On one of her last days of high school, Maddie Oliver read a letter from her sixth-grade self. In the first lines, sixth-grade Oliver wished that when she saw the letter again, she'd be an 18-year-old headed off to play Division 1 college basketball.
Oliver is realizing that dream. She graduated from Norwell two weekends ago and will head to James Madison in late June. But she would never have guessed how her recruiting process — one of the more bizarre, drawn-out endeavors in this Class of 2025 — would play out.
"People kept asking me, 'Does this feel like a weight off your shoulders?' And that really can't be more true," she said. "It physically felt like a weight was off my chest, because I just had constant anxiety all the time."
Oliver announced her college commitment just two weeks before graduation and the day after her senior prom. Her first offer didn't come until February. She's still not completely sure what her scholarship entails, but she knows she's guaranteed a roster spot. To reach this point, Oliver has overcome personal loss, self-doubts about her basketball goals and multiple years of struggle and stress to secure her future.
"Being on the phone 24/7, trying to get through my senior classes, trying to train, trying to just balance everything was just so much," she said. "Even talking about it — it's like an anxiety response I think, but it just spikes everything, because it really was such a stressful time."
Oliver was on a solid trajectory after her freshman year at Norwell, following the lead of her older sister Grace. But she was blindsided by the sudden death of a close friend before sophomore year began. Oliver had to choose between processing her grief and forging ahead through the grassroots season — her friend's funeral, for example, occurred during one of the summer's biggest showcases. Oliver said that about 10 colleges were showing interest at the time. But she withdrew from the sport as she grappled with the loss.
"It kind of just put things into perspective for me because I just wanted to spend time with the people around me," she said. "I kind of just started to resent basketball a little bit. I don't even know necessarily why, but I think it was just because I was like, 'Why am I even doing this? Nothing's guaranteed.' I think it was just a couple months — obviously, the shock of it was insane — but it just put like a lull on everything for me, and I kind of just went silent for a while. I was talking to these coaches, and it was just kind of like I just stopped playing that summer."
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Around the same time, Oliver began feeling the pull from NEPSAC. She started touring prep schools the spring of her freshman year, the same time Grace chose to reclassify and transfer to Nobles, and nearly followed her sister. But Oliver didn't want to add an extra year of high school that would come from reclassifying, and she didn't want to leave her town and friends.
Oliver returned to the Clippers as a sophomore and reignited her love of basketball. She won South Shore League MVP that winter, then went back-to-back with the award as a junior while surpassing 1,000 career points and leading Norwell to its first state championship appearance in 35 years. But her recruiting momentum sputtered. Sure, coaches were interested — Western Kentucky along with multiple other schools came to watch the Clippers practice during Oliver's junior year — but talks never left the talking stage.
"I've been on the phone with coaches the past five years, but it was never complete. I was always just looking for my first offer, but it would be just talking," she said. "Which was frustrating, because the talking only does so much."
It wasn't just Oliver in disbelief. Norwell coach Matt Marani couldn't understand why coaches would validate her talent but not extend an offer. He started to see how much the college transfer portal was mucking up Oliver's recruiting process.
"We would talk to tons of them, and it was constantly the same answer, which was, 'We're going to wait until after the portal.' And they all expressed a ton of interest and a lot of positive things about Maddie," he said. "I would even ask questions like, 'Are you not seeing the Division 1 player like I'm seeing?' And they were like, 'Nope. She's definitely placed correctly. This game's for her; she can play at this level.'"
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By senior year, Oliver started watching the other stars in the Class of 2025 make their college decisions while she held out. Marani admitted he was "freaking out, 100 percent" as Oliver respectfully declined Division 2 and 3 interest to chase the elusive Div. 1 chance. He watched Oliver dominate against a Sacred Heart commit when Norwell played a holiday tournament in Florida, but the staff wasn't swayed enough to offer her. Oliver began applying to colleges as a standard student.
At this point, the 6-foot forward had started to doubt her talent. Grace helped get her back on track.
Oliver has always appreciated her older sister's support and blunt, honest advice. Grace had gone on to earn national ranking status and played her freshman year at Colorado (she has since transferred to Wake Forest). Last winter, Colorado head coach JR Payne asked about Oliver's recruiting progress, and she and Grace took a look at the tape. Both were shocked that Oliver hadn't received an offer.
"It was almost like her getting kind of frustrated for me, that made me be like, OK, this kind of makes a little bit more sense," Oliver said.
But the payoff, through a remarkable coincidence, was closer than they realized.
Norwell brought aboard Jay D'Entremont as an assistant coach this past winter. Marani was lamenting to D'Entremont about Oliver's recruiting struggles, and D'Etremont said he could try passing along her film to a friend he knew at the college level.
"He said, 'Well, do you want me to reach out to my friend at James Madison?'" Marani recalled. "I stopped and was like, 'Jay, you have a friend at James Madison? I've called almost every other college in the country — you have someone at James Madison?' He's like, 'Yeah, the head coach is a good friend of mine,' and I was like, 'Yes, please call him.'"
That head coach, Sean O'Regan, expressed immediate interest in Oliver's game. He stayed in touch with her for about a month and surprised her with her first offer, following an hour-long pitch of the the school in a Zoom call, in February.
"I remember the next three weeks, I was looking up every single thing to do with James Madison — looking at every video of the school. I just got obsessed with it," Oliver said. "It was just such a surreal moment and just completely changed everything for me."
The journey wasn't over. Oliver didn't want the excitement to control her finding the right fit. She and her MCW Starz coach, Mandy Carter-Zegarowski, worked the phones through the winter. Coaches kept halting at a scholarship but sang genuine praises. One assistant at Quinnipiac felt so badly that they were out of scholarship spots that they called a nearby coaching connection — ultimately leading to Oliver's second offer from Central Connecticut State the next day. Along the way, she won her third straight South Shore League MVP award and steered the Clippers to another Div. 3 runner-up finish.
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The calendar flipped to May, long after most seniors have chosen their next path. Oliver was down to James Madison and Central Connecticut State, with American and Holy Cross also interested. She visited the JMU campus and loved it. The morning after her senior prom, she walked downstairs and told her parents she was done with the process.
"It was just like, 'I just can't keep doing it to myself,'" she said. "I know I already have an amazing spot waiting for me. Why not just take it?"
Throughout the last four years, Oliver has stubbornly charted her own way to Division 1. She watched Grace shine at Nobles and admitted that if she had listened to most voices around her, she would have transferred to prep school. Oliver and Marani often fielded similar questions from college coaches: Why is she still uncommitted, and why hasn't she reclassified and gone prep?
In the weeks since committing, Oliver can finally relax. She got to spend prom and graduation with friends and teammates she's known since she was seven years old. And though it took inordinate years of stress and sacrifice, she got the basketball future she dreamed of. One reason Oliver stuck it out: she wanted to prove, to herself and other athletes, that a path like hers is still possible.
"I think that I needed someone at that time to kind of show you don't need to do certain things like everyone else is telling you to do," she said. "And also, just being able to make decisions based on yourself and what will make you happy."
