Mike McDonald Interview: Chess, Marathons & Looking Back on Poker

– What's the story with Cayman Islands? Do you live there now? How did you end up on the team?

Yeah. I moved to the Cayman Islands about five years ago. When I moved here, there was very little chess. We've had a chess club, which met at this wine bar, which is actually pretty cool. I guess if you went through the world and saw hundreds of thousands of chess clubs, and you think of what setting most of them are in, this wine bar on a tropical island in a kind of a heart of the financial sector is a very cool setting for a chess club, but the chess itself wasn't that great. Not many youths were higher than 1200 on chess.com – perhaps, two or three in the whole country. And there were only about four FIDE rated players. Even though my chess was a little rusty, if the strongest players showing up were maybe 1600-1700 chess.com, I had a decent shot.
I don't like chess without a clock. I just feel like the time is the resource. Whoever's losing, they take more and more time. I'll play bullet, rapid, blitz, or classical, but I don't like blitz that turns into classical, and there was a bit of that. There were also not many tournaments. Over the last few years things got more organized. We had the Cayman Championships in 2024. Or maybe there was one before I participated, when I was just not playing chess. I played 2024 Cayman Championships and I got second place. When the previous Olympiad was going on, I'd been on the island a little under three years. And I think the rules (I don't know if these are Cayman rules or FIDE rules) were something like you had to have been a resident in your country for three years, or be a national champion. And I'd been, you know, 32 months in and second in the national championship, so I missed the 2024 Olympiad. But after that I hit my time eligibility and also won the national championship.

I've been fairly active with chess the last year and a bit, played just about every weekend tournament we have, go to the weekly chess club most weeks, just getting more into it. And now the number of kids that are over 1200 on chess.com is probably like 40. It's been a really good growth in youth chess in the last few years, that's been really nice.

– Do you and the team have coaches?

Online I'm coached by Eric Hansen, but its not seriously training chess, I don't think. It's more like a golfer or tennis player who is always getting lessons and is never really improving. I played the Olympiad and probably got three or four hours of lessons being like 'Hey, Mike, you need to stop effing this up'.
Anyway, he is my coach, and also Cayman Islands national team has a coach IM Jomo Pitterson, with whom we do a weekly Wednesday night call where we'll do various tactics or positional things. He gave advice on openings we should play and helped with some of our prep at the Olympiad. Both Jomo and Eric are my coaches online.

– I noticed that every member of the team in the Open section gained rating, so I guess the team's performance can be considered a success?

Yeah, I was kind of thinking about that. That was quite nice to see. Every country and every club thinks they are underrated, but if our men's team gained about 80 rating, and the women's team gained about 150, it's nice to bring a few hundred points back to the country! It's less fun when the youth school travel to some tournament, get away a hundred rating points, then they come and farm it off me.
I think we all played a pretty good tournament. Not saying we played amazing, but maybe Olympiad brings in some overrated players. I think there are some people who only play one tournament every two years. Maybe they were a 2200 twenty years ago, but not anymore.

Also, our Board 3 is one of the worst players I've ever seen with the clock. In a 60+30 format he might be more like an 1800, and in a 90+30+30 format he might be more like a 1900 kind of guy. When we'll have a 6 or 8-round classical tournament, he often flagging two of the games, one in an equal position, one in a better position, even with the 30-second increment. So I think his raing being 1830 or something isn't very reflective of his actual level. I'm not saying he should be 2100 or anything, but for him the more time the better, while for me 60+30 or 90+30+30 are all the same, I don't think it affect my playing strength. If there are 1000 men in the Olympiad, I'll guess he is one of the top 20 who benefits the most off of the increased time. That's a bit of a factor.

And then I think our Board 1... He's been teaching chess for a long time. He is a little bit older than me, but I don't think he played much tournament chess from the time he was 12-14 years old. He didn't think he could be the best player in Jamaica, but when he moved to Caymans, he figured he could be the best player in Caymans. So I think for him, when he plays some of our local tournaments, maybe he doesn't play to the best of his ability. When he and I play chess, are games are about equal, but when we talk chess, I learn a lot from him, and he doesn't really learn anything from me. I think his chess understanding might be more like a 2100, but I get everything out of myself, and I don't feel the same about him when he plays local tournaments. But playing at the bigger stage, I think he brought more seriousness.
And also, Shaun, our Board 4, I just think was a bit underrated. He had a bit of a drop, and I think of him as an 1800 player, but at the Olympiad he was like 1730, which doesn't really feel right for him.
As for me, I think I am at my rating. I am closer to 1850 than to 1950.

