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Matt Holliday has lived a charmed baseball life. His oldest son, Jackson, could be next.

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Matt Holliday has lived a charmed baseball life. His oldest son, Jackson, could be next.​


Jacob Unruh
Oklahoman

STILLWATER — Leslee Holliday is prepared for another move.

The moving company arrives this week. They’ll bring boxes and tape. They’ll load the truck. They’ll head down the road.

As the wife of former MLB star outfielder Matt Holliday, she's seen it happen dozens of times. But this time the distance is short.

They’re not even leaving Stillwater.

“This is where we wanted to raise our family,” Leslee said.

For nearly four years, Oklahoma State has made this home for the Hollidays. But until now, it was technically temporary.

Their custom-built home is permanent.

Baseball has driven the entire Holliday clan for decades. It united them in Stillwater more than 40 years ago, then sent them on different paths around the country.

But the sport has made the family whole again at OSU.

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Matt, now retired, is the volunteer coach for his older brother, Josh, who is in his 10th season running the program his dad, Tom, once led. Tom is now an analyst for in-house TV broadcasts. Matt’s high-school-aged sons, Jackson and Ethan, are committed to the Cowboys.

Three generations separated by only a few miles are continuing their legacy.

“This is what my family does,” said Ethan Holliday, a 15-year-old freshman. “We’re going to play baseball and we’re going to be successful. That’s what our goal is.”

As the college baseball postseason begins, no family will be in a bigger spotlight. The Cowboys — despite a late-season swoon — remain contenders to make the College World Series. And Jackson Holliday, the oldest of Matt’s three sons, faces a momentous decision about his future. A projected top-five overall pick in July’s MLB Draft, the uber-talented shortstop could forgo his college career like his father. Or he could play for his family.

Baseball might again spread the family out, but that decision will come later.

For now, the Hollidays are making the most of their time together.

“The idea of moving back to Oklahoma and getting back involved with this baseball (program) and still having the freedom to be a much more heavily involved dad and husband,” Matt said, “it was a good mix for me.

“I didn’t know exactly what I would be doing when I was done playing ball, but I’m pretty happy with the way this situation is around here.”

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A new face of the family​

Tom Holliday could only hear giggling.

He searched his Austin home for his 2-year-old grandson and found him on the back porch. Jackson was having the time of his life swinging away with a plastic bat at a ball on a rope.

“He was always hitting something,” Tom said with a laugh.

Straw wrappers rolled up and a butter knife became batting practice tools at tables. Breadsticks were excellent bats in restaurants. Socks rolled into balls worked well in living rooms.

It all became a show.

Throw something at Jackson, and he’d undoubtedly hit it.

“He had the greatest eye-hand coordination that I’ve ever seen in my life,” said Tom, who coached college baseball for 40 seasons.

Even Matt noticed. If he fell into a hitting slump during his early years with the Colorado Rockies, there was Jackson at home swinging.

Everything was pure.

“I would be struggling and trying to watch his movements because they were just so natural but yet so mechanically sound,” Matt said.

Jackson became a regular at the ballpark with Matt, spending more time in clubhouses than the family rooms and focusing from the stands while wearing a tiny glove.

A new face of the family​

Tom Holliday could only hear giggling.

He searched his Austin home for his 2-year-old grandson and found him on the back porch. Jackson was having the time of his life swinging away with a plastic bat at a ball on a rope.

“He was always hitting something,” Tom said with a laugh.

Straw wrappers rolled up and a butter knife became batting practice tools at tables. Breadsticks were excellent bats in restaurants. Socks rolled into balls worked well in living rooms.

It all became a show.

Throw something at Jackson, and he’d undoubtedly hit it.

“He had the greatest eye-hand coordination that I’ve ever seen in my life,” said Tom, who coached college baseball for 40 seasons.

Even Matt noticed. If he fell into a hitting slump during his early years with the Colorado Rockies, there was Jackson at home swinging.

Everything was pure.

“I would be struggling and trying to watch his movements because they were just so natural but yet so mechanically sound,” Matt said.

Jackson became a regular at the ballpark with Matt, spending more time in clubhouses than the family rooms and focusing from the stands while wearing a tiny glove.

And Jackson’s obsession with baseball only grew.

“I think in his being and soul he’s always loved baseball,” Matt said.

It didn’t take long for Jackson to become a star.

Jackson played travel ball wherever Matt played but primarily in Florida, Alabama and Georgia. The extreme skill elevated him wherever he went.

Following Jackson’s eighth-grade year at Jupiter (Florida) Christian, the family spent the 2018 summer in Stillwater. They were mulling the idea of moving back as Jackson played with a summer team for Stillwater High.

He never struck out that summer, wowing his future teammates.

“He was probably our best hitter then,” Stillwater High coach Jimmy Harris said.

After Matt finished his playing career that October with one final run in Colorado, he and his family moved from Jupiter to Stillwater. He joined the OSU coaching staff as a volunteer assistant.

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Jackson became the starting shortstop for the Pioneers as a freshman. He hit the travel-ball circuit in the offseasons. Last summer, he was named a Perfect Game All-American.

And he steadily rose up the draft boards.

The next star to carry the Holliday name had arrived.

“Our whole family’s well known, in baseball at least,” Jackson said. “It’s good to wear it with pride.”

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