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Bernie Williams Q&A: Why retirement has been more meaningful than Yankees career

The former MLB All-Star talks about his involvement in music, player celebrations and the time he annoyed Derek Jeter on the team plane

Bernie Williams knows New York Yankees fans don’t want to hear this. This is a fan base that is, of course, accustomed to success. Twenty-seven World Series titles. Forty American League pennants. An estimated $4.6 billion valuation.

But Williams, who appeared in five All-Star Games and four of those 27 coveted championships when he donned the pinstripes from 1991 to 2006, doesn’t put any of those accomplishments (not to mention a batting title and the 1996 American League Championship Series MVP award) above what he’s been doing in his decade-long retirement from baseball. No, he didn’t move into management or television like some of his former teammates. Nor did he become a real estate mogul or restaurateur.

Williams, 50, instead turned to music and musical education.

“Out of all the World Series rings and all the home runs and all the hits that I’ve ever done as a Yankee,” Williams told The Undefeated, “this part of my life, to me, it’s a lot more meaningful because I have an opportunity to make that much of an impact.”

Since his last season in the majors 13 years ago, Williams, a trained guitarist, has successfully transitioned from professional athlete to renowned musician and musical advocate. He’s released two jazz albums, The Journey Within and Moving Forward, the latter of which was nominated for a Latin Grammy Award in 2009. In 2016, he graduated from the Manhattan School of Music with a bachelor’s degree in jazz guitar. Alongside national organizations like Turnaround Arts and the National Association of Music Merchants (NAMM), Williams has used his platform to advocate for federal funding of music and arts programs across the country, including being instrumental in the passage of the Every Student Succeeds Act in 2015, which prioritized music and arts as part of what’s deemed a “well-rounded education.”

During a trip to Washington, D.C., for NAMM’s annual musical education advocacy fly-in at the U.S. Capitol, Williams stopped by The Undefeated’s office to talk about baseball, his native Puerto Rico and the time he annoyed Derek Jeter on the team plane.

This interview has been edited and condensed.


How did your talk with Rep. Max Rose, D-N.Y., go on Capitol Hill?

It went well. It’s not a difficult task to talk about how important music and arts is. Everybody’s kind of in agreement with it, but just when it comes down to make decisions and to fund different programs and to make sure that they understand that we are there, we’re a presence. That’s the main thing: trying to make sure we’re a positive influence in their decision-making when it comes to arts and music.

I have to imagine this is a bipartisan issue.

Whether you’re from either side of the aisle, we’re talking about a great thing for kids, a great thing for community. That shouldn’t have a party. (Laughs.) It’s a common good, man. We’re talking about things that are good for everybody in this country.

Increases in musical education funding, according to the National Association of Music Merchants, have had positive impacts on student learning, teacher dedication and student behavior. What benefits have you seen yourself?

I could talk about a lot of stats from my personal life and how much music and arts impacted my upbringing to be the person that I am today: professional athlete, former Major League Baseball player with the Yankees and all that stuff … but I think the biggest example that I could probably mention is one thing that happened a few years ago:

As a [Turnaround Arts] artist, I had a school in Bridgeport, Connecticut, and it was a middle school. And we had an opportunity to perform in the White House in front of Mrs. Obama, because it was obviously her initiative. And we had those kids going into this room to wait for their chance to perform; the first lady comes in, and she takes a picture with the whole crew. And after she left, they completely realized the whole situation that they were in, and then this collective outpouring of emotion that sort of came through. People were crying for about 10 to 15 minutes. I got choked up myself. It was insane.

And, to me, that epitomizes what I was there for and how much of an impact that experience is going to have on those kids, that they will take that for the rest of their lives.

How long have you been doing the congressional fly-ins?

This is actually my 10th year. … This is actually one of the things that I really point out in my calendar as one of the most important things that I do during the course of the year, because we’re changing policies here. I believe there’s the Every Student Succeeds Act that was passed in 2015, and it makes music and arts part of a core curriculum. I was a part of that process.

Out of all the World Series rings and all the home runs and all the hits that I’ve ever done as a Yankee, this part of my life, to me, it’s a lot more meaningful because I have an opportunity to make that much of an impact, at least in my mind, and thinking that I had a really positive impact in this whole process.

“To be able to actually have some sort of part in determining the future of the education of this country, there’s no comparison,” said Bernie Williams. John Cordes/Icon Sportswire

How do you think New Yorkers would react to you saying those four rings aren’t as meaningful?

I would stand by my words. (Laughs.) I would challenge them because to bring entertainment to people is important, especially going through the things that we have gone through as a nation, obviously 9/11 and things like that, but to be able to actually have some sort of part in determining the future of the education of this country, there’s no comparison there.

