The favored sport of the star left fielder for the Boston Red Sox is not played on grass and dirt. It’s played on hardwood with two baskets and a big orange ball. Andrew Benintendi was a four-year starter on his high school basketball team, averaging nearly 25 points a game during his final two seasons. But he figured—at 5-foot-10—he’d never quite measure up on the court.
“Basketball is my favorite sport, but I knew pretty early on that I wasn’t going to have the size to play,” Benintendi says. “But it’s still my favorite. I enjoy watching it now. I can’t really play.”
During the short offseason—made even shorter by Boston’s triumphant World Series run—Benintendi could still be found catching basketball games in person. But it’s on his terms. Is he in a luxury box at TD Garden? Nope. Maybe courtside at a Xavier University game near his hometown? Not quite. He’s in a nondescript high school gym in Madeira, Ohio, watching his 14-year-old sister Lilly play.
“She went to every single game of mine growing up. She had to because she was so young,” Benintendi says. “It’s cool to just go back and watch her play.”
IN FULL SWING: Andrew Benintendi, Photographed for the Improper Bostonian by John Huet at JetBlue Park at Fenway South in Fort Myers, Florida
A low-key setting and time with family and friends is mostly how the 24-year-old prefers to spend his days off. Growing up, when he wasn’t playing baseball or basketball, he’d be hanging out at the neighborhood pool or playing in a whiffle ball league. Now, when he’s done with his early-morning offseason workout, he’s more apt to go play golf or video games.
“It’s pretty boring,” he says. “Which is what I like.”
On the field, however, Benintendi’s anything but boring. The University of Arkansas product was named the college player of the year in 2015 before the Sox drafted him with the seventh overall pick that June. Fourteen months later, Benintendi had shot through the organization and reached Boston thanks to his combination of defense, base-running and hitting. In his first playoff at bat that year, he hit a home run—becoming the youngest Sox player to homer during the postseason. In the two full seasons since, he’s filled the stat sheet with homers and steals while playing in front of the Green Monster—the latest in a long line of stars to man left field, from Ted Williams and Carl Yastrzemski to Jim Rice and Manny Ramirez.
But while it seems the outfielder was always destined for stardom, his teammate Brock Holt saw a quiet kid when Benintendi first arrived in the clubhouse during a trip to Seattle in 2016. Holt helped educate Benintendi on off-field etiquette, especially because he wasn’t even invited to big-league camp during spring training and was coming directly from playing AA-level ball in Portland.
“That series, he just asked me, ‘What should I wear to the field? What time should I get on the bus?’ Stuff like that,” Holt says. “He asked good questions, and he stuck once he made it. He gets it. He understands what he’s supposed to do. And he stays out of people’s way because he doesn’t like any attention.”
There’s a lot of evidence behind Benintendi keeping a low profile. His only big purchase after earning a $3.6 million signing bonus in 2015 was a Ford F-150 truck. On plane rides, he sits next to Holt and usually slips on his headphones and watches a movie. The close friends often enjoy breakfast together on the road as well. Initially billed in the media as a sort of matinee idol because of his looks, Benintendi’s hardly been the man-about-town in his two-plus years in Boston.
“I’ve heard a lot of people think that I’m kind of a douche because I don’t really say anything, whether it’s the media or fans. But I just like to keep to myself and go to the field, do my job and go home,” Benintendi says. “I don’t like all that extracurricular stuff.”
With the fan base locked into last season’s playoff run, however, he couldn’t escape the attention. His diving catch to win Game 4 of the ALCS saved the Sox from a loss that would’ve tied the series against Houston. It would go on to become the Associated Press’ Play of the Year and, in the moment, it elicited a big scream and some jumping from the mild-mannered Benintendi.
“For someone who doesn’t really show a lot of emotion, it was fun to see that side come out and see how excited and fired-up he was,” Holt says. “He had so much fun, and it was great to see him get excited and enjoy it.”
And during the World Series, Benintendi had a few more highlights, both of which he’s quick to shrug off. He collected four hits in the first game of the series—a win against Los Angeles—to which Benintendi replies: “The four-hit game was a bit skewed because I had two bloopers. It wasn’t as good as it looked.” He made another catch in the second game of the series that drew instant comparisons to Michael Jordan’s iconic Jumpman logo or a grand jeté in ballet, but Benintendi also downplays that highlight: “I don’t want this to come off as arrogant, but I feel like I’ve made catches like that before. I think it was just the stage it was on. Obviously, in the playoffs with the media, everything is amplified.”
But one thing that Benintendi won’t downplay is winning the World Series. When the final out was made on Oct. 28 at Dodger Stadium, Benintendi was joined on the field by his parents and two younger sisters. They exchanged hugs, posed for photos with the trophy and hung out to soak in the atmosphere—but not for too long.
“I was like, ‘Dang, let’s get inside so we can start popping bottles and stuff,’ ” Benintendi says. “The parade and hanging out with all the guys for the next couple of days after was really fun. It’s a long season and when you can win it all, it’s something special.”
While the team gears up for an encore to its 108-win season, Benintendi finds himself in a role that he hasn’t often filled with the Red Sox: Leadoff hitter. Although he spent a couple of weeks atop the lineup last season while Mookie Betts was injured—and he was successful there—he hasn’t consistently batted in the leadoff spot since college. When he was in that role for Arkansas, he was focused more on reaching base and less on hitting for power. That perspective led to an up-and-down freshman season—one of the last times he’s really struggled in his baseball career.
“After that season, I went home, worked out and came back about 15 pounds heavier. I just said, ‘I’m going to drive the ball to the gaps and stop getting the prototypical leadoff hitter mentality,’ ” Benintendi says. “Now, I’m not trying to do what I did my freshman year at Arkansas when I hit leadoff. I’m not going to change anything. I’m just moving up a spot.”
Along with a fresh lineup slot, Benintendi’s got a fresh haircut—and it’s short. If Benintendi’s known for anything beyond the field, it might be his hair. Holt sounds like a scout describing the next Babe Ruth when he opines on his teammate’s mane.
“He can rock the short hair, he can rock the long hair. It’s dark. It’s full. It’s thick. It’s curly. He’s at the top of the mountain when it comes to hair. … He had it long a couple of years ago, and it looked fantastic. He’s got it short now, and it looks fantastic. He doesn’t do anything. He’s not in the mirror fixing his hair or doing anything crazy,” Holt says. “We’ve got some guys losing their hair, so I think some guys are envious of what he’s got going on up there.”
Benintendi says the obsession with his hair dates back to his time playing in college, but he cautions those who are awaiting the return of his flowing locks. “I always get asked now, ‘When are you growing your hair out?’ And I don’t think I’m ever going to grow it out like that again.”
As for if less hair portends a Sampson-like decline, Benintendi’s not buying it for 2019.
“I’m just looking forward to getting the season started,” he says before reflecting on his quick ascent of the past few years. “It’s hard to believe that only four years ago I was drafted. It’s been a whirlwind.” •