A legendary baseball love story began with a blind date in November 1998.
That’s when 18-year-old Matt Holliday met 19-year-old Leslee Smith in Stillwater, Okla. Matt, drafted by the Rockies in the eighth round of the June draft, had recently completed short-season rookie ball in Arizona. Leslee was a student at Oklahoma State.
Nearly 27 years later, their two sons have a chance to become stars.
Last Sunday, Ethan, 18, a recent graduate of Stillwater High School, was taken by the Rockies with the fourth overall pick of the Major League Baseball draft. In 2022, Jackson, now 21, was the first overall pick. He debuted with the Orioles last April at the tender age of 20 and is now their starting second baseman.
From their famous father, the boys learned how to thrive in the batting cage and on the diamond. Matt was a seven-time All-Star, but ask just about anyone in Stillwater, and they’ll tell you that Leslee is the family’s superstar. She’s raised Jackson, Ethan, Graycn (15), and Reed (12) with a game plan and a tender touch.
“We are ‘Team Holliday,’ ” Leslee said.
She’s centered the family’s life on her deep Christian faith. Last offseason, the Hollidays took part in a mission trip to the Dominican Republic with Compassion International, a Christian child sponsorship organization.
“She doesn’t get enough credit, but then, she doesn’t need it,” Ethan said. “She knows who she is, and she has always been the centerpiece of our family. Jackson would say the same thing; my dad would say the same; and Reed and Graycn would say the same. She’s incredible.”
Added Jackson, “I don’t even know where to start. It wasn’t just about her taking us to all of our games and all of that. It’s the way she handled the chaos of the four kids, with grace and joy.
“It was very easy to grow up with somebody you consider your best friend as a kid; somebody who was your mom, as well. She let us enjoy growing up, playing baseball and just being kids.”
Oklahoma State University volunteer baseball coach Matt Holliday and his family at a Stillwater High School game. Pictured with Matt are, from left, Jackson, Leslee, Reed, Ethan and Gracyn. (Photo courtesy of Holliday family)
‘Hope Floats’
The Hollidays are baseball royalty in Stillwater.
Matt’s father, Tom, was the head coach at Oklahoma State from 1997 to 2003. That position is now held by Matt’s older brother, Josh. The family boasts four Oklahoma Gatorade Player of the Year winners: Josh in 1995, Matt in ’98, Jackson in 2022, and Ethan this year.
A baseball legacy is only part of what makes the Holliday family thrive.
“From Matt, you are going to get all of the baseball stuff, but when you get to know the Holliday boys, they are not just baseball players, they are a lot of other things, multifaceted,” said Billy Jones, who just completed his 12th season as Stillwater’s varsity assistant coach and director of baseball operations. “Leslee is the other part of their life, and she’s a big reason they are so well-rounded. Not that Matt isn’t part of that, but Leslee is their safe space.”
It would’ve been impossible to see it all coming on that casual first date back in 1998.
“We got set up by a friend,” Matt recalled from the Holliday home in Stillwater. “We went to one of those cheap movie theaters where they used to show movies on a second run, out of the main theaters.”
Leslee, laughing, chimed in.
“It was a $1.50 movie, and at the point, Matt didn’t know, financially, how it was going to go,” she said.
Does Leslee remember the name of the movie?
“Of course,” she said. ” ‘Hope Floats,’ with Sandra Bullock and Harry Connick Jr. Great movie.”
Prophetic, too.
Matt and Leslee were married on Dec. 30, 2000. Now, nearly 25 years later, after four kids, Matt’s 15 big-league seasons, two World Series, seven All-Star games, and 316 career home runs, the parents reside in baseball heaven.
“It’s a joy,” Leslee said. “I’m savoring these days, just like I did on the T-ball fields, and coach-pitch fields, and high school fields. It’s been pretty incredible.”
Leslee grew up on a ranch in Higgins, Texas. Her father, Steve Smith, raised cattle and quarterhorses. The family moved to the small Oklahoma town of Chickasha (pronounced Chick-kuh-shay), and Leslee graduated from Chickasha High School, where she played basketball, tennis, softball and soccer. She was also a cheerleader.
“Go ‘Fightin’ Chicks!’” she said with a laugh. “In my school, you pretty much had an opportunity to play every sport.”
Leslee’s side of the family has its own rich sports heritage. Her mom, Janice (Fenimore) Smith, played collegiate softball at Oklahoma State and Northern Colorado. Her younger brothers, Matt and Zach, were both high school football stars.
But it was her great-uncle, Bob Fenimore, who was most famous.
Fenimore, known as the “Blonde Bomber,” was a two-time All-American football player at Oklahoma A&M College (now Oklahoma State). He finished third in the 1945 Heisman Trophy vote.
“He was a very, very kind man,” Matt said.
