The story sounds too good to be true until you see the kid’s swing and think, maybe.
Little Jackson Holliday was just like his dad: obsessed with hitting. From the time he could put a bat on his shoulder, Jackson was looking for a pitch to hit. Father and son would slip downstairs for basement batting practice, and because Matt Holliday was a burgeoning All-Star consumed with the science of the swing, he couldn’t help but notice his son’s setup and mechanics.
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“He’s in a better position than I am,” Matt said. “I’m trying to play in the Major Leagues, and I’m taking tips from a 2- or 3-year-old.”
It was perfection only a father could see. Impossible to be true in a literal sense.
Except when Jackson Holliday steps in the batter’s box now, his hands are quiet, his stance is relaxed, and his swing explodes without obvious effort. He is the most highly touted prospect in baseball, so easy and natural at the plate, it’s as if he’s been doing it his entire life.
Which, maybe he has.
Holliday has been swinging plastic bats in Major League clubhouses since he was old enough to walk. On Wednesday, he’ll finally get to swing the real thing on the field.
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The Baltimore Orioles are calling up the 20-year-old phenom less than three weeks after sending him to Triple A at the end of spring training. The infielder had hoped to make the big-league roster out of camp, but his mother helped put that pursuit into perspective: even if he opened the season in the minors, she told him, he’d be on the cusp of the big leagues far earlier than anyone could have imagined. Her advice was to enjoy the experience no matter where he was assigned.
“So, that’s what I’m doing,” Holliday said in the early days of spring training. “Just enjoying it and not putting pressure on myself. Just going out there and playing and having fun with these guys.”
That’s the way he’s approached it his whole life.
The name on the back of Holliday’s jersey should hang heavy, its eight letters carrying the weight of history. Matt was one of the best hitters of his era. Matt’s father is a decorated college coach, and his brother is the head coach at Oklahoma State. He has a cousin who is also a coach and an uncle who’s a scout. Matt’s second-born, Ethan, is one of the top amateur hitters in the country.
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But it’s first-born Jackson who burns brightest at the moment. He’s stepping into the Orioles’ lineup less than two years after graduating from Stillwater High School in Oklahoma. His every at-bat will come with the kind of hype and attention very few his age have ever experienced.
At Stillwater High, Jackson had a baseball coach, Jimmy Harris, who loved slogans and mottos. He’d often invent or find different phrases to motivate his players. During Jackson’s senior year, Harris gave the team shirts with the words “Pressure is a privilege” on the front. His best player had been living those words his entire life.
It may be what’s kept Jackson steady and comfortable on this mad dash to projected fame and stardom.
“I think a reason why he’s so good is I don’t think he was trying to live up to that (name),” said Cleveland Guardians prospect Jake Fox, who played with Holliday on the high school travel-ball circuit. “He was just trying to be himself.”
It takes a lot, though, to stand out in Matt Holliday’s shadow. Matt was a seven-time All-Star with a World Series ring, a batting title, and four Silver Sluggers across 15 major-league seasons. Matt learned the game from his father, and passed that love — and, clearly, some genetics — on to his sons.
As a high school senior, Jackson broke J.T. Realmuto’s national record for hits in a season, with 89 base hits. He was the No. 1 overall draft pick in 2022, and last year blew through four levels of minor league baseball. Last fall, he became the fourth player ever to have been named both High School Player of the Year and Minor League Player of the Year by Baseball America. This spring, he had a middle locker squeezed among the many young position players who have made the Orioles franchise relevant again. He had a .924 OPS with a couple of stolen bases in spring training and a .333/.482/.595 slash line in 10 Triple-A games to start this season.
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“Sometimes you get here and get starry-eyed and go through the motions,” reigning Rookie of the Year and new teammate Gunnar Henderson said. “But it seems like he knows what he wants to do and goes out and tries to do it each and every day.”
Jackson was born in December of 2003, just four months before his father’s big-league debut with the Colorado Rockies. In Denver’s clubhouse, a young Jackson would use a plastic bat to hit Wiffle balls off the walls, and if a ball ricocheted into the locker of one of his dad’s teammates, Jackson would run up to that player and wait for him to throw it. Jackson just wanted to hit it again.
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“He had a great swing as a kid, I’m telling you, man,” former Rockies shortstop Clint Barmes said. “He swung hard, and he hit that thing hard. He didn’t hold anything back.”
When Matt became a leading MVP candidate in 2007, the New York Times wrote a feature story not so much about him leading the Rockies to the World Series, but about the hitting exploits of his 3-year-old son. Josh Fogg, a Rockies pitcher, predicted then that Jackson would be a first-round pick.
The preschool perfection of his swing was only part of the scouting report. Jackson was quiet but passionate. Barmes remembers him eating meals and stopping to swing his fork like a bat. Jackson used to entertain the team by mimicking the batting stances of different players around the league. He was always watching, always listening. He rarely needed to be taught the same lesson twice.
“Very mature early on and easy to parent,” Matt said.
Jackson witnessed not only the tireless work that made his father an All-Star but also the talented teammates who came and went without the same staying power. Jackson was living the life of an MLB star while learning it could not be taken for granted.