– Which of your games at the Olympiad is the most memorable for you?

I guess, my game against Nicaragua, round 6. I played against Arauz Espinoza, 2041 (view the game here).
I feel when I play chess I am mostly a tactical player, and think of myself as a poor positional player. I do tend to try and mess the games up, make them as tactical as possible most of the time. In this game he played very quickly and much better tactically than I did, and I felt positionally he played quite poorly. A bit rushed with some of his moves. I was happy when I played Qxe6.

Quite an unnatural move, but it helped me equalize, and I don't think he analyzed it, assuming that I'll play a more natural fxe6.
And then I completely mishandled trading off the minor pieces to get into an endgame. I was trying to calculate, but positionally I played into a lost endgame. For me it was a good example of playing against someone whose rating is not that different from mine, where I shouldn't just try to outcalculate people.
Couple of times a year I'll get paired against a 2300 player, and it doesn't really matter what I do, I'm gonna lose. But here it was a game against a beatable opponent whose rating is not that different from mine, who played a somewhat poor game, and somehow I played an even poorer game. He let me get back into the game two or three times, and each time I mishanded my time.
This is a good example that there are players who are stronger than me whom I could beat in a positional fasion. And trying to make the game more tactical, especially against younger players, is not always the best way. If I were to play this guy a match, I should probably favor a more positional setup than I like. This is why this game stood out to me – a beatable opponents not on his best day, but my approach to the game set myself up for a failure.

– Have you already analyzed your games?

Not yet. I had a 4-day trip after the Olympiad, so I will dig into those games some time this week. During the Olympiad, I just checked briefly for blunders with Stockfish, but this is not a proper analysis, of course.

– Did you have a chance to use your famous stare during the games?

Haha! One thing worth mentioning, I really don't enjoy eye contact! People hate when I stare at them, but I bet I hate it more than they do, nine times out of ten. I never enjoyed it, I just think it will like help me a little bit. And chess – first of all, it's my hobby, I'm not nearly as serious with chess as I was with poker.
However, once I feel my position gone from equal to winning, I do kinda like looking up at the opponent, just to see if they feel the same way, haha. I like looking at the person more than staring at their eyes.

My Round 11 game was one of the worst games I've had in terms of blowing a better position. And that was where my opponent had no poker face whatsoever. He was very much showing on his face that he is just done with the game, If my rating was 2200, he probably would have just resigned. But I totally went from my opponent just looking so dejected, looking like why am I even here, into him winning the game, haha!
(View the game here)
I'm very glad that it was Round 11. If that happed in Round 7 or 8, it might have been tougher to recover from. But not having to play any more chess after blowing that position was a little bit nice.

I missed the strength of Qb6+. When I was debating how to recapture on h6, capturing with the bishop felt more natural, but I was a bit low on time and just thought, ok, let's recapture with the knight. And I just totally missed the strength of Qb6.
I was looking at a few lines, and I think I saw a position where I can get into a queen and pawn endgame up like two pawns. And I think I got greedy. At this point I only had 10 minutes on the clock, and I wanted to visualize the position that is like dead won, but didn't see any in my calculations. I think there were one or two positions where I could've calculate further or evaluate them better.
I think if we were played a 3+2 blitz, I probably would have incorporated Kh2, just as a rhythmic move defending against Qb6.

But with the 30-second increment I was too focused on looking for a more precise calculation rather than let him have the ball on his court. And I think I overlooked a few ideas in a row to give him an upper hand there. That was quite demoralizing.
So, I don't do staring in chess. Maybe I would if I didn't like my opponents, but I like most of my opponents. Every now and then I play a poker homegame and have the instinct to stare, and I'm: wait, I don't have to do this! This isn't my job anymore! I can just play poker for fun, and it's kinda nice.

