If you saw any of the coverage of the $5K Seniors High Roller event at this year’s World Series of Poker (WSOP), you might remember the player with the Cookie Monster t-shirt and matching card protector.
That was Mark Checkwicz of Massachusetts, and when the last card was dealt he was the one left holding all the chips. For topping a field of 680 players aged 50+, Checkwicz collected $573,876 - a significant step up from his previous biggest cash of $26K.
“I can't find a reason to be unhappy when I'm playing the game,” Checkwicz told the WSOP immediately after his win, “It's just so perfect. Poker is so beautiful and really there has to be a winner and a loser and I appreciate both sides of the equation. That's what makes it work.”
This zen-like approach to the game has helped make Checkwicz a lot of friends in the past few weeks. We spoke with him about his recent win, what comes next and - of course - the whole ‘Cookie Monster’ thing.
On using his table image to win a WSOP bracelet…
Listen, the plan from the very beginning of the tournament is this silliness. How are you going to take me as a good poker player? I’m just silly. It’s deflection. I have fine-tuned this shtick from day one, that Cookie Monster moment. I’m not bragging, it’s just a fact. I am able to convince people I don’t know what I’m doing when, in fact, I know exactly what I’m doing at a poker table. And the ‘people part’ of it, you know as well as I do, there aren’t many people that can pull this off, it’s a special talent.
The bottom line is: if they like me, there’s a small range of hands they won’t play because they don’t want to take me out. Whatever that is, I don’t know what that range is, but I know there are hands. If you like me, you don’t really want to be the one to take me out.
Mark Checkwicz, winner of the $5K Seniors High Roller
On the origin of the 'Cookie Monster' persona…
I have a son with Down’s Syndrome and when he was about seven years old we were shopping in a Sears. We’re going through these aisles and my son, Andrew, spots a Cookie Monster outfit, but it’s for adults. We explained to him and he had a little bit of a meltdown. But, we’re good parents so we go down to the kids section – we’re just going to buy him a Cookie Monster outfit. And there’s nothing in Sears for kids for Cookie Monster, but there’s this adult top. So, I wore it for him and it cheered him up. He was happy again. I would wear it around the house.
My mom and I would go to Foxwoods every Saturday, that was our tradition. And one day I say to my wife, ‘I’m gonna wear the Cookie Monster down to Foxwoods.’ And she’s like, ‘You are not.’ Now she’s just throwing red meat at me because as soon as she says that I’m definitely doing it.
I had this plan that I’m going to hide the Cookie Monster shirt underneath my coat and keep the beanie in my pocket. I’m going to wait for the right moment to be like Clark Kent and reveal my Cookie Monster while saying, ‘Me all in.’
And the moment came, it was so beautiful. I have pocket eights and the flop came down 
. He checked, I bet, and he called. I’m putting him on ace-king. The turn came an ace and he checked again. I bet and he raises me. This is it: I’m going to do the ‘Me all in’ thing.
I stand up and I put the beanie on, I take my coat off – nobody knows what’s going on. I do it, I say, ‘Me all in,’ and the guy snap-calls me with a set of aces. And it’s like, ‘Wow, that went terribly.’
Well, you can guess the ending – I hit quads and the place exploded. I became the Cookie Monster, that’s the origin story.
Brought to you by the letters W, S, O and POn what’s next…
My wife’s a school teacher. She’s supposed to retire in nine years, our financial advisors that dig into this said this is how you get the full retirement. I promised her that if we win, we’re going to put some money away that will grow to equal a year’s salary. So, in eight years, if she wants, she can just walk away.
Other than that, paying off debt, getting a new roof. The tournament scene in our area is not great. Foxwoods has neglected tournaments for the most part and they increased the rake significantly. I’m old school, I don’t like greediness. Look, charge whatever you charge, but don’t put this extra 5% down here in the fine print. That’s shady. You don’t need to be shady with poker players. Foxwoods poker… I was a legend there and they blocked me on Twitter because I criticized them.
I’m coming back next year for the second Seniors High Roller and winning it. I’m the only person with a chance to do that. I may play the Super Seniors if it runs again because I’m over 60 and I have a tremendous edge. Some of them fall asleep but I have tremendous energy for a 62-year-old.
I’m gonna go back to cash games, $2/$5 grinding. I min-buy every time. I’m sustainable because I min-buy. I let other people bring the money to the table, I’m in no hurry. So, when I play tournaments, I know how to play the short stack. Why should I bring the money to the table if they’re willing to bring more?
This is who I am. The whole thing is so simple, but nobody will listen to me. All these young guns have come and gone, I’ve seen them all. Maybe they’re more talented than me, but they are not smarter than me.
You can follow Checkwicz on X, where he is known as Steamboat Cookie Monster.
