Winning AFTER a Trip to Mohegan

Every time I go to a Mohegan Sun Casino, something significant happens in my career.

My first trip to a casino outside Las Vegas (which I only went to for the MLB Winter Meetings & Job Fair) was to Mohegan Sun in Connecticut. It was August of 2010, and I was on a road trip with the Hudson Valley Renegades.

The ‘Gades were playing the Connecticut Tigers at Dodd Stadium in Norwich. We stayed at a hotel about 15-20 minutes away from the casino, and had some extra time before a night game. One of my past broadcaster partners and I stopped at a nearby Wal-Mart to buy cheap polo shirts. (I wasn’t going to be caught dead wearing a team polo in a place like that.)

After discussing some research by a Princeton professor about gambling odds, we decided that Deuces Wild Video Poker was where we would spend most of our time. It apparently has the best odds to win of anything in a casino (among table and video games). After about half an hour of waffling back and forth between being up two dollars and down ten, I decided it was time to try a few different games.

I made my way over to the Black Jack table, in hopes of earning money a little more quickly. After a few stupid hits and stays, a mysterious side bet caught my eye. One of the other players at the table kept putting a dollar down on it, and every once in a while, he would get five or more back. Since it was getting close to our agreed-upon leaving time, I made a bold bet. WIthout fully understanding what the side bet was (which was pretty dumb of me), I dropped a five dollar chip on it. I got a pair of nines, and the dealer’s up-card was a nine as well. If the dealer’s card had been between my two original cards, I would have received a fair payout. Because I had not just one but two matching cards, I ended up with $120 despite losing the actual hand. (The dealer had 19.)

The next day in the hotel, I noticed an @ reply and subsequent direct message on Twitter from a guy who was a year behind me at BU, but I had never met. That was the beginning of a two-week discussion that netted me a job with the Liberty Mutual Coach of the Year. The compensation from that job was enough to allow me to keep my low-paying baseball gigs and actually have a roof over my head. I also got a call that day from a Providence Bruins broadcaster about my application to be an intern there…


A road trip to Maine and Pennsylvania with the P-Bruins gave me another chance to win some pocket change, and again preceded some news about a potential game-changer in my career. Last month, the second stop on our three-city tour was Wilkes-Barre. It’s home to Mohegan Sun at Pocono Downs, a much-smaller casino than its Connecticut counterpart. After the six-plus hour overnight bus ride from Portland to PA and a nap that lasted beyond noon, I headed over for a chance to turn a small percentage of my meal money into a small percentage of student loan principal.

After watching one table game for a while, I was ready to jump in with a specific system of betting. The game was similar to Roulette, but a bit less complicated. Instead of betting on numbers, a color, odds/evens, thirds, or halves, you simply bet on which payout you think will come up: 1-to-1, 2-to-1, 5-to-1, 10-to-1, 20-to-1, and the two individual big payouts, both 42-to-1. The odds of those payouts coming up are only slightly lower, so with a little bit of luck, it’s not hard to break even or make a little money over a long period of time.

The best part about this “Wheel of Fortune” as they called it, was that the minimum bet was one dollar. Score!

I devised a plan to break even, win big, lose big, win a little bit or lose a little bit on every single round. Instead of rooting for one number to come up, I rooted for all BUT one number to be chosen. I put five bucks on 1-to-1, nothing on 2-to-1, and one dollar on each of the other payouts (which was another five in total, because the largest payout had two separate spots). It cost me $10 per round, and I almost always broke even at the absolute least. Because of the combined odds, I would avoid losing any money about 70 percent of the time. Almost 50 percent was breaking even, and the other 20 percent were winning between one buck and 42.

I decided that if I ever saw three twos in a row, I’d stop. They never came in more than an hour at the table, though. I won three times on the 42-to-1 payout, including once with a random choice to place two chips there.

After returning from the road trip $95 richer, I got some bad news. The position I had fought so hard for at HubSpot had been filled. Despite the effort of everyone who helped share my love letter to the company and half a day of in-person interviews, I wasn’t the newest employee on First Street.


This past Saturday, I went to Mohegan in Connecticut again. I didn’t have any big wins, but it was still a great day. There is exactly one Wheel of Fortune in the three-casino complex, and it took forever to find. Unfortunately, the odds were different, the payouts were slightly different and the minimum bet was way higher. Any one of those factors could have ruined my system alone, so the collection of all of them plus some bad luck early assured that I wouldn’t beat the house this time.

Despite being down for the day, it was a nice escape capped off by a free Kris Allen concert. I couldn’t have told you anything about the dude Saturday at this time, but the concert was energetic and fun anyway.

I hope I’ll see the next number on my career wheel soon. Anything but a 2!

One comment on “Winning AFTER a Trip to Mohegan

  1. Marilyn Gagalis
    April 29, 2013 at 1:35 pm #

    Good Luck! Gambling on a job may prove more enriching than gambling for cash!

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