“I feel like in baseball, they don’t expect you to be a normal person,” Chisholm tells me in mid-January from The West Hollywood EDITION, tucked away in his California training cocoon. “They want you to feel like you’re above the normal person. Which I hate, because I’m not.” 

Instead, Chisholm has made the sport feel like him. He’s brought the tunnel fit swag of the NBA and the NFL to a league most known for its dogged uniformity. This has been perhaps most pronounced in his choice of jewelry. The All-Star has a taste for the finer things — an iced-out Audemars Piguet, an array of Rolexes, including two-tone Datejusts and gold Presidentials. He’s got chunky, diamond-encrusted bracelets, and of course, the pièce de résistance: a custom bejeweled chain with a mammoth pendant depicting “Luffy,” the main character in Chisholm’s favorite anime, One Piece. 

But Chisholm’s wardrobe is only fractionally as thrilling as the magic he conjures in the field and at the plate. I advise all who have yet to search “Jazz Chisholm 2025 highlights” on YouTube to reprioritize. Over five full seasons in the big leagues, Chisholm has done it all: impossible diving stops at second; precise darts cannoned across the infield from third; flyballs tracked down from centerfield. He has averaged .250, hit 108 home runs, and slapped in 308 RBI. All this, done with flair. There are few prettier swings, and arguably no better bat flips in the game. 

It was this combination — obvious talent, undeniable productivity, an entertainer’s sense of showmanship — that brought the most famous franchise in the game calling. In the summer of 2024, the New York Yankees coughed up three promising minor league prospects to acquire Chisholm. He wasted no time impressing. In his first three games as a Yankee, he sent four balls over outfield fences, becoming the first Bronx Bomber in franchise history to hit so many home runs in that kind of timespan. 

In his year and a half in New York, Chisholm has become a favorite in the bleachers and in the locker room. He stands just under six feet, with the solid but lithe build of a Caribbean sprinter and the impish disposition of a younger brother. Yankee fans and teammates have grown accustomed to his dimpled grin in the dugout, usually accompanying some act of cheeky mischief. During an early season win last April against the Kansas City Royals, cameras caught Chisholm taking a joking nibble out of famously stoic hitting coach Pat Roessler. 

Chisholm had apparently adopted the biting ritual in spring training. “I’m just showing love,” he told New York Daily News by way of explanation. The 66-year-old Roessler had another interpretation: “He’s nuts.”

Chisholm’s irreverent presence has made the Yankees feel fresh, even buoyant. It has also brought people like me back to the game. It was the sight of Chisholm — a Black Caribbean man in a purple shooting sleeve, custom Jordan cleats, glittering chain spilling out of his pinstripes — that re-ignited my long-dormant Yankee fandom in the summer of 2024. I had all but given up on baseball as a venue to engage with colorful, stylish personalities. But to see a player doing his thing in the bastion of baseball heritage reminded me of the greats who first got me interested. Players like Barry Bonds and Sammy Sosa, whose own inimitable style permeated everything from their towering swings to their dangling earrings. 

Coming off the most productive year of his career with one of the most famous sporting franchises in the world, Chisholm is on the precipice of a new chapter. At 28, some would say he’s entering his baseball prime. He’s also entering a contract year: 2026 is his final season under contract with the Yankees, after which he’ll become a free agent. 

Chisholm tells me he would love to spend the rest of his career in New York. Whether that wish comes true depends largely on if he can turn in another stellar performance. Add to all of this his recent engagement to girlfriend Ahna Mac, and Chisholm is staring down the gauntlet of his own future. 

Luckily, he’s a confident guy. 

It was Chisholm’s grandmother, a professional softball player, who first introduced him to the concept of smacking a ball with a bat. She would take him out to the diamond every weekend and guide him through hitting and fielding drills. “She was like a superstar to everybody,” he says. “So I just wanted to be like Grandma.”

Chisholm’s family soon realized he was more talented than their Caribbean island could accommodate. After a breakout performance at the Cal Ripken Little League World Series, Chisholm says two Florida high schools recruited him to play. However, as he tells it, one was prohibitively expensive, and the other was too close to the potential distraction of his extended family in Orlando. That’s how, at age 12, Jazz Chisholm Jr. got shipped off to Park City, Kansas. 

One might think that going from the white sands of Nassau to the white suburbs of Wichita would be a shock to the system of an adolescent Black kid. But Chisholm didn’t feel that way. “I enjoyed it. I felt free every day,” he says. “I’m living with a host family, and they really let me do whatever. ‘Okay, you want friends to come over? You can have friends come over. Oh, you want this new video game? You can have this new video game.’” This was a far cry from Nassau, where his parents were stricter and funds were tighter. 

