Yankees Mag: Grace Notes

The two infielders stood maybe 25 yards apart, trying to ignore the cold that enveloped them. Whipping a baseball back and forth to loosen up their arms on this frigid April day in New York City, they took a few steps closer to each other with each relay. Just 20 yards now separated them. Then 15.

The 35,000-plus fans that would eventually fill most of Yankee Stadium were largely absent, likely huddled up somewhere warmer until first pitch. Same for many of the Yankees and Athletics players who would soon take the field and do their best to perform under these conditions. An expanse of perfectly manicured green grass and a sea of power-washed blue seats gleaming in the late afternoon sun were, for the most part, all that surrounded Jazz Chisholm Jr. and José Caballero as they continued their ever-shrinking game of catch, now from 10 yards apart. Then 5.

The two players have known each other basically since they were kids in the Arizona Diamondbacks organization — Chisholm was part of the team’s 2015 international free agent class; Caballero a seventh-round pick out of Chipola College two years later. Both have overcome long odds to get to this place, one of baseball’s highest temples, hailing from homelands with short lists of big leaguers, and where having a catch in 40-degree weather is not even possible, outside of a walk-in refrigerator. Now too close for overhand throws, they fire sidearm tosses to each other. Then, just steps apart, they shovel-pass the baseball back and forth using only their gloves until there is no space left between them at all. It’s at this point that the 28-year-old Chisholm and 29-year-old Caballero hug it out, breaking into wide smiles as they perform an elaborately choreographed series of high fives culminating in a simultaneous shredding of air guitar that is quite — in Bill & Ted parlance — excellent!

It’s a comical charade, done for no one’s amusement but their own.

“We play the game hard and with passion,” Caballero says, “but we try to remind ourselves that it’s a kids’ game; it’s something to have fun with. That’s when our best comes — just having fun — and we start in the pregame.”

From the looks of it, one would never suspect that both were hitting below .200.

For Chisholm, a slow start at the plate this season was compounded by a couple miscues in the field that, in the minds of some, he struggled to adequately explain and a five-game losing streak that brought the Yankees back to the pack in the AL East. When those factors all converge, Chisholm’s detractors come out of the woodwork. Oftentimes, their enmity is based on their perception of the second baseman as being too brash, too flashy, too cocky.

The truth is, that bravado is part of what makes Chisholm so special. Not every ballplayer is cut from the same cloth, and what works for your favorite humble superstar just isn’t ever going to be en vogue for a player whose moniker is synonymous with the freest form of musical expression. Every player has statistical goals in mind; Chisholm is one of the few who will share them publicly, even if they’ve only been done once before in the history of baseball.

“The sky’s the limit for Jazz,” his manager, Aaron Boone, once told reporters with a wry smile. “Go ask him, he’ll tell you.”

By propping himself up and being his authentic self 100% of the time, Chisholm has risen to the pinnacle of his profession in perhaps the most demanding market in the sport. And for the most part, he has thrived.

“When he gets going, he’s one of the best players in the game,” says three-time MVP Aaron Judge. “You can’t dispute that.”

Those who take the time to dig beyond Chisholm’s bold statements and even bolder outfits may be surprised to discover that at his core is a young man whose values — faith, family, winning — closely align with some of the greatest to ever put on a Yankees uniform. He is someone who believes that if he’s going to reach his ultimate goal of winning a World Series, there’s only one way to do it.

His way.

***

Every Yankee takes their own path to the Bronx, but Chisholm might be the most unique player ever to put on the pinstripes.

When Jasrado Prince Hermis Arrington Chisholm Jr. was born on Feb. 1, 1998, in Nassau, Bahamas, it had been 15 years since there had been a Major Leaguer from the archipelago nation just east of the Florida Keys. André Rodgers — a former cricket player who spent 11 seasons (1957–67) as a shortstop in the National League — was the first, and while his success spurred the game’s growth at the grassroots level, only a handful of players followed the trail Rodgers blazed from Nassau to the Majors.

Chisholm grew up in the heart of the capital city in the hardscrabble Coconut Grove neighborhood known locally as “the Grove” — not to be confused with the similarly named tourist destination just a few miles (yet worlds) away. The Chisholms were “definitely not a rich family; very paycheck to paycheck,” the two-time All-Star says. “But at the same time, we learned to enjoy it.” Raised by his parents and grandparents — two of whom are pastors — and surrounded by siblings, cousins and other members of his extended family, Chisholm says he “learned how to have fun every day, to smile every day, to thank God for all the blessings that He gave us every day.”

Chisholm also learned that if he wanted something, he had to work for it — but that didn’t mean it couldn’t still be fun. He recalls not having candy money for the corner store, so he’d chat up the clerk and finagle a deal to run an errand in exchange for the item. “We couldn’t buy it, but my grandma showed us from a young age how we could get around and enjoy it every time; make it a fun thing and never a boring thing, no matter if it’s work to you.”

