Jackson Holliday's major league dream now a reality with Baltimore Orioles (2024)

Ben HutchensThe O’Colly

Editor’s note: This story was originally published in The O’Colly, the student-run newspaper at Oklahoma State University in 2022. With permission, the Tulsa World re-published this story that year. It's being re-issued today after Holliday was called up Tuesday night to the major leagues.

Whenever Tom Holliday reached for a straw wrapper, his grandson Jackson Holliday would reach for a butter knife.

Tom needed to entertain his table full of grandchildren as they waited on their food, so he went for what he knows best: baseball. Even when his wife, Kathy, quietly protested the odd behavior, the Hollidays transformed the table into a baseball diamond.

Tom crumpled up the wrapper and flipped it to Jackson who would hit it with his “bat.” If they lost the wrapper Jackson would find another one to keep the game going.

“Of course, I got my wife saying, ‘Stop it.’ No, I’m not going to stop it,” Tom said. “You want to have dinner?”

Baseball has gripped the Holliday family for generations. Tom, former OSU baseball coach, got into the game because his dad was a “baseball rat.” His two sons, Matt and Josh, both played professionally and now coach at OSU.

Jackson, son of Matt and a senior at Stillwater High School, is one of the latest baseball rats the family produced. After this weekend, Jackson, a highly ranked MLB draft prospect, will face a choice similar to the one his father faced 24 years ago.

Say no to family and college or delay professional baseball aspirations.

In 1998, Matt was the third-ranked quarterback in his high school class. Les Miles, offensive coordinator at OSU, wanted him to lead the Cowboys on the football field, and Tom wanted him to hit cleanup on the diamond. The Colorado Rockies drafted him in the seventh round, later than his talent warranted because there was speculation he would play collegiately.

Once Miles left for the NFL, Matt’s options narrowed. Tom said just by watching the Pittsburgh Steelers together on Sundays he could always tell Matt was enamored with professional sports. Matt chose to pass on college and sign with the Rockies.

“There were a few more slightly different factors in my decision than his,” Matt said. “But, obviously, the similarities would be he has to make a decision on whether he wants to be a professional as an 18-year-old or if he wants to come to college. So yeah, in some ways it is a little similar.”

To Jackson, the situations aren’t identical, but he is still able to draw on the experiences his dad had for guidance.

“I wouldn’t say put myself in his shoes but kind of learn from his experiences and what he was able to do out of high school and become pro and how he handled it,” Jackson said. “It was just kind of good for me to be able to learn.”

Josh and Matt grew up at Allie P. Reynolds Stadium, a great environment to raise kids, Tom said. To spend time with their dad they went to the ballpark. Still, Tom didn’t want to force the game on them.

“(It was) December, 30 degrees and they wanted to go hit,” Tom said. “It’s not like we just rammed it down their throat. We let them choose it.”

Jackson has also grown up around baseball. He was 1½ years old and hitting plastic golf balls with a Little Tikes bat. Whenever he hit one into his grandparents’ fish tank, he ran around going crazy.

“It’s not like we have a thing in the refrigerator that says: Baseball: If you eat it, you’ll play it,” Tom said. “It’s not that easy. But it’s the sport that we kind of all have chosen to fall in love with.”

Jackson spent his childhood following his dad’s 15-year MLB career. Matt and his wife, Leslee, enrolled Jackson in a Florida school that had online options similar to a college. It allowed the family to be flexible, following Matt on several road trips throughout each season.

“We didn’t go too long without seeing each other, so that was kind of our thing,” Matt said.

Jackson spent hours in MLB clubhouses, soaking everything in. At only 3 years old, he could imitate the swings of the players he watched.

“Jackson kind of became like a circus thing,” Tom said. “‘Hey, watch Matt’s kid, watch this, ‘Show me Matt Carpenter’s swing.’”

Jackson has gone from imitating big league swings to possessing one. He is the top shortstop prospect in the upcoming MLB draft.

Jackson said he doesn’t get tired of people asking him what he’s going to do. He said his family has talked about having two “Plan A’s”, playing for his family and with his friends at OSU or starting his professional career.

