Jonathan Jaffe: WPT Champion and Heads-Up Poker Specialist

In the world of professional poker, it is incredibly difficult to achieve the longevity that has been maintained by PokerCoaching.com coach Jonathan Jaffe. Since establishing himself as one of poker’s best heads-up sit & go players in the early 2000’s, Jaffe has gone on to excel in just about every variation no-limit hold’em has to offer. A proven cash game crusher and reigning champion of the recently resurrected World Poker Tour (WPT) Alpha8 super high roller tournament, Jaffe’s commitment to study and execution provides results regardless of the game being played. A seasoned poker coach who can be found hosting webinars when he isn’t winning on the felt, the countless hours of strategy content provided by Jaffe reflect years of dedication to the game of poker. In preparation for his next big contribution to cash game content on PokerCoaching.com, Jaffe took the time to chat with me about the upcoming Advanced Cash Game Course and reflect on his career.

Poker Origins, Poker Friends, and Leaving College Early

Born and raised in Longmeadow, Massachusetts, the early days of Jonathan Jaffe are reflective of many poker pros who were in their teens or early twenties during the Moneymaker Boom.

“I was a freshman in high school when Chris Moneymaker and the 2003 World Series of Poker was going on,” Jaffe said. “All the guys in my high school who liked either sports or games also seemed to be into poker. ESPN did such a good job creating all these storylines and archetypes in a really fun way. We were all like ‘whoa’. It wasn’t like basketball where you can’t really emulate Michael Jordan, but I can go into my basement with my boys and flop a set of fours just like Phil Ivey. Poker has that accessibility where you can jump in and start winning in the short term, and that was really appealing to a bunch of young guys with big egos.” 

Even at an early age playing for small stakes with friends, Jaffe could tell his poker abilities were better than most.

“We played a lot of $5 to $10 buy-in cash games and $5 to $10 tournaments. Everybody thought they were the greatest in our little circle, and I was no different,” Jaffe recalled. “Poker in the early 2000’s really fit me nicely. If I had come up in the poker climate of today, I think the need for developing strong technical skills would have been too great a barrier of entry for me. When I was starting out, if you had a good strategic mind and could get a good feel for your opponent’s strategy, that could go a long way. I wasn’t reaching out to other players or looking at 2+2. I can tell you I had already been a professional for years before I saw my first preflop chart. I was just carving out different ideas, and my ego definitely got in the way of letting myself learn technical skills.”

In his adolescence, Jaffe met individuals who would later go on to become his pro poker peers. Growing up with fellow WPT champion Brian Altman, Jaffe would also cross paths with high stakes tournament crusher Nick Petrangelo.

“Nick and I met when we were 17,” Jaffe said. “We had a few strange connections, it took us a few times to actually get together. We first met at a home game hosted by my college floormate who knew Nick. We quickly realized we were the only two guys who had much of a clue, but we didn’t hit it off in any friendly way. Two months later my step-mom came into my room and said ‘We just gave a ride home to your friend. Do you remember Nick Petrangelo?’ It turned out that Nick missed a train coming home from New York, and he was asking people at the station for a ride. My parents gave him a ride home, got to talking, and he recognized a lot of me in my Dad and asked them if they had a son.”

After another mutual friend informed both Jaffe and Petrangelo of each other’s poker prowess, the two eventual poker pros would finally come together to discuss strategy.

“My childhood friend was his prep school roommate,” Jaffe said. “He kept telling both of us how they had this other friend who was also really good at poker. Eventually, Nick decided he needed to investigate, and we then started hanging out and watching each other play.”

Jonathan Jaffe following his seven-figure win in the World Poker Tour Alpha8 for One Drop (Photo Courtesy of PokerNews)

The Genesis of Iftarii

At the age of 16, Jaffe would use the pay he received from working as a summer camp counselor to make his first deposit on PokerStars. Not wanting to alert his parents to his intentions of gambling online, he secured a money order from his bank and deposited $200 to the site. Starting with online no-limit hold’em tournaments and cash games, Jaffe eventually found his way to heads-up sit & go’s two years later. 