– At what age did you start playing chess?

I learned how the pieces move really young. My memory as a kid was sort like I always remembered knowing how to play chess. My dad must have taught me the moves when I was 3 or 4. And I think I knew en passant existed, but never knew how it worked. Maybe I played a five games of chess when I was 3 or 4, and then none at all until I was 11. I think my neighbor got into playing chess at that time, against ChessMaster 7000 or 8000. He was getting into it, and then I got into it and found there is a business in our town that was giving chess lessons, group lessons where you work your way through things. I started doing that when I was probably 11 or 12, and I really dove right in. I got pretty hooked on chess for the next 3 to 4 years. And then I found out about poker right before my 15th birthday. I continued playing chess on my high school chess team and stuff for another year or so, but I would never study chess and wouldn't go play like three hours of blitz before bed. It used to be: I have free time, let's play chess, and it went to “let's play poker”.
So, I was in chess for 4 to 5 years as a teenager, but once I started playing high stakes poker and I've graduated high school, I played zero chess until the 2018 World Championships. I watched that on Twitch. I've been out of poker for a few years, and I like to compete at, I like to have some goals to work on. So I got back on chess.com.
Weird thing, I didn't see any of Magnus Carlsen's career. I knew he is the second youngest grandmaster, and the only thing I saw was when Anish beat him, when he was 16 or something and thought to be the next Magnus Carlsen! I really was so focused on poker that didn't pay any attention outside of it.
Didn't really see Anand being a World Champion, didn't see Magnus dethrone him. I was just solely focused on poker from 2004 to 2018 and missed the whole Magnus era – a bit strange thing to hear from someone who is just 37 years old!

– Are you still a semi-retired poker pro? Or is it full retirement? No WSOP return planned?

It's been full retirement for 10 years. I don't think I played a tournament in 4.5 years, and I don't think I played a WSOP in 7 or 8 years. It's been quite a while there. It's interesting how little I miss it! Competing at quite low-level chess or competing at quite low-level marathon running kind of makes chemicals in my brain fire in a similar way, and I feel excited by that competition.
I don't really think I ever cared that much what stage I'm on in poker. Whether I'm playing a $250k Superhighroller against Phil Ivey, or playing a $22 rebuy online, it never felt that different to me. And when I look at my peers, I feel that for most of them the favorite part of their poker career is when they played at the highest stakes, competing with the best in the world, competing on TV, and things like that. For me, I think, my favorite stage in poker was working through the ranks. The first 3-4 years, when there is always the next level, you hitting the next achievement, and so on. Can I get from $100 games to $200 games? Then to $500 games? I enjoyed playing at the high level as well, but I don't think I enjoyed it as much, as when I was learning and improving every day. In that regard, I don't really miss world class competition at all.
Once in a few years I have a brief thought that I could get good at poker again, after watching a poker video or playing a home game. But then I realize that I don't think I would enjoy getting to a level lower than I was at my peak, and I don't think I would enjoy the effort level required to get to my old peak. And maybe it's even impossible for me to get as good as I once was.
It was an amazing chapter in my life, but not really one I think about. There are people whom I've known for years from chess comminuty or running community, who have no idea about my poker career. Even in Uzbekistan – it's always a little bit funny when during the tournament a few big name chess player would come talk to me. Peter Svidler is probably the most notable one. Someone told me Hans Niemann wanted to meet me, although we didn't end up chatting. There were some other strong GMs. And I think everyone in the Cayman team would always be a little bit surprised when a 2700 would come and chat to me. Like, WTF?
I'm not opposed to talking about my poker career, but I don't like to forcefully bring it up. “Oh, this reminds me when I was playing Daniel Negreanu!” – “Oh, nice to see this young GM! This reminds me of how I became the youngest EPT winner of all time!” It's not really relevant in conversations. It's a closed chapter in my life. If anyone asks a poker question, I am happy to answer, but it's just not that relevant.

– Looking back, are you satisfied with the choices made regarding your poker career? Anything you wish you would have done differently?

