Moving 1,500 miles from home to pursue your dreams is never an easy decision, especially for a teenager.
Bailey and Olivia Breen of South Thomaston, who are 17 and 13 respectively, said goodbye to their friends and family three weeks ago to join Montverde Academy’s prestigious prep basketball program in Central Florida.
Following in the footsteps of Maine basketball stars Cooper and Ace Flagg, the Breen sisters recognized that the opportunity to play for a perennial national championship contender and fully prepare themselves for the Division I level was too good to pass up.
The Breens both stand at roughly 6-foot-2 and have drawn the attention of schools such as Boston College, Providence College, Bryant and UMaine, flexing their size and versatility in elite AAU tournaments around the country. Transferring to Montverde was the logical next step for both of them, but it comes at a cost: the sisters had to uproot themselves at a young age and must go all-in on their pursuit of basketball excellence.
“From a mentality’s standpoint, you have to be a totally different animal,” Bailey said. “We have a 3-hour practice, a 1-hour lift and an hour and a half of open gym every day. Our easiest day is a hard day for the average person.”
She added, “I didn’t have to leave Oceanside for my college career, but this puts me in the best position to walk in and make an [immediate] impact in college, without any what-ifs. I had to be a big girl and grow up at some point.”
The decision was difficult for both sisters, who left home at critical junctures in their adolescent lives.
Bailey is entering her senior year of high school, and sacrificed the opportunities to win Miss Maine Basketball and defend her second state title at Oceanside, alongside her longtime teammates and father Matt Breen, who is the Mariners’ head coach.
Olivia is entering eighth grade and won’t even get the chance to suit up in Mariners threads. Moreover, she’ll be at Montverde without her older sister for four more years after this one.
“It was hard for both of us,” Olivia said. “I came here to be the best player I could be — the three straight national championships [Montverde has] persuaded me. The pace is faster, but playing against other D-I commits is where I want to be.”
Olivia originally made her decision to transfer back in April, after a campus tour during a family vacation to Florida. She then sustained a dislocated shoulder in May — which has sidelined her for the first few weeks of practice and is nearly fully healed — but ultimately decided to finish her recovery away from home.
Bailey had been on the fence about transferring for two years, previously shying away from a roster spot at Tabor Academy in Massachusetts last year. It took her “until the night before” the sisters flew down to Florida in August to fully commit herself to transferring.
“I was leaning toward staying, but everyone in my close circle was pushing me to go,” Bailey said. “Even my dad. For someone to say that in that position, I had to have trust in him.”
Matt was a two-time Kennebec Valley Conference Player of the Year at the now-defunct Rockland High School and went on to earn All-Conference honors at Husson University. After graduating, he returned to coach at Rockland/Oceanside, where he has accumulated 257 head coaching wins. He won his first of two gold balls when Bailey was a freshman in 2022.
He admitted seeing his daughters transfer to Montverde was a “double-edged sword.”
“It’s hard, but as a parent you want to provide them with the best opportunities,” Matt said. “It was the right move.”
The sisters will mitigate their homesickness by taking weekend trips to Maine at least once a month, and also have the privilege of rooming and practicing together.
Bailey plays for the Eagles’ “national” (varsity) team, and Olivia is one of just two eighth graders on their “gold” (junior varsity) team. The two squads scrimmage together and are both coached by Matt Shewmake, who played basketball at Louisiana Tech and has assistant coached at the Division I level.
Each team has roughly a dozen players, who come from all over the country and even overseas. One of Olivia’s teammates will be the daughter of Maine Basketball Hall of Famer Andy Bedard, who is a freshman on the gold team and also happens to be named Olivia.
“It’s an international school, and it’s nice to have those connections,” Olivia Breen said. “Everyone is really welcoming. I’m excited to play with them.”
The sisters have been encouraged by Shewmake’s vision and their teammates’ friendliness.
“Shewmake sees me as more than just a tool in a basketball factory. He believes in me like my dad does and he has a good vision for how I can make an impact,” Bailey said. “I love my teammates; there’s no jealousy or drama. There’s not one person on the team who doesn’t pass the ball. They’re really good players, and really nice people.”
