Jonathan Jaffe Talks About His Career Year On High Roller Circuit

Jonathan Jaffe has been on a red-hot winning streak for the last 12 months, cashing for more than $4 million worldwide. The Massachusetts native started off his 2023 campaign with a victory at the PokerStars Caribbean Adventure, and then cashed for nearly $1 million at the Triton Vietnam series in March.

Then this summer, the 36-year-old banked $1,537,600 by taking down the WPT Alpha 8 for One Drop high roller at the Wynn, at the time telling reporters that he still had yet to process the career-best win.

“I’m still kind of in poker mode and just going through the motions right now, but I know I will feel good.”

Jaffe didn’t have long to wait before his next trip to the winner’s circle, outlasting a field of top players in the $50,000 Poker Masters finale. It was another $756,000 for Jaffe, who then added more than $1 million with another win and deep run at the Triton Monte Carlo series this October. He now has nearly $11 million in career live earnings.

It’s hard to believe that just a few years ago, Jaffe was considering quitting poker and finding a different career. The former online heads-up specialist said that he never really had to work hard on his game away from the tables, but that complacency had let the game evolve past him.

During the COVID lockdowns, an old friend, who just happened to be one of the high-stakes circuit’s best players, inspired Jaffe to dig deeper into the game. Soon after that, Jaffe felt his passion for poker return, and the results came quickly.

Card Player caught up with Jaffe to pick his brain regarding the evolvement of his game and the joy he now finds in coaching players to new levels of success.

Craig Tapscott: Can you share some of your poker beginnings for those who don’t know your story?

Jonathan Jaffee: I had similar roots to many people my age after the Chris Moneymaker boom happened. I was in high school in Longmeadow, Massachusetts, and poker was getting popular. My friends and I would hold small tournaments multiple times a week.

CT: Do you still stay in touch with some of those players?

JJ: Yes. One of them was [three-time World Poker Tour champion] Brian Altman. He came from my town.

CT: Did you gravitate to online play during that time?

JJ: I put a few $100 on PokerStars and ran it up to a decent amount, enough where it was more than a distraction from schoolwork. I knew then that I wanted to do this for a living. My parents let me drop out after the first semester of college, and I started playing full-time. It was around this period that I decided to become a heads-up professional.

CT: I read you had a lucky swap to help build your bankroll at the time.

JJ: I did. I was just 19 years old at my first PCA event, and I had a five percent swap with my friend, John Ford, who was also a heads-up specialist. He got third [in the main event] for about $550,000. That swap was a good influx for my bankroll during that period.

I took the extra money and said, ‘If I lose it, I lose it.’ And I took shots playing $5,000 and $2,000 sit-n-go’s, and it went well. I felt at the time that I was as good or better than the guys playing the highest stakes on PokerStars. I was kind of shocked by my progress, in a way. I think within the next year or two, I felt like one of the top players on the site.

CT: You’ve since become one of the top MTT players in the world. What were you learning during this period playing primarily heads-up that would eventually transfer over to your MTT game?

JJ: Good question. The game was so different 15 years ago. There wasn’t much out there, especially for heads-up play.

CT: And not even precise ranges to play at any given position at the time.

JJ: Not at all. It was pre solvers. There weren’t clear hand ranges that were agreed upon. There wasn’t much agreement on how you might play preflop or flop strategies. But you still had all these different approaches floating around. So, you were constantly adjusting to your opponent. And I don’t think anyone, me included, could have done a great job of describing what they were doing well back then.

CT: Why was that?

JJ: You learned more subconsciously than anything in the sense that you’re just kind of getting a feel for the game. It translated into the idea that players had no suitable material to learn from. It was on-the-job training. It played to the people who naturally gravitated to strategy and picked up on player tendencies and patterns. My recognition skills were very good. It didn’t have much to do with who was studious or who was trying the hardest. I think it was a lot more about natural talent [at the time].

