‘I always wanted to follow in my dad’s footsteps’: Inside the MLB draft journey for the sons of two former major leaguers

ONE OF ELI WILLITS’ earliest baseball memories is of playing catch with his father, Reggie, in the Angel Stadium outfield. In late June, Eli again took the field that his dad called home during six seasons with the Los Angeles Angels during a private workout with the team, which has the No. 2 pick in the 2025 MLB draft.

“Eli was working out last week for the Angels. For me, it was surreal. He was hitting and taking ground balls, and my boys have been doing that with me since they were little,” Reggie Willits said. “Me, Jaxon and Eli would go out to left field and we’d take BP out there; they were so small. That way, they could hit homers into the bullpen. It was a surreal moment for us as a family. I played my whole career in that stadium.”

Ethan Holliday was born in 2007, the same year that his father, Matt, finished second in National League MVP voting for the Colorado Rockies, and fondly remembers taking a trip to Busch Stadium with his brother, Jackson, when Ethan was 6 or 7 to see their dad star for the St. Louis Cardinals. Both of those teams hold picks in the first five selections of the upcoming draft, but there is no guarantee that Ethan will be available by the time Colorado is up at No. 4 or St. Louis one pick later.

The two Oklahoma high school stars have a lot in common: They’re both sons of former major leaguers who also have brothers excelling in the family business. They’re both expected to hear their names called early in this year’s draft. And they have even formed a tight friendship through baseball.

But for all the glamour that comes with potential stardom, both have learned from their fathers how much work behind the scenes is needed on the road to the top of the draft.

“‘Do you like your name above the locker?’ Yes,” Eli remembers responding to a series of questions posed by his dad about a decade ago. “‘Do you like going out there in front of 50,000 fans?’ Yes,” Eli said. “‘Do you want to get up at 4 a.m. and go work out?’ No.” Eli said while laughing. “But that’s what it takes, and I always wanted to follow in my dad’s footsteps. … I’m very grateful for that chance.”

THE HOLLIDAYS ARE the established first family of Oklahoma baseball, helping to raise the profile of a state not known as a hotbed for draft prospects.

Matt hit .299 with 316 home runs over 15 years in the majors, and his brother Josh is the head coach at Oklahoma State (following the footsteps of their father, Tom, who coached the Cowboys for 26 seasons). Ethan’s brother, Jackson, added to the family legacy by becoming the No. 1 overall pick in the 2022 draft and plays second base for the Baltimore Orioles.

I first noticed Ethan when he was a freshman at Stillwater High. He was batting behind his brother, whom dozens of scouts were there to watch. Ethan already stood out.

Lastly, Jackson’s younger brother 3B Ethan Holliday was really impressive in general before you realize he is a 15-year-old freshman. Here’s a homer and some BP cuts: pic.twitter.com/WWrnYwRnUT

— Kiley McDaniel (@kileymcd) April 27, 2022

Being the younger brother of a top prospect has given Ethan a window into the draft process that most players don’t experience. He has seen Jackson go through the transition from teammate to becoming the No. 1 pick to making his big league debut, and that has eased Ethan’s transition into his draft process.

“I was his wingman that year. I got to be in his meetings, be with him in games and practices, when there were 40 scouts coming to every game and everyone had their camera up when he hit, I was right there with him,” Ethan said. “It’s obviously a little different going through it myself, but that definitely took some weight off.”

Jackson’s quick ascent — he ranked No. 1 on my top 100 prospect list in 2024 — also helped shine a spotlight on Ethan early in his high school career. Ethan has been the most well-known player on any field he has been on for at least a year. Before his senior season, he became the first high school player to sign an NIL deal with Adidas, the brand Jackson signed with once he turned pro.

But despite the apparent advantages of his baseball lineage, it hasn’t all been easy for Ethan. To some scouts, he underperformed last summer on the showcase circuit against the best high school pitchers in the country. Entering the spring, some in the industry questioned whether he would deliver on his potential and the hype tied to his last name.

When asked an open-ended question about the evolution of his swing and not mentioning that narrative, he clearly was aware of it in his response.

“In high school, you face a good pitcher, and their plan is to throw offspeed because they don’t trust their fastball,” Ethan said. “In the summer, the pitchers are coming in for one inning and throwing as hard as they can. It’s different. I never got anything other than spin in high school, so making the adjustment for the summer was difficult. My dad has really helped me with my approach, my swing.”

As you might expect from someone who has had a recent major league star to turn to for baseball advice, Ethan handled the topic like a pro. He had a huge high school season, and those offensive concerns have subsided because of his performance.

Despite some wondering whether Ethan would have a big spring, most scouts were optimistic because Matt is considered one of the better swing coaches in the sport. His son has taken up his dad’s penchant for picking up on the components of a swing.

“I’ve had a leg kick my whole life,” Ethan said. “One day in the cage, I was messing around and watching video of Barry Bonds and his toe tap. Then, I was toe-tapping and hammering balls anywhere I wanted, and I hit four barrels in the next scrimmage. Nothing has changed with my swing path or where my hands are, it just felt great, so I went with it.”

When Matt talks about hitting, it’s easy to see why he is so respected, with wisdom gleaned from playing with some of the best players of his era.

“I’m fascinated by the swing, the mechanics of the swing, how it’s tied to your brain, the approach, and how it all works together,” Matt said. “If your timing is not good, your swing will break down because when you’re late, your body freaks out; it knows. It’s going to change your front side a little bit, and the bat will get long. … I love to talk about the swing. I love to learn.”

