What Is Chess Hustling & How Much Do Chess Hustlers Make?

Chess Guides / By Andrew Hercules
chess hustling

Chess hustlers are players who compete at the chess board for money. Most of them can be seen hanging out in parks, mainly in New York City.

Some may talk a ton of trash, cheat and play for small amount of money, while there are others that actually make a good income from the game.

Chess hustling is a fixture of New York street life that has been referred to as the “largest growth industry” in the city. While gambling in chess is technically illegal, chess hustlers are largely ignored by legal authorities. In fact, some of these players across areas of New York city are heavily featured in popular newspaper articles and websites, giving them a unique brand of fame.

Watch video below of GM Maurice Ashley vs NYC Chess Hustler

How Much Do Chess Hustlers Make?

So you might be asking, how much do chess hustlers really make? Well, that will mostly depend on the players level of skill. A highly skilled chess hustler who knows the ins and outs of the game can make up to USD$400 per day with enough tourist traffic. The hustler can charge $3 for a no wager game, and if you want to bet, the winner gets $5. Hustlers can also offer 30 minute lessons for $20 as another stream of income. 

I know, $400 a day from chess hustling might seem like a lot of money, and it is. But do most hustlers make this amount of cash each day?

…Definitely not

The amount of money you make from this type of sport will again depend on your skill, the number of tourists visitors, your location and the amount of work you put in. Success is not guaranteed.

How Good Are Chess Hustlers?

One key thing you should know about chess hustlers is that they aren’t quite good. Most of them are usually class C or B players at best. What they excel at is 5 minute chess on their own turf, where they do everything they can to distract you. Quite frequently, they make illegal moves and badger you with commentary.

If you are beating them quite frequently, they’ll just say ‘no more!’.

These hustlers have a goal of how much money they wish to make in a single day. It’s not a great living but they can obviously pay enough bills to get by in a manner that they deem acceptable.

If you are a class C player in your local club, then you stand a chance. However, you should keep a few things in mind when playing against chess hustlers:

1. Avoid Opening Blunders 

Play a stout, mistake-free chess opening. These chess hustlers love a pawn advantage in an endgame with 1 minute left on the clock.

They make their money pushing wood! They aren’t endgame experts. They just know a passed pawn must be pushed, and honestly that’s all it takes to win against most people.

They ache for you to make one tactical mistake. So don’t. If you’re black, play something you know that is rock solid and strategic such as the Pirc defense, Close Caro-kann or anything that limits their tactical chances.

If you’re white, play something equally mundane like the London or Queen’s Gambit Declined (something stout)

2. Steer Away From Complications

Avoid tactical engagements unless you know you can come out on top. Every move is about frustrating them. You’re waiting for them to overextend, because they will. Why? Because they’re really only a mediocre club player and that’s what mediocre club players do. Just let them come to you.

3. Exploit their weaknesses

Be tactically brilliant. They are, so you need to be as well. They will make a mistake. Spot it. Exploit it.

That sounds simple, and it kind of is. I win about 80% of my games with street hustlers. They usually only will play 2 games with me.

Playing speed chess waiting for the lesser player to make a mistake is a dicey move if you aren’t sure they are the lesser player. But when you are, it’s easy money … but only for 1 or 2 games.

Do Chess Hustlers Cheat?

It’s very hard to get away with cheating in chess. On the other hand, I’ve heard about one chess hustler who abruptly abandoned his game in excuse to take the “rest room”, he was never to be seen again. This may be considered cheating if you are in a winning position and are about to win the wager.

Fortunately for me, I’ve never been dealt with that experience. I have to say that the majority of chess hustlers do NOT cheat. That’s not what makes them a chess hustler.

A chess hustler makes money from playing chess in an informal setting. That’s all that there really is to it. You agree to play for money, we agree to take your money. That’s it. The hustle all comes down to knowing your skill, finding a niche to exploit and capitalizing on your opponents’ weaknesses.

It’s a speculation to think that chess hustlers cheat and for many chess hustlers, it’s not part of their repertoire. The stakes are too high and their opponents are pretty mad at them anyway and to be caught cheating could result in injury or at least loss of a source of revenue.

For some, though, when their opponent is the only other person present and they think they can get away with it, they can do something that might happen anyway, like a Knight landing on a wrong square or a lone Bishop ending up on the opposite color (to the hustler’s benefit).

I can recall an incident that reportedly happened at a local chess club. A local player of expert strength had the sadistic habit of playing slowly (even in speed chess) and getting in severe time trouble but was then able to rip off a series of moves in very little time, often resulting in a winning combination.

A hustler who had never seen him before and who was losing quite a few bucks grew so agitated at losing a string of games this way that he pulled out a gun and aimed it at the guy.

The local player spoke loudly, “You’re not going to shoot me in front of all these people, are you?” All the players looked at the guy with the gun and ducked under the tables. The agitated player put the gun away and quickly exited.

Chess Hustlers In Prison

Some cases, you can encounter a chess hustler who is really good. So good that you can hardly believe what you are witnessing. One such player is Claude Bloodgood (1937-2001), who is famous and notoriously known for killing his mother. Some say it was his step-mother.

Although he was in prison, it didn’t mean the end of scamming for Claude Bloodgood. He almost became the highest ranked chess player in the U.S. through trickery.

This happened in the year 1996. America’s chess world discovered that Bloodgood who was a convicted murderer, a man who once played 2,000 chess games simultaneously by mail from his prison cell, who claimed to be a former Nazi spy, had suddenly become the No. 2 rated chess player in the country.

He wasn’t really. He was good, but never that good. Chess officials denounced Bloodgood as a fraud. They said he had manipulated the chess rating system from his maximum-security prison cell. The chess establishment couldn’t strip Bloodgood of his rating — he had earned it, albeit dubiously — so they simply erased his name from the ratings list in 1996.

Bloodgood was a student of the game, specializing in unorthodox openings. He even wrote several books about openings:

Bloodgood was a prolific writer, and his collection has several manuscripts of his work. He was well known for his unorthodox chess openings and had several books published, including The Tactical GrobNimzovich Attack: The Norfolk Gambits and Blackburne-Hartlaub Gambits.

What Ratings Are Chess Hustlers?

Chess hustlers ratings are typically around 1200-1800 rating points. Many of them have no idea what their rating is. They think they are higher rated then they actually are.

When I was 15, I played against the weakest guy in the Washington Square Park and he was probably 1200. When I starting beating him I moved to the next strongest, and so on. When I started playing in tournaments, I ended up around 1500.

There was an old man there called Arcarty. I watched him play in the last New York Open around 2004 or 5. His rating was 2100+ FIDE. He was considered a master by the park denizens.

Most of the hustlers are homeless and drug addicted. One guy who has played there for around 20 years is a middle eastern guy who was pretty weak, and is now about 2000. He spends his days smoking a lot of weed and hustling.

Will Chess Hustling Survive in 2021 and Beyond?

It doesn’t look too good for the world of chess hustling, especially in the times we are living in today with covid, social distancing and lockdowns. Chess hustling is becoming more and more outdated.

Today, most chess games are played over the the internet on popular chess apps such as lichess.org and chess.com. I do wish that someone could make an app where chess players can make wages and bets virtually through legal means. That would be pretty cool 🙂

But for the time being, chess hustlers will have to turn to another source of income besides their usual New York street life hustling.

Andrew Hercules

Hercules Chess, launched in 2020, is a website that teaches you about chess. We started as a chess blog and became a chess training platform in early 2022.

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