The Pursuit: A Jackson Holliday Story

From a young age, everyone in Jackson Holliday’s life knew he was likely going to grow up to play professional baseball.

“He just had a really fundamentally sound swing at two years old. People would stop and watch his swing, players on the team would stop and be like, ‘That’s not normal.’ He had a good swing and he could barely walk,” said Matt Holliday, Jackson’s dad. “He was always playing ball, and he was swinging at everything. He would pretend like everything was a bat. He was obsessed with all things baseball from a very young age.”

Jackson accomplished a lot during his time playing baseball for Stillwater High School, following in the footsteps of his dad and uncle, Josh Holliday.

He was named the 2021 Central Oklahoma Athletic Conference Defensive Player of the Year as a junior. He also played in the Perfect Game All-American Classic at Petco Park that same year.

“During my senior season, I was playing really well and got a lot more attention than I did during the [prior] summer. I got stronger and played well. I say probably halfway through my high school season I knew I had a chance to be a first-round pick,” said Jackson.

While being scouted for the 2022 MLB Draft, Jackson set the amateur national record for hits in a season with 89, surpassing the now Philadelphia Phillie J.T. Realmuto’s record he set in 2010. In 2021, Jackson was named the Gatorade Player of the Year, an award which both his father and uncle received. He also earned ABCA/Rawlings Gold Glove in 2021 and 2022.

“Jackson has a very long-game approach to his career. He respects the game. It is very hard; he is competing against some of the greatest players in the world at a really young age,” said Leslee Holliday, Jackson’s mom.

Always swinging a bat led him to become the No. 1 prospect in the country before the 2022 First-Year Player Draft. On July 17, 2022, at 18 years, 7 months, and 13 days old, Jackson Holliday was drafted No. 1 overall by the Baltimore Orioles. Ten days later, Holliday signed, becoming the third number one overall pick in Orioles history.

“It has always been his dream. It has always been something he has strived to do, and I was proud of him. It has been incredible to watch him. I am so proud of him and so proud to be his brother,” said Ethan Holliday, Jackson’s younger brother.

Spending quality time together as a family is the most important thing for the Holliday’s, or, as they refer to themselves, Team Holliday. Each one of them takes pride in supporting one another through their endeavors, whether it be life or their baseball and athletic careers.

“During Matt’s career, a non-negotiable was for us to stay together as a family. I am so grateful that we did that,” said Leslee. “During Matt’s career, wherever he played, we went. The boys played baseball in whatever city Matt played in. We made it like we were going to live there the rest of our lives because holistically, it was really important to keep our family engaged in the city and involved and support him the very best we could. I am so glad we did that because it meant the kids got to see a very good example of what it meant to stay together as a team and as a family.”

“It was awesome to have them there. I have been watching my dad play for so long and for him to be there watching me play in a park that he played in a World Series at [Fenway Park] was pretty awesome,” said Jackson.

“When we got married, I said ‘Jax, we just have to get a dog. You leave me during the day, I am by myself. I need a little buddy’,” said Chloe. “He said we could only get a dog if we named him Cocoanut because we saw it on the street at Spring Training one day and I said sure we can name him Cocoanut.”

“There is a street in Sarasota [Florida] called Cocoanut Ave. and I told Chloe we could get a dog if we named it Cocoanut,” said Jackson. “That is where his name came from. I think it fits his personality pretty well.”

“I am a big fan of Jackson and Chloe and their relationship. She is quiet and really strong and a great teammate. I love watching them do life together. They are a great team,” said Leslee.

Teammates are important to the Holliday family, whether it be actual teammates who have played with Matt, Jackson, Ethan, their extended family, or their many visitors.

“Our family is expanding. We have all kinds of people staying with us. I am a mom of many. Family is very important to us, and it has a very broad definition,” said Leslee. “The guys in the clubhouse and their wives and their kids, it is a village. It is a family that extends beyond your last name.”

“I enjoy being able to live on the land and be close to family and have that community of baseball,” said Jackson. “For me, being able to be around guys that want to play in the big leagues and want to do it for a long time. Being able to do that with Ethan and guys like Roman [Anthony]and Aiden [Meola], that’s what we like to do – surround ourselves with people who have similar goals.”

“He is really good at golf and has gotten very into it. He is watching golf videos every time I go over to his house. He has got a very good swing,” said Matt.

“Having dinner with our friends and his parents and siblings every night is awesome,” said Chloe.

“I am so impressed with him. He is my oldest, so it is a very interesting season in parenting when you look at your kid and you are in awe of how they are able to handle the highs and lows of it,” said Leslee.

“I do not know what the futures holds but I do know that a non-negotiable for him, which I am very proud of, is his work ethic and his integrity and how much he cares about the people in the locker room,” said Leslee.

“I want him to enjoy it and take it day to day and work hard at it and play the game and have fun. If you process it out and you take it day by day by day, you’ll have a really good career,” said Matt.

“I just pray for him to stay healthy and achieve everything he wants to achieve. I just want to be there and support him through everything, in baseball and out of baseball,” said Chloe. “I just want to be there for him in this life together.”

“I want to be able to help the team win and have a winning year. I want to play in the playoffs and hopefully make it to the World Series. I like to set high goals. I’d like to win a Gold Glove. I have my work cut out for me. That’s my goal. I want to be an All-Star caliber player, and I'd like to have a great year and contribute and help our team win,” said Jackson. “God has a plan for me and baseball is something that he has blessed me with the ability to do, and I am going to work as hard as I can to do that, and whatever happens, happens.”