It was late October 2007 and the Colorado Rockies were preparing to face the Boston Red Sox in the World Series opener at Fenway Park. This was the first World Series appearance in franchise history for the National League’s Rockies and the national media were on the prowl looking to identify the Series’ biggest storylines.
An obvious target on the Rockies side was their terrific 27-year-old leftfielder Matt Holliday, who in 2007 led the NL in hits (216), doubles (50), batting average (.340), total bases (386) and RBI (137); he would finish as runner-up in the MVP balloting to the Phillies Jimmy Rollins.
Tyler Kepner, the highly respected, longtime award-winning baseball writer for the New York Times, did in fact decide to feature Holliday in a piece that was published on Oct. 25, but he took a slightly different angle. He introduced to his readers Holliday’s then-3-year-old son, Jackson, who was an endearing presence on the field during the Rockies’ pregame routine and often in the postgame clubhouse.
Jackson Holliday, now a 17-year-old junior at Stillwater (Okla.) High School and a top national prospect in the prep class of 2022, had a knack for mimicking a big league player’s batting stance, Kepner reported. Matt Holliday would call out a player’s name – David Ortiz or Nomar Garciaparra as an example – and the toddler Jackson would get into that player’s stance.
“When you’re imitating big-leaguers at 3 years old,” Jackson’s grandfather, Tom Holliday, told Kepner, “obviously you’re a pretty good showman.”
Jackson’s mom, Leslee Holliday, has fond memories of her son going through the routine as well. The young family was at the 2007 MLB All-Star Game in San Francisco when Garciaparra came up to bat and Jackson began replicating all the equipment adjustments Nomar famously made before settling in. Unbeknownst to Leslee, Garciaparra’s wife, soccer great Mia Hamm, was sitting right behind her.
“She tapped me on the shoulder and she was like, ‘That’s the most amazing thing I’ve ever seen,’” Leslee recalled during a phone conversation with Perfect Game late last week. “And I was like, ‘I know, right?’ It was just crazy.”
In 2007, the show that Grandpa Tom spoke about was still very much in its infancy. As the year 2020 mercifully descends into the history books – not a minute too soon for a lot of us – Jackson and his entire baseball-centric family are making sure the show goes on at the highest levels of amateur baseball. It’s a Stillwater baseball legacy that seems destined to thrive for generations to come.
Jackson Holliday, a 6-foot-1, 170-pound primary shortstop with sure hands, a spring in his step and a fluid lefthanded swing, is an Oklahoma State commit who is slotted at No. 34 overall (No. 7 shortstop) in Perfect Game’s class of 2022 national prospect rankings.
And he is the son of Matt Holliday, a 7th Round pick of the Rockies out of Stillwater High – the same school Jackson attends – in the 1998 MLB June Draft, a seven-time All-Star and a career .299 hitter with 468 doubles, 316 home runs and 1,220 RBI over 15 seasons – 14 with the Rockies and the Cardinals.
Matt Holliday, a leftfielder, made his major league debut with the Rockies in mid-April 2004 when Jackson was four months old; he played his last game on Oct. 1, 2018 when his oldest son was a 15-year-old high school freshman.
In other words, Jackson Holliday was raised in the nation’s major league ballparks, getting his first figurative big league cup of coffee at a time when milk and chocolate-chip cookies ruled the day.
“We’ve got to experience a lot of different places and meet a lot of different players, which was really cool,” Jackson told PG. “Just getting to watch them was really cool … and it was a really good experience getting to travel and meet all these players and learn about what they do to get ready for games and for seasons.”
Matt and Leslee married young when Matt was already playing in the minor leagues as a 19-year-old, so Leslee went along for the entire ride while her husband navigated every level of professional baseball. She saw first-hand as the professional players, including those as talented as Matt, dealt with the ups and downs the game presents at every turn, especially in those early years.
She feels like those experiences give her an advantage with Jackson from the perspective of watching Matt go about his business for so many years.
“So as a parent, something that I think is very important from my relationship with Jackson is to just not be too involved,” Leslee said. “I think it’s important to encourage work-ethic and important to encourage a big perspective but I never wanted our relationship to ebb and flow on his success or failure.”
Matt Holliday takes the same approach while also acknowledging he feels blessed that he was able to provide his oldest son with opportunities and experiences that are available only to the children of active big-leaguers. He also feels fortunate that he was with the Rockies for six years and the Cardinals for eight, two very family-friendly organizations.
“The freedom I had to bring in the boys and let them be around the environment and be around their dad and be around my friends and the game (was special),” Matt told PG during last week’s group phone conversation that included Leslee and Jackson. “And seeing me and others with a passion for baseball, it’s almost natural that that kind of rubs off.”