I have to admit that whatever was available, I was ignoring. I was arrogant and not interested in other people’s opinions all that much. Mainly because things had been going well for me, I could get away with that approach. But then I would have my reckoning not too long after that period, about five years later.

CT: What was happening?

JJ: Over the next few years, people were getting excellent data from their HUDs. People were comparing notes, and the most rudimentary solvers were beginning to form. Now the studious people were taking over, and it was much less about innate talent.

The solvers were carving out what might be the best preflop ranges while I was still playing differently preflop every day. I was watching my results get worse and worse, and I was enjoying the game less and less. At that time, I was also more interested in other life things, and my passion for poker was waning.

CT: How is that possible?

JJ: Anything’s fun when you’re one of the best. It becomes less fun when you’re just watching yourself degrade. I had been coaching some players, which kept my interest in the game, but aside from that, I wasn’t playing all that much.

CT: Did you stay in touch with any of your local poker friends?

JJ: I kept a close connection with my friend Nick Pertrangelo, who went a completely different route. As my game was starting to degrade, Nick began to branch out beyond my previous poker tutelage. He was learning from other people and was absorbing some great information and applying it to his game.

His goal was very different from mine. He was looking to have success in the biggest tournaments in the world. He took his competitive nature and channeled that into wanting to be one of the best in the game.

[Editor’s Note: Petrangelo succeeded, and to date has cashed for more than $32 million, mostly in high roller events.]

CT: Were you curious about what information he had been learning and applying as he started having more success?

JJ: I would say everything was more grounded in theory with Nick, and the concept of balancing was more critical. When you’re thinking about exploiting, you’re going to do it because this player doesn’t understand the situation. But when your opponent is playing a little bit more robotic, you can’t make this kind of soul read and say – they never have a huge hand there when they call.

The concept of balancing was becoming more universal and not just something that a few of the best players were employing. As balancing ranges became more common, exploitative strategies became less effective, and that had been the crux of my strategy approach previously.

CT: What was the turning point in your conversations with Nick that brought your passion back for the game?

JJ: It was last summer. Nick had convinced me to go to Cyprus to play the Triton events. I decided I finally had a real reason to put in a lot of study effort, as I was going to be playing with the big boys. The studying became very applicable again. Because these players are good, I can’t just kind of run them over with rudimentary exploits.

It gave me the motivation I’d been lacking to try to improve as a player. That was a real turning point for me. I enjoyed the game again. The studying just felt like this esoteric endeavor in the past. I don’t reasonably need as much studying or solver material to play my best game in a $3,500 WPT event. [Editor’s Note: Jaffe won the CAD$3,500 WPT Montreal main event in 2014.]

But if I’m going to play $700,000 in buy-ins against the best players in the world, I’m going to need to know my shit.

CT: Can you share some of what you were focusing on?

JJ: I was trying to learn heuristics for different kinds of setups. I learned to understand the difference between what 30- and 20-big blind play look like in a more nuanced way.

I was also getting very familiar with ICM (Independent Chip Model). Anyone playing the high rollers, their studying is going to be highly concentrated on ICM because that’s where the big money mistakes can happen. But also because you are in ICM situations so frequently. Making a final table is not an aberration. You’re always there, and I needed to study these scenarios more closely.

CT: Can you tell me what you have enjoyed most about being a coach.

JJ: I think one of the gratifying parts about coaching is trying to find the communication style that will work with each student. Because if they’re just looking at a solver output, it can be very daunting to try and make a pattern out of all these different shades, and looking at the grids can be pretty intimidating.

The most satisfying thing as a teacher is when you can see it click for them, and there’s a crescendo of knowledge they’re grasping. That’s very rewarding.

CT: Where do you see yourself in 20 years?

JJ: I really like writing. This past year I’ve been researching a book about the high-stakes tournament world. I’ve been interviewing a lot of players. It’s been fun. And I’ll continue to coach as long as I find that interesting. But in 20 years, I have no idea where I’ll be. I think the only thing I know is that I don’t know. ♠