Bernie Williams Traded Center Field for a Jazz Degree

Bernie Williams spent 16 seasons chasing down fly balls in center field for the Yankees. These days, every August, he swaps his glove for a guitar and plays a sold-out jazz set at a small winery in the Hudson Valley.

Four Rings and a Retired Number

Williams played his entire career with the Yankees, from 1991 to 2006, and helped the team win four World Series titles between 1996 and 2000.

He made five All-Star teams and won four Gold Gloves in center field. In 2015, the Yankees retired his number 51 and unveiled his plaque in Monument Park.

Back to School at 47

Williams had been playing guitar since childhood, but he wanted a real music education. He enrolled at the Manhattan School of Music, sitting in classes with students less than half his age.

"Most of these great musicians weren't even born when I was playing baseball," Williams said. "I feel that I needed to earn their respect, not for what I did before, but for what I'm doing now."

He earned his Bachelor of Music in jazz performance in 2016, at age 47. "It was really challenging," he said. "I thought I knew how to play guitar before I came here."

A Grammy Nod and a Night at Lincoln Center

Long before he had the degree to prove it, Williams was already recording. His 2009 album Moving Forward reached No. 2 on Billboard's jazz chart and earned him a Latin Grammy nomination for Best Instrumental Album.

In 2024, he went further still. Williams made his New York Philharmonic debut at Lincoln Center, performing his own composition under conductor Gustavo Dudamel at the orchestra's spring gala.

Every August in the Hudson Valley

Williams now sits on the board of trustees at the Manhattan School of Music. But the show he keeps coming back to isn't at Lincoln Center.

Since 2021, he has returned each summer to Millbrook Vineyards & Winery in the Hudson Valley for a jazz concert with his band. In 2026, it was the fifth year running, and tickets sold out.

"Returning to Millbrook Winery and being a part of something that blends music, wine and community is always one of the highlights of my summer," Williams said.

Each year the winery also releases a new vintage of Bernie's Blend, a red wine Williams helps craft with the head winemaker, its label designed by his daughter, artist Beatriz Williams. The 2026 label shows a guitar passed between two sets of hands, one older, one younger.

The Yankees legend who once chased fly balls under the lights at Yankee Stadium now plays guitar under the stars at a winery two hours north. He is there again next August.