One of Bernie Williams’ most memorable conversations with the late George Steinbrenner had nothing to do with baseball.

About eight or nine years ago, the Yankees suspended their annual Family Day at the Stadium, an event during which the players were able to bring their children to play around on the field.

Williams’ wife, Waleska, was upset because the couple’s kids always looked forward to going, so the center fielder decided to take action. First, he went to manager Joe Torre, who told him the decision came from the top.

So he called The Boss.

“I don’t think he was expecting a call from me,” Williams, who is promoting MasterCard’s new Reserved by MasterCard program, told a group of six bloggers at a recent roundtable discussion in Midtown Manhattan.

“I said, ‘Mr. Steinbrenner, how you doing?’ He said, ‘Good. What can I do for you?’ I said, ‘Well, I heard that we’re not having Family Day this year, and I was wondering why we’re not having it because I know my kids are looking forward to it, and I’ve been one player that I don’t really ask for much, but I’d really like you to reconsider this decision because it’s really important for me and my family.’

“He said, ‘OK, I’ll get back to you on this.’ And I think it was because we won that day, he said, ‘OK, we’re going to have Family Day tomorrow.’ “

Williams felt he had earned the right to be honest with the owner, like during a more serious conversation with Steinbrenner a few years earlier.

In 1998, Williams helped lead New York to its second World Series title in three years, becoming the first player to capture a Gold Glove, batting title, and ring during the same campaign. After the season, the outfielder, who began his career with the Bombers in 1991, became a free agent.

“Being part of the Yankees for [eight] years, with no options of doing anything, not having the free will to decide my own destiny, I think I sort of owed it to myself to at least be able to explore the possibility to maybe just see what’s out there,” Williams explained. 

The D-Backs, Tigers, and rival Red Sox were courting Williams, who thought it was pretty cool to be a part of the free market.

“But at the end of the day, I had been with the Yankees for such a long time—I was so used to the city, the system, my teammates—I was like deep down inside, I knew I just wanted to be a Yankee,” he said.

While the negotiations were ongoing between Williams’ agent and the organization, the player himself decided to call Steinbrenner from his home in Puerto Rico.

“‘I don’t think they’re getting it done the way I want to get it done,'” Williams told the owner. “‘I just want you to hear from me that I want to remain a Yankee and I want us to work this out,’ and he said, ‘What do you want?’ “

Williams explained to Steinbrenner that he desired a contract similar to the one Mike Piazza had at the time with the Mets. So the owner discussed it with his people and within a few hours, he returned with an offer that ended up being signed at seven years, $87.5 million. The five-time All-Star would win two more titles and play out the rest of his career in New York.

That tenure came to an end after the 2006 season, which the veteran had played under a one-year, $1.5 million deal.

The Yankees invited Williams to spring training in ’07, offering him the opportunity to earn a spot on the roster, but he wanted a guaranteed spot and turned down the invitation.

The lifetime .297 hitter hasn’t played in the big leagues since, but he has never officially retired.

“The first year or two, I was going through somewhat of an existential crisis,” Williams said about his life after baseball. “It takes some time to adjust and you have this possibility of maybe playing for another team, and you start missing the game. Going through the World Baseball Classic [in 2009], I was like, ‘I can do this again,’…but I sort of kept it open, I think maybe trying to fool myself into thinking that maybe one day I could come back. If it’s not this year, maybe next year I’ll definitely make it official.”

And maybe after that happens, Williams’ No. 51 will be hung in Monument Park next to the likes of Babe Ruth, Mickey Mantle, and former teammate Don Mattingly.

“I have no expectations as far as that goes. That’s their decision to make,” said the 1996 American League Championship Series MVP. “I have my experiences, the years that I’ve played with them, the World Series rings, the batting title, the Gold Gloves. Even though I left in not the best terms, I’m able to feel that I’m still part of this great organization…The number would be icing on the cake.”

Williams is keeping plenty busy away from the game of baseball. Last year, the classically trained guitarist released his second major album, Moving Forward, which earned him a Latin Grammy nomination.

The 42-year-old attended a performing arts high school, and always carried a guitar with him throughout his baseball career. During rain delays or after batting practice, he and ex-teammate Paul O’Neill, who plays drums, would retreat into the paint room at the old Yankee Stadium for their very own jam sessions.

“Even though my skill level may not be there, just to have the opportunity to [perform], to me, it is a blessing,” said Williams.

He’s being awfully humble because the San Juan native is probably the only person ever to win a World Series and have an album reach No. 2 on the U.S. jazz charts.

Follow me on Twitter at JordanHarrison .

Jordan Schwartz is one of Bleacher Report’s New York Yankees and College Basketball Featured Columnists. His book Memoirs of the Unaccomplished Man is available at,, and

Jordan can be reached at

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