Unfazed, Boston Flannery smirked at his catcher.
It was the 7th inning of a tight game, and Brunswick School’s newest closer had just watched one of his pitches get smacked over the fence for a home run. Brunswick, the college prep school in Connecticut that Flannery had just transferred to, found themselves only up by one run.
Brunswick coach Johnny Montanez was surprised when he saw Flannery smirk after the homer. He hurried to the mound and had a few choice words for his closer.
But Flannery wasn’t shaken. He collected himself and proceeded to strike out the side in just 10 pitches to end the game – a game where he also threw 94 mph for the first time. For reference, the MLB’s average four-seam fastball velocity in 2022 was 93.9 mph. Most teenagers aren't throwing 94 mph in a high school baseball game.
But more than the flashy pitch velocity, it was Flannery’s ability to stay composed when meeting adversity that impressed Coach Montanez.
Mental toughness and resilience were coveted traits for a position where even an inch of error can lead to disaster. And that day, Boston Flannery proved that his laser-focused mindset was unflappable.
In early 2023, Flannery is a senior at Brunswick School and committed to playing baseball for the University of North Carolina in the fall. No longer a closer, he’s now converted to a starting pitcher and has his sights set on a baseball career after college.
But while his name might be gracing the back of MLB jerseys in a few years, his journey to get there all started with a jersey he, himself, didn’t recognize.
When he was nine years old, a friend's jersey caught his eye. But it wasn’t a New York Yankees or a Boston Red Sox jersey. Rather, it was a youth travel baseball team.
His friend’s passion for the game piqued his own interest. And for the first time in his life, Flannery tried baseball for himself. “From the minute he started playing Little League,” Keith Flannery, Boston’s father, recalled, “he was one of the best on the field with no instruction.”
Others soon noticed. Several travel team coaches approached Flannery, and soon, Boston and his dad found themselves on the road – taking overnight trips every summer with travel teams. After games, his dad would go over his performance. But it was Boston who was always hardest on himself, always aching to get better.
Maybe he shouldn’t have thrown that particular pitch on that pitch count. Maybe he knew he shouldn't have allowed that cheap hit off of him.
But Flannery always had the ability to erase it from memory and move on. Always focus on the next pitch – because failure is just part of the journey, he constantly reminded himself.
“You can hit .300 and you’re a Hall of Famer,” Flannery explained. “Meanwhile, you’re getting out