Will Whalen ’23 is a mild-mannered world politics major by day, but master of the mean, meowing chess bot Mittens by night. Whalen, who moonlights at Chess.com as a creative strategy lead, had the idea to create the cute kitty chessmaster that plays an aggressive game and took over the chess world earlier this year. The formidable feline proved to be a fierce and frustrating opponent on Chess.com, where Whalen will go to work as director of audience development after graduation.
Tell us about your personal history with chess.

I started playing chess in high school; I decided to keep coming back because the advisor of the club bought Oreos every Wednesday and Friday. Over time, I started to fall in love with the game and how empowered people could feel while playing. I started playing competitively against other schools and used Chess.com as a resource. Once we were all sent home for the pandemic, I applied for a social media assistant position with Chess.com and have been working there for the last two-and-a-half years in various roles. 

Will Whalen ’23

Major: World Politics
Hometown: Needham, Mass.
High School: Noble and Greenough School

What exactly is Mittens? How did the idea come about?

Mittens was originally a pitched joke that ended up getting very out of hand. Every month, Chess.com releases bots [apps that create dialogue and interact with players in different ways in the style of their characters and play] in different themes for what we think players will take to — holiday bots with Santa and reindeer in December, for example. In the past, we’ve done AI parodies of billionaires, and in January, the theme was cats. The idea was to make a cat with a very silly name (I pitched “Bubbles” or “Mittens”) and massive eyes, and then to make that bot very, very hard to beat. The goal was to defy expectations and catch high-rated players off guard.

How did you turn this idea into reality?

A number of other people helped out. Sean Becker, the current lead of the bot process, wrote Mittens’ interactions with players to start incredibly calm and cuddly and then devolve into madness. In most matches, Mittens starts by giggling at the player and ends by quoting Nietzsche. That was Sean’s pursuit alongside numerous contributions with the other people on the writing team: Director of Written Content Colin Stapczynski, Pedro Pinata, and Nathaniel Green. The art for Mittens was done by Marija Casic. 

Did you expect anything like the popularity Mittens achieved? What was it like to see that happen?

Absolutely not. We knew it would be a fun bit for content creators, but we never expected it to blow up as it did. In the first few days, it felt surreal. The first pieces of content that YouTubers such as Levy Rozman (GothamChess), Hikaru, the Botez Sisters, and many others put out made me think that we really had something awesome. We ended up overtaking the top Google search result in the United States for “Mittens”— over people shopping for the actual article of clothing — in January, which was when I realized that things were REALLY going off the rails. It was a thrill to see it happen, and I was thrilled that the team had created something for the entire chess world to unify against. 

What is/has been your role at Chess.com?

After my year or so with the social media team, I began to write social media and content campaigns for sponsors in major events, such as Coinbase in the 2021 FIDE World Championship. A lot of what I do is to help connect outside sponsors to our audience and create content ideas to make our audiences jibe together. I’ve also been leading our marketing efforts for events for nearly a year. 

Do you plan to continue working at Chess.com?

Yes! I’ve accepted an offer as Chess.com’s director of audience development and will be going full-time in late June. 

How have your experiences at Hamilton influenced your work at Chess.com?

The greatest advantages that I’ve had in this kind of job as a Hamilton student have been close relationships with professors and being forced to be on my toes in smaller, high-level classes. The study of empathy is what interests me in school, and my classes, especially in the Government Department, have reflected that. I’ve mentioned Professor [Erica] De Bruin a number of times as someone I had a close relationship with for years  —she has helped me strategize how to balance school and work.

Did anyone beat Mittens?

A number of people! Mittens was strong but not fast: You could out-speed the bot if you played with a short enough clock to complete the game.

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