“Dude, someone started a Reddit forum about your Instagram chess photo.”

More messages started coming in, and that sick feeling in the stomach started to kick in. What the hell have I done now!

“Queen on’er own color Webb!”, said my friend Nick, co-founder of Zocdoc, a great chess player.

Then I looked at the photo in question which had started to break down in tears like a CIA detainee being tortured endlessly at an obscure black site in the Middle East.

F*** me, white queen on black square opposite side of the board.

But wait! It’s not my side, Miguel’s fault! Doom on me, my photo!

The picture in question Is Here.

I was playing a few locals, and then we put the board together for a quick shot for the gram. I should have checked but didn’t.

We are witnessing the greatest war tragedy in modern Europe but there are enough people out there willing to still trash someone for simple mistakes.

I found myself thinking, “F*** me, I need to really be careful on my photos shoots!”. Then I realized five seconds later and thought, “No, f*** that, this is real life. People are not perfect, I’m NOT perfect and I don’t want to live my life like some Instagram model posing at the latest travel hot spot wearing clothes and handbags that could cost more than most people’s rent for a year!”

But we all can and should be better to each other.

I love chess. I’m a slightly above-average 1600 player. Blitz, I’m clawing my way up.

I play chess daily, about an hour. It’s a great mental activity. I love it, and I found chess again as a forty-something dad whose son had become a great player and was doing his first semester at the University of St. Andrews, on the chess team, and living with me in Puerto Rico during the pandemic.

My kids rock and they are lucky to have a great mom also. I’m so grateful I get along well with her and her husband.

And I am fortunate to consider all my children friends, they’re just freaking fun to hang out with.

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Olivia has a passion for creating things like me and self-made at fourteen, Grayson is the family athlete and future finance whiz, and Hunter my oldest is super into computer science, entrepreneurship is an active NFT fund investor (he started the fund), and a 2000 plus chess player and President of the team at St. Andrews.

I taught him the basic rules as a kid, and he taught me how to really play and love the game during our time in Puerto Rico.

We’d get up, do our morning workout, work all day, him at school and me running my media business or writing and we’d finish off the day with a few hours of chess and make dinner together. Maybe a surf session if it was good, which in the winter is often.

Of course, we both watched Queens Gambit together, a great show and I’m thankful for what it has done to the young community of chess players in America.

Hunter and I playing a game over breakfast.
Hunter and I played a game over breakfast.

I grew up surfing the heavy beach breaks of Ventura harbor, lived in the water as a kid, and later as a Navy SEAL. I have been in some heavy conditions and it was a proud day to see Hunter paddle out in double overhead conditions, get caught inside, have his leash break and handle himself.

After the pandemic, Hunter and I hit up the chess club south of Washington Square Park, and the park players of New York. He was nervous his first game, soon that gave way to confidence as he started beating the Washington Square players and graduated to Union Square, where the real action is.

I took a few lessons and learned some nasty queen sacrifice mate openings. Union Square is tough chess, straight-up street trash-talking fast-moving blitz chess. No high brow allowed here, although some of the better park players make a great living teaching white-collar players. I took a few lessons and even won a game when my opponent blundered his queen and I traded down fast and mated him.

Playing a local in Harvard Square while finishing up my business school program.
Playing a local in Harvard Square while finishing up my business school program.
Hunter and I playing with the locals in Mexico City. Such a great community of players in CDMX.
Hunter and I playing with the locals in Mexico City. Such a great community of players in CDMX.

Hunter is off at University now but we have a standing Sunday evening game on Lichess.org.

I love the game, my friend James Altucher and I try and play weekly. He schools me and is a great teacher and a master. Thank you for the bishops opening James! I also play regularly with my friend Allan who works media for Wheels Up!

“Run it, Allan!”

I love the community of players. I’ve played in dodgy clubs in Mexico City, the hustling parks of New York, and the chess Baths in Budapest.

And if I can stoke the gossip fires of Reddit chess forums with an out-of-place queen posted on Instagram, the game is better for it.

Thank you to the mods of r/Chess on Reddit for yanking the post down like a 1000 yard target on the sniper range, I just signed up for the forum so glad this happened the way it did.

I remember Elon Musk’s interview on Rogan when Joe asked him what the world needs more of.

“Kindness”, he said. I couldn’t agree more.

See you on Lichess 5/3 Blitz!

RedCircleSEAL out.


This story was originally published in Brandon Webb’s Blog.