Born for this: Holliday grew up ready for MLB career

*This story was originally published on Wednesday, April 10, 2024, prior to Jackson Holliday's much-anticipated MLB debut.
*

The regulation white ping-pong ball bounced back and forth over the net until, finally, it picked up velocity and caromed hard off the northwest corner of the table, surely headed for the ground.

Except Jackson Holliday swooped in, intercepted it and delivered a backhanded shot that narrowly clipped off the edge of the opposite side of the table, leaving his opponent (fellow Orioles prospect Heston Kjerstad), nearby onlookers and even himself in a bit of disbelief.

He’s even good at ping-pong, too.

“I’m in the top five, maybe,” said a smiling Holliday, looking around and evaluating the competition in Baltimore’s Spring Training clubhouse in Sarasota, Fla. “Only about five people play, so I like to consider myself top five.”

The 20-year-old showed no sign of fatigue in any sense late in a spring in which he was in the eye of the national spotlight. He’s the son of a former big leaguer, a former No. 1 overall Draft pick and the top prospect in baseball. And he did dozens of one-on-one interviews with media members, all wanting to know if he thought he was going to break camp with the O’s.

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But Holliday remained relaxed. Following his round of ping-pong that day, he sat in his chair, arms crossed, visibly unfazed by all of the attention. A high-pressure spring? Maybe for some. Not for the kid who has spent two decades with one objective in mind: becoming an MLB player.

It did not happen on Opening Day -- despite a stellar Spring Training -- but the dream became a reality on April 10 as the Orioles called up Holliday for his Major League debut at Fenway Park.

“My goal was to play in the big leagues as long as I can remember,” Holliday said. “It’s something that I’ve dreamt about for a long time.”

***

Matt Holliday’s MLB career began April 16, 2004 -- only 134 days after his son, Jackson, was born. His firstborn started playing the sport himself not too much later.

When Jackson was young, his grandfather -- Matt’s dad, Tom -- was in the midst of a long college coaching career that spanned five decades. From 2004-06, he had a three-year stint as the pitching coach at the University of Texas.

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Matt can recall an instance in which Tom tied a string to a Wiffle ball and hung it on the porch of his Austin home so that Jackson (not even 2 years old at the time) could hit it with a bat.

“He used to hit it, and it would go round and round and round, and he’d hit it again,” Matt recalled.

Like many kids, Jackson played other sports, too. He says he enjoyed basketball until he “stopped growing.”

“I was never tall enough to be an NBA basketball player,” said Jackson, now 6-foot. “So I liked basketball in about eighth grade, but baseball was always what I wanted to do.”

Of course, it was. Jackson grew up with the behind-the-scenes big league access that every kid wishes they could get.

Matt played for the Rockies from 2004-08, and as soon as Jackson was old enough to handle it, he tagged along with his dad in the clubhouse and often onto the field for batting practice. When he neared preschool age, he played catch with Colorado players such as Ryan Spilborghs, Troy Tulowitzki, Cory Sullivan and Garrett Atkins.

The Holliday family (which features Matt’s wife, Leslee, and two more sons, Ethan and Reed, and a daughter, Gracyn) moved around a bit. The bulk of Matt’s career was spent in St. Louis (2009-16), but he also had stints in Oakland (‘09) and New York (‘17).

When Matt rejoined the Rockies for his final MLB season in 2018, Jackson was 14 -- old enough to join in on fielding drills and scoop ground balls alongside Nolan Arenado and Trevor Story.

“He was in that prime sponge age, where he could go out there and take grounders with Nolan and Trevor and could really learn, and then apply some of the things that they were teaching him,” Matt said. “He’s always had guys that he’s got to be out on the field with and pick their brain.”

***

There was never any doubt whether Jackson had the tools to be a good baseball player. He skipped past tee-ball and was playing kid-pitch Little League before the required age. But as he began his career at Stillwater (Okla.) High School in 2019, he was a bit undersized.

“I always told people, ‘When his strength matches up with his skill, he’s going to be an unbelievable player,’” Matt said. “Once that man-muscle kicked in, he was really going to take off, and his game would really excel.”

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That happened as Jackson entered his senior season in 2022. He was already an MLB Draft prospect -- and committed to play at Oklahoma State University if that didn’t work out -- but he wasn’t yet in the conversation as a potential No. 1 pick.

The Orioles, who owned the top selection that year, were early in the process of identifying players who may have progressed over the winter when they sent area scout Ken Guthrie to Stillwater in early February. He quickly reported back with an update on Jackson Holliday.

“I remember distinctly,” said Brad Ciolek, who was Baltimore’s director of Draft operations from 2021-23. “He said to me, ‘Oh hey, I just want to give you a heads-up. We’re always talking about guys that take a leap.’ He said, ‘This kid has done that. And more.’”

A handful of other O’s scouts made trips to watch Holliday. They reported back the same thing: He was bigger, stronger and overall more polished in his game.

