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2018 Gambling Olympics: Which Math Expert Can Win at Connect Four?

2018 Gambling Olympics: Which Math Expert Can Win at Connect Four? article feature image


  • Connect Four is one of 12 events in the inaugural Gambling Olympics and takes place Monday, July 9.
  • The game has been mathematically solved since 1988 and can be consistently won by whoever goes first if they know what they’re doing.
  • The Three Donkeys, along with The Prop Bet King, are self-pronounced Connect Four aficionados.

The 2018 Gambling Olympics is a two-day, 12-person contest taking place in Las Vegas on July 9-10. The buy-in is $2,500, and the winner gets $10,000.

Before, during and after the Gambling Olympics, we will provide extensive coverage via participant profiles, event breakdowns and live in-person analysis. Be sure to follow all the action in the Gambling Olympics section of the site.

How Does One Win the Connect Four Challenge?

The Connect Four challenge will be bracket-style with matchups chosen at random. Contestants will compete in a best-of-three series, with the two most dominant performers (judged by fewest pieces used to win) earning a bye. The final standings for losers are based on pieces used; this isn’t an “if you ain’t first, you’re last” type of situation.

There are more than 4 trillion unique ways to fill a standard board, and nearly 2 trillion ways to win. Per Wikipedia, James Allen and Victor Allis each independently solved the game within 15 days of each other in 1988. There’s literally a game solver online that lets you view and execute the winning strategy after each move.

Basically, whoever goes first in the game can mathematically guarantee victory if they know what they’re doing (or can click a hyperlink). The first move literally decides everything (again, assuming Player One plays perfectly):

This means the Connect Four challenge will need to be approached with poise and the ability to stick to a mathematical process rather than blind confidence.

Who wins Connect Four?

Adam Levitan dubbed Connect Four his strongest event because, “We’ve been running sims.” When asked how many hours of prep he’s put into this, Levitan responded, “Lot of time in the lab on Connect Four and Yahtzee. Unquantifiable hours.”

It’s safe to assume “we” refers to the two remaining members of the Three Donkeys: Jonathan Bales and Peter Jennings. They’re long-time sharps in the underground Connect Four scene.

A lot of great things going on at the Sloan Sports Analytics Conference, but the most important and what everyone's talking about is that I'm up $500 against @CSURAM88 in Connect 4

— Jonathan Bales (@BalesFootball) February 23, 2018

An exhaustive Twitter search revealed additional contestants have dabbled in the Connect Four rat race over the years.

It’s unlikely the rest of the contestants are complete amateurs in Connect Four, although we can’t rule out the possibility some may have seen this tournament coming years ago and smartly went out of their way to not expose their secret skill on social media.

Where’s the Value?

Connect Four is a game seemingly built on experience and muscle memory. The entire field is used to putting in hours to #grind in their respective degenerate lifestyles. Still, each of the aforementioned contestants with verified experience could very well hold a slight edge considering they reportedly had somewhat consistent practice over the last calendar year.

Jennings deserves a very long look due to his noted gambling experience with NBA point god Chris Paul, which means there’s a non-zero chance he’s learned Rajon Rondo’s unbeatable Connect Four trap. Of course, Jennings noted that Ingram is his pick to finish dead last overall because, “He has a ton of talent for this event, but I don’t think he is going to put in the work.”

Laying +600 odds on each of the three donkeys along with the prop bet king wouldn’t be the worst idea ever. Ultimately, it’s hard to bet against the guy with seemingly the most experience and who has additional motivation thanks to trash talk from a long-time rival.

My Pick: Ingram +600

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