When Jackson Holliday spoke with PG late last week he was on his way to basketball practice at Stillwater HS, a sport which he also enjoys. In fact, he said, he plans to continue to play hoops the remainder of his prep career just to kind of mix things up sports-wise during Oklahoma’s winter months.
But baseball provides the guiding light and Jackson faithfully follows its beacon. With the deep roots the extended Holliday family have established both in the Stillwater and Oklahoma State communities nothing else could have possibly been expected.
Jackson’s grandad and Matt’s dad, Tom Holliday, was the Cowboys’ head coach from 1997-2003 and led them to the 1999 College World Series. His uncle and Matt’s brother, Josh Holliday, took over as head coach of the program in front of the 2013 season and took the Cowboys back to the CWS in 2016; Matt has served as a voluntary assistant coach with the program since his retirement in 2018.
Oklahoma State has long been among the best in its conference – most recently as members of the Big 8 and the Big 12 – and it opened up a $60 million, state-of-the-art O’Brate Stadium in February only to have the season cancelled by the coronavirus pandemic.
“It was really exciting to be able to commit here and keep playing for my family,” Jackson said. “With the new stadium and everything, it’s going to be really fun. It’s like a big-league stadium; it’s pretty awesome.”
The young Holliday still has two more seasons left to play at Stillwater High before he can start thinking about life in the Big 12 and he’s excited about that, too. All things considered, there really isn’t anything better than playing with your high school buddies on the same field where your dad first grabbed the attention of MLB scouts.
After his 2020 spring season at Stillwater High was cancelled by the pandemic, Jackson jumped right into the summer travel ball season, playing with the Oklahoma-based Sandlot Scout Team 2022 at the PG 16u National Elite Championship in Hoover, Ala.
That was the first of three PG tournaments Jackson Holliday played in with Sandlot over the summer, and he earned all-tournament recognition at two of them: the PG 16u National Elite and the PG 16u World Series.
He also had the opportunity to play up at five PG national championships with the Florida-based Scorpions 2021 Founders Club and Scorpions Marucci Franchise Team.
While playing with the Scorps, Holliday was named all-tournament at the PG 17u National Elite Championship in Hoover, the Ultimate Baseball Championship Powered By PG and Baseball America in Hoover, the PG WWBA 17u National Championship in Marietta, Ga., and the PG WWBA Florida Qualifier in Fort Myers.
The Sandlot Scout Team 2022 boasts a roster made-up almost entirely of top 2022 Oklahoma prospects. They include fellow OSU recruits in lefthander Brennan Phillips (No. 192-ranked) and righthander Kade Shatwell (No. 277), who are joined in the Sandlot’s dugout by Oklahoma Sooner commits in righthander/infielder Bauer Brittain (No. 228) and catcher Peyton Roberson (t-500). By all accounts, there is no animosity shared between the Cowboy and Sooner recruits; that can wait.
While playing with the Scorpions 2021 Founders Club, Holliday was part of a roster that featured 23 top-500 guys from the class of 2021, including OSU commits Zach Ehrhard (t-500) and Aidan Meola (No. 140); Jackson was the only 2022 rostered with the team.
“It was a good summer. We got to stay in Hoover and Atlanta for two weeks at a time and play lots and lots of games; it was great for both teams,” Jackson said. “I played on a really good team with the Scorpions and I played on a really good team with Sandlot. It was fun to get to play with some of the older guys with the Scorpions and some of the kids that are coming to OSU on the Sandlot.”
And Holliday himself enjoyed a standout – if not even a breakthrough – summer and early fall on the travel ball circuit. Playing in 36 games, he hit .355 (27-for-76) with 11 extra-base hits (2 HRs), 23 walks, 25 runs, 20 RBI and 16 stolen bases; his .510 OBP was eye-popping.
Jackson is the oldest of Matt and Leslee’s four children, having just celebrated his 17th birthday earlier this month. He is joined at home by two brothers, 13-year-old Ethan and 7-year-old Reed, along with his 11-year-old sister, Gracyn. Ethan, Leslee told PG, is already showing signs of being a pretty talented ballplayer himself.
One of the beautiful things about being a part of a baseball family, Leslee told PG, is that they’ve become excellent packers and excellent travelers. She and Matt loaded up the whole crew this summer and spent a lot time together in PG hotspots like Atlanta, Hoover and Fort Myers.
“It’s just kind of a traveling circus around here, and I love it,” Leslee said with a laugh. “The cool thing about baseball is the families. During Matt’s career it was the families that made it such an enjoyable experience and it’s the same with youth baseball, getting to know the parents and the brothers and sisters. It’s just been so much fun.”
Matt Holliday didn’t play with a travel ball team when he was Jackson’s age but he was invited to the USA Baseball National Team Trials in Joplin, Mo., when in high school. He said that was really his only chance to see where he stood amongst his peers, an opportunity today’s teenaged players are given for weeks on end during their summers of play.
