THE WORLD'S LARGEST AND MOST COMPREHENSIVE SCOUTING ORGANIZATION
| 2,384 MLB PLAYERS | 15,801 MLB DRAFT SELECTIONS
2,384 MLB PLAYERS | 15,801 MLB DRAFT SELECTIONS
Create Account
Sign in Create Account
Tournaments  | Story | 12/21/2020

'Holliday' spirit sparkles in Stillwater

Jeff Dahn
Photo: Jackson Holliday (Perfect Game)

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.”
Give us your feedback
Tournaments | Story | 12/17/2025

15u Tourney All-American Team
Jason Phillips
Article Image
Hitter of the Year: Landon Bonner The 2028 class saw many players from across the country take the next step in their development as they entered the High School ranks. There were huge performances from highly ranked players on the PG circuit as well as some under-the-radar guys who burst onto the scene. Landon Bonner came into Sophomore National as a Top 500 ranked player and after an impressive showing, left with all eyes on him as a rankings riser in the class. The left-handed hitting shortstop from The Colony, Texas, had a summer to remember with All-Tournament Team selections in three of his next four events culminating with a historic performance at the 2025 PG 15U WWBA National Championship. The Hebron High School prep went 20-for-24 in nine games for 5 Star Mafia 15U Black with four homeruns and 12 runs batted in. He also scored 17 runs and finished with a mind-boggling 2.500...
Read More
Tournaments | Story | 12/16/2025

16u Tourney All-American Team

AJ Denny
Article Image
Hitter of the Year: Koa Romero is the Hitter of the Year for the 16u group, as he would come to every premier event of the summer and earn All-Tournament honors (Beast of the East, 16/17u WWBA, Jupiter) in every single one. Over 82 plate appearances, Romero would pump ten homeruns with forty two RBI and sixteen walks, good for a .378 average and 1.339 OPS. The performance on volume at the best events of the year pushed Romero over the edge here, as he’d hit a pair of homeruns in Jupiter (one of them at 112 EV) as an underclassmen and collect double digit hits in BOTH WWBA events with a combined six jacks over the two tournaments. It was a summer that combined performance and winning on the biggest stages for Romero. It’s a quiet left-handed swing that packs a punch. He would reap the benefits of his performances, earning a commitment to LSU and jumping to the #74 prospect in...
Read More
College | Recruiting | 12/15/2025

Recruiting Notebook: December 15

John McAdams
Article Image
Tucker Rice (27 MS) bumping up to 91; living hi-80s from real fast arm. Good SL @ 77-79 w/ depth & sold w/ intent. Loads of traits & strikes. #WWBA @PG_Uncommitted @PG_DeepSouth pic.twitter.com/DEjFqRcsIY — Perfect Game Scout (@PG_Scouting) July 6, 2025 Tucker Rice, RHP, Class of 2027 Commitment: Alabama Alabama has continued to stay red hot in the recruiting trail ever since August 1st rolled around on the calendar and have continued to stack major pieces in their ’27 class. They dip into Mississippi to land one of the premier arms and one that’s stood out on the circuit for quite some time. It’s a fast arm and the athleticism certainly shines working down the slope. The velocity has continued to tick up over the last calendar year and reached into the low-90s towards the end of the summer. He’s confident in his changeup and the breaking ball is...
Read More
Tournaments | Story | 12/15/2025

17u Tourney All-American Team

Vincent Cervino
Article Image
There’s a lot of talent throughout this 2026 class, filled with the big-name stars, to talent that spreads across the nation. It’s been a lot of fun seeing these prospects grow and develop over the years, from the days of watching some of these guys at the 13/14u days at events on the circuit, to now where they are all graduating seniors in 2026. There’s been new faces who have popped along the way over the years, even in 2026, where some players who were relatively undiscovered, have come out and made a name for themselves with a statement performance. Between the familiar and the new, there’s a lot of names on this list that are going to be quite regularly talked about on the circuit, and for good reason.  Whether it’s PG All-Americans or not, there’s a lot of names with superstar potential at the next level. We’ve got 14 PG All-Americans...
Read More
Tournaments | Story | 12/13/2025

Finest in the Field: Class of 2029

Tyler Russo
Article Image
Finest in the Field: Class of 2026 | Class of 2027 | Class of 2028 These guys might just be entering high school, but they've certainly already made a name for themselves on the national circuit, especially with their abilities on the defensive side of things.  C: Xavier Rodriguez (Logansville, GA) Rodriguez is a polished defender with real arm strength behind the dish, while showcasing the ability to impact the baseball with authority to all fields evident by thirty of his sixty-five hits going for extra-bases including seven bombs. He handles high-level pitching extremely well, commands his staff and his offensive prowess makes him a true two-way asset. 1B: Cooper Knight (Buda, TX) Knight is a smooth operator at first base with plenty of range, fluidity and agility in his footwork around the bag. Add-in a rocket for an arm, the ability to change slots and to...
Read More
Tournaments | Story | 12/12/2025

