Homewood-Flossmoor phenom Dillon Head expected to be picked in first two rounds of MLB Draft

Public evaluators and league scouts are expecting Homewood-Flossmoor’s Dillon Head to have his name called in the first two rounds of the MLB First-Year Player Draft on Sunday.

When that happens, the first descriptors will settle on the 18-year-old center fielder’s raw ingredients: the athleticism, which Head sensed was a cut above his peers from an early age, that fuels his defense; the top-of-the-scale speed that inspired countless pick-off throws whenever he reached base, which was more than half the time during his senior season.

“Ability is one part of that, but once you get to those elite players, what are you going to give up to be great?” Homewood-Flossmoor coach John McCarthy said. “Every player has that decision to make. For him, I know he’s decided to be a great player. It’s evident in everything he does.”

Head’s parents put him in tee ball at age 4, beginning a trend of facing off against older kids. When his personal hitting coach, Chris Cunningham, first saw him, Head was 10 years old on a 12-and-under ACE team. Being in junior high and receiving attention not just from McCarthy but major colleges is when Head “started to know” and solidified his decision.

Because it’s a decision for a teenager to mix in 40 weeks of hitting practice a year at Willowbrook Village Sports Performance Center with Cunningham and weight training at IMR Athletics in Lynwood, while playing travel baseball, completing his classes at Homewood-Flossmoor and leading his team to state regionals. The constant grind of baseball appeals to Head, whose mindset is attuned to a sport defined by failure.

“There’s always something to chase after,” Head said. “That’s the excitement about it. Never being satisfied, never being complacent.”

The chase, Head openly states, is about eventually playing in the majors. Though with a commitment to Clemson in hand, Head says he’s content for it to be a low-speed one. Whether Head sneaks into the back of the first round or lands in the middle of the second as some evaluators expect, he is in line for a seven-figure signing bonus. But speaking a week after his high school graduation, Head was ambivalent, reasoning he was reporting early to Clemson no matter what happens this month.

The loaded schedule suits Head, who finds himself coming home at the end of a full day of work and still picking up a bat and miming his swing. Fittingly, a standout hit tool drives Head’s first-day projections.

“He’s probably in his career struck out a total of 10 times, it’s unbelievable,” McCarthy said.

“He handles velocity at the top of the zone as good as anybody I’ve ever seen, so that’s different for a lefty,” Cunningham said.

The separator will be how teams see the 5-11 Head projecting physically and what power they can expect him to develop. Steadily adding strength since the pandemic wiped out his freshman season, the bar for Head’s offense remains lower as long as he remains a true center fielder.

But Cunningham and Head have worked to add the ability to extend his arms and drive the ball middle-away to his direct-to-the-ball line-drive approach predicated on making use of his game-wrecking speed.

“For being [a] 185-pound dude, he can hit the ball a long way,” Cunningham said.

“I used to just think hitting balls hard, you’ve just got to be real strong and swing for the fences,” Head said. “When it’s really like, getting backspin, getting stretched in your arms and legs swinging. It’s more than just being the strongest guy out there. Because you see in the big leagues, it’s all dudes all shapes and sizes hitting balls 400-plus feet. So it’s really just not only being strong, but having the technique behind it, too.”

If Head enters professional baseball, a long developmental path awaits. Riding the bus in minor-league baseball is a stark departure from organizing the home-run celebration and walk-up playlist for his high school teammates, or hitting batting practice thrown by his father, Gary, from behind a U-screen (since he shattered his father’s pinkie with a comebacker at age 12).

But recalling all the times Head shrugged off rough games and moments makes his coaches think handling adversity is where their pupil will really shine.

“He’s as good of a kid as I’ve ever had with handling failure,” Cunningham said. “He’s actually incredible about it. It’s kinda scary.”

As Head stands at the precipice of a higher and more demanding level of baseball than at any point in his life, he is more than the sum of his raw tools. His baserunning is the product of fastidious work on his first step breaks, his over-the-shoulder drills shine in center as much as his pure speed. Rather than bat speed or mechanics, Head tracks his offensive improvements through learning pitch sequences and opposing plans of attack.

“The little things,” Head reasons, “are ultimately what turn into the big things.”