A Funny Chess Hustling Gone Bad Story!
Back in the 80's, the prestigious NY Open was probably the strongest and richest Open Chess Tournament in the world. One year, a strong IM from South America came to NY City to compete in this event.
He arrived a couple of days early for sightseeing and perhaps make a few quick easy bucks by hustling chess players at the famous Washington Square Park. There is no way anyone in the park would know who he is as there was no internet back then.
He glanced around the park to pick on his "easy" target. After a short moment, he spotted a “scrungy unshaven man” (who looked like a homeless person) in the corner. This man was giving $5 to $1 money odd (so you pay $1 and if you beat him, you get $5) as well as 5 minute to 1 minute time odd.
So the IM thought to himself that it was his lucky day. Not only the he was getting 5-1 money odd but also 5-1 time odd. So he flopped down a $5 bill on the table. The older scrungy chess player looked up at this IM, slowly took a puff or two at his cigarette, and said OK.
The IM lost the first game and the “scrungy unshaven homeless man" did not even use 30 seconds on the chess clock. He said to himself that it must be pure beginner's luck. So he flopped down a $10 bill this time for another chess game thinking that he will get his money back. Once again, he lost and his “scrungy unshaven homeless” opponent barely went more than 30 seconds.
Now the IM was very angry. How lucky can this "homeless guy" be? So this time he flopped down a $20 bill. There is no way I can lose to this joker 3 straight times, he thought. Once again, he lost. So he mumbled to himself that this was unreal. There is no possible way he could lose 3 straight game to some "scrungy unshaven homeless" guy, right?
He tried his luck again, this time with a $50 bill. It took a little bit more effort from the “old scrungy unshaven homeless” man but the IM once again lost. He got up, left the park, went back to the hotel room, packed his bag, and went home without playing in the NY Open. He said to himself that if he cannot beat some “old scrungy unshaven homeless” guy in the park with 5-1 time odd, why even bother to play in the NY Open.
The IM basically gave up chess after that. The “old scrungy unshaven homeless man” was a former 2,600 top 10 chess player in the world and an incredible blitz chess player (back at that time, 2600+ would be equal to nearly 2800 today).