Ashley ElleWhen you meet Jason Grilli today, what you notice first isn’t the All-Star pedigree or even the easy smile of a man who’s pitched in the biggest stadiums under the brightest lights. What you notice is the way he listens. Not the celebrity kind of listening (the nod-along, just-waiting-to-speak kind) but the full, leaned-in sort that says: I’m actually here with you.
And maybe that makes sense. Because Grilli, 48, has lived the kind of life that forces presence. The son of a Major League pitcher, a 15-year veteran of The Show, a man who’s blown out his knee, rebuilt his soul, written two books, launched a wine company, and is now enjoying life in a barn in the rolling outskirts of Pittsburgh—he’s not chasing noise anymore.
“Growing up, I just wanted to be like my dad,” Grilli says, leaning back in a leather chair inside his airy, rustic home filled with an eclectic mix of sports memorabilia, Star Wars collectibles, and wine. “He happened to be a big league ballplayer, but that’s not what made him my hero.”
Grilli’s father, Steve, pitched for the Detroit Tigers and Toronto Blue Jays in the 1970s, later opening a sports bar in Syracuse, New York, a place where Jason grew up watching the game from the other side of the bar. “I’d see these guys come in, all these guys I collected on baseball cards, just sitting there eating wings,” he says. “It wasn’t like, ‘Oh, I want to be famous.’ I just wanted my own baseball bag. I wanted my own card.”
That longing to build something of his own has followed Grilli through every chapter of his life, from declining a Yankees draft offer at 17 to pursue college ball at Seton Hall, to reinventing himself after injuries nearly ended his career, to crafting his post-baseball identity with Rock‘N Ball Wines, a boutique wine brand rooted in Italian heritage, storytelling, and soul. “You wear your name on the back of your jersey your whole life,” he says. “And then one day, that jersey comes off. You’re going to be out of that jersey longer than you’re in it, so you have to make good choices for your future. Who are you when it comes off? That’s the real test.”
Grilli was a first-round draft pick by the San Francisco Giants in 1997, the fourth overall pick. His rise was quick, but it wasn’t painless. There were injuries. Multiple Trades. And yet, one thing stayed consistent: his mindset.
“I just knew,” he says, with the conviction of a man recounting a love story. “People ask how I knew baseball was the thing. I don’t know how to answer that. It’s like when you find the love of your life. You just know.”
Baseball wasn’t just his job—it was his commitment. “While other kids were at parties, I was at home with two TVs on, recording Nolan Ryan and Roger Clemens on VHS. That was my Friday night.” »
In high school, his father (worried he wasn’t enjoying the perks of youth) once dropped him off at a party down the street. “He goes, ‘Come on, you need a life!’” Grilli laughs. “But I just wasn’t into the reindeer games. I was like, ‘They’re gonna be watching me one day.’ That was my mindset.”
That kind of intensity might sound isolating, but Grilli insists it made room for a different kind of connection, one rooted not in popularity, but in purpose. “I tell kids all the time: know where you’re going. If you can see it, if you can taste it, it’s already half yours.”
That tunnel vision met its greatest test in spring training one year when a non-contact injury nearly ended his career. “My leg just exploded,” he recalls. “I dropped like someone shot me. I thought, ‘This is it.’ It was a death that day. My knee was literally on the back of my leg.”
He was sent to the famed Steadman Clinic in Vail, Colorado, where he underwent surgery. But what rebuilt him wasn’t just the scalpel, it was a stranger. A 17-year-old girl, beautiful and limping, who sat across from him in the rehab facility. She popped off her prosthetic leg and changed his life.
“I thought my career was over, and then here’s this girl, lost a limb, almost died, and she’s laughing. She became a Paralympian. I’m sitting there like, ‘What the hell am I complaining about?’ That girl, Breanna McMahon, she’s in my book. She gave me strength.”