And the fact is, Jackson’s rise to this point was not predetermined. He was not always the most highly touted player as a kid. He was good, certainly — talented and highly regarded for his baseball I.Q. — but he was small. (And he still looks young; his dad points out that Jackson doesn’t have a hint of facial hair.)
It wasn’t until Jackson’s junior and senior years of high school that he added quite a bit of muscle to his technique. His back got a little wider, his legs a little stronger, and his arms a little thicker. As Jackson grew, his stock soared. He spent his senior year bouncing to national tournaments and showcases while moving quickly up every team’s draft board.
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“You always knew it was just a matter of time,” said Red Sox prospect Roman Anthony, who knew Jackson when they were kids in Florida and became especially close to him when they were on the travel circuit as teenagers.
On one of Jackson’s first days back in high school after a fall stint with Team USA in 2021, Harris had the Stillwater team running sprints in the outfield. Jackson wasn’t necessarily the fastest player on that team, Harris said, but he remembers Jackson winning every race that day.
“I don’t know what his point was,” Harris said. “But I took it as he’s fixing to show everyone that he’s going to do what he’s supposed to do. He’s going to carry balls and pick up trash just like everyone else.”
Jackson had carried himself that way since childhood. Jackson was 5 years old when his father was traded to the St. Louis Cardinals, and he’d just turned 6 when Matt signed a seven-year deal to stay in St. Louis long-term. The Holliday family began to spend their offseasons in Jupiter, Fla., where the Cardinals hold spring training, but they enrolled Jackson in an elementary school that specialized in remote learning so that he could attend classes virtually when the whole family uprooted to Missouri at the start of each season.
Matt Carpenter talking about working out with Jackson Holliday, Matt Holliday and Ethan Holliday on @MLBNetwork:
“If you want to feel bad about where you are as a hitter, go hit with the Holliday family.”
— Sam Dykstra (@SamDykstraMiLB) March 11, 2024
Many professional baseball families let their lives revolve around the sport, accepting distance and separation as inevitable parts of the game. The Hollidays tailored their lives to exist within baseball. Home was wherever Matt was playing. The family traveled often, going to as many games as possible — home and away — and when Matt signed a one-year deal with the Yankees late in his career, the entire family (four kids at that point) moved into an Upper East Side apartment. Matt’s wife, Leslee, told the Get in the Game podcast that they would sometimes have family dinners at 11 p.m. just to have some time together at the end of a long day. That was Jackson’s life until his freshman year of high school, when his father retired.
“He was around grownups as a child,” Matt said.
Maturity came with the territory, and as Jackson outgrew his plastic bats and began to play real baseball games, the Hollidays knew he was entering a fishbowl. His emerging talent was impossible to ignore, and his last name only amplified the attention. The entire experience was combustible, primed for potential jealousy and ego that could tarnish the sport that had been central to Jackson’s entire life.
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But neither Jackson nor his dad said they could recall a truly negative experience from Jackson’s amateur days.
“There was nothing gross about it,” Matt said.
Teammates were friendly. Opponents were respectful.
“A few times it’s kind of funny at the beginning,” Jackson said. “But then I think people just recognize you as Jackson, just as a person.”
In St. Louis, Jackson played for a youth travel team called the Tide. In New York, he joined the Fury (on the recommendation of one of its alums, Harrison Bader, Matt’s former teammate). He played for a while on a Florida-based team called the Scorpions. He was picked for Team USA’s 18-and-under squad. And he had his high school team in Oklahoma.
Over and over again, Jackson had to introduce himself to new friends and teammates, and over and over again, the experience was the same.
“Jackson was a great teammate and a great person at such a young age,” said Kaden Peer, a freshman outfielder at the University of Missouri and one of Jackson’s early Tide teammates. “Always showed up to practices and games with a smile on his face.”
It was hard to resent a kid like that, especially when his dad was in the stands introducing himself as just some guy named Matt.
“If his dad was playing it up like that about his kid, maybe (there would be resentment),” Fox said. “But they’re such a humble family. They were never bragging in any sort of way.”
Jackson’s brother Ethan is a little more fiery, but Jackson is quiet by nature. He’s wired to keep his head down and go about his work. Friends today describe Jackson as even-keeled and humble. His dad calls him “pretty simple” and “hard not to like.” Jackson likes movies and fishing and golf. He plays his dad in pickleball, and he’s not much for social media. He met his wife, Chloe Cox, in high school; the two were married this winter. Jackson knows who he is and what he’s about. His confidence doesn’t require outside validation.
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Before his second game of spring training, Jackson saw the opposing lineup and texted his dad. The Atlanta Braves were playing their regular lineup, with Ronald Acuna Jr. leading off, Austin Riley in the three-hole, and Matt Olson batting cleanup. Jackson said he stood at second base that day and kept track of all the 40- and 50-homer seasons as they came to the plate.
It was more appreciation than adoration. These were the guys he’d watched every October since high school. That wasn’t lost on him, even as he began to assert himself as one of their peers.
“Just trying to be grounded and taking it day-by-day and being where my feet are planted,” Jackson said. “That’s the approach that I had last year, and it got me to where I am today.”
Pressure is a privilege, and Jackson Holliday’s been looking for a pitch to hit since the day he was born.
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(Top photo: Julio Aguilar / Getty Images)
