A Chess Story

This is a story about chess, childhood, growing up, and the things that happen in between.

When I was in the 6th grade I was a competitive chess player. I’d fly all around the country playing in tournaments. My life was something straight out of Searching for Bobby Fischer, but a little more intense and a lot more real. In 1999 I was playing in the national championship tournament. I started the tournament on Board 5 (equivalent to 5th seed), and drew to a lower rated player in the 4th of 7 seven rounds (he was in the 1400 range and I was in the 16/1700 range at the time, if I remember correctly). I ended up winning nationals that year with a score of 6.5 out of 7, and the person I drew to in the 4th round tied for second place.

As silly as it may seem, winning nationals has always been one of the proudest achievements of my life. It’s nice to have something under my belt that no one can take away from me. Sometimes I think about what would have happened if I hadn’t drawn that match early on in the tournament. Would I have still won? Would I have lost? Would I still be me? Who knows. All I know is that I stopped playing competitively shortly thereafter and I was okay with that. By the time I retired I had played against Hikaru Nakamura, hustled the hustlers in Washington Square Park, met most of my chess idols, and fulfilled my chess dreams. My chess career peaked at the age of 13. All things considered, that was probably a good thing.

Fast forward ten years to April 2010.

Several weeks ago I was toying around on LinkedIn and stumbled upon a familiar name: Josh Weinstein. I scoped out his profile and sure enough it was the same Josh Weinstein I drew to in the 4th round of nationals a decade earlier. I was pleasantly surprised to learn that Josh had gone on to do some great things himself. He became the National Speed Chess Champion, the student body president at Princeton, and the founder and CEO of a company I admire called GoodCrush. He also ended up in the NYC startup scene, and we now work walking distance from one another.

I shot him a note saying, “Pretty sure we played each other at nationals.” He immediately responded with “Pretty sure you won.” And that was that. We got lunch the next day and hit it off. It was as if the past ten years hadn’t existed and we just finished a marathon series of post-nationals blitz games. Josh has come a very long way since the 6th grade and it’s great to see him doing so well.

This week Josh and I went over to Shake Shack to grab some lunch. When we were waiting for food I asked him when we were going to play chess again. ”e4!” he said. The last game of chess I played in my head was over ten years ago, sitting next to my chess coach at a friend’s Bar Mitzvah. The way mental chess works is you say your moves out loud and play the entire game in your head. There is no physical chess board, only an image of it and the pieces in your brain. You either play the all the way through, or the first person to make an illegal move loses (this usually happens before someone is checkmated). The last time I played, my coach made an illegal move around 15 moves into the game. I held bragging rights after that. Damn that felt good.

“e6,” I replied. Four moves later we were playing a variation of the French Defense. Much to my surprise I could still do it. My mind was still sharp and my ability to visualize the board was still there. (Unfortunately, my knowledge of openings has completely deteriorated.) We sat down for lunch a couple moves into the game and postponed it.

On the way back to work we picked up the game via text message - still no board. The image of the pieces remained fresh in my head. For the rest of the day we continued to sporadically exchange text messages with our moves - sometimes with 2-3 hour breaks - but we never lost sight of the position. Finally, walking home from work, I offered Josh a draw. I was down two pawns entering the endgame (clearly a losing position). He texted back, “Why the hell would I take a draw?” I told him to accept it for old time’s sake to which he responded with a big fat “LOL”. I took that as a polite “yes” and the game was over.*

Some things stick with you for a lifetime. It’s nice to sit back and appreciate the way things work out.

*If you’re interested, I wrote out the game below - it’s not an exciting one by any means, but I’m thrilled that I can still visualize a game of chess. Josh played white. I played black.

1. e4, e6 2. d4, d5 3. Nc3, Bb4 4. Nge2, c5 5. ed5, ed5 6. a3, Bxc3 7. Nxc3, c4 8. Qf3, Be6 9. Bd2, Nf6 10. Bg5, Nbd7 11. 0-0-0, 0-0 12. h3, a6 13. Bxc4, dc4 14. d5, Bxd5 15. Nxd5, Qa5 16. Bxf6, Nxf6 17. Nf6+, gf6 18. Qxf6, Rad8 19. Kb1, c3 20. Rxd8, Rxd8 21. Qxc3, Qxc3 22. bc3, Rd2 23. Rf1 DRAW