Um, that's a good question!..
I took a year off at one point. Doing that was stupid. If life is a journey and you take it year by year, maybe I had to take that year off to gain some perspective or something, but looking back at my poker career now I would have just said: this is something you are really good at, you are competing at a high level, and someone else is going to work their ass off the next year. So, it was a pretty dumb thing to do.
I think that I also would have benefited from – how would I describe it? Golf is a good example. A lot of people prefer practicing something they are already good at. They are bad at putting, but can drive the ball well, and they keep practicing their drive. When I look at my poker, I think I was somewhat that way as well. I would often lean to the things I am naturally good at. And I was a bit careless with the things I'm naturally weak or undisciplined at.
I am quite good at coming up with my own strategies or taking a fairly new strategy and iterating on it. Basically, when everyone shit at poker, I think I am really good at dominating someone as much as possible. As people get better and better, and it comes to picking the exact right combos, especially using a solver-type input or simpler pre-solver tools, I think I am not naturally good at that, and also I have quite a low discipline at working on my weaknesses.
Yeah, I think I am maybe more gifted than most people at learning poker in a short period of time, but I didn't use as much discipline working on the things I am less gifted or just average at – and usually you are supposed to work on them more.
At the ultra high level of poker, I'd see people who are definitely more gifted than me in their memory of hands. Or, in particular, and it really stands out for me, some people are different in the way how they parse the information: “Okay, this guy checks too many flops, therefore he'll be too value-heavy with his turns bets”. All strong poker players are good at taking one small piece of date and make good inferences of it. But when you see the best players, they really stand out. Someone like Trueteller, or Sauce, or Ike. When you see, how much they are better than you are, it can be somewhat intimidating.
I was maybe more gifted than some of the best players in quick calculation, rapid mental math, but I took for granted the things I was good at, and was a bit of a hater of some things other people were good at. What I didn't do is – “these guys are so good at their inferences that I just have to outwork them!” What they can learn in 50 hours with a solver, I can learn in a 100 hours, and if I spend 150 hours, I can start beating them. Spending zero hours instead wasn't a good choice.
Even if solvers hurt my ability to get to the top or stay at the top, I probably should have been more diligent with using them, in order to at least pass other people who were similarly lazy.

So, those would be my two regrets. The actual duration of my career – no, I don't regret cutting it short or anything. I think I wanted to give poker everything I can with the intensity to compete with the best in the world. I had very little time when I actually thought I'll be the best player in the world, but I had a couple of years of sort of thinking that was viable, and the sort of intensity required to pursue that.
Overall, I am happy with what I achieved, happy with the level I reached, and don't really care if I could maintain that level for another five, ten or twenty years.

– The way you describe your strengths and weaknesses, it looks like you are naturally predisposed to mixed games!

In Canada the tax situation is better for playing in the countries other than the US, and the mixed games are so much American-dominated, playing in Las Vegas, etc. I do think if I was American, I likely would have become a mixed games player. There are so many forms of luck in life that don't exist because I was born 50 kms north of the border. Probably because of that I became a tournament player instead of a mixed-game player. I was always mindful of logistics, taxation, and things like that, and decided not to get seriously into mix, but maybe mix would have been good for me.
Mixed games also have such a good longevity. I remember at some point players poured so much time into Chinese poker, but people barely play Chinese anymore. However, in the moment it felt like dedicating your life to Chinese poker made more sense than working on mixed games. But they've really stood the test of time, which wasn't obvious at all in 2008-2012.

– What are you doing now, besides your hobbies?

Um, not much, to be honest! Which is kind of nice. Investor, I guess, is the main thing. I am not doing nothing, but I have a freedom to take two weeks off for a tournament and not be too bugged about it. For all I know, maybe a year from now, maybe five years from now, I'll be fully focused on something and putting 60-hour weeks, you know. I'm not opposed to starting some sort of business in the future, but right now I am kind of relaxing.

– Are you on Huck Seed’s level for running?

Oh. Definitely not in shorter distances. I don't know what longer stuff Huck's done. Maybe we could try racing each other in half marathon or something like that. I haven't run a sub-3-hour marathon, but I've run 3 hour and 0 minute marathon – 3 hours and 25 seconds in my last one.