By mid-to-late March, Ciolek informed general manager Mike Elias that Holliday was somebody the team should consider at No. 1 overall. As the July Draft got closer, the Orioles had compiled nearly 20 reports on Holliday, all of them glowing.

When members of Baltimore’s front office made a pre-Draft visit to the Holliday household, it became even more clear what the club should do.

“You want to make sure that you’re going to get a guy that is confident in his own abilities, that is comfortable in his own skin,” Ciolek said. “When we sat down with Jackson and his family, he completely just blew us away in terms of his overall maturity, his ability to conceptualize everything, how he envisioned how his career was going to go, how goal-driven he was, how ambitious he was.”

On July 17, 2022, in Los Angeles, the pick was delivered: Jackson Holliday was now a Baltimore Oriole.

“When the Orioles decided to take him, you start diving into their Minor League talent,” Matt Holliday said. “They were coming off a bad season, but people were starting to recognize how much young talent they had.”

***

After getting his first small taste of pro ball in 2022, Holliday had a rapid ascension in ‘23 -- both up the O’s Minor League system and up prospect rankings.

Last June, Holliday became MLB Pipeline’s No. 1 prospect, a title he still held as of his promotion. It was a deserved honor in a year in which he climbed all four of Baltimore’s full-season Minor League affiliates -- Single-A Delmarva, High-A Aberdeen, Double-A Bowie and Triple-A Norfolk.

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Holliday continued a new Orioles tradition, too. They’ve now had a No. 1 overall prospect in three straight years. Catcher Adley Rutschman began the season ranked ranked No. 2, but was No. 1 at the time of his MLB debut in May 2022, then infielder Gunnar Henderson was No. 1 heading into his ‘23 rookie season.

So if there’s anybody who knows the pressure Holliday could potentially feel early in his debut big league campaign due to all of the external expectations, it’s these two new teammates, one of whom is also a former No. 1 Draft pick (Rutschman in 2019).

“It’s all perspective, the information you choose to let in,” Rutschman said. “I think he does a great job with it. He seems like he has good people around him, and it seems like it doesn’t affect him too much.”

“You’ve just got to try and block it out, just go out there and stick to your process, don’t let any of the external factors get into your head, and allow yourself to adjust to the big leagues,” Henderson said. “He’s got a good head on his shoulders.”

Rutschman and Henderson had two of the more memorable debuts in recent O’s history.

On May 21, 2022, Rutschman soaked in the atmosphere at Camden Yards and then tripled for his first MLB hit. He went on to be the runner-up in American League Rookie of the Year voting.

Later that year, on Aug. 31, Henderson debuted in Cleveland and homered in his second at-bat, also losing his helmet on the swing. In 2023, he became the first Orioles player to win AL Rookie of the Year since Gregg Olson in 1989.

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Now that Holliday is embarking on his own big league journey -- joining a Baltimore team that went 101-61 and won the AL East last season -- he’s hoping to emulate his fellow former No. 1 prospects.

“Obviously, they’ve had unbelievable starts to their career, and that is my goal, is to be able to try to win the Rookie of the Year, or come in second,” Holliday said. “It’s really cool to be able to watch what they’ve done, and that’s the footsteps that I want to follow in.”

***

Following another heated pingpong match this spring between Holliday and Kjerstad -- a fierce, burgeoning rivalry at the table -- the two had a clubhouse conversation with Ryan O’Hearn.

Holliday asked O’Hearn a question -- what was his first MLB hit? The veteran first baseman recalled he went deep in the second at-bat of his debut for the Royals on July 31, 2018.

Kjerstad told a similar story, regaling the tale of his first hit from last Sept. 15.

“Oh yeah, mine was a homer,” Kjerstad said. “That’s what I dreamed about as a kid.”

Holliday can’t get as specific when imagining how he’ll achieve the momentous feat. That isn’t to say he doesn’t want it to be memorable.

“I haven’t thought as in detail, but definitely looking forward to that day,” Holliday said. “Hopefully, I make something fun happen.”

With “that day” nearly here, Holliday can set his goals a bit higher. After all, he’ll have achieved the first step of his lifelong objective by stepping onto a big league field -- familiar turf to somebody of his pedigree -- this time as an MLB player.

Holliday’s new focus? Leading the Orioles to their first World Series championship since 1983.

“That’s my goal,” Holliday said. “You want to play in meaningful games as long as you can. I know, growing up in the clubhouse in St. Louis and New York and a little bit in Colorado, like, that’s what they did. For as long as that I can remember, it was postseason baseball.

“That’s what I’m hoping for, and I hope that Baltimore has to look forward to.”

If there’s anybody who will endlessly work to make their baseball dreams a reality, it’s the highly competitive, driven, determined, born-for-this-moment Jackson Holliday.

“You put the time in, you eat right, you sleep right, you lift, you train, you work out,” Matt Holliday said. “He just continues to try to get better and go out, perform and do what he loves to do -- which is play baseball.”