Sports Illustrated’s annual “Where Are They Now?” issue catches up with the stars and prominent figures from yesteryear—past features have included Sammy Sosa, Brett Favre, Dennis Rodman, Tony Hawk and Don King. The 2019 issue features an inside look into the new life of Alex Rodriguez, Yao Ming’s mission for Chinese basketball and more.

The tradition of Youkilis men providing alcohol to America’s parched goes back almost a century. During Prohibition, Morris Youkilis was a bootlegger who ran booze across the border for Samuel Bronfman, the Canadian kingpin who founded the Seagram Company. That gave Morris enough money to open a bar in Cincinnati called the Brown Derby, the proceeds of which allowed him to bring over, one by one, his 10 siblings from Romania. Nearly a century later, Morris’s great-nephew Kevin is also in the beverage business—but aboveboard, as the owner of Loma Brewing Company in Northern California.

Of course, Kevin was an All-Star infielder before he was a brewmaster—Youk’s 10-year major league career, most of which was spent with the Red Sox, just happened to coincide with the early-2000s craft beer explosion in the U.S. He did charity events with Boston’s Harpoon Brewery, and he often explored the expansive selection at Marty’s Fine Wine, a liquor store just off the Massachusetts Turnpike in suburban Newton. “They put me in the right direction of figuring out the styles I liked,” Youkilis says. And with a job that took him all over the country, he could put that knowledge to practice, sampling the wares at Boulevard Brewing Company in Kansas City, Cigar City in Tampa, Surly Brewing Company in Minneapolis and countless others. “If you got to play in San Diego,” he says fondly, “that was always a great trip.”

However, there was more to the visits than putting away a few brewskis. Youkilis has long had an intellectual curiosity. “He’s always been willing to learn, to adjust, to sort of go with the flow,” says Dan Reineke, a former baseball teammate at the University of Cincinnati who is now Loma’s general manager. At the tail end of Youkilis’s career, he could have stayed in the States and played in the majors; instead he signed a deal to play in Japan in 2014. “If I hadn’t won the World Series and gone to All-Star Games and all that—if I was chasing something—I probably would have stayed,” he says. “Going over there, it was just really about the experience and getting to do something unique and fun.”

So all of those brewery trips, including the ones in Japan (scouting report: “a lot more lagers, but outside Tokyo there are also a couple of craft breweries”), were about accumulating suds knowledge. “Basically putting it in my back pocket,” Youkilis says. “I was researching and studying and saying, Hey, when, I finally take off the jersey and the spikes, I’m gonna look into owning my own.”

Kohjiro Kinno

As it turned out, the time to take off the jersey came sooner than he thought. Plantar fasciitis in his left foot was making him miserable, and after 21 games with the Tohoku Rakuten Golden Eagles, he decided to retire. Within two years he had his own place up and running, serving beer and gastropub fare in Los Gatos, a Silicon Valley town near where he and his wife, Julie (Tom Brady’s sister), had moved a few years earlier. In the summer of 2017, a year after it opened, Loma was named Commercial Brewery of the Year at the California State Fair.

Originally Youkilis partnered with his brother Scott, an accomplished restaurateur in San Francisco. When Scott tired of the lengthy commute, Youk turned to Reineke, his former college roommate in what they refer to as “the baseball house.” (Both mysteriously use air quotes when bringing it up.) Youk describes the house, which accommodated up to five players, as “kind of the Animal House of the University of Cincinnati.” Its location—tucked away, and next to a frat house—kept the cops away. The beer consumed on-site was copious and decidedly non-craft. “A lot of Natty Light, and Hudepohl from Cincinnati,” says Youk. “Basically the most beer we could get for the amount of money we could raise.”

After college, Reineke went into the restaurant business, while Youkilis pursued his baseball dream. Despite the fact—or maybe because of the fact—that he looked very much like a guy who enjoyed his Natty Light, Youk would go on to become one of the most popular Red Sox players of his generation. He was drafted by Boston in the eighth round in 2001 after hitting .405 as a senior. The scout who signed him, Matt Haas, referred to him, tactfully, as a “thicker-bodied guy.” Others were less delicate. His coach at U of C, Brian Cleary, went with “pudgy.” A’s general manager Billy Beane called him simply “a fat kid.”

But he could hit. What Youk lacked in buffness—and he did work himself into very good shape during his career—he made up for with incredible eyesight: 20/11. (Ted Williams had 20/10.) It helped him pick up the spin on pitches, which allowed him to determine if they were going to end up in the strike zone. He averaged more than a walk a game in his last two seasons as a Bearcat. In the days before OPS was a thing, that only caught the attention of a few baseball minds, but Beane was one of them.

