Yankees Legend Bernie Williams on Aaron Judge, Life After Baseball and the Power of a Good Nickname

Opinions expressed by Entrepreneur contributors are their own.

Ted Williams once said of his swing: “God gets you to the plate, but once you’re there? You’re on your own”.

Well I don’t believe in God, (mostly because I’m a White Sox fan) but the Splendid Splinter did add: “If you don’t think too good, don’t think too much.”

That I can relate to.

So when Poland Springs (the official water of the New York Yankees) extended an invite featuring a guided tour of the Yankee Stadium’s museum and Monument Park, followed by taking batting practice with the four-rings-flaunting, lifetime-.297-batting-average-owning, 287-homerun-hitting, five-time-All-Star appearing, four-Gold-Gloves-wearing, shirtless-heckler-hushing, ALCS-MVP-earning and Latin-Grammy-nominated Bernie Williams? This ChiSox sucker was in.

Not wanting to embarrass myself completely, I took a lesson at The Baseball Center, a world-renowned hitting facility that has had many an MLB great in its cages. “Easiest thing is just head down, eye on the ball,” preached Mike “Jellybean” Belmont, who was a college pitching prospect before a career-ending shoulder injury. “The second thing is to keep your feet still and stay balanced — you don’t have to swing as hard as you can, just make it smooth and easy, control the bat, and have confidence. A lot of baseball is swagger.”

Great advice that, alas, I never got to put to the test as the clock ran out on batting practice before I could step in the cage and show Mr. Williams my chops. But I did get some time with the man to pick his brain on all things baseball, wine and chance encounters that lead to great investments.

ENTREPRENEUR: What have been some of your better post-baseball money moves?

BERNIE WILLIAMS: Oh wow. That’s a really interesting question — but I have no idea what I’m talking about. [Laughs] I will tell you a story: It was probably at the near-end of Covid and my financial people from UBS told me at this point in time, these things are worth investing in: The cruise line industry, the airline industry and semi-conductors.

Please tell me you went with the semiconductors.

Ha, we did semiconductors! I didn’t think the cruise industry would bounce back as quickly as they expected, but with the semi-conductor industry we ended up making a healthy profit within less than two years.

Speaking of sound financial strategies: How is Millbrook Vineyards going?

The winery is going good! I’m not really that big of an investor. Yet. But I had the opportunity to make my own blend. They made 51 cases [note: Bernie’s retired number is 51] and it actually sold out. So now it’s a collectible. Wine is sort of like vintage cars and vintage guitars in the sense that they manage to keep their value.

Didn’t you randomly discover the place while on your motorcycle and tearing through Hudson Valley?

Yeah! I just kind of stumbled upon it during one of my rides and ended up spending three or four hours there, enjoying the scenery, having some wine and talking to the general manager of the place. They had great live music and the next thing you know I’m launching my own blend of red wine and playing music there, myself. Now we’re gonna have a fall launch of a white wine and I think it’s gonna be along the lines of a chardonnay. I’m really excited about it!

During your research, did you confirm the widely held belief that red really does make for more of a hangover than white?

[Laughs] Look, I think it’s less on the type and more on the amount.

Considering fellow Yankee, Aaron Judge’s, historic single-season homerun odyssey, [at the time of this interview, Judge had drilled 60 dingers], do you believe the benchmark to beat is Roger Maris’s 61 or Barry Bonds’ steroid-clouded 73?

I think it’s 61. Look, as much I like Barry, [Mark] McGuire and [Sammy] Sosa? It seems like they did something they are not supposed to do. In my opinion? I’ll take 61.

As a musician, which player-intro song did you hate the most?

Probably when David Wells was pitching. He was, like, a hard-rock Metallica guy. Especially on the day that he was pitching? He’d blast, like Anthrax stuff in the locker room.

Staying with annoying earworms, which Yankee perennials did you hate less: “Cotton-Eyed Joe“or “YMCA“?

Hate less? “Cotton-Eyed Joe”. I didn’t mind it cause we heard it a lot when I was in the minor leagues. They started the “YMCA” groundskeeper thing when I started playing. But, yeah.

With regards to your legendary center-fielding predecessors: Did you ever run into Joe DiMaggio or Mickey Mantle?

Mickey Mantle is a yes. He was always my hero even though, as a young player, coming here, I was mostly more into the 70s-era Yankees: Chris Chambliss, Bucky Dent, Thurman Munson, Willie Randolph, Ron Guidry, Reggie Jackson, all those guys. But when I got here is when I got a good sense of the overall history of the team and got to hang out with Mickey during an Old Timers Day. It was around ’93 or ’94 and I was taken into the coaches’ room. Now Mickey didn’t wanna hang out in the clubhouse, ’cause that’s where everyone would be all over him. I see him there, shake his hand and tell him what a fan I was. He knew who I was!

Of course he knew who you were!

But I didn’t know that he knew! He was so gracious, man. Still the coolest guy in the room and he signed a ball for me with “To Bernie: You’re great. Mickey Mantle”. So I bring it to my apartment in Jersey at the time, my two-year-old sees the ball and starts scribbling on it! So that ball has my, now, 32-year-old son’s scribbles on it and Mickey Mantle’s signature.

That’s almost as bad as what happened to Babe Ruth’s ball in The Sandlot.

[Laughs] Well it’s infinitely more valuable to me than pretty much anything else, I will never sell it, scribbles and all.

Music-wise: You had signed with Paul McCartney’s music publishing firm: Was he disappointed to find out that this switch-hitting center fielder wasn’t a left-handed guitarist like he is?

Well, I don’t think he was “disappointed” —

— There aren’t many of those southpaw strummers out there.

I was just so taken with him. I mean, he’s like royalty! I met him in the most vulnerable of circumstances. It was at the end of a game, towards the end of my career, and in those years, afterward, I’d look like the Michelin Man, all covered in ice packs. I got my knees all iced up, my shoulder iced up and I’m walking towards him like the mummy. But he was just great. I’ve met Bruce Springsteen, James Taylor, Bon Jovi, all those guys. I was surprised to see that they were as excited to meet me as I was to meet them because they were my musical heroes.

Final question: I have yet to hear a Bernie nickname that I like, so wanted to throw a couple super-cool ones by you that I came up with. The first one is Bern Notice. You know, you get a standing double and yell at the pitcher “That was your BERN NOTICE!!”…

Okay, okay, I like that.

Second one involves your number: Fifty-FUN.

Alright, alright.

You clearly hate it. Lastly, The Clutch Oven.

Ah, man, I think I may go with Bern Notice.

Not Clutch Oven?

Nah. Well…? Nah.