The conversations about his future mostly take place around the family dinner table. Leslee said the family’s favorite meal she cooks is bison filets, sweet potatoes and greens.

“I have to cook a lot,” Leslee said. “There’s a lot of calories that those boys consume, and so I just make a lot of food and we just play cards and eat and laugh about whatever went on.”

She said with both her boys on the same baseball team there are no shortage of stories, and she savors the time listening to them. The card game of choice is spades, although occasionally rummy gets mixed in.

When it is just the family playing, Matt and Leslee are always on a team. The games are laid back.

“Sit around, shoot the breeze and just enjoy each other’s company and hang out,” Leslee said.

Ethan Holliday, Jackson’s younger brother and a freshman on the Stillwater baseball team, is the loudest voice at the table.

Ethan said he is the most talkative one in the family and, predictably, talks to Jackson about his plans all the time. The brothers are close, and Ethan knows that soon they won’t be living under the same roof.

“I mean, he’s leaving,” Ethan said. “He’s going to either Oklahoma State or somewhere in either Florida or Arizona. So, I just got to prepare myself that he’s leaving and just got to know that he’s got big plans. God has big plans for him, so I just got to root for him.”

Ethan said he doesn’t know if he’s ready for his brother to leave. He said because of his dad’s MLB career he thinks he is prepared for it but knows it will sting a little at first.

On Sunday, Jackson will hear his name called in the first round of the draft. He will have to say no to either his uncle or his dream of professional baseball.

“That’s going to be a tough day in the Holliday house,” Tom said.

Josh said it wasn’t difficult recruiting Jackson and Ethan, both of whom are signed with OSU.

“Bottom line is, my nephews, they’re the closest things you have in life to extensions of your own children,” Josh said. “So, they’re very precious and I’ve watched them grow up since the day they were born.”

As he has matured, Jackson has trained with the Cowboys. At a fall practice last season, he worked into the batting practice rotation, not missing a beat in the talented OSU lineup. Playing for his uncle and alongside the people he considers friends would be a comfortable transition.

“I think (Josh) just wants what’s best,” Jackson said. “I love him, and I’d be happy to play for him and have an opportunity to be great.”

If there were ever an 18-year-old ready for professional baseball, it would be Jackson. The million-dollar signing bonus, the no-name town minor league grind, the weight of providing for a family through athletic performance, Jackson has seen it all.

The maturity Jackson exudes after the game ends stands out just as much as his lateral quickness on the infield or opposite field power.

Tom shared the story of a New York Mets representative he knows flying in to watch a Stillwater Pioneers game. The man had a five-minute conversation with Jackson and told Tom he had the best make-up of any prospect he had talked to, and he had talked to only the 10 best kids in the country.

Jackson ended the conversation telling the scout he would be back in three years because Ethan is going to be good too.

Jackson is already conscious of what he eats. He takes further care of his body by getting up three mornings a week and lifting weights before he goes to school.

“You have to teach college guys that and they don’t like it,” Tom said. “But he’s already got that at 18 in high school.”

Jackson never appears rushed. He has time for everyone after games, hanging out by the net behind home plate for all who want to chat.

“(Jackson is a) clean-looking kid, you know, got his girlfriend, got his truck, Got his dogs. I mean, he’s got just about what any guy would want to be able to say he has a whole life,” Tom said. “I mean, he’s different.”

The jarring maturity, Tom says, comes from the time Jackson spent with his dad around MLB. Win or lose, whether his dad went 3-for-4 or 0-for-4, Jackson was allowed to be in the clubhouse, and he has taken on his father’s levelheaded personality.

Matt Holliday said he thinks the maturity is part of Jackson being the firstborn. He said Jackson has always been a mature, humble kid who just likes baseball.

Kids with those traits, who are also talked about as generational athletes, don’t come around often.

Well, maybe they do in the Holliday household. And maybe there is a reason for that.

“I think Matt and Leslie did a really, really unique job at exposing those kids to it, but never let it become too big for them,” Tom said. “And no time ever, ever let the family values slip away. Never.”