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My Visit to Toronto's Best Chess Bar
Please note: You don't need to dress like James Bond to get in to the bar.

My Visit to Toronto's Best Chess Bar

SheldonOfOsaka
| 19

Welcome, everybody to another idiosyncratic edition of the Osaka Papers.

If you're anything like me, then you play the vast majority of your chess online, and never so much as lay eyes on an opponent, as convenient as this is, it does however leave something to be desired. On the other hand, tournament over-the-board chess can be somewhat intimidating: near silent playing halls, rated games, a dead serious atmosphere...it can all be a little much.

There is however an alternative - Jazz and Chess night at 915 Dupont: unrated games, friendly opponents, no clocks, jazz, and an unlimited supply of great whiskey. I heard about this veritable chess oasis, during the FIDE Candidates, which took place a few months ago in Toronto, Canada. Luminaries of the online chess world, such as, Sagar Shah, Nemo and Levy Rozman, played a number of casual games at the bar, seeing this I vowed that the next time I was in Canada, I would make it a priority to take a day trip to Toronto and enjoy a few games.

But before we get to all of that, how about a few pics to prove that any of this actually happened.


A pic of me taking a pic...

I stopped by Young and Dundas, Toronto's town center and found a number of giant chess sets.

Jazz & Chess night is every Monday from 6:00-11:00PM.

Retro decor and Great Jazz music create an incredible atmosphere.

Players who were moments ago told to act natural while I awkwardly hovered over them taking pics.

Jazz & Chess Night


As some of you may have guessed, I live in Osaka, Japan...O_o...but I'm originally from Hamilton, Ontario, Canada; a working class town located about an hour west of Toronto. So, on my latest visit to my hometown, I made a day trip to Toronto in order to check out the City's best chess bar.

915 Dupont is located in an industrial building near the corner of Ossington and Dupont, getting there from the city center was relatively easy, a combination of subway and bus got me there in about 20 minutes.

What I found was a chess player's dream, friendly staff and patrons, cool decor, great music, and above all CHESS. There were a large number of chessboards available and what's better, people playing chess everywhere. The players were incredibly diverse seemingly made up of every color and creed, what's more, the genders were equally represented, most tournament halls are quite male dominated, but not here, females made up close to 50% of the players.

Most importantly, all skill levels were welcome, beginners mixed with hardcore fanatics, without any of the snobbishness one might expect from a highly competitive activity like chess.

So, I strutted in, laid out my chessboard and didn't have to wait more than a minute before someone asked me for a game.


Devin's Defence


My first opponent was Devin, I told him my backstory (the whole blogger deal...) he was a little taken aback, that anyone would be mad enough to travel from Japan for a game of chess, but I assured him that I was indeed that mad...

Devin's playing skills seemed to be typical of the patrons of 915 Dupont, in that, he understood tactics and development but lacked a little in the defensive department, allowing me to pull-off a neat tactic in our first game.

Black's last move has allowed a Mate in 10, can you see how I brought the game to quick conclusion?


The board was reversed and we dully played a second game...

The game was progressing nicely, when I decided to exploit a pin on the king, in order to win a pawn. At this point, Devin thought long and hard about what to do - brought out his smartphone and took a picture of the position before playing his move...

As it turns, out he played the wrong move and went on to lose another game to me...O_o...

Perhaps you can do better, what is White's best defence in this position?


Checking on Jeff



My next and final opponent was Jeff...whom I must admit I was very confident of beating. My confidence sprung from two sources. First, Devin whom I had just beaten twice, beat him in the game prior to our own. Second, and more importantly, Jeff would announce "Check", whenever he had an attack on my king...O_o...

OK, maybe I'm being a bit of chess snob, but announcing check in a real game is something you do when you haven't played much OTB chess.

In actuality, our first game was quite close, and only superior endgame skills saw me through to a win.

Can you forcefully transition to a won endgame?


At this point in the evening, it was getting late and I needed to be heading back to Hamilton, so I decided that this would be my final game of the night. I was a couple whiskeys deep, which I believe gave me a little bit of liquid courage when it came to going all out in attack.

What follows is a great example of Jazz Bar Chess.


And that was it, that was my visit to 915 Dupont Jazz & Chess Night.

I had an amazing time, and it was definitely one of the highlights of my vacation in Canada. It is one thing to meet like minded people online, but its far better to have a chance to get out of your home and create relationships face to face.

For anyone living in or visiting the Toronto area, I would highly recommend stopping by 915 Dupont for a friendly game of chess.

As always thanks for reading...and wait, I almost forgot...


Add Me On Instagram


I have recently created my new Instagram page SheldonOfOsaka_Chess where I will be displaying my latest Chess Prints. All of the prints are available on Redbubble.com and can be printed on anything from t-shirts to stickers.

Here are a few of my best selling products.


The Magician

A Game of Chimps

Astro Cat Plays Chess While the World Burns

As always, thanks for reading, and feel free to share these games and puzzles with your friends down at the library or jazz bar.

Cheers, SheldonOfOsaka.