As National League finalists appeared on MLB Network for the Manager of the Year Award announcement on Tuesday night, Chicago Cubs Manager Joe Maddon looked on comfortably from an Italian restaurant in Tampa, Fla. His gray hair swept across his head like a wave. He had his sleeves rolled up, his shirt splayed open, a silver chain sticking out.

Behind him, a fireplace was ablaze.

“Enjoy the red wine,” one commentator told him. “I know you’ll have more than one glass.”

In his first year with the Cubs, under the weight of new expectations and a century-old curse, Maddon kept his young team at ease, leading it to a 97-win season, its best in seven years. Maddon received 18 of the 30 first-place votes for the award, finishing well ahead of the Cardinals’ Mike Matheny and the Mets’ Terry Collins, who received three first-place votes.