After graduating high school, Jaffe already knew what he wanted to do in life, but the desire of Jaffe’s parents for him to attend college would cause a minor detour in his path to becoming a poker pro. Willing to work it out with his parents, Jaffe eventually agreed to attend university and began his brief stint in higher education. 

“I promised my parents I would attend college despite being self-sufficient money-wise due to poker,” Jaffe shared. 

“I attended Westfield State University, it was a college twenty minutes away from my house. My Mom said to my Dad and me ‘You guys have to start your college search’ so we went there because it was close. We got to the parking lot, and there was a tour starting. I turned to my Dad and I said ‘Look, if we don’t have to do the tour and can go to lunch, I’ll go here.’ And he said ‘Okay’.”

After enrolling at Westfield State and attending for a semester, Jaffe finally received his parent’s blessing to drop out and pursue a career in poker.

“I asked my Dad every night if he was ready to let me drop out,” Jaffe shared. “After my first semester they let me out, I was free to play for a living.”

Finally able to devote all of his time to poker, Jaffe fully immersed himself in the world of online poker, along with some memorable live cash game sessions.

Make the best preflop decisions with Jonathan Little’s Push/Fold Charts!

The Cash Game Career of Jonathan Jaffe

While Jaffe was making a name for himself playing online heads-up sit & go’s, he also earned a seat to an incredibly lively private cash game. Recalling some of his more memorable moments at the cash game tables, Jaffe shared how his straight-laced, 18-year-old self found a seat in what could only be called a Degen Game. 

“Early on out of high school, I was fortunate to be plugged into a pretty cool private game,” Jaffe shared. “In some ways, I was in over my head. I was a straight-edged 18-year-old who had never smoked weed or anything like that, and I was playing in a game that started at midnight and ended at 8 AM. Guys would occasionally do cocaine off of the table, and I even got partially paid out in fake money once. Regardless, it was still a great game and a lot of fun.”

With success, Jaffe eventually moved away from the lively game as he continued to move up stakes playing online heads-up sit & go’s. While Jaffe would build his career on being one of the best online heads-up sit & go players, eventually the game variation became less profitable and accessible. Looking for a new way to make a living from poker, Jaffe transitioned to playing tournaments full-time, but not without making some money in the cash game streets.

“In 2013 I walked into the Bellagio just looking for something to do,” Jaffe said. “I decided to play cash and sat down at $25/$50 and it was a very good game. There was a very good action rec who would sit with $100k and the game was incredibly deep stacked. I did not know if I was going to be a winning player due to how aggressive I usually was, but I played five or six sessions and it went well. From there, my ego spun that into ‘okay, I’m a good cash game player’.”

A few years later after moving to Florida, Jaffe’s boredom would lead him back to the cash game arena. 

“I was looking for something to do to augment the coaching and backing I was doing. I kept my eyes on Bravo, and saw that there was a $25/$50 game running at The Isle at Pompano Beach,” Jaffe said.

“I made my way to the casino and saw that it was actually a $25/$50/$100 game. I only had about $17,000 on me, but I decided to sit down with that. They all looked at me kind of funny. There were a few recreationals but the rest seemed like pros, but I didn’t know who any of them were. I played really aggressive, basically broke even, and just a couple of days later one of the pros found me on Facebook and invited me to play. Clearly, he thought I was good action, and I was fortunate enough to stick in this private game. The recreationals took a liking to me, and half the pros thought I was a whale. The other half were like ‘don’t do this, this is not a good idea.’ Eventually, all the pros came to the conclusion that inviting me had in fact not been a good idea.”

Jonathan Jaffe following his WPT title win in 2014 at Playground in Montreal.

Being a PokerCoaching.com Coach and the Advanced Cash Game Course

In 2008, Jonathan Jaffe would go toe-to-toe with the man himself, Jonathan Little. Heads-up in the WPT World Poker Finals at Foxwoods Casino, Jaffe and Jonathan faced off for the $1.1 million top prize in what would be a marathon of a duel. Despite heads-up play beginning at 10:30 PM, both Jonathans would play a total of 275 heads-up hands over the course of five hours, a WPT record at the time. At the end of the marathon heads-up showdown, Jonathan would come up on top after his A-Q bested Jaffe’s A-10 during the final hand. 