After the tweaks to his swing, Ethan enters the draft with plus-plus power and has also improved defensively as a shortstop. He could be the top pick and should be off the board by no later than the No. 4 selection.

THE WILLITS FAMILY lives in Fort Cobb, Oklahoma, where they own and operate the Double Seven Ranch, run by Reggie’s wife, Amber. Fort Cobb has between 400 and 600 residents, depending on the source. When I spoke with Eli less than a month before he likely will become an early first-round MLB draft pick, he had helped move 200 bales of hay the day before.

This isn’t lost on scouts I spoke with, or even Matt Holliday, who said, “I admire the hard work that the farm takes. I appreciate their family’s work ethic and what it takes to operate a real farm.”

Eli has a full workload, between training, baseball games, practices and work at the ranch. He has grown an inch this year — he’s now up to 6-foot-1 — and added 8 pounds of muscle since I scouted him at a tournament in April. He also took on a heavy course load to finish high school in three years so that he could reclassify into the 2025 draft. Eli won’t turn 18 years old until December, making him the youngest prospect expected to be drafted this year, a historical factor in projecting success for high school prospects.

Reggie initially didn’t like Eli’s idea of reclassifying because Reggie had switched jobs, from coaching for the New York Yankees to the Oklahoma Sooners, to be home to be with his kids.

“That’s why I decided to get out of pro baseball, [Jaxon] was about to be a senior in high school, and I hadn’t been able to see him play. I wanted to experience his senior year,” Reggie said. “When [Eli] came to us and he wanted to reclassify, that was a hard decision for us as a family. At first, I said ‘no chance.’… I wasn’t really into that. It took some convincing.”

While the family was going through the reclassification decision, Eli’s success on the field during workouts with top college players from his father’s Oklahoma squad (his brother Jaxon is also the shortstop) helped convince Reggie that his son would be ready for the next level.

“We had some infielders get banged up, and we were short there at OU. We started throwing Eli out there so we had some leeway and didn’t run our guys into the ground in the fall. He got some at-bats. He’s been practicing with us since he was 14. He was getting lots of live at-bats by 15.”

Eli remembers those first few live at-bats. “The first hit I got, I was 14 years old facing a 24-year-old pitcher. I was just trying to do my best. I want to embarrass them, really … Age doesn’t matter, I want to show I’m the best player on the field.”

Eli did well in 15 to 20 scrimmage at-bats and that started to ease his dad’s concerns that his son would be overmatched by older competition. “I came home and told my wife, ‘I feel like he could play for us as a 15-year-old, so I’m pretty sure as a 17-year-old, he’d be all right if he reclassified.'”

Sooners right-hander Kyson Witherspoon is a projected early first-round pick, and Willits got to face that level of pitcher as a high schooler. Willits has held his own in these matchups, which helped him improve.

“I had more confidence going into the summer [showcase season] because I know I’m not going to see another Kyson on the mound there,” Eli said.

Similar to Ethan turning to his dad for swing advice, Eli gained invaluable experience while tagging along with his dad when he was a coach with the Yankees from 2018 to 2021.

Though watching Aaron Judge take BP up close sounds like a pretty cool perk of having a dad in coaching, the biggest influence might have come in learning from then-Yankees coach Carlos Mendoza, who is the New York Mets manager and regarded as one of the best infield coaches in the game.

“I wouldn’t be anything like what I am defensively without Carlos,” the younger Willits said.

Eli is a well-rounded player, one who is above average at almost everything on the field, except for power. He’s not the biggest, strongest or fastest player in this draft class, despite entering the draft as one of the best prospects.

THERE ISN’T A LOT of time for social activities as both players prepare for life as professional baseball players, but Willits and Holliday take a break from baseball by texting each other.

“We don’t talk about the draft. We leave baseball out of it, and just talk about our lives,” Willits said. “We both like to fish, so we talk about fishing a lot … Last summer is when we really started playing together and getting to know each other. Ethan’s now a great friend of mine.”

They were also Team USA teammates in Panama at the WBSC U-18 Baseball World Cup Americas Qualifier.

“In Panama, we hung out every day before and after the games, the bus, the locker room, we’ve talked basically every day since then, but I didn’t see Eli in person again until Edmond [high school baseball tournament],” Holliday said.

The Edmond tournament turned into the scouting event of the year because Willits and Holliday participated. Stillwater and Fort Cobb-Broxton, where the two prospects play high school baseball, are a few hours apart and the schools compete in different classes. The round-robin event at Edmond Santa Fe High School’s field just outside of Oklahoma City provided a midpoint for scouts to see both players. Willits and Holliday impressed multiple high-level scouts in attendance from almost every team picking in the top half of the first round, even if their stats from those games weren’t gaudy.

When will the two run into each other on the diamond next? Holliday thought about the possibilities.

“That would be awesome if the next time we saw each other was the big leagues,” Holliday said. “Probably the minor leagues? Whichever team gets him is super lucky. He’s a stud.”

Willits and Holliday laughed when I asked about a potential friendly rivalry regarding who will be drafted higher. Both said that couldn’t be further from the truth.

“We’re both from Oklahoma. Oklahoma doesn’t get enough credit for the talent it produces,” Holliday said. “We’re super pumped for each other; we’re each other’s biggest fans. There’s no bad blood, no rivalry, no Bedlam feud.

“We’re just two boys that really love baseball and are proud of Oklahoma.”