“Spend any time with him and he’d tell you all about it,” Leslee added. “He was very proud of what he did for Oklahoma State.”
But Leslee’s hero is her father, and their relationship, in turn, molded the Holliday boys. Steve and his daughter often rode the range together, talking about life.
“I really enjoy spending time with him, and I wanted my kids to have the same experience,” Leslee said. “Even though our life looks different than the one I grew up with, the one thing I wanted was to make sure that our children had an opportunity to be around their dad.”
The `non-negotiable’
Matt’s career took him from Colorado to Oakland to St. Louis to New York City, and back to Colorado. There were multiple minor league stops and 20 spring trainings. Ethan was born in Tucson, Ariz., during spring training 2007.
When Leslee and Matt were at the hospital, Rockies teammates Cory Sullivan and Garrett Atkins babysat Jackson. Sullivan drove Jackson to the hospital to see his mom and baby brother.
When Matt and Leslee started their family, and Matt’s career took him across the country, she had a hard-and-fast rule: the family would live together all the time. If that meant renting an apartment in Oakland for half a season in 2009, or living in bustling New York with four kids for Matt’s 2017 season with the Yankees, so be it.
If that required Leslee to become a master traveler, juggling suitcases and baby strollers through airports, that would happen, too.
“That was non-negotiable in our marriage,” she said. “Wherever Matt was, that’s where we were going. I’m so grateful for that decision because Matt is an incredible father. I wanted the kids to know him.”
Leslee’s steadfast rule is a big part of the reason why Jackson and Ethan chased their baseball dreams.
“Leslee created an atmosphere where they would get excited about baseball and what I did,” Matt said. “She did an amazing job of allowing the kids to see my job as a positive and something they wanted to do.
“I have seen the kids of other players, sometimes resenting what their dad does because they never saw him, and he missed all kinds of things. If I had to put a bow on it, I’d say that Leslee created an environment where the kids grew to love baseball and my job.”
Jackson and Ethan played on summer travel ball teams, attended showcases around the country, and spent countless hours on the fields and in the batting cages at Oklahoma State. But they haven’t burned out on the game. Baseball is a love, not a have-to.
“That’s absolutely it,” Jones said.
The Stillwater High coach grew up in Los Angeles with Todd Marinovich, who became the ultimate cautionary tale of what can happen when intense focus on athletic achievement overwhelms a young prodigy.
Marinovich, a rifle-armed quarterback, was selected by the Raiders out of Southern California in the first round of the 1991 NFL draft. Then his life fell apart. His father, Marv, groomed Marinovich from infancy to be a star QB. But, according to a 2019 Sports Illustrated story, “Todd Marinovich was ‘the test-tube QB’ the first half of his life, a drug addict since.”
Jones saw it up close and personal.
“Marv was one of my coaches, and I saw the way he treated Todd vs. how he treated us,” Jones recalled. “We would go out to McDonald’s and stuff, but Todd had to have this special diet. He was forced to do all of this special training. You could see the burnout coming long before it happened.
“But with Jackson and Ethan, and their happiness, I think a lot of it has to do with their spirituality. They have a deep Christian faith, and their family is so centered, it’s not just about baseball. It’s pickleball. It’s golf. It’s education. It’s all of those things. They are very well-rounded, and Leslee and Matt deserve credit for that.”
‘Ready for the world’
Ethan, 6-foot-4, 210 pounds with room to pack on muscle, had an astounding senior season at Stillwater High, hitting .611 with a 2.038 OPS, 19 home runs and 64 RBIs.
Impressive, for sure, but that’s not what defines the Rockies’ first-round pick.
“I know Ethan really well, and he’s an amazing kid,” Jones said. “When we talk, it’s usually not about baseball. It’s about music or other things. Ethan is really into reggae.”
Leslee was not surprised when the Rockies picked Ethan; most draft experts had predicted it. Still, she was emotional.
“It’s exciting and you can’t help but get sentimental,” she said. “I mean, the day after Matt and I got married, we drove to Colorado for a winter development program. We lived in the basement of Kurt and Tammy Wells’ home in Littleton.
“We feel like we grew up with the Rockies organization. Jackson was born in the organization. So was Ethan. There are such sweet memories for us there. So I’m thrilled for Ethan. I can’t wait to see him in Denver. I love Coors Field. I think it’s the greatest ballpark in the league.”
She vividly remembers the 2007 season when Matt was the leading man in Colorado’s Rocktober run to the World Series. “Magical” is how she describes it.
There is no telling when Ethan will make his own Coors Field debut, but when he does, he’ll know where to look for his mom in the stands.
“The thought of moving out of this house and not having my mom around is sad,” said Ethan, who will soon begin his professional career in the Arizona Complex League. “But my mom helped mold me into someone ready for the world. She means everything to me. She’s incredible.”
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