Even with being on the receiving end of a heads-up loss to FieryJustice, Jaffe would eventually coach Jonathan as well as join Team PokerCoaching.

“Jonathan was one of the first people to ever hit me up for coaching,” Jaffe said. “He asked me to coach him in heads-up. I’m not sure what all we did or if it was one session or three sessions. Not that long after, and maybe this had been Jonathan’s plan the whole time, he asked me to do some videos for Float The Turn. Many years later, after Jonathan started PokerCoaching.com, he offered me to come aboard and do some coaching. I was intrigued, and now I really enjoy it!”

Contributing to PokerCoaching’s quizzes, courses, and challenges, by far the most popular content put out by Jaffe is his webinars.

“Going into it, I was thinking a lot more about being a perfectionist and pumping out videos where everything was correct,” Jaffe recalled. “I could say everything that I wanted, but it took a lot of time and the product came off a little bit more sterile. Jonathan suggested webinars from the get-go, and they are a billion times better. What I really enjoy is the interaction, being able to go back and forth and ask the audience and see what they say about a different spot. I try to react to that and give them some different answers to their questions. It ends up being a really pleasurable experience for me. I really appreciate all the members that come to the webinars, it makes it more fun for me when I have a big crowd.”

Jonathan Jaffe playing $1/$3 with PokerCoaching members
at the 2022 company meet-up game.

Heads-Up Cash Games and Jaffe’s Upcoming Book on High Stakes Tournaments

While Jaffe continues to provide popular webinars to students, he has also been collaborating with coaches Jonathan Little, Brad Wilson, and Justin Saliba on PokerCoaching.com’s upcoming Advanced Cash Game Course. Specifically focusing on heads-up cash game section of the course, Jaffe looks forward to helping students improve their play when only facing one opponent.

“Members are going to come out with a better understanding of how the heuristics change at different depths and what kinds of combos they want to be using for check-raises on the flop,” Jaffe said. “Learning just how dirty turn play gets compared to what other players are doing, there is going to be a lot of familiarizing with overbets both on the turn and river.”

“There’s just a ton of information when you are adjusting to playing heads-up deep-stacked cash because you have to fight it out with so many b******* hands. What every member takes away will be different, but there is a wealth of information when you are trying to get good at heads-up. I’ll do my best to unload as much as possible in a clear manner.”

As Jaffe continues to develop the upcoming Advanced Cash Game Course, he also has plans to eventually release a book detailing the behind-the-scenes of the high roller poker tournament scene. Drawing on his experience as well as interviewing other high stakes tournament pros, Jaffe hopes to provide poker fans and players a glimpse into the world of the nose bleeds.

“The book is about the culture of the high rollers,” Jaffe explained. “It’s meant to be a look behind the curtain from someone who plays them about what it is like. It’s not meant to be a big commercial book that draws in people who don’t play poker, I think a lot of the PokerCoaching members are the heart of the audience.” 

With the goal of providing a book PokerCoaching members would want to read, Jaffe hopes members are willing to provide feedback on what they would like to learn and read about in the book.

“It would be cool to solicit some ideas from PokerCoaching members,” Jaffe said. “I’m curious what people want to know about, I might get some interesting surprises!”

If you would like to support Jonathan Jaffe and contribute some ideas on what you would like to read about in his eventual book on poker’s high roller tournament scene, please comment below this article!

Conclusion: Get Ready For The Advanced Cash Game Course!

A special thank you to Jonathan Jaffe for taking the time to discuss his career, the game of poker, as well as the work he has been doing on the upcoming Advanced Cash Game Course. Be sure to check out PokerCoaching.com’s newest course, set for release this November. In the meantime, if you are in need of cash game content and can’t wait until November, check out Jonathan Little’s preflop strategy for crushing cash games!