Will AI win Scuttleball 2026?

by Craig Leweck, Scuttlebutt Sailing News
When Conan O’Brien hosted the 2026 Academy Awards, it was his second consecutive year, but he expects it be his last. “I am honored to be the last human host of the Academy Awards,” joking about how AI is taking over. “Next year it’s going to be a Waymo in a tux.”

The ChatGPT app has made me a dog trainer and physical therapist, and with any luck, the 2026 Scuttleball Champion. Out of  curiosity, I am using AI to select the winners for my March Madness bracket. We are riding this magic carpet of technology; the basketball pool for sailors can too.

The 2026 College Division I Men’s Basketball Tournament has finalized the 68 teams to compete, with the first round beginning on March 19. This is when Scuttleball begins too, with completed entries to be submitted no later than five (5) minutes prior to the start of the first game.

Since the ChatGPT app already knew I was a Gonzaga fan (don’t ask me how), they had the school doing very well in my bracket. When I explained that I was more interested in winning the pool, they applauded my approach.

“Good call,” it noted. “In March Madness pools, the goal isn’t loyalty – it’s probability,” before adding how Gonzaga was statistically over-picked every year. Tell me about it.

The top seeds in the four regions are Duke, Arizona, Michigan, and Florida. While the Gators are the reigning national champions, their road toward the title will have games in Houston and likely against the #2 seed Houston Cougars. Brutal!

The last four schools to get into the Tournament were North Carolina State, Texas, SMU, and Miami (Ohio), while Oklahoma, Auburn, San Diego State, and Indiana were the first four teams to miss the dance. Better luck next year.

Early Scuttleball entrants include Kathy Alven (2024 champ) and Matt Brock (2025 champ), eager for the taste of champagne again.

There are rules to Scuttleball, but we made none of them. Managed by CBS Sports, participants earn points for each winning team correctly picked, with points awarded increasing with each round of the Tournament. Participants may create up to three (3) brackets total.

There’s no entry fee and the winner receives personal bragging rights and recognition in Scuttlebutt Sailing News. With AI, you really do not need to know anything to compete. It’s almost game time, register here.