That was just one of the valuable lessons his elders taught him. Although he inherited a healthy dose of athleticism from his father — Jasrado Chisholm Sr. was a star sprinter in his youth — Jazz was awed by his maternal grandmother, Patricia Coakley, who taught him the game of baseball. A member of the Bahamian national softball team who played into her 60s while contributing to the growth of the sport at the youth level, Coakley was “a superstar” in young Chisholm’s eyes and remains so today. His positive attitude, his confidence, his comfort in the spotlight — all of it came from “Grammy Pat.” When the rest of his family scoffed at his dream of becoming the next Bahamian to reach the majors, she supported him unequivocally.

His love for baseball grew like wildfire as he played every weekend in the Freedom Farm Baseball League, often with kids several years older. He soaked up knowledge of baseball history, and at night, as the rest of his family nodded off to sleep, he’d stay up watching the only team on cable in the Bahamas: the New York Yankees.

“I tell you, about eight o’clock, everybody wanted to go to bed, but not me — I’m in the living room watching Robinson Canó,” Chisholm says as he stands in front of his locker in the Yankees’ clubhouse, mimicking the eight-time All-Star’s smooth left-handed swing. “I’m trying to do that.”

A chance encounter with another former Yankees infielder further solidified Chisholm’s belief that he was destined for big-league stardom. Not long after Gary Sheffield’s 22-year career ended in 2009, the nine-time All-Star was visiting the Bahamas when he saw some baseball diamonds in disrepair. That’s Gary Sheffield! Chisholm thought as he ran over to introduce himself.

“He told me, ‘I’m thinking about revamping these fields,’” Chisholm recalls. “And I said, ‘Hey, I’m about to go play. Stay here and watch my game.’ He stayed, I hit two home runs, and he was like, ‘I’m going to make sure you’re good, kid.’ Now, he’s like my uncle. Me and Gary are like this.”

To further Chisholm’s education and his Major League prospects, his family enrolled him at Life Prep Academy, a Christian boarding school in Wichita, Kansas. He had spent time visiting family in Florida, so the United States wasn’t totally unfamiliar, but the Midwest was a far cry from anything he had experienced.

“Oh my God, it was crazy,” Chisholm says. He wasn’t totally on his own; six Bahamian boys from his Little League, including two of his cousins, went to Life Prep that year. But Chisholm was the youngest in a group where “there was not much going on as far as smart ideas or smart decision making at all. There was bad decision making every day.”

At such a formative age and in an unfamiliar environment without his parents or grandparents around to watch over his every move, Chisholm began to figure out who he really was in high school. And although he admits to having a “wild” side, he also was a self-proclaimed math nerd — “Numbers were super easy,” he says — who partied with everyone. But he realized that when he wasn’t playing baseball or football or basketball, he didn’t just want to sit around someone’s house watching TV. He wanted to get outside and explore, go on an adventure. Sometimes, if no one was willing to join him, he’d do it alone.

“I was very much an everybody person, but I was also a loner at the same time, which I’m still like,” Chisholm says. “If anything gets into my [mind], like anything weird is going on around me, I tuck myself in. I stay away from everybody, and that doesn’t bother me either. If I’m good with the group that’s around me, I’m the outside guy. If I’m not, it’s just like, unnnnh. In Kansas, I was kind of both.”

Back in the Bahamas when school was out, Chisholm continued to develop into his own person and feed his imagination. He didn’t yet have the means to purchase the designer clothes that caught his eye, so he got creative by painting and customizing the clothes his family could afford to fit his own sense of style.

“I was always an ‘out there’ guy, never wearing what everybody else is wearing,” he says. “As a kid, if anybody wore this brand, I wore a different one. I had to do everything myself.”

His fortunes changed on July 2, 2015. That day, Chisholm’s family, along with coaches and other Freedom Farm players, gathered for a press conference in Nassau, cheering on the 17-year-old as he signed a professional contract with the Diamondbacks for a reported $200,000. Wearing a red vest and red bow tie to match his No. 3 Arizona jersey and cap, Chisholm stepped to the podium and spoke from the heart without so much as an index card to glance down at.

“First of all, I’d like to thank God,” the teenager began in a bygone Bahamian accent that Yankees fans would not recognize as belonging to Chisholm. After thanking the Diamondbacks for believing in him, he then delivered sincere gratitude to his grandmothers, Coakley and Judy Chisholm; the many coaches who helped him along the way, addressing each one by name; and the friends and family in attendance.

Chisholm concluded by channeling the Sunday sermons he had attended growing up, delivering a passionate message that sparked reactions of approval from the congregation before him.

“For the younger Bahamians coming up,” he said, “I just want to be a stepping stone for you all, to open the doors for you to do better. It’s through hard work and determination (that) you all can do anything. We are strong, Bahamian people. Thank you. God bless all.”

***

There might not be an athlete in all of sports who knows what it feels like to be staring down free agency and produce an otherworldly season better than Aaron Judge. In 2022, with his Yankees contract set to expire after the World Series, Judge went out and set the American League single-season record with 62 home runs, winning his first AL MVP Award. Two months later, he was back at Yankee Stadium to sign a nine-year megadeal and accept the title of Yankees captain.

