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STILLWATER, Okla. — 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.”
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.
Jackson would perfectly imitate David Ortiz’s hand movements in the batter’s box. He could nail the wackiness of Nomar Garciaparra’s routine. He could hold a bat well above his head like Craig Counsell. He even had a perfect impression of his father’s batting stance.
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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.
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.”
Ethan Holliday stood in the on-deck circle and yelled at the home-plate umpire, partly in anger but also in defense of his brother.
Jackson had just struck out looking to end the game, sending Stillwater to a tough one-run loss to Bixby on a questionable strike.
Ethan wasn’t going to stand for it.
But Jackson walked over, put his arm around his younger brother and walked him to the dugout.
Grace in defeat.
“He needed to see his brother handle failure,” Leslee Holliday said. “Those little moments like that for a mom were really cool. Lessons I can’t teach Ethan, Jackson picked it up.”
For the better part of the past year, Jackson has been Ethan’s mentor. The brothers are three years apart in age but best friends.
Jackson is the star of today. Ethan is the star of tomorrow.
And playing on the same team — like Josh and Matt did once at Stillwater High in the 1990s — was incredibly rare but special.
“That was my favorite thing,” Leslee said. “I loved it.”
Jackson, who is around 6-feet-1 and 185 pounds, played shortstop. Ethan, who is 2 inches taller, manned third base.
They batted consecutively in Stillwater’s batting order, Jackson hitting second and Ethan third, as they made a potent offense go.
And their unique personalities shined.
Jackson is the quiet and serious brother, like Matt.
“My dad and Jackson are not really grouchy but observing us,” Ethan said.
Ethan is naturally boisterous and loud, mirroring Leslee.
“Ethan’s a little more out there, kinda loud and competitive,” Jackson said. “You can see it when he gets angry. He’s great.”
The mix of personas is challenging for a father who coaches.
Nearly every day, Jackson went to O’Brate Stadium to hit with Matt before practices or games. Jackson encouraged guidance from a seven-time All-Star who works in the offseason with close friends and current pros Nolan Arenado and Matt Carpenter.
Ethan, though, made life tough at times for his father. Ethan only wants coaching from Matt at certain points.
“I get a little hard-headed,” Ethan said.
But the family balances each other out on and off the field.
“Everybody needs a Matt in their life. Everybody needs a Jackson in their life,” Leslee said. “You gotta have that anchor.”
Of course, on the field, the brothers starred this spring for the Pioneers, with Jackson setting a national record for hits in a season with 89, passing a record 88 hits tied by Carl Albert’s J.T. Realmuto in 2010.
Jackson also had 52 extra-base hits and 79 RBIs while stealing 30 bases.
Ethan drove in 53 runs and had 23 extra-base hits in his debut spring.
“Ever since the fall, every day has been awesome,” Ethan said. “The fact it’s coming to an end is sad.”
The brothers certainly savored their lone spring together. It made both better.
“It’s probably been — as far as baseball goes — my favorite memory so far, getting to play with him,” Jackson said.
‘Two Plan A's’
Sitting in a draft meeting with a major league team around a week ago, Leslee Holliday had a huge realization.
Jackson is on track to be a professional athlete in the coming months.
“He’s always been a really good player, and he's always been one of the better players on the team,” Leslee said. “In my mind, you just go enjoy watching him. When you do this lifestyle, there’s a humility built in that you don’t make assumptions.
“Professional baseball is such a competitive lifestyle, and it’s very hard. To assume that Jackson’s name will be called, that just doesn’t feel right to make those assumptions.”
In this case, there is little doubt Jackson’s name will be called in July.
And that creates an interesting decision.
Jackson could go pro and start his career, just like Matt did when he was a seventh-round pick in 1998. Or Jackson could stay in Stillwater and become a hometown star for at least three seasons.
Either is appealing.
“We have two Plan A's,” Jackson said. “If the opportunity comes, it’ll be great. If not, I’ll get to go to OSU and play with a lot of my friends, my uncle and my dad.”
Matt and Leslee have worked to keep everything in the moment. Thinking too far ahead won’t help.
But Jackson has been preparing for this moment almost his entire life.
“It’s definitely a tough decision,” Jackson said. “My family is all here. It’d be a big step, but I know what it takes, I think, to be a big leaguer. It’ll be fun when that decision happens, and I’m excited.”
Matt and Leslee, who also have a 12-year-old daughter and 8-year-old son, have encouraged Jackson to make the final decision when it’s presented.
“As we get closer to the draft and start to understand what it is or isn’t going to look like, I think he’ll have a better idea, we’ll have a better idea of what that decision will look like as far as what’s on the line or what’s not on the line,” Matt said.
“We're going to try to enjoy the last month or two of his sort of — I don’t want to call it freedom — but one way or another baseball’s going to get serious starting in July or August, whether he comes here or goes out and plays pro baseball.
“It’s an exciting time, but as a parent it’s also hard.”
For an uncle hoping to coach his nephews, the next few months could be anxious. Instead, Josh Holliday is finding the positives.
“I think Jackson’s just had that blueprint burned in his mind, and he’s just followed it,” Josh said. “He’s just had a great senior year of high school. Where this takes him, it’ll be exciting to see. But we’re really proud of him.”
And for a grandfather who has a bucket-list item to one day coach a grandson, the opportunity might have to wait. Tom Holliday coaches Chatham in the Cape Cod League each summer. He recently worked to get Jackson there with him this summer until the draft, but league rules denied the dream.
Instead, Tom will settle for watching Jackson at the next destination.
Where that is, nobody knows just yet.
But home will likely always be Stillwater.
It was once Jupiter, where dolphins swam near their back patio each morning. Now, ocean views have been replaced by Oklahoma grasslands, dolphins by wild turkeys and deer.
Life in Oklahoma isn’t too bad.
“We’re here,” Leslee said. “We’re going to be here for the long haul. We get to be around family. You just can’t replicate that.”
Follow Jacob Unruh on Twitter at @jacobunruh.
This article originally appeared on Oklahoman: Former MLB All-Star helping son Jackson Holliday prep for July draft