Inside Jackson Holliday’s MLB draft journey
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- ESPN MLB insider
Author of “The Arm: Inside the Billion-Dollar Mystery of the Most Valuable Commodity in Sports”
AT FIRST, HE was a mascot, and then he was a marvel, and now, more than a decade after he first toddled into a major league clubhouse, Jackson Holliday’s transformation is complete. He talks like them. He looks like them. He plays like them. And on Sunday night, when his name was called first in Major League Baseball’s amateur draft, it codified his newest identity: one of them.
He is far from the only one with a familiar surname to join the latest crop of big league aspirants. There is Druw Jones (No. 2 pick on Sunday, the No. 1 player in the class), son of Andruw. And Cam Collier (potential top-5 pick), son of Lou. And Justin Crawford (potential top-10 pick), son of Carl. Elijah Green (the No. 5 pick) and Kumar Rocker (No. 3) have dads who played in the NFL. The fathers of Brooks Lee (No. 8) and Tucker Toman (first-rounder) coach college baseball.
But no one in this draft, or any recent draft for that matter, has a baseball legacy that runs as deep as Holliday’s. His dad, Matt, the seven-time MLB All-Star; his grandfather Tom, a college coach for four decades; his uncle Josh, currently the coach at perennial power Oklahoma State — Holliday was born into baseball, enmeshed by it. And no place fostered that more than the clubhouses that helped rear him.
At 3 years old, Holliday regularly ambled around the Colorado Rockies’ locker room, plastic bat always in hand. Even then, his lefty swing was so pure The New York Times shouted it out before Game 1 of the 2007 World Series. Two years later, Holliday’s father started an eight-season run in St. Louis, where the son grew from preternaturally talented kid to gifted preteen. After that, a year in New York, where as a 13-year-old Holliday befriended a Yankees rookie named Aaron Judge. And then in his dad’s final year, back to Colorado, where a new generation of Rockies — and a teenage Holliday, more fully understanding of the expectations on his dad — learned to appreciate what Matt represented.
“I didn’t have to look up to someone I didn’t know,” Holliday said. “He was there every day.”
Great baseball dad, it must be said, does not necessarily equal great baseball son, even if the 2022 draft seems to suggest otherwise. They do populate baseball: Fernando Tatis Jr., Vladimir Guerrero Jr., Bo Bichette, Ke’Bryan Hayes, Joc Pederson, Cody Bellinger, Bobby Witt Jr., Jeremy Peña. The nature element certainly doesn’t hurt a kid’s chances, but a nurturing complement is imperative. Jones didn’t become the consensus top prospect and Holliday No. 2 on Kiley McDaniel’s draft board by accident. They ascended, alongside Collier and Crawford, based on years of hard work, going from talented prospects with good bloodlines to the future elite of the sport.
“There was always a bond there just knowing our dads got to experience what we want to experience,” Holliday said. “We all play our games like our dads did. And we all have an advantage over everyone else: being raised in baseball.”
THE RAIN PELTED Jackson Holliday, and the cool air stung his skin, and as much as his body cried for shelter and relief, his mind told him to look to his right, over at third base, where Nolan Arenado was fielding ground balls, impervious to the elements. A couple of years ago, Arenado had flown to Oklahoma to offer the latest master class in the education of Holliday and his younger brother Ethan. And as he stood at shortstop, all Holliday could think to himself was: This is what my dad is talking about when he emphasizes the importance of work.
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At the same time, Arenado was astonished by Holliday’s methodology. He was still just a kid, more lithe than his father, but his approach still sticks with Arenado. During batting practice, Holliday wasn’t looking to impress anyone. He didn’t care about hitting the ball over the fence. He would spit on pitches he didn’t like, waiting for a ball to travel into the strike zone to lace it to the opposite field.
“Sometimes I still swing at balls,” Arenado said recently, “and he was trying to make sure he was swinging at strikes.”
