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Jackson Holliday was destined to be a star baseball player in high school, and a veteran starter for one of the top high school baseball programs in Oklahoma knew it would happen before Holliday was even in high school.
Holliday spent time playing with Stillwater High over the summer as a rising ninth grader. That was when his family lived in Florida while they were figuring out the future in the closing months of his father’s MLB career.
Seven-time all-star Matt Holliday was putting a cap on his 15-year career in a 2018 playoff run with the same Rockies organization that had drafted him in the seventh round in 1998 out of Stillwater High.
“(Jackson) was always about whatever was best for the family, and we just felt like getting back closer to home,” said Matt Holliday, who hit .299 with 316 home runs and was the left fielder for the World Series-champion 2011 Cardinals.
“He just handled it all really well. Even at that age, his humility and just his wanting to fit in and to play and be part of the team. I think that’s sort of how it all went down.”
Without any hesitation, Stillwater High’s starting shortstop at the time, senior Jackson Ford, told head coach Jimmy Harris that he would make way for the oldest son of the program’s most famous alum to assume the role as a freshman.
“(Ford) came up to me, he says, ‘Coach, move me to third (base) and I’m good,’ ” Harris said. “I was like, ‘So you think Jackson is a varsity player?’ He says, ‘Coach, come on. He’s going to be our shortstop.’ . . . So the transition was really easy.”
It was a moment of the many layers that created the foundation that has seen Jackson Holliday rise to become one of the top prospects for the 2022 draft and earned him the honor of Baseball America High School Player of the Year.
“I definitely thought I could have a chance after having a great high school season, but it’s really exciting to reach a goal,” Holliday said of the honor. “Obviously, you want to be the best, and it’s very exciting.”
Holliday had a historic senior season in Stillwater.
The son of an MLB all-star, nephew of Oklahoma State baseball coach Josh Holliday and grandson of longtime baseball coach Tom Holliday notched 89 hits in 2022, setting a new national record that had stood for over a decade.
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The record Holliday eclipsed for hits in a season was previously held by Oklahoma prep J.T. Realmuto of Albert High in Midwest City. Realmuto has Oklahoma State ties himself. He is the nephew of Oklahoma State’s legendary wrestling coach John Smith, who is one of just three American wrestlers to win two Olympic gold medals.
According to Holliday, his father shared with him late in the season that he was within reach of the national record. And as the games wound down, the chances to eclipse Realmuto, now an all-star catcher with the Phillies, grew slim.
Getting past the milestone down the stretch was no easy task for the 6-foot-1, 175-pound shortstop.
With the end of the season fast approaching, the Pioneers landed in one of the toughest postseason regionals in their classification. It featured three of the top senior pitchers in the state—Owasso’s Brennan Phillips and Kyndon Lovell as well as Southmoore’s Daniel Satterlee. All three had Division I commitments.
Holliday positioned himself for an opportunity to break the record by going 3-for-3 at the plate in an extra-inning game against Owasso. He doubled off Phillips early in the contest before getting an instrumental two-out RBI double to tie the game in the top of the seventh.
He then hit a leadoff home run in the top of the 10th inning—but Owasso would tie the game in the bottom frame and eventually win it in the 11th—which put him two hits away from the record heading into an elimination game.
He took advantage of every at-bat in the game against Muskogee High in what turned out to be a five-inning run-rule win for Stillwater. A double in the first moved him to within one of Realmuto, with the tying hit being an RBI single amidst a nine-run second inning.
Jackson led off the fifth and final inning needing only one more hit to set the record. And even though he was destined to get at least a few more at-bats with another meeting against Owasso, he wouldn’t have to risk it when he ripped an 0-2 pitch to left field for a triple to set the new mark.
It proved pivotal for his place in history. Owasso, the eventual Oklahoma state champions, held Jackson hitless in a lopsided matchup that ended Stillwater’s season.
“It was definitely a little bit more challenging than some other teams that we had to face, but to be able to do that against really good competition made it even better,” said Holliday, who bats lefthanded.
It shouldn’t be much of a surprise that he was able to eventually set the new mark in such a fashion.
He had been juggling pressure all season.
As one of the top prospects in the 2022 draft cass, he saw the numbers of scouts at every game grow between his junior and senior seasons.
The daily turnout was three to four times the number from the previous year, sometimes including top executives looking to get a closer look.
And that still didn’t faze him.
In 40 games, Holliday hit .685 with an on-base percentage of .749, thanks to drawing 33 walks on the season against just seven strikeouts.
But the biggest leap in his game came from an increase in power.
With the guidance of his father, he built on his frame by gaining about 10 pounds prior to his senior year. Coupling that with a small tweaking of his swing, he saw his home run numbers leap threefold from the year before.
The solo shot against Owasso in the regional tournament was his 17th of a campaign in which he had one week when he hit five over a four-game stretch, including three in an important district game against Tulsa Union.
“Being able to play on the (showcase) circuit last summer, being able to play against the best kids in the country, the game kind of just slowed down for me,” Holliday said.
“(I was) looking for pitches that I can do damage with throughout each at-bat, and not missing was important for me—getting my pitch, and being able to put a good swing on it. When you hit the ball hard, good things happen.”
The latest transformation for Holliday has roots in the pandemic year that canceled sports around the world.
At a time in his growth when Harris, who has coached for 21 years and won four state championships, has said he typically sees the biggest leap in development from high school players—the sophomore season—Holliday could have seen that growth stunted without having a year of baseball.
However, he and his younger brother Ethan, who started at third base this season as a freshman for Stillwater, had the opportunity to work on their craft without the daily routine of in-person schooling and team practices or games.
“All we had was time, really,” Matt Holliday said, “so whether it was starting to work out and a chance to lift weights every day or get a chance to hit and really kind of work on mechanical things a little bit, you start to use that time and make the best of it . . .”
“Obviously, it wasn’t ideal, but we used it as best we could to try to get better, and he did a really good job of making some adjustments and getting stronger.”
Jason Elmquist is the Stillwater (Okla.) News Press sports editor.
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