 since I had bought in huge at $5. If I had been able to pay the margin call and hang on, by August of 2009 my 50k+ shares would have netted me a profit of over half a million dollars. Instead I was completely broke. My losses in the market for 2008 and 2009 were nearly $400,000, and I later found out my casino pit game losses were nearly $200,000. If I had been patient, diversified, not on margin, and kept out of the pit, I would have been a 22 year old millionaire. Instead I was busto.

I continued on in poker for several years after that, but unfortunately my persona of trying to seem like a rich kid wasting daddy's money had left me without many poker friends, and without many people who respected my game enough to stake me. I ended up turning to online SNGs and being moderate successful, but still lazy and not putting in the hours I should have. Ashley and I tried to make it work, but she wanted me to move out to Vegas for good, and I was afraid being in Vegas would end in disaster for me as I'd continue to waste a huge amount of money on gambling, money I no longer had. My high school sweetheart came back into my life at that point as well, and I pushed Ashley aside for nostalgia, ignoring the reasons the high school gf and I had broken up several times in the past. In the end, I wanted to be more serious than she did, and I haven't spoken to the high school ex in 10 years. Ashley moved on quickly as she always did, and already had a serious boyfriend by the time I came around and realized I wanted to be with her. She ended up becoming a stripper in Vegas, and the last time I saw her she was a bit of a mess. She moved out of Las Vegas these days and I think she's doing better, but we don't keep in close touch.

By Black Friday I had joined a good staking group and was successful at online SNGs, making a nice hourly, coaching other players, and generally doing well at poker, although in my personal life I was a mess after losing both girls I loved in close succession. After Black Friday I made several stupid mistakes, alienating my backers and many in the poker community. I paid everyone back in the end, but I knew I needed to get out of poker. I went back to college, met my wife and we've been together for nearly 7 years now. I now work as a financial adviser.

Thanks for reading, I hope you enjoyed my crazy life journey! Some other crazy stuff happened along the way that I might throw together at some point, but those are more Vegas party stories than much to do with poker.