None of this surprised Matt. When Holliday was 2 years old, his grandfather tied a whiffle ball to a string and hung it on the porch. He swatted at it like a kid with a piñata, whacking it until it lost its shape. “Ever since he was a toddler,” Matt said, “he had a natural ability to get his body in a position to hit the ball well.”
After Ethan, three years younger, arrived, the brothers soon became regulars at the ballpark. This was the life Matt had known: his father, Tom, found his greatest success, including a College World Series title, in an era where coaches did everything, from recruiting to raking the field. The park is where Matt learned the value of the grind, a tenet he believed was found in abundance at his workplace.
“I wanted them to grow up like I grew up: at the baseball field,” Matt said. “To see good work ethic, to see bad work ethic. But the predominant thing for me is I wanted to be with them. I wanted them to be involved. We’re not going to do this remote family.”
The clubhouse is a place with excessive energy and scant rules. It is, in other words, a child’s dreamland. The best days were the wins. Kids couldn’t go into the clubhouse after a loss, but a win meant Holliday got to see his dad and his dad’s buddies, swing a bat, play some Golden Tee.
Matt and his wife, Leslee, were 23 when Jackson was born. Matt was the first of the new generation of Rockies to have kids, so for Troy Tulowitzki and Garrett Atkins and Ryan Spilborghs, Holliday served as talisman and test subject. He loved baseball as much as they did — maybe more.
“It’s about access to playing and practice — and when practice turns into fun,” Spilborghs said. “Players and coaches love to throw and hit grounders or fly balls to kids, so it becomes constant play. Jax grew up in the cages.”
Going to St. Louis didn’t change that. There it was with Jon Jay, Chris Carpenter, Adam Wainwright and Matt Carpenter, who to this day will send bats to the Holliday boys. Holliday bowled over all of them with his skills and know-how and curiosity. Ethan was the wild one, with personality and verve to spare, while Holliday studied the littlest details of the big leaguers who surrounded him.
“If you’re around a bunch of elite professional athletes, even the smallest sponge is gonna pick something up,” Cardinals general manager John Mozeliak said. “And Jackson was much more than that. He watched. He listened. Whenever they were around, they made you smile because they were just always going. They loved having a bat in their hands. They loved to swing it. If they didn’t have a bat in their hands, they had a ball — and we had to remind them: no throwing a ball inside the building.”
By the time Matt retired after the 2018 season, Jackson was a month into his freshman year at Stillwater High, where his father and uncle had gone. He was only 5-foot-9 and 145 pounds, but Matt spoke to him the same way he would a rookie who just arrived in the big leagues. If you want to spend your life playing baseball, he would say, you have to be one of the 750 best players in the world. And that takes a lot more than spending hours in a big league clubhouse.
IN MAY 1998, Matt Holliday skipped his senior prom afterparty. He had a workout with the Pittsburgh Pirates the next day, his father reminded him, so he went home early, crushed the tryout and thought he was going to Pittsburgh with the 15th pick in the draft. Instead, the Pirates took Clint Johnston, a two-way player out of Vanderbilt who topped out at AA. Teams picking later in the draft thought Matt would go to Oklahoma State to play both football and baseball, but his uncle Dave, a scout with the Rockies, suggested Colorado take a flier on him in the seventh round. Twenty years later, Matt retired with a .299/.379/.510 line, 316 home runs and 1,220 RBIs.
Jackson Holliday is a lot like his father: reserved, focused, almost myopic. He’s willing, if necessary, to pass on things in service of the game. He doesn’t drink. He’s not one for parties. He fishes. He golfs. He watches movies with his girlfriend. Most of all, he practices and plays baseball.
When Stillwater returned to in-person classes in late 2020, Holliday, then a junior, opted to remain home. He could finish schoolwork on his own time and tailor baseball work around it. Holliday had grown to 6-foot-1 and a stout 180 pounds. His speed remained. His glove was still natural. And all those hours he’d have been in a classroom, instead spent with his father in the cage, had upgraded his swing from pretty to punishing.
