Austin Prep standout Dylan Cunningham ’28, previously identified as New England’s top uncommitted prospect, has committed to University of Virginia baseball. The opportunity to contribute as both a pitcher and position player, a strong connection with the coaching staff, and guidance from Austin Prep alumni helped make Virginia his choice.
Before every start, Dylan Cunningham ’28 takes a moment behind the mound to pray.
“I say a prayer behind the mound just to kind of thank God for letting me be there and be in the situation that I’m in,” he said. “It kind of just gets me going. Gets me locked in for the game.”
The Austin Prep right-hander now knows where he hopes those starts will take him next. Cunningham, identified by New England Baseball Journal as New England’s top uncommitted prospect earlier this fall, has committed to the University of Virginia.
His fastball has reached 95.1 mph, but Virginia offered something beyond a place to pitch: the opportunity to keep hitting, too.
Dylan Cunningham’s Rise Took More Than a 95 MPH Fastball
Cunningham grew up playing Revere Little League, starting around age six, and has lived in Peabody, Massachusetts, since kindergarten. By the time he entered Peabody High School, his fastball had climbed into the mid-80s. College baseball began to feel like a realistic possibility.
He later transferred to Austin Prep, reclassifying into the Class of 2028. Strength training and mechanical adjustments helped his velocity climb, but another change proved just as important.
“At the beginning when I came in here freshman year, I was just throwing it as hard as I could,” Cunningham said.
The next step was learning to be “a pitcher, not a thrower,” developing his other pitches and maintaining his effectiveness longer into games.
The results followed. Cunningham led Austin Prep in innings pitched in 2026, reached 95.1 mph at the Prep Baseball Future Games, and participated in the USA Baseball National Team Development Program.
During the Cougars’ New England Diamond Duel championship run, he earned two victories, improving his record at that point to 4–1 with a 0.55 ERA and 43 strikeouts.
At Austin Prep, Cunningham Became the Competitor Who Wants the Ball
Austin Prep Head Baseball Coach Jonathan “JP” Pollard ’97 describes Cunningham in terms that apply equally to the mound and the batter’s box.
“My scouting report would be ultra aggressive, ultra competitive, always wants the ball, always wants the at-bat,” Pollard said.
That willingness to take responsibility has become part of Cunningham’s identity within the team.
“He’s found a leadership within the team where guys know when the game’s on the line, he wants the ball,” Pollard said.
Cunningham found teammates who shared his ambitions and made the work easier to sustain.
“There’s always somebody that’s willing to throw, hit with you, lift with you,” he said.
The competition extends beyond practice, but he sees it as productive.
“It doesn’t cause arguments or anything,” Cunningham said. “It’s kind of just pushing each other to work harder.”
Away from baseball, those same friendships carry over to golf, fishing, and pickleball.
Cunningham Chose Virginia for a Two-Way Opportunity and Familiar Faces
Virginia first called Cunningham on August 1, the opening recruiting day for his class, while he was attending a baseball event in California. He reached out to former Austin Prep catcher and captain Bradley McCafferty ’26, who had recently joined the Cavaliers, to ask about visiting.
Cunningham ultimately visited Virginia and Auburn before ending his search.
“I found where I wanted to be. I knew it was UVA,” he said.
Virginia’s résumé includes the 2015 NCAA championship and seven College World Series appearances. For Cunningham, the connection with Head Coach Chris Pollard and his staff mattered more than the program’s history alone.
“That coaching staff was great to me and was great to my family,” he said.
The opportunity to contribute as both a pitcher and position player also helped settle the decision.
“I’m gonna keep doing it for as long as I can,” Cunningham said. “So I’m gonna be working from both sides.”
After his official visit, he had the unique opportunity to consult with two Austin Prep alumni with Virginia experience: McCafferty and Evan Blanco ’22, who pitched for the Cavaliers from 2023–2025.
McCafferty offered his perspective without pushing Cunningham toward Virginia. Having already worked together as a pitcher and catcher, they also brought an established relationship to the possibility of becoming teammates again.
“He knows me and I know him very well,” Cunningham said.
With its championship success, player development, and college connections, arguably Austin Prep is the best high school baseball team in Massachusetts. For Cunningham, those connections provided firsthand perspectives on what could come next.
With Virginia Ahead, Cunningham Has a Comeback to Make and a Role to Earn
Cunningham still has two years at Austin Prep and a recovery to complete. After experiencing discomfort in his throwing arm, he underwent an MRI and, following consultation with New York Yankees team physician Dr. Christopher Ahmad, had Tommy John surgery.
He expects to contribute with his bat during the 2027 Austin Prep season while working toward a return to the mound.
“I’m not gonna be sitting there doing nothing,” Cunningham said.
Choosing Virginia has given him room to focus on that process.
“I can just focus on my recovery and take the time I need,” he said.
When he reaches Charlottesville, he understands that a commitment is only the beginning.
“Everything has to be earned.”
Brett Rudy is a trailblazer in the world of baseball. As the founder of Baseball Is My Life and co-founder of Charity Hop Sports Marketing, he’s dedicated to elevating the sport and supporting the athletes who play it. With a passion for making a difference, Brett has created successful philanthropic initiatives like Charity Wines and 100 Innings of Baseball for ALS. He’s also the mastermind behind the Corked Bat Collection, Cooperstown Classic at the Baseball Hall of Fame, and Winterball for Toys for Tots. When he’s not working to improve the game, Brett can be found playing outfield in the Boston Metro Baseball League, living and breathing the sport he loves.