A visit to Cuba in April 2015 presented a new challenge and opportunity for Jake and Kids on the Ball. Troubled by the state of the courts at the National Tennis Center, Jake set forth on a mission to resurface them. Through the financial generosity of KOTB friends and supporters, 10 courts were renovated in what has been only the second brick-and-mortar project to be undertaken by an American organization since the Eisenhower Administration. In April 2017, in an event covered by the Tennis Channel, Kids on the Ball was joined by Martina Navratilova and Stan Smith to celebrate the renovation

Since that first trip, Kids on the Ball has brought dozens of adult players to hit with Cuban youth in an enriching, apolitical environment. On every trip, now more than a dozen, Jake brings the games he has made famous on the courts of Vermont-- like Doubles Top Dog, Approach and O-U-T-- all of which foster a shared appreciation for the power of tennis to forge Cuban and American friendship and respect.

KOTB regularly provides sneakers, racquets, nets, string and balls to Cuba’s National and Junior Tennis Teams. Following Covid, Kids on the Ball returned to Havana in July and November 2022 to reconnect with the players and coaches and to restart its quarterly visits, which now include a stop at the Nicolás Estévanez Murphy Primary School, where KOTB’s coaches play the same games with the same equipment as they do back home in Vermont.