– Ouch.

I'm hoping to go into low 2-50s in my next one, mid 2-50s would be great as well. I run probably 8 or 9 hours a week. I'm more into running than I'm into chess, but those are my two main hobbies. I quit drinking a year ago, which definitely helped!
Everything I do, I do a bit excessively. For a few years drinking was the thing I chose to do excessively, and quitting that has been good for the lifestyle in general, but also just for running. The number one thing to improve in running is to run a lot, and number two is don't drink. It just helps so much for your recovery! It's not really the running that makes you a better runner, it's the recovery from the running – how your muscles repair, how your heart and lungs adapt to this.
When you look at these fast marathon runners, it's almost comical how fast these guys can go for two full hours. They go for two hours with the speed very few people could run for one minute, and many people can't run at their top speed for one second. But when you are running 15 hours a week, your heart and lungs adapt so much, by years and years from recovery. Unlike muscles, your heart and lungs are not visible, and it's not obvious that the guy sitting next to you has the healthiest heart in the world.
So, quitting drinking helped a lot with running, and also helped with weight loss. It just snowballs in a good direction.

– I assume you know your VO2max?

My watch tells me it's 57. It's based on training in hot weather, cause I live in a hot, humid place year round. When I go and run a cold race, I always get a boost. I would guess if I were to go and spend a month training somewhere with good running weather, it would go up a few points, like up to maybe 59 or something.
If you take people, who run marathon time around me, I would guess there is nobody under 50, and if you see someone over 65, that means they have quite a bit of untapped potential. I'm sure there are people who have a 75 VO2max, who run a marathon similar to me, but it just means they should be running 2:35, and they just don't have the lifetime miles. And if we were to go race a 5 km, the person with the 70 VO2max would beat me by a minute and a half, maybe by two minutes, basically regardless of their training. Maybe they are playing soccer, or do cycling, or swimming, and barely even run, but they'd still crush me completely.
It's a very common thing in running – playing the thief of joy. Say, I've been running for two years, you've been running for six months, and you beat me by an insane margin and post about it on reddit – but you have 15 years of near-professional cycling training under your belt. And it converts really well. All those Nordic skiers with VO2max approaching 100 can just show up and give a top 1% time in any local race. Magnus Carlsen can't just play Go or Scrabble at the top level. If he plays go tomorrow, he'd probably be below average in a go tournament.

– There is a Japanese Shogi player, Yoshiharu Habu, a legend of the game, who tried working on regular chess for a short while, and quickly advanced to an international master level.

So some games are really close to each other.'

Oh, interesting, I didn't know that. It's kind of cool and awesome.
In chess, by the way, some people also have a history of playing, but pretend that they don't. You played at your local school chess club with strong youth players, maybe didn't get a FIDE rating, but maybe you were 1600 strength. Now you come back to chess when you are 30, you play for three months, get 1600 Elo and start telling people that you've only been playing chess for three months. I feel like I see it a decent amount. Probably more in running than in chess, but quite a bit in both. It's almost like they want to steal the joy of someone else's progress by misleading about their own progress.

– Well, everybody wants to look talented.

Yeah, exactly. But I think poker taught me that being talented is... is kind of nothing. What you really wanna do is be the best you can be and achieve the most you can achieve. And your talent is really kind of worthless. If you are of equal ability to someone, and you have more talent than they do, it means they achieved more than you have, and their decisions have been better than your decisions.
I think of Stephen Chidwick as a decent example. I always felt he was one of the most underrated poker players. When people were listing off their top-10s, I'd always put him in a conversation, but I wouldn't hear many other people talking about him. Now, fast forward to this era, he is one of the absolute best, and it would be kind of crazy not to list him in any kind of a shortlist. I would think of him as someone who can achieve much more than a more talented person over a 15 or 20-year window through extreme dedication and staying level-headed, staying away from your biases. He stayed diligent for a long period of time, when very few people have. He is definitely one of the top players, and his success comes very much from the things he's earned. He'd be a perfect example of a career that you can be very proud of.

Mike McDonald Interview: Chess Olympiad, Marathons, & Looking Back on Poker