The Most Interesting Chess Instructor in the World

Let’s be honest, chess instructor sounds like an awfully dull occupation. To be fair, about 99% of the time, this assumption is spot on. Dan Heisman, National Master (NM), resides in that one percent. The Wynnewood, Pa. native has traveled the world thanks to an impeccable reputation as one of the best chess instructors in the United States. In October 2009, Heisman traveled to Abu Dhabi, instructing the game of chess to a Sheik for an entire week. He’s a painter, an author, a guest speaker. Football coach John Heisman was his great-grandfather’s first cousin. (Yes, he’s related to THAT Heisman).

Heisman has twice appeared on "The Howard
Stern Show."

When Howard Stern needed advice on positioning during the end game of his Internet match against an opponent with a 1950 rating, he called his personal chess tutor: Dan Heisman. Chess instructor Dan Heisman, NM may very well be the most interesting man in the world.

How did this come about? Some simple Googling and a phone call. Stern called Heisman after looking up chess instructors online and asked him if he knew any tutors in the New York City area. Heisman, after the initial shock of a celebrity dialing his phone number faded, mentioned that he could tutor Stern via the Internet with a simple software download. Stern downloaded the software and a partnership was born.

“Howard was one of my best students,” Heisman said in a phone interview. “I say that not because he was the most talented, but because he worked at it. He never took my advice or criticisms personally. He always knew I was trying to make him better. With other students, most students actually, this is not the case.”

Instructing via the Internet has its challenges. On his radio show, Stern mentioned how Heisman employs the Socratic Method. That is, he loves asking questions. It helps him get inside the mind of the player, understanding his or her reads and reactions. Through the Internet, these questions may rub a player the wrong way.

“I was instructing this one player who made a mistake and it cost him big,” Heisman explained. “So I asked him, ‘what were you thinking?’ But I did not mean that in a sarcastic or rude way. I actually meant, ‘what was your thought process here?’ I wanted to know what the player was thinking so we can correct the process.”

The player was furious, surmising that Heisman was taking a personal shot. He got defensive and an argument ensued. This never happened with Stern. Stern had the innate ability to recognize and learn from constructive criticism. It helped Heisman that Stern had a strong passion for the game. He would read books, listen to Grand Masters online. Stern consumed himself with chess.

“Howard was relentless,” Heisman said. “He wanted to get better. He asked me questions. He was into it. I thought maybe this would have lasted three or four lessons. This lasted three full years.”

Stern would play chess for five to six hours a night.

On his show, Stern admitted he would play on the Internet Chess Club (ICC) for five to six hours a night. Consider this exchange between Stern and his radio co-host, comedian Artie Lange. (Courtesy of Confessions of a Chess Novice).

Lange: If you look at Playboy Playmate's list of favorite things, chess is rarely on the list.
Stern: What's wrong with me? I'm dating a supermodel who's in the bedroom and I'm sitting at the computer playing chess.

After one year, Heisman improved the chess-obsessed Stern’s ICC ranking from a paltry 900 to an above average 1500. By July 2009, Stern’s ranking reached 1685. He would regularly compete with players who had rankings upwards of 1900, a rating on par with some of the best chess players in the world. Heisman helped improve Stern’s board vision, tactical vision and thought process. According to Heisman, Stern all but eliminated his mental errors and rarely traded pieces that resulted in a loss.

On his radio show, Stern praised Heisman.

"Dan’s a good teacher. A really great teacher. Gets an imbecile like me from 900 to 1500.” (Courtesy of Confessions of a Chess Novice).

Stern is known as an outlandish character on his radio show, a “shock jock” if you will. Outside of his show, he is a private, charming and gracious guy, according to Heisman. In fact, every year, Stern invites Heisman and the winner of one his chess tournaments onto the show to promote the ICC, the United States Chess Federation (USCF) and the Holly Heisman Memorial Fund. The Holly Heisman Memorial Fund is a charity started in honor of Heisman’s wife who passed away from breast cancer in 1994. Heisman could not have been more appreciative of Stern for this gesture. In May 2009, Heisman was live on the air with Stern for an hour and 40 minutes talking chess. One would think that this airtime would be a huge benefit to the ICC, USCF and Heisman himself. Stern reportedly averages as many as 5 million loyal listeners every day.

“I may have gotten one or two more clients because of my appearance on the show,” Heisman admitted. “It’s not exactly our demographic.”

Stern has since moved on from chess. The signs were there. Like a girlfriend no longer interested, the phone calls slowed, as did the Internet lessons. According to Heisman, photography is Stern’s new obsession. No goodbyes. No regrets. For the most interesting chess instructor in the world, a new adventure certainly awaits.