As intoxicating as his new freedom was, the baseball side of things took some adjusting to. Life Prep, his new school, wasn’t exactly a sports powerhouse. There were maybe 300 kids total, Chisholm says. And while the school did have strong international talent and often faced stiff competition, the scouts who attended games were rarely there to see Chisholm and his teammates. He took this as a challenge. “I was seeing guys that we played against being signed to Ole Miss, signed to Florida, and I’m like, ‘Bruh, I’m better than these guys,’” he says. 

Eventually, he says, many of the scouts began to agree. “They’d be like, ‘I did not expect someone else to be better than the guy I came to watch,’” Chisholm recalls.

Indeed, Chisholm sometimes progressed too quickly for baseball’s grinding hierarchy. Due in part to a quirk of the Bahamian education system, he graduated from Life Prep at just 16. This made him ineligible to play college baseball or to be drafted into the pros. Instead, he was forced to go home to the Bahamas for a year. At his stepfather's suggestion, he played in a talent showcase in the Dominican Republic. It was there, alongside such names as Vladimir Guerrero Jr., Fernando Tatís Jr., and Juan Soto, that he was truly able to test himself. “I still didn’t feel like I wasn’t the best,” he says. “I just felt like there were some guys with my [level of] talent.” 

I ask Chisholm about finally signing with the Arizona Diamondbacks at 17 and getting his shot in the minors. Was it a relief? “My first year? When they sent me to rookie ball? I was mad as hell,” he laughs. He didn’t see why he had to start from the bottom. “I thought to myself, ‘You got that guy ahead of me?’” 

But — unlike the other American sports where younger and younger stars are cashing in, signing deals, and hopping to the majors — baseball maintains a rigid system of apprenticeship. You start at rookie ball and work your way up to high-A until eventually, hopefully, you get invited to The Show. 

Thus began a somewhat humbling period for Chisholm. In the middle of his second year playing for a single-A team, he tore his meniscus — a season-ending injury. Then, in the offseason, he was surprised to learn that he wouldn’t be promoted. Frustrated but not discouraged, he made sure to dominate the following season. By the All-Star break, he was on his way to earning Minor League Player of the Year honors. 

The farm team director for the Diamondbacks finally relented and promoted him to the high-A Visalia Rawhide — with one caveat. “He said, ‘[For the remaining 30 games in the season], I need you to hit .300 and give me five more home runs,’” Chisholm recalls. “I hit .330 and gave him 10.”

By the time the Marlins came calling, Chisholm was more than ready. Halfway through his second season, he was leading all national league second baseman in home runs, RBIs, and slugging percentage, earning his first All-Star selection. Still, he says, Miami was never quite home. Chisholm has been candid about feeling isolated there, and about his suspicions that his flamboyance may have rubbed some older teammates the wrong way.

Ironically, it’s been as a Yankee — the club most known for its stuffy traditions — that Chisholm has felt the most license to be himself. He credits the example set by the team’s captain, Aaron Judge. “That’s when the narrative switched,” Chisholm says. “Nobody’s more credible than Aaron Judge. That’s ’cause Aaron Judge is a normal guy. 

“Judge’s attitude is: once you’re here and do what you gotta do on that field, nothing else matters,” Chisholm adds. “We can tighten up a few things off the field, but we ain’t gonna tighten up everything. You’re still a person. Go enjoy your life. Go do your thing. Do whatever you gotta do, but do it smart.”

He says he tries to talk to Judge every day — not just about baseball, but about “real life stuff,” too. That, outside of his friends, Judge is his favorite player to interface with. “He’s cultured, but he’s also super professional,” Chisholm says. “Who better to learn from?” 

He’s bonded with the rest of the team, too. In New York, Chisholm says, it’s “a family vibe. It’s a family of actual brothers.” 

Alongside his brothers, he has played some of the best baseball of his life. His first year with the team, they made it all the way to the World Series before being smited by Shohei Ohtani and the Los Angeles Dodgers. Last year, they flamed out in the divisional round against the Blue Jays, but this year, with a contract to earn and the wind at his back, Chisholm is more motivated than ever.  

Speaking of which, he has to get back to training. Before he goes, I ask him what he thinks of the baseball purists who accuse him and his cohort of young, drip-conscious stars of tainting America’s great pastime. 

“They make me feel like I’m supposed to be wearing a suit and tie all the time,” he says. “My job isn’t to put on a suit and tie. My job is to put on a uniform and get in that dirt.”