I Flew to New York to Play Hustlers
Note: I did not actually go to New York and Boston just to play chess hustlers.

I Flew to New York to Play Hustlers

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We've all seen the videos on YouTube, a chess hustler playing a "beginner" in the park, only to realize that this "beginner" is actually a master. Though I've always wondered, what is a chess hustlers rating? Obviously, this question can be answered with a quick Google search, but that would be no fun. The more practical way to answer this question is to actually play against a hustler! In this blog, I will discuss my experience playing against chess hustlers in New York City and Boston, and finally be able to answer the question, what is the rating of a chess hustler?

New York City

A cringe picture of me in Times Square, New York City.

New York City chess hustlers have been a staple of Washington Square Park for decades. It is rumored that a young Bobby Fischer used to go to the park to play chess. When I first arrived at the southwest corner of Washington Square Park, I spotted an empty board with a chess hustler sitting across the table. I sat down and "Beanie Man" explained the chess hustling guidelines. The hustler explained that if I won the game, nothing would happen, though, if he won the game, I would have to "donate" five dollars. Here's how the games went. 

Game 1 vs. Beanie Man

I wasn't sure what to expect playing against a chess hustler, from what I've seen online, I knew that he would play an unconventional opening. I was considering pretending to be a beginner, though if I lost that would be quite embarrassing. I decided to play my own game and here's how it went. 

Quite a balanced game, judging from this first game, I would give my opponent an online blitz rating of 1800. Although values my opponent's rating at 1950, it also values my rating at 2400 which is clearly inflated. I initially thought hustlers would be much more aggressive and go straight for the attack, but "Beanie Man" seemed quite reserved and made a few positional mistakes before blundering the c8 bishop.

Game 2 vs. Beanie Man

Washington Square Park, New York City.

Following the first game, I am more confident that I could win, knowing that this chess hustler isn't extremely strong and could easily blunder. Although this game was much harder to win, my opponent definitely put up a fight. Let's see how it went down. 

This game was definitely more balanced compared to the first, instead of winning off a tactic, I had to trade and eventually get into a winning rook endgame. Even though I did not play the best, my opponent made it quite difficult for me to win, I would give my opponent a blitz rating of 2000. I wish that the hustler would be more aggressive, as it is hard to judge someone's rating when they are always passive.

Overall, I would say that this hustlers blitz rating would range between 1800-2000. Something that I noticed is that this hustler was not talking any smack, on YouTube, I often see hustlers talking trash or attempting to entertain/distract their opponent.  Though after winning the second game, the hustler must've realized that I was a waste of his time and that he would be unable to beat me, I was not offered another rematch. 

Game vs. Johnny

Washington Square Park, New York City.

Having previously watched a video by Anna Cramling, I immediately recognized "Johnny" sitting at his table waiting for an opponent. I approached him and asked if he would be interested in a game, he charismatically said yes, though I had to pay a five-dollar fee to play him. Knowing that he would be fun to play against, I decided to pay five bucks for one game. Here's how the game went.

I can't tell if I had gotten scammed or not, I had just paid five dollars hoping for a good game of chess, only for it to end in Johnny blundering a queen. Now despite this oblivious blunder by my opponent, I would give Johnny a blitz rating of around 1600 judging from the opening and the games he played against Anna Cramling. After this game, I had decided it was time to leave the park as I realized that New York chess hustlers were not as strong as I thought.


Boston, Massachusetts home to 4.5 million people.

I decided to search for New York's strongest chess hustler, Russian Paul. However, I was unable to find him during my two-day trip. So instead, I decided to visit Cambridge, Massachusetts. Why? Because Cambridge, Massachusetts is one of the smartest cities in the world, home to two prestigious universities, Harvard and MIT. Due to the common stereotype that chess players are academically smart, that must mean that I will find stronger chess players. 


Harvard University founded by John Harvard in 1636.

Harvard University is a private Ivy League university in Cambridge, Massachusetts. My cousins had told me that there were chess hustlers at Harvard Square, so I decided to go see for myself. Unfortunately it was quite cold that day so I decided to go in the Richard A. and Susan F. Smith Campus Center to get breakfast. I then spotted a chess hustler named Doc setting up a board in the café. I asked if he wanted to play, and he proposed a bet. A five dollar match, best of 3, the time control being 5 minutes without increment or delay. I do not support gambling, but I reluctantly decided to accept Doc's bet. 

Game 1 vs. Doc

The Richard A. and Susan F. Smith Campus Center

After this game, I thought I was going to get an easy five bucks. I was pretty dominant in this game except a few inaccuracies in the opening, I would say Doc has a blitz rating of 1600. However, some people call him a grandmaster of trash talk, as he would not stop talking during this blitz game. Though, he decided to finesse me and change the time control from 5 minutes to 2 minutes. Here's how the next game went.

Game 2 vs. Doc

I played so well to get a winning position, and then once I got a winning position, I sold in every possible way. I missed the free bishop on f1, then allowed counterplay, and for a second had a drawn position. Although of course since Doc had changed the time control, I flagged with mate in 4 on the board. However, something extremely interesting happened right as a finished this game. A boy behind me asked if he wanted to play, I turned around and it was none other than Tanitoluwa Adewumi! 

Tanitoluwa playing a time odds game against Doc.

If you don't know who Tani is, then I suggest you read these articles about his amazing story and his current chess journey to the GM title. Although once Tani started spectating my third game, I immediately fell under the pressure and just started hanging pieces left and right. The game was so bad that I don't even want to show it. Although, if this blog gets 2000 views, I'll post the game in the comments so you can all laugh at me playing like an absolute patzer. 

Final Thoughts

A picture taken by me on my flight back to San Diego.

Overall, I would say that the average strength of a chess hustler is a blitz rating of 1800. They have been playing the game for a while and will understand basic positional ideas and be able to spot threats and tactics. Although from my experience, they are not the best defenders and can often overlook some ideas and motifs. I would say that playing against a chess hustler isn't a chess game, but more of an experience. Johnny was very talkative and fun to play against, and Doc was simply rambling about his intrusive thoughts. Thank you for reading, and as always, see you next time. 

14-year-old aspiring national master.