Scout Stories: Part 5

AJ Denny
Article Image
Best Game I Saw: The Dream NTL 18U vs. MBA Scout Team Murphy Jupiter always brings out the best, and we got fireworks from the jump. Turner Marshall gave The Dream an outstanding 4+ innings of work on the mound, holding a lethal MBA team at bay with Chance Dixon, Derrick Carter, and Ellis Appling providing an offensive spark out of the gate for the Georgia based boys. However, it was only a matter of time before the talent on the other side got going, as MBA erased a 3-run deficit in the 5th to take a 4-3 lead led by a Parker Loew HR. The Dream then took command again in the Top of the 6th, before MBA punched right back with a huge 5-run inning in the bottom half capped off by a clutch RBI single from Matthew Kerrigan, ending a wild sequence with tons of notable performances from two very competitive rosters. Best Tournament Performance I Saw: Surely someone has already brought this...
Read More
College | Story | 12/12/2025

College Notebook: December 12

Craig Cozart
Article Image
Nebraska Cornhuskers 2025 Highlights: The Cornhuskers were a difficult team to figure in ’25 as they finished with 33 wins, played just .500 (15-15) in the Big Ten but had some big wins at various times during the season and got hot at the right time. They knocked off then #16 Vanderbilt in the second game of the year, beat #5 Oregon State 2-out-of-3 at home in late March and then got hot at Charles Schwab Field in Omaha to win the Big Ten Tournament. They beat Michigan State in a 10-inning thriller before taking care of #4 Oregon, knocking off Penn State and then shutout #13 UCLA to punch their ticket to the Chapel Hill Regional. Head coach Will Bolt has now led his alma mater to three conference titles and three NCAA Regional appearances during his six years in Lincoln. No different than when he was a player, Bolt’s teams play with passion and toughness, this was never more...
Read More
Tournaments | Story | 12/12/2025

Finest in the Field: Class of 2028

Troy Sutherland
Article Image
Finest in the Field: Class of 2026 | Class of 2027 You like athletes? You like defenders who can impact a game at any given point? Look not further than this class as it's loaded from coast-to-coast with elite defenders all over the diamond.  C: Brogan Witcher, Bakersfield, CA Our scouting staff got several strong looks at Witcher whether that was at the Summer Kickoff, Sophomore National or the Underclass All American Games where he showcased his strong overall skillset and especially his advanced ability behind the plate. His 6-foot-3,180 pound build looks like one that will fill in quite nicely and be that big and physical catcher’s frame. His arm talent is undeniable where he gets it out quick and runs it up to 79 mph on throwdowns to 2nd (1.84 pop). Besides the standout catch/throw ability, we’ve seen him frame/receive strong arms and block it well during...
Read More
Softball | Softball Tournament | 12/11/2025

PG Softball "Toys 4 Tots" Fundraiser 18U division

Dave Durbala
Article Image
BURLINGTON, IA - 2025 Perfect Game Softball Toys 4 Tots Fundraiser One Day, December 7, 2025. Kicking off the holiday season, six teams participated in this one day, 3 game guarantee tournament in the 18u Division. We would like to thank those that donated a toy, and know that they will be distributed to area underprivileged children through a local charity organization. Following are some of the top performers from the weekend. Earning Tournament MV-Pitcher was Jolee Strohmeyer (2026 Dubuque, IA), a RHP/UTIL with tournament champion Lady Expos Blue. Strohmeyer shows hitters a consistent and repeatable motion and delivery with good use of the legs in the drive phase, and a quick and aggressive arm whip. Working with a six pitch mix of fastball, change-up, rise, drop, curve and screw, Strohmeyer topped out at 60 mph, and showed good movement  as she worked her rise and curve just out...
Read More
Tournaments | Story | 12/11/2025

Scout Stories: Part 4

Tyler Henninger
Article Image
Scout Notes: Part 1 | Part 2 | Part 3 Best Game I Saw: Hudson Reed (‘26, GA) torches this ball to deep CF for a solo 💣. Generates easy power that plays to the big part of the yard. Middle of the order traits #UBCWest @PG_Georgia @PG_Uncommitted pic.twitter.com/UXqDVFmUBx — Perfect Game California (@California_PG) June 18, 2025 I was fortunate enough to see a lot of highly competitive games with loads of talent on the field, the game that sticks out to me the most was Alpha Prime 2026 vs. ZT National Prospects at the UBC West. The game was an efficiently played affair with arms dominating on both sides. Graham Schlicht was masterful for Alpha, striking out 12 hitters over 5 dominant innings. PG All-American Julian Cazares came out of the pen blowing smoke, touching 97 mph with the fastball. On the other side, Jake Carbaugh surrendered just one hit and...
Read More
Loading more articles...
About Perfect Game :: Contact us :: Terms of Use :: Privacy Policy :: Testimonials :: Job Opportunities
Copyright 1994-2025 by Perfect Game. All rights reserved. No portion of this information may be reprinted or reproduced without the written consent of Perfect Game.