In Michael Lewis’s 2003 book Moneyball, which followed Beane through the ’01 and ’02 seasons, the GM refers to Kevin as Euclis, the Greek God of Walks—which is funny, because nothing in that appellation was entirely accurate. Youk isn’t Greek: Several generations back, a Jewish relative (whose surname was Weiner) fled Romania to get away from the Cossacks and wound up in Greece, where he adopted the Youkilis name. Nor was he a titan: As former Sox manager Terry Francona once said of his husky slugger, “I’ve seen Youkilis in the shower, and he’s not the Greek God of anything.” And while he had a good eye, Youk’s greatest offensive weapon wasn’t the base on balls. He finished in the top 10 in the AL in slugging twice and averaged 23 home runs and 94 RBIs per 162 games.

Winslow Townson

A peripheral Idiot on the curse-breaking 2004 Red Sox, Youkilis was a mainstay on the ’07 World Series–winning team and made his first All-Star appearance the following year, when he hit .312 with 29 homers and the AL’s fourth-best OPS, .958. His third and final All-Star season was ’11, when the Sox collapsed down the stretch amid stories of pitchers eating fried chicken and drinking beer—likely not of the craft variety—in the clubhouse during games.

Three seasons later his career was over. Coming to grips with the fact that he couldn’t go on was tough, but the break was clean. Visit the Loma Brewing Company and you won’t see a single piece of baseball memorabilia on the wall. Youk is there five days a week, but, unlike Sam Malone at Cheers, you won’t find him in a Red Sox Starter jacket. “He was very adamant about that from the beginning,” says Reineke. “We separate the baseball Kevin and the brewery Kevin. He wants this to stand on its own.”

That’s not to say that Youkilis doesn’t follow the game. At a Fenway Park ceremony commemorating the 10th anniversary of the 2004 championship team, he got to talking with Theo Epstein—the GM of the team who became president of the Cubs in ’11. Epstein offered him a job as his special assistant, so every February Youk goes to spring training, where he instructs hitters and throws BP. Coaching is something he has thought about, but for now he has no interest in getting back into the grind of a big-league lifestyle that would take him away from his three kids. He’s happy coaching Little League, and his focus is on Loma.

The one nod to baseball you’ll find in the restaurant comes in the name of one of the brewery’s most popular beers: Greek God of Hops, a double IPA with more punch (9.0% alcohol by volume) than Jason Varitek at his chippiest that edges out Jew-Jitsu as the most cleverly named of Loma’s beers. (Greek God of Hops is also Youk’s Twitter handle.) “We want half of the [beer list] hop-forward,” Youkilis says. He has a say in the beer recipes, but he largely leaves things in the hands of Brogan Hunter, one of the few female head brewers in the business. “I was like, ‘Make funky beers, do whatever you want,’ ” he says. “ ‘We’ve got our core beers here, so do some crazy stuff. If it fails, no big deal. It’s not a failure, it’s a learning process.’ I always see everything as a learning process.”

Youk’s own curve has been steep, but rewarding. “The reason I love this is that I think all athletes need to get into something they don’t know really well after [their playing career], because whatever you do in life, when you become the best in your field, you all of a sudden have this natural feeling that you know way more in life than you actually do,” he says. “Then when you get in the real world, you realize, Oh wow, I don’t know as much as I think I do. This has been very humbling for me, to have to really understand how a bar works, really understand how people work, how to manage them, how the kitchen works, how taxes on a business work . . . .”

Kohjiro Kinno

Talk to him and it’s clear he’s catching on. He can go on at length about all sorts of beer-related topics, like how lagers, while nice and crispy in the summer, don’t work as well from a business standpoint because of the amount of time they take up in the fermenting tanks. (Six weeks, or about twice as long as an IPA.) And when he realized that the event space in the back of the restaurant was largely unused during the day, he turned it into a coffee shop, using coffee beans roasted by a guy in Portland, which is perfect, Youk explains, because after the beans are roasted they need to rest for three days, which allows them to arrive in Los Gatos just as they’re ready for use. That’s now grown into a whole new enterprise, Loma Coffee Company; Youkilis is planning on opening a brick-and-mortar shop in Portland later this year.

The future of his beer business is getting the brews distributed. Three of Loma’s beers will be available this summer in the Bay Area, and thanks to a deal with Harpoon, two can be bought in Massachusetts and Rhode Island. One of the three for sale in California is Youk’s Kolsch. Its can features Loma’s mascot, Leo the Cat, riding on the running board of a Prohibition-era truck that’s hauling barrels of contraband.

“It’s about my family,” Youkilis says. “It’s a dedication to a family that did a lot of crazy stuff just to get everyone over here.”