The actual games played at the Little League World Series make up just a fraction of the players’ time spent in Williamsport, Pa.
Read more Willow Grove Park Mall is in the process of being sold
For the most part, the players are ushered between various media appearances and practice, which sometimes can be overwhelming for a group of middle schoolers. However, when they have downtime, the players can interact with — and even befriend — peers from all over the world.
East Side, a 12-and-under baseball team from West Chester, is making the most of the opportunity.
“It’s kind of cool watching them engage with the international players,” East Side coach Bob Hennessey said. “Our bunkmates are [from] Japan. It’s kind of cool to watch those boys interact, not through language, but through signs and just handshakes and stuff like that.”
On Friday, East Side, representing Pennsylvania and the Mid-Atlantic region, will face a team from New Jersey — Bayonne Central Little League, representing the Metro region — in the West Chester squad’s first matchup of the Little League World Series (7 p.m., ESPN). Left fielder Paul Cowperthwait previously told the Inquirer the team is living “every 12-year-old’s dream.”
“These are kids that we always thought were special from Day 1,” Hennessey said. “We continue to have that belief in them, and here we are now at the Little League World Series, which is something that we thought was possible, but you don’t really know until you get to this point.”
After clawing out of the loser’s bracket in the Pennsylvania state tournament, East Side cruised through the Mid-Atlantic regionals, winning all three of its matchups.
East Side’s victory in the Mid-Atlantic championship was the most dramatic of the three wins, as it defeated Wilmington’s Naamans Little League, which is roughly a 30-minute drive from West Chester, 3-1.
With two out in the game’s final inning, East Side pitcher Ryan Donnelly slid to grab a short roller before making the throw at first to get the Naamans runner out. A prolonged review that lasted approximately four minutes allowed the team to celebrate twice — after the play initially was made and once the replay confirmed the outcome.
“I think it was sweet to have that second celebration,” Hennessey said.
West Chester to Williamsport‼️
Pennsylvania advances to the LLWS in its home state 👏 pic.twitter.com/H5ANOLXwsp
— ESPN (@espn) August 14, 2026
East Side is looking to keep the good times rolling against Bayonne Central. The North Jersey team is preparing for its second game of the Little League World Series, after defeating Bridgewater Joe Lazaro Little League of Massachusetts, 2-1, on Wednesday.
The tournament is double-elimination, so East Side’s championship chances are not over if it loses Friday. They’d play again on Sunday with a win, or on Monday in an elimination game with a loss.
An ‘awesome experience’ for Hennessey
Hennessey, whose son, Ryan, plays for East Side, has coached the same set of players in West Chester for the past five years.
“I started coaching them when they were 8, so to watch them grow from little guys to almost young men has been a very cool experience,” the elder Hennessey said. “Obviously, I’m coaching my son as well, so to see him grow along with the other kids, it’s just been an awesome experience for me and the other coaches.”
Hennessey is especially proud of how the team has handled their newfound attention since arriving in Williamsport last Saturday. According to the coach, the team has become increasingly comfortable on camera since first being exposed to the media circuit during the Mid-Atlantic regionals.
And coaching his son has made the whole experience even more special for Hennessey — even if it poses its own challenges at times.
“Coaching your son, obviously, is tough,” Hennessey said. “I feel like at a younger age, they listen to you more, they appreciate your feedback. But the older they get, the less likely they are to listen to you.”
To combat this, Hennessey and his assistant coaches — who have children on the team — put a simple rule into place: No coaching your own son. Since implementing the rule a couple of years ago, the coaches have been able to break through to their own children.
“My dad coached me growing up,” Hennessey said. “I always appreciated him coaching me and just being there to help me out to kind of show me or tell me the things I was doing right or wrong. And I think, maybe, [Ryan] doesn’t understand it now, but I think you know down the road he’ll understand things I said to him and the reasons why I said it. And hopefully he’ll appreciate that down the road.”