Baseball, wine and jazz at Millbrook Winery

Throughout the history of Major League Baseball, precious few greats have been considered five-tool players. New York Yankee Bernie Williams was one of them.

To be considered a five tool player, one must show exceptional proficiency in five categories: hitting for average, hitting for power, running bases, fielding and arm strength. But there’s another tool Williams possesses that didn’t make it to the back of his baseball card: his mastery of jazz guitar.

On Aug. 1 at Millbrook Winery, that elusive sixth tool will take center stage as Williams and his Band of Friends return to the Vineyard for a night of jazz, wine and possibly a baseball reference or two.

Williams is best known for his legendary career with the Yankees. During his 15 years with the Bronx Bombers, he won four World Series championships, four Gold Glove awards and one Silver Slugger award in 1998, the same year he won the American League batting title, making him the first player in history to win a Gold Glove, a batting title and a World Series in the same year. Oh yeah, he was also an MLB All-Star every year between 1997 through 2001.

But while his work on the field is well known to New Yorkers and the broader baseball world, he almost took the musical route through life.

Williams first picked up a guitar when he was just 8 years old and was immediately taken by the magic of music. He was so passionate about it that he attended a performing arts high school in his hometown of San Juan, Puerto Rico. By the time he made it to the big leagues, he was known as the guy with the guitar in the locker room.

That reputation soon reached the Yankees’ fan base, with commentators telling stories of Williams and his outfield teammate Paul O’Neill’s jam sessions. O’Neill set up a drum kit in a paint room at the old Yankee Stadium, and the two would play together through rain delays, sometimes getting visits from New York City’s musical greats while they waited to play ball. MSG Network, which aired Yankees games at the time, even ran a promotional ad featuring the two World Series champions jamming together on a blues riff in their batting practice uniforms.

But unlike O’Neill, whose drumming is a hobby at best, Williams is a serious musician. During an appearance with Paul Simon at a charity event, Simon surprised Williams and his band by playing “Mrs. Robinson,” a song they didn’t know and hadn’t practiced. But just a few lines in, Williams was taking solos and riffing on Simon’s choruses with expert musicianship.

While Williams’ music is the main draw for the event on Saturday, the relationship between the All-Star and the winery goes beyond the performance. The collaboration started in 2021, when Williams visited the vineyards and instantly connected with then-general manager Ian Bearup, bonding over baseball, music and wine. They quickly decided to team up and create a custom variety they call Bernie’s Blend. This year’s bottle, featuring art from Williams’ daughter, Beatriz, is a blend of Cabernet Sauvignon, Merlot and Cabernet Franc and will be released at the performance on Saturday night.

While the VIP ticket levels are all sold out, as of press time, bring-your-own-lawn chair spots are still available. The wine will be available at the vineyard and online throughout the year at millbrookwine.com.