Jackson Holliday was just 3 years old when Rocktober rocked Colorado in 2007 and he provided a joyful spark to the Rockies’ clubhouse.
Next month, the 6-foot-1, 185-pound shortstop from Oklahoma’s Stillwater High School is projected to be one of the top five players selected in the major league draft.
“It’s kind of surreal, and bittersweet,” said his father, Matt Holliday, a seven-time All-Star who was the runner-up for National League MVP in 2007. “People say that the days are long and the years are short . Man, you really start to see that when your kid gets into their junior and senior year of high school. You start to wonder where the time went.”
The kid who used to send Wiffle balls soaring through the Rockies’ clubhouse is now 18 and facing a huge, life-altering decision.
The young power hitter, who set a national high school record for most base hits in a season, could sign a lucrative deal and get as much as an $8 million bonus with the major league team that drafts him. Or he could choose to attend Oklahoma State, where family ties run deep. His dad is a volunteer coach at OSU for his older brother, Josh, who just completed his 10th season as OSU’s head coach. Jackson’s grandfather, Tom, spent 26 years as a coach at OSU and was head coach from 1997 to 2003. He’s now an analyst for the Cowboys’ in-house TV broadcasts.
If Jackson seems remarkably well-prepared for his hard life choice, it’s a credit to how his parents raised him. On this Father’s Day, he’s very much aware of that.
He calls his dad “my best bud.”
“My mom and dad just made it easy for me,” Jackson said. “They never put extra pressure on me and they never made it hard. I thank them for that. They always let me be a kid and allowed me to keep loving baseball.
“I mean, they have been through it all, with my dad’s career and everything. So I know I have them in my corner. I know they have my back, no matter what decision I make.”
When Matt and Leslee Holliday were married on Dec. 30, 2000, they made a pact that family, and their strong Christian faith, would be their first priorities, regardless of where Matt’s baseball career took them. As it turns out, Matt played for the Rockies, Athletics and Cardinals, was a batting champion, and launched 316 home runs during his 15-year big-league career. He helped lead the Rockies to their only World Series in 2007 and won a World Series title with the Cardinals in 2011.
“Our kids always knew they were Matt’s first priority,” Leslee said. “I think that’s a particular blessing, especially when you are around baseball so much. It can be all-consuming. All of our kids always knew that their dad would drop anything to be with them if he was needed.”
Matt and Leslee have four children: Jackson; Ethan, 15; Gracyn, 12, and Reed, 8. Ethan, already two inches taller than his older brother, just completed his freshman year at Stillwater High and is also considered a baseball prodigy.
Jackson, who hits from the left side, hit .685, launched 17 home runs, drove in 79 runs and stole 30 bases as a senior at Stillwater High. He was named the Gatorade Player of the Year for Oklahoma. His 89 base hits eclipsed the mark of 88 set by current Phillies catcher JT Realmuto in 2010.
Through the years, Jackson has been tutored by a number of his dad’s former teammates, including Nolan Arenado and Troy Tulowitzki, both of whom remain close friends with Matt. Last year, Tulowitzki, now an assistant coach at the University of Texas, spent more than an hour with Jackson, teaching him some of the finer points of playing shortstop.
“With that family, as solid as it is, and with Jackson’s focus and passion, the sky is the limit,” Tulowitzki said.
Tulo first met Jackson when Jackson was just a toddler. Plastic bat in one hand, Wiffle ball in the other, Jackson would beg Tulo, Brad Hawpe and Ryan Spilborghs to pitch to him. Then, pint-sized Jackson would take big-league swings, whistling the ball to the far end of the clubhouse or bouncing the ball off the noggins of unsuspecting reporters.
His father looked on with a bemused grin.
“I have faint memories of that,” Jackson said. “Maybe I’ve heard about it more than I actually remember it. But we are moving into a new house right now and my mom is going through all sorts of old pictures. She’s been showing me a lot of stuff. It’s pretty cool.”
Matt recalls those moments with wistfulness.
“A lot of my old teammates and media members still bring that up,” Matt said. “They talk about this little guy in the clubhouse with his big plastic bat, imitating major league players’ swings, and hitting the Wiffle ball really hard, with this technically sound swing.”
Jackson loved mimicking the stances and batting approaches of David Ortiz, Nomar Garciaparra, and even his father.
Matt, drafted by the Rockies out of Stillwater High in the seventh round in 1998, recognized early on that his son had special baseball talent.
“I remember being in the basement of our rental house in Denver,” he recalled. “I was in a little bit of a slump and I was pitching the Whiffle ball to ‘Jax.’ He was just 3 or 4 years old at the time. I remember thinking, ‘His swing, mechanically, is better than mine.’
“It was pretty incredible. And while I couldn’t have predicted that Jax would be a high draft pick, I did know that he was obviously skilled at a very young age.”
Jackson’s passion for the game blossomed as he got older.
“In his soul he’s always loved baseball,” Matt said. “And I think being around players in the Rockies’ clubhouse, and then the Cardinals’ clubhouse, really helped shape his passion and his love for practicing. A lot of that started way back then.”
While Matt could see Jackson headed toward baseball stardom, Leslee was too caught up in the moment to realize it.
“I’m very naïve, fortunately, or unfortunately,” she said with a laugh. “It only recently dawned on me that, ‘Oh my graceful, we might do this whole baseball thing again.’ But I have enjoyed all of it. I have enjoyed the heck out of Jackson. He’s been so fun to watch.”
The Hollidays have always led a hectic life, what with Matt’s 15-year career in the majors and summer travel teams for Jackson and Ethan. Last summer, Jackson was named a Perfect Game All-American and that’s when his name shot up the draft boards.
But his dad always tried to keep Jackson, indeed his whole family, connected and grounded.
Last summer, Jackson was playing in a tournament in Atlanta and Ethan had games in Hoover, Ala., about a three-hour drive away.
“I think this tells you something about my family,” Jackson said. “My game was in the morning and Ethan’s was in the afternoon. So we drove from Georgia to Alabama, just to make sure we had a family dinner. Then we drove back to Georgia. And then we did it all again the next day.”
Matt and Leslee have had long conversations with their son about his next step in life. They hope — no, make that they believe — that they have prepared him well.
“The one thing I can offer him is my experience and what it’s going to take,” Matt said. “But we want this to be his decision. Ultimately, it will be his path.
“We look at it like he has two Plan As and there is really no bad choice here. If he wants to play for Oklahoma State and be around me and his uncle every day, and play in significant college games and a brand-new stadium and be three years along toward his college degree, that’s great.”
And what if Jackson wants to dive head first into a pro career at age 18?
“That’s also a great option,” Matt said. “That can always be a great adventure and an exciting time. We are trying to let him navigate this in his own mind and we want him to do what’s right for him.”
The dad is confident that his son is ready to become a young man.
“I don’t think any father could be prouder,” Matt said.