He began journaling during his recovery. Not to write a book, just to remember. “Relief pitchers have to have short memories,” he explains. “You blow a game, give up a home run, you’ve got to be ready to pitch again tomorrow. So I started writing stuff down, because I wanted my kids to know what I went through. And also because I forget things. A lot.”
The writing became Just My Game, a memoir that reads like a conversation: raw, funny, and wise. His second book, Unlocking the Power of NIL, is a road map for college athletes navigating the uncharted territory of monetizing their name, image, and likeness.
“Every kid’s a brand now,” he says. “But nobody’s telling them how to protect themselves. I had 12 financial advisors, four agents, relationships that went south. Nobody gives you a playbook for that.”
The NIL book, now adopted into a University of Pittsburgh curriculum, comes with a workbook and is designed less to preach and more to protect. “I just want to help. If one kid avoids a bad deal, it’s worth it.”
If baseball was the book, wine might be the epilogue—and it’s a good one. Rock’N Ball Wines is Grilli’s latest act, a boutique label rooted in Italian soil and personal pride.
“Every athlete wants to be a rock star,” he grins. “And every rock star wants to be an athlete. So I blended both.” »
The bottles feature grapes like Cesanese del Piglio and Bonarda dell’Oltrepò Pavese, some tied to other iconic names like Yogi Berra and Francisco Cervelli. “The Yogi label benefits the Yogi Berra Museum and Learning Center,” he says. “Every bottle donates to a charity of the namesake’s choice. That’s the halo.”
The labels read Share Your Roots, and that’s not just a slogan. “When I played for Team Italia, I got my Italian citizenship. There’s something about honoring the name on the front of the jersey, but especially the one on the back. That’s your legacy.”
The wine venture has given Grilli something he didn’t know he needed: another team. “That’s the hardest thing after you retire,” he says. “The clubhouse goes away. The text threads. The guys. You think you’re okay. And then it hits you.”
He’s deeply hands-on with the brand, but also dreams big: goals include seven varietals by June, private label collaborations, exclusive offerings in MLB suites. And yes, even a wine tasting and party at the Rock & Roll Hall of Fame in Cleveland.
But even as he scales the business, it stays grounded, like him. “Wine isn’t a party drink. It’s storytelling. It’s vulnerability. It’s sitting around a table and just talking like we’re doing now.”
Grilli didn’t grow up in Pittsburgh (he was born in Detroit and raised near Syracuse), but he chose it. After his playing days with the Pirates, where he became a fan favorite with his signature fist-pump, he decided to stay.
“I could’ve been anywhere. I had a place in Florida. But Pittsburgh just…it just drew me in. I met people outside of baseball that were just good people. I wanted to raise my kids here.”
His property – part home, part clubhouse – has become a local legend of its own. There are always kids around, food in the fridge, music playing. “I wanted to be the house that everyone wants to come to,” he says. “And it is. Prom pics, bonfires, holidays. That’s the important stuff.”
Faith, too, is central. “Baseball chapel changed me. It was the first time I heard the Bible taught in a way that made sense to me. The music, the stories, it really woke me up.” Now he’s up early every morning reading scripture, highlighting verses. “That’s my time with God. Just me and the Word.”
Grilli’s home isn’t just filled with memorabilia. It’s filled with purpose. Framed jerseys, bottles with stories, and laughter echoing off the rafters. It’s not about fame,” he says. “It’s about impact. That’s what sticks.”
When asked what’s next, Grilli’s answer is simple. “More of this. More connection. More meaning. I’ve done the stadium and lights thing. Now I want people to drink something I helped create, I want to know that what I’m doing brings people together.”
He sees Rock‘N Ball as more than a product; it’s a platform. “I want to sit at a table with people of every background, path, story, and just say: ‘What’s your name? What’s your story?’”
At one point during our time together, he turns serious. “People say, ‘Where are they now?’ about guys like me. I’ll tell you where I am. I’m in a barn, drinking wine, watching my kids grow up, building something that matters. That’s where I am.” •
Rock’NBall Wines are available at rocknballwines.com