“I think it’s motivating,” Matt said. “I think it’s good for these kids to get out and play against the best kids in the country and to see them and to kind of size themselves up a little bit; see what they need to work on and realize that it’s a big pool. If their goal and their dream is to play in college and potentially in professional baseball, there’s a lot of work to be done.”
Perfect Game’s national class of 2022 prospect rankings is filled with middle-infielders – 10 of the top 44 overall are primary shortstops. It’s a list that features No. 4 overall Termarr Johnson (Atlanta, Ga.; uncommitted), No. 5 Jayson Jones (Savannah, Texas; Arkansas), No. 8 Cole Young (Wexford, Pa., Duke), No. 13 Gavin Kilen (Milton, Wis., Louisville), No. 19 Nazier Mule (Paterson, N.J., uncommitted) and No. 28 Dominic Hellman (Mill Creek, Wash., Oregon), all of whom are currently slotted in front of Holliday.
By performing at all of the PG national championship tournaments and also at the 2020 PG Junior National Showcase in Hoover in June, Holliday has been able to spend time around his equally-talented peers while they swap stories, talk a little baseball – among other topics – and plan their paths moving forward.
“I’ve gotten to know quite a few kids and it’s real cool to watch them play and root for them and be able to interact with them,” Jackson said. “To know that they’re the top kids in the country is pretty cool...It’s real neat because you’ll be playing against them for years to come. Building a relationship with them now will most likely carry on for many more years.”
As parents, Matt and Leslee thoroughly enjoy watching their son embrace the social aspects of the game at the places where all these new relationships are built and friends practically become family. The experience of watching the traveling families interact at PG events reminds Leslee of the days on the road when Matt was in the big leagues and the way the players’ wives and their children would form a tight-knit community of their own.
“It’s super rewarding to see that Jackson is bonding over sports and teamwork and things like that,” she said. “Those kind of relationships usually last and they’re based on a really good foundation.”
Matt also loved being in attendance at the big tournaments in Atlanta, Fort Myers and Hoover where he had the chance to watch other young players perform a high that almost belied their age.
And there was another reason he enjoyed it. Many of his big-league contemporaries also have sons performing at PG events and impromptu reunions can breakout at any time. This summer alone he was able catch-up with Craig Counsell (father of Brady Counsell), Andruw Jones (Andruw Jones, who also goes by Druw Jones) and Jason Werth (Jackson Werth) among others.
“No. 1, it makes you feel a little bit old," the 40-year-old Matt Holliday said. “But No. 2 it’s nice to connect and see some old friends and also get a chance to watch some really good baseball.”
Development is key at this stage in Jackson Holliday’s still-young career and Matt Holliday is being hands-on when it comes to aiding that development. With his family ties to the OSU program, Matt is able to utilize the Cowboys’ facilities when working with his sons, which can certainly be beneficial.
As Jackson gets older, his dad said, he’s going to have to continue to get stronger and strides were made on that front over the summer. Jackson’s weight is currently listed at 170 pounds and Matt said he’d like to see him around 185 by the time he’s a high school senior.
“We’re going to encourage what he’s passionate about,” Matt said. “The fun part is that he wants to be really, really great at baseball and I want to encourage that...I’m available to him for whatever he needs to chase those dreams and thankfully I’ve had the opportunity to see firsthand what it takes to play at the highest level.”
Leslee Holliday remembered that when Jackson was just “a little bitty guy” how he would swing just about anything he could fit into his hand like it was a bat. When brushing his teeth as a 3-year-old, he’d be swinging the toothbrush; while enjoying a burger, French fries and a drink, the fries and drinking straws would take on new lives as bats.
This was when Jackson was at the age The Times’ Tyler Kepner first took notice of this precocious youngster, the toddler who would be hanging out with his dad’s big league teammates one minute and imitating their batting stances the next.
Jackson Holliday may have garnered attention at a young age but he certainly never sought it out; Matt and Leslee always made sure their son stayed grounded – no pressure, no expectations.
As Matt said, it’s only natural to want your kids to be able to identify something they want to pursue with a special vigor and if it happens to fit into a realm that was also the targeted pursuit of most everyone in their family, well then, that’s all the better.
And soon, it now seems likely, Jackson will be playing his junior season out on the same Stillwater High School field that his dad played on a little more than 20 years ago before moving on to a 15-year big-league career.
“He’s just always loved it,” Leslee said of Jackson. “As a mom, no matter what it is, it’s cool to see your kid passionate about something...and for them to want to learn and work. That’s the thing about both my (older) boys that’s fun is that they’re passionate about baseball and they’re willing to line their actions up with their words.”