What Happens When a Chess Player Mistakes a Grandmaster for a Beginner: It’s Pretty Delightful

Vaca­tion­ing in New York City last sum­mer, Anna Cram­ling, an Inter­na­tion­al Chess Fed­er­a­tion mas­ter swung by Wash­ing­ton Square Park, to see about scor­ing a pick­up game with one of the reg­u­lars.

Her oppo­nent, Jon­ny O’Leary, a native New York­er who learned the rules of the game from oth­er Wash­ing­ton Square habitués while work­ing main­te­nance jobs in the sur­round­ing build­ings in the mid-80s, is a gar­ru­lous sort, shar­ing his phi­los­o­phy of life as the game pro­ceeds.

Luck­i­ly he believes that the human inter­ac­tion and the oppor­tu­ni­ty to learn make even los­ing games a win­ning propo­si­tion because Cram­ling whoops him pret­ty hand­i­ly.

Flash for­ward a cou­ple of sea­sons.

Cram­ling, bun­dled up in a par­ka and warm stock­ing cap, heads back to Wash­ing­ton Square with her mom in tow.

O’Leary is more than will­ing to intro­duce the elder Ms. Cram­ling, now 60, to the Game of Kings. He loves teach­ing begin­ners, even if they have no mon­ey to put down. He is so eager to show her the ropes that he dic­tates four of her first five moves.

His extro­ver­sion may be his down­fall here.

In our expe­ri­ence, folks who call mid­dle-aged women they’ve just met “Mom” tend to under­es­ti­mate and talk over them.

Sur­prise! Pia Cram­ling is a Grand­mas­ter of Chess, who once held the title of best female play­er in the world.

“Mom” humbly fol­lows direc­tions, mov­ing her knights and bish­op as instruct­ed and pre­sum­ably clamp­ing down on her tongue as O’Leary schools her begin­ning strat­e­gy and the names of the pieces.

To his cred­it, he seems absolute­ly thrilled when the Cram­lings’ ruse is revealed, eager­ly call­ing for anoth­er game even as he vol­un­teers that he’s nowhere near as good of a play­er.

(“Get the old man,” his bud­dy Doc glee­ful­ly inter­jects.)

Their shared love of chess burns bright.

The Cram­lings com­pli­ment O’Leary on his gen­eros­i­ty as a teacher, no doubt mind­ful that his immer­sion in the game looks dif­fer­ent from theirs. (Anna’s father is Grand­mas­ter Juan Manuel Bel­lón Lopez and she has been accom­pa­ny­ing her moth­er to tour­na­ments since she was a baby.)

O’Leary may appear to draw a bit of a blank when Pia Cram­ling men­tions World Chess Cham­pi­on Ana­toly Kar­pov, but he’s rubbed shoul­ders with grand­mas­ters Max­im Dlu­gy and John Fedorow­icz at the Wash­ing­ton Square Park chess simul, and he was very inter­est­ed in her Elo rat­ing, the U.S. Chess Federation’s sys­tem for assess­ing play­ers’ skills.

“She has a brain that’s not from here!” he cries admir­ing­ly to any­one with­in earshot.

After wit­ness­ing some oth­er play­ers’ over­ly cocky, unsport­ing, and rude behav­ior in Anna’s oth­er filmed street match­es, we def­i­nite­ly agree that Jon­ny O’Leary is the “Grand­mas­ter at the social aspect.”

Watch more of Anna Cramling’s chess relat­ed videos, includ­ing her mom’s encoun­ters with oth­er Wash­ing­ton Square Park reg­u­lars here.

Relat­ed Con­tent 

A Free 700-Page Chess Man­u­al Explains 1,000 Chess Tac­tics in Straight­for­ward Eng­lish

Man Ray Cre­ates a “Sur­re­al­ist Chess­board,” Fea­tur­ing Por­traits of Sur­re­al­ist Icons: Dalí, Bre­ton, Picas­so, Magritte, Miró & Oth­ers (1934)

Mar­cel Duchamp, Chess Enthu­si­ast, Cre­at­ed an Art Deco Chess Set That’s Now Avail­able via 3D Print­er

– Ayun Hal­l­i­day is the Chief Pri­ma­tol­o­gist of the East Vil­lage Inky zine and author, most recent­ly, of Cre­ative, Not Famous: The Small Pota­to Man­i­festo and Cre­ative, Not Famous Activ­i­ty Book. Fol­low her @AyunHalliday.


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  • Howard Dee says:

    Fas­ci­nat­ing and pos­i­tive human inter­ac­tion. Instruc­tive, both re life and chess. Kudos to Anna for encour­ag­ing John­ny to express his social phi­los­o­phy and to O’Leary for being so respect­ful, hum­ble and such a good sport!

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