The Trip of a Lifetime with Kash Gillespie

Feb 10, 2026

Most middle school students spend their free time gaming or scrolling TikTok, but Oakwood Middle School eighth-grader Kash Gillespie is always looking for ways to stay active. A standout basketball player and elite baseball talent, Kash recently returned from a once-in-a-lifetime experience in the Dominican Republic, playing with The Warehouse Warkats 17U team. This international trip pushed him into a new level of competition, culture, and personal growth.

When the invitation arrived in August 2025, Kash didn’t hesitate. Before his family could even finish the question, he was already saying yes.

A Surprise Start

After landing in Boca Chica, Kash had been in the country for only minutes when he spotted MLB star Elly De La Cruz at the airport. Kash was the only player brave enough to ask the Cincinnati Reds shortstop for a picture, setting a tone of confidence for the week ahead.

Training Dominican-Style

The first full day began with a 7:00 AM beach workout led by Dominican coaches. The session was intense: no water breaks, conditioning in deep sand, and even catching and throwing coconuts. It was a shock to the system that revealed how seriously baseball is treated in the DR.

"We worked on hitting bottle caps with broomsticks, which is super tough. The bottle caps move like crazy!" Kash noted. These unique methods reshaped his approach to the game. He now takes warm-ups more seriously, incorporating game-type throws, like the "Derek Jeter" jump-throw, into his routine.

Inside the Guardian’s Academy

The team also visited the Cleveland Guardians’ Dominican Academy. Kash met prospect Angel Martinez and toured facilities where players attend English classes decorated with preschool-style flashcards. Since many local athletes arrive with only an elementary education, the visit was a powerful reminder of the different paths to professional baseball between the US and the DR.

Games Unlike Anything Back Home

Throughout the week, Kash faced older, stronger players who looked more like grown men than teenagers. The fields ranged from modest to run-down, but the passion was unmatched. Since many opponents spoke only Spanish, Kash’s team relied on hand signals to communicate.

Memorable game highlights included:

Sudden Crowds: Local children and neighbors would gather out of nowhere to watch, sometimes bringing sound systems to announce the game in Spanish.
Mid-Game Snacks: During the third inning, a Coke and crackers were delivered to players and parents as a tradition.
Scout Appearances: MLB scouts would appear mid-game, prompting teams to swap in top prospects immediately to be seen. "When I was pitching, I’m pretty sure I faced the same guy three times in two innings," Kash laughed.
Creative Fixes: Teams used whatever was available to keep playing, once even using a seat cushion as first base.

Facing Elite Talent

Despite being the youngest player on the trip, Kash held his own against pitchers throwing 85–90 mph. He struck out three batters in one game, broke his first wood bat (which he proudly brought home as a souvenir), and had several strong swings against a top prospect whose video was later sent to MLB scouts. When asked about a particularly tough at-bat, Kash’s personality came out: “He was throwing 90... what did you want from me?”

Life Beyond the Diamond

One of the most impactful moments occurred during a visit to a local village. Seeing dirt roads and children with limited resources painted a stark contrast to life at home. The team spent the afternoon painting a tin house and passing out candy. "I didn't realize how rough the area was," Kash shared. "The houses were small with dirt floors. I didn't expect to see that."

Kash also played in San Pedro de Macorís, the hometown of his former coach and family friend, Andres Perez. Realizing he was competing on the same field his mentor once did made the experience deeply personal.

Representing Oakwood with Pride

Whether Kash was facing 90 mph fastballs or pitching in front of MLB scouts, Kash showed maturity beyond his years. He represented Oakwood Middle School with resilience and humility, returning home with lessons and memories that will last a lifetime.