On Wednesday, Rilling traveled to Stamford to host a lunch at Zodi's 19th Hole restaurant for the boys basketball team from Westhill High School after he lost a bet with Stamford Mayor David Martin.
The Westhill High boys basketball team beat Norwalk High School in the FCIAC finals earlier this year.
"It was an exciting time for Norwalk," Rilling told the Daily Voice. "That was the farthest the team has gone. They played hard, it just wasn't meant to be. But it was close all the way, and at the end Westhill put it into high gear."
The teams played twice this year, with Westhill winning both meetings by four points.
"That was one of the safest bets I made all year," Martin joked. "Norwalk gave us a run for the money, but Westhill came through."
Westhill made it to the state championship game, where it lost, 51-50, to Fairfield Prep. The team finished with a record of 25-2, and had a 22-game win streak before the loss in the state final.
At Wednesday's lunch, Westhill players Joshua Gordon and Voshon Natteal joked: "The pizza tasted excellent on Norwalk's tab, and Mayor Rilling looks good in that Westhill T-shirt."
Click here to follow Daily Voice Norwalk and receive free news updates.