You’re talking about doing a thing that is going to last for years and years to come, and some people are going to be great beneficiaries of that kind of effort. To be a part of that is like legacy stuff. It’s like you look back on your life and say, ‘What have you done during the course of your life that was actually really meaningful?’ And if I have to compare the home run that I hit in the 1996 ALCS or this stuff? I mean, there’s a no-brainer to see what’s more important.

What was it like the first time your teammates were made aware of your musical talents?

When I was playing with the Yankees, I usually took my guitar everywhere, and I played in the lounge after batting practice and I would go into the MTV Hits channel and just play along with all the hits. Even without saying a word, they started creating this appreciation for what I did because it was something completely different than they could ever do, and they sort of let me alone. A clubhouse can be kind of cruel at times.

Bernie Williams (left) and (sometimes) duet partner Derek Jeter (right).

Did they ever get annoyed with the playing?

Yeah. All the time.

Who got the most annoyed?

I was sitting right behind Derek Jeter on the plane rides, and it was funny because I would bring my guitar and I would start playing right in the back of the plane. And some days, if he was in a good mood, he would join in on a couple of tunes. But sometimes you’re tired, and he’s like, ‘Dude, I’m trying to catch some z’s here. It’s a five-hour trip. You’re going to play the whole time?’ For the most part, everybody understood that’s what I did, and they respected me for that. As I got older and got more tenure on the team, it became more of a staple kind of thing.

What were some of your walk-up music choices?

None. I had no music choices to walk to the plate, because [of] two reasons: I felt that all the old-school players never really had music to go to the plate, and two, having a musician’s mind, I thought it would be too distracting for me to listen to the music and then just facing someone throwing 95 mph. There’s a lot of music in silence as well. And Miles Davis says, ‘It’s the notes that I don’t play are the ones that are most valuable.’

The Chicago White Sox’s Tim Anderson has put player celebrations in the news recently. What are your thoughts on players expressing themselves on the field?

I have mixed feelings about it because I sort of grew up in a generation that was maybe the last of that generation that was very conservative about their performance on the field. Baseball has always been the last sport that would take some sort of change. But, with that said, baseball is, certainly like any other sport, a reflection of society. And at this point in time, society is very different than it was 20 years ago. Even 10 years ago.

I think the players are reflecting the changes that are happening, all this joy and celebration. When you take an opportunity to do that in the old days, you actually knew that it was wrong, that it was a thing that was frowned upon. And if you did it, you did it with an intent to create some sort of turmoil and create some stuff. Nowadays, I think because it’s just kind of what’s happening now, people are just taking it as ‘We need to make this a little bit more interesting.’ The beauty of baseball is the fact that it takes all kinds of personalities, all kinds of behaviors, and you can’t say which one is right and which one is not. As long as you keep putting those numbers up, they don’t really care what you do.

You have been very instrumental in the recovery efforts of your native Puerto Rico in the aftermath of Hurricane Maria in 2017. How many times have you been back to the island since?

Plenty of times in the last two years. Probably … 20 times. I go back and forth. I still own property there, still have relatives there, my brother, siblings, my nephews. I do have a strong connection to the island still.

It’s moved out of the news cycle over the past two years. What do people need to know about what’s still going on on the ground there?

The rebuilding phase is over. It’s now trying to get back to normalcy and get all the services back: utilities, power, water. And there’s still a lot of people that have sort of fallen through the cracks in the mountain range and the most remote parts of the island that are still having a lot of problems with their lives. There’s still a lot of stuff that needs to be done, so I would encourage people to find out how they could help and do the best that they can to try to get the island back to the way it was and probably better. But as far as the tourists and hotels and all that, the island is operational now.

Does it feel like, because Puerto Rico isn’t a part of the mainland, that Americans have turned a blind eye to fellow Americans there?

I think in many ways it has, but I think it’s probably because of lack of education, perhaps. I think it’s a lot of people that didn’t even know that Puerto Rico was a part of the United States. People still ask me to this day, ‘Do you need a passport to get there?’ It’s like, ‘No, you don’t. It’s part of this country.’ (Laughs.) So I think a lot of it had to do with people not knowing the full information about the island, and it’s kind of sad that it took something like this to bring attention to it and the situation that it was. But it’s never too late. I think that if there’s a silver lining about this is that we can actually have things on the table now and people know about it, and if you know, you have a choice: you either act upon it or you choose to ignore it.

Martenzie is an associate editor for The Undefeated. His favorite cinematic moment is when Django said "Y'all want to see somethin?"