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Home for the Hollidays: Matt Holliday's unlikely return to Stillwater

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Stillwater native Matt Holliday is joining his brother, Josh, on the Oklahoma State baseball team's coaching staff

Next to the Gundys and Smiths, the Hollidays are Oklahoma State and Stillwater royalty.

Tom, the patriarch of the Holliday family, had a historical run as a baseball coach at OSU that spanned 25 years.

Josh, the oldest of the Holliday siblings, followed in his father’s footsteps and took the reins of the Cowboys in 2013 after stints as an assistant coach with several college teams.

Then there’s Matt, the baby brother, who’s back in Stillwater when it might seem most unlikely. 

Matt could have lived anywhere he wanted. He had a big, beautiful house in Florida, but returned to the place he called home to be an assistant coach.

While Matt grew up wearing OSU’s signature orange and black and spent numerous days at Allie P. Reynolds Stadium, he never suited up for the Cowboys in a college game.

Matt was a larger-than-life athlete playing football and baseball for Stillwater High School. When it came down to his career path after high school, Matt had nearly every school calling him with scholarship offers in both sports, including, of course, Oklahoma State University.

The thought of playing college football and baseball intrigued him.

But that wasn’t his dream. 

“It was a very difficult decision,” Matt said. “As an 18-year-old, you’re trying to decide whether you want to play football and baseball at the university you grew up around. My dad was the head coach at the time and my brother was on the team. Sure, it was definitely a difficult decision, but as a kid, as long as I could remember, my goal was to play in the major leagues.

When the Colorado Rockies selected Matt in the seventh round of the 1998 Major League Baseball Draft, he said it was finally his chance to live that dream.

“When the Rockies gave me the opportunity and invested an amount of money that I knew it would give me an opportunity as a high school kid,” Matt said. “You know it’s going to be difficult and you’re gonna have ups and downs and you’re gonna have tough seasons, but if they’re invested in you, you’ll get opportunities even if you struggle.”

The Right Decision

Flash forward almost two decades and Matt was coming close to the end of a successful career that included seven All-Star selections, four Silver Slugger trophies and a World Series championship in 2011 with the St. Louis Cardinals. 

Matt finished a one-year stint with the New York Yankees in 2017. He had his worst season as a batter, was 37 years old and a free agent. It could’ve been his time to hang up the jersey, but Matt knew he still had it in him to play again.

Matt and his wife and kids spent time in Stillwater during the summer of 2018. It was the first time in 14 years that he wasn’t playing baseball.

It was surreal to him. 

He had more time to spend with his family because he wasn’t on the road so much. Matt said it was great to spend more time together with Josh and Tom. But he still had that aching for baseball. 

One day when Matt was with his brother, Josh brought up the possibility of finally donning an OSU jersey.

“I mentioned to him that summer, ‘Hey, whenever you think you’re done playing in the major leagues, would you ever want to coach?’,” Josh said. “He said, ‘Yeah, I think I would, but it would kinda be a matter of timing as far as the right timing for something like that.’”

The offer was on the table for whenever Matt finally decided to retire. Then the Rockies gave him a call, and Matt knew it was something he couldn’t turn down.

Matt signed a minor-league contract with Colorado on July 28 and made it to the Rockies starting lineup less than a month later. He played an integral part in the Rockies run to the postseason, but they were eliminated in the National League Division Series.

The Next Chapter

After two decades of professional baseball, Matt decided it was finally time to step away from the game. As much as he still wanted to play in the MLB, Matt said it was time to be with his family more.

“My kids were getting older and I missed a lot of time away,” Matt said. “But at some point, you have to make that decision where you have to decide kinda the pros and cons. While I feel like I could hit in the major leagues, I just feel like it's time to be home and be there for my kids.”

Matt and his family had been moving from house to house and city to city for the duration of his career in the MLB. After Matt finished his career with the Rockies, they were living in Jupiter, Florida, but not for long.

After long talks between Matt and his wife Leslee, they decided to trade in the sand and beaches of Florida for the familiar red dirt of Stillwater.

Tom had spent time with Matt and his grandchildren in Jupiter before making his way back to Stillwater. Four days after he returned, Matt called his father to tell him the big news.

“(Matt) called me and said they were coming back here,” Tom said. “I was like, ‘To visit?’ Matt said, ‘No, we’re moving.’ It was a little bit off guard. We had no idea that he was gonna come back up here to live. So when they did, it was good because we had everyone right here at home.”

As he continued to talk to Matt, he still didn’t have a clear understanding as to why he wanted to come back.

“Quite frankly, I thought Matt and Leslee liked Florida,” Tom said. “They had a big, beautiful home. I don’t know, it’s just one of those feelings when you’re happy that family wins out.”

It was the first time since Matt and Josh were teenagers that the Holliday family was permanently located in Stillwater. 

The newly found time together in Stillwater brought Matt and Josh closer than ever. Now the two weren’t just seeing each other during the holidays when both were preparing for their respective baseball seasons. Matt’s move to Stillwater kickstarted their relationship again.

“(Having Matt in Stillwater) has probably been the most rewarding part on a personal level,” Josh said. “Just the time that you get to spend with your family. The last two years between Matt’s family, my family, my parents, Matt’s in-laws and my in-laws, this is the most family time we’ve had together in the last 20 years.

“For a great stretch of time there, we were all chasing our work and our careers and raising our families and that took us to all different parts across the country. Now baseball has allowed us to come together as a family once again.”

Baseball, The Connector

The three Holliday families frequently come together as one for family outings and dinners. They no longer have to wait for Christmas to spend time together. Matt and Josh’s children get to spend more time with their cousins and grandparents. 

Matt said his family had their anniversary of staying in the same house for a full calendar year. It was the first time that has happened since Matt was a teenager. 

He hopes Stillwater will be his home for the foreseeable future, and he hopes to help Josh win what their father came close to numerous times: a College World Series championship.

Baseball was the catalyst for the separation between all three Holidays, but it is also what brought them all back together in Stillwater. If you ask Matt, he’ll say he wouldn’t trade this time he has with his family for anything.

“Just being around the people you love the most is very valuable,” Matt said. “You start to appreciate that the older you get. We appreciate our time together and it’s nice to spend that quality time with family."

“This life moves pretty fast, so to be back here and be around family has been something that I’ve really enjoyed.”