By the time Holliday reached his senior spring this year, the reports from scouts started to tell a new story about him. This wasn’t potential anymore. It was present. The ball leapt off his bat. He set a national high school record with 89 hits, exceeding by one a fellow Oklahoma prep: J.T. Realmuto, now a three-time All-Star in his ninth big league season. In 40 games, Holliday batted .685/.752/1.392 with 17 home runs, 30 stolen bases, 33 walks and seven strikeouts. Few high school seasons ever have eclipsed it. And Matt believes it’s simply the beginning.
“When his strength and man muscles collide with his skills,” he said, “he’ll really have a chance to be special.”
What stood out to Matt as much as the numbers was how Holliday conducted himself as his star rose. People were watching his every move, seeing how he would respond to a bad call — waiting, phones in hands, for a public failure. Holliday dashed those hopes quickly. He chatted up kids on second base. He never pimped home runs. He needed to refuse, Matt and Leslee told him, to give anything to those seeking ammunition.
“I need to represent myself with super-high standards,” Holliday said. “I try to do the right thing and treat people with respect and class.”
It’s a common travail for sons of big leaguers, kids of privilege, to avoid the silver-spoon label. Jones famously reacted to an “overrated” chant this spring with a massive home run on the next pitch. Collier skipped his senior year of high school, went to junior college and raked, and has more than held his own in the Cape Cod Baseball League against players on average 3½ years older than him. CC Sabathia’s son Carsten, a slugging infielder committed to Georgia Tech, is a potential pick. No challenge, be it mental or physical, has proved too great for them.
“My parents have made this process really easy,” Holliday said. “Right now, we’re just sitting in a parking lot about to work out. We’re taking it very lightly. You would never know the draft is about to happen. We’re enjoying our last normal summer together.”
That summer entails lots of travel ball for Ethan and ultracompetitive putt-putt get-togethers — 12-year-old Gracyn Holliday, the sole girl among the four siblings, is the most cutthroat of the bunch — and Holliday’s maturity manifesting itself in all kinds of ways, like when he gets on his parents for not keeping good-enough track of the youngest Holliday sibling, 8-year-old Reed, who has a tendency to wander.
“He’s a better parent than we are,” Matt said, and he was halfway serious, though he knows better. Without those foundational years in clubhouses, all the lessons Holliday learned far younger than most would instead be part of his teenage experience. He tested out, paving the way for a skill-intensive approach that few others could even attempt to pull off. Who else has carte blanche to go up the road to the gorgeous new stadium of a perennially strong college program and hit at any time? Who else, when he’s in Jupiter, Florida, can ask for a cage to take swings and wind up at the Cardinals’ complex, doors wide open not just because of who his dad is but of who he has become?
Holliday went No. 1 to the Baltimore Orioles, who were contemplating five players, Green, Jones and Lee potentially among them. Arizona took Jones at No. 2, the first time in history two sons of major leaguers have gone 1-2. Holliday has spent his life in this game, has known for years he wanted to play baseball for a living, and now he is officially doing so. He is here because of all those who carried him along the way — and because, over these past three years, he carried himself to new heights.
“I don’t think he’d be as prepared as he is for what’s to come if he didn’t grow up in the game,” Matt said. “And as a parent, I wouldn’t be as comfortable with him potentially going out into that world if he didn’t know it.”
He knows it all right, up and down, inside and out. Baseball is in his blood, just like it is in Druw Jones’ and Cam Collier’s and Justin Crawford’s and plenty of others’. From afar, Arenado and Judge and Carpenter and Wainwright watch with pride, satisfied that the little kid they once knew — the mascot, the marvel — has turned into something altogether different. Not necessarily what he was destined to be but rather what he made of himself: finally, officially, one of them.
The author of 5 books, 3 of which are New York Times bestsellers. I’ve been published in more than 100 newspapers and magazines and am a frequent commentator on NPR.