With a contract that expires after this season, Chisholm is in the same boat. But early on, he wasn’t getting the same results. It was a small sample size, but after 17 games, his OPS was .485, 331 points lower than his .816 mark as a Yankee entering the season. Outwardly, Chisholm remained unwavering in his belief that he would heat up along with the weather, just as he had in 2025 when hit .160 through the first 20 games and wound up an All-Star with a Silver Slugger Award. But in a quiet moment at his locker, the impending free agent admits that seeing his paltry early-season numbers displayed on the newly refurbished super-high-definition 100-foot-wide video board in center field while he’s standing in the on-deck circle does not exactly fill him with confidence.

“I’m ready to tell them to take that [thing] down,” Chisholm says.

The thought that he could be torpedoing a nearly once-in-a-lifetime opportunity was killing Chisholm, but not because of the money at stake. That has never been why he plays the game.

“Either you go help a team win or not,” he says. “Home runs are cool, but I hate when it’s just a counting game. Especially now, I’m in my — what’s this called again? — free agency year? So, now, it’s like a lot of things matter. But to me, I hate that things matter in that way. I just want to go out there and play baseball and have fun. I don’t want to hear, ‘Hey, you’ve got to do this to get this.’ How about, ‘Hey, let’s go be first in the league, and you get this.’ That sounds great to me. I can go out there and make winning plays. Just go play.”

Did the team’s captain see his teammate pressing? Maybe a bit, which was natural given the potential enormity of Chisholm’s next deal.

“I could sit here and tell you it didn’t weigh on me (in ’22), but that’s a lie,” Judge says. “Obviously, I’ve got a job to do on the field, and I’d tell everybody, ‘Hey, I’m focused on my job.’ But we’re all human. You’ve got that in the back of your mind. Jazz just needs to continue to play his game. I think that’s what it comes down to. Play your game, have fun. Do what’s gotten you in a position to be a free agent and have an opportunity to pick where you get to play.

“Everybody goes through slumps like this, or moments like this, where things aren’t going your way. You could probably take my last 10 years, and you could find a stretch of 100 at-bats out of the 600 at-bats that I get in a season where things aren’t going my way, but you look at the end of the year, and your numbers are there, your stats are there, whatever it is. So, you’ve got to be a goldfish. You’ve got to forget the negative, try to stay focused on the positive and enjoy every day. And I think that’s one thing that he does a really good job at.”

No sooner does Judge offer his assessment than Chisholm comes bounding through the clubhouse door, a pep in his step as he breezes toward his locker, proudly displaying the bag of sour gummy candies he has procured to share with his mates.

“You see? He’s a guy that never changes,” Judge says, smiling. “He brings the charisma, he brings the energy, the confidence you need to have when you’re playing for 162 games. You need to have a short memory and always be positive.”

“He brings a flair and a style to the field with him every day, which I think is a good thing,” Boone says. “He’s himself, and we certainly want him to be that. He loves being a Yankee, loves his teammates, and he loves to go out there and put on a show.”

***

Chisholm’s next start comes the following day, April 15 — Jackie Robinson Day. Every player and coach across Major League Baseball wears No. 42 to honor Robinson, but Chisholm takes it a step further, hiking up his pant legs and tucking them into his socks just below the kneecap, the same way Jackie did. The day begins with him and Caballero playing catch, having fun, savoring the moment, appreciating their opportunity, high-fiving, rocking out.

It ends in jubilation.

Trailing the Angels, 4-3, with one out in the ninth, Chisholm hits an infield pop-up that drops between the shortstop and third baseman, then steals second base. After Jordan Romano’s full-count fastball to Austin Wells is challenged but confirmed a ball, Caballero steps to the plate. With Chisholm and Wells attempting a double steal on a 1-2 count, Caballero strokes a double to center field. Chisholm scores easily, and Wells, chugging all the way, slides home a split-second ahead of Angels catcher Logan O’Hoppe’s tag. Yankees 5, Angels 4.

“We did say, ‘This one’s for the back end,’ the 6-7-8-9 [hitters], you know?” Chisholm says of his conversation with Caballero after the walk-off win. “We know we’ve all been struggling a little bit. We’ve all been relying on each other to get better. … It was good to see the guys at the back end who haven’t been doing well come in and help us win a game, especially after waiting on it for the first three weeks of the season.”

He pops his diamond studs back in his ears and makes his way toward the exit, then off into the New York night. Maybe he’ll hit the town with some friends or go out to dinner with his fiancée or record some vocal tracks over the beats that his cousin has produced for him. Whatever it is, Chisholm will get his mind off baseball for a few hours by diving into one of his many other passions. Then he’ll come back the next day and do whatever he can to help the Yankees win.

He is living out his dreams, on his terms.

“I just do whatever I want to do — have fun, enjoy life,” he says. “It only comes once.”

Nathan Maciborski is the executive editor of Yankees Magazine. This story appears in the April 2026 edition. Get more articles like this delivered to your doorstep by purchasing a subscription to Yankees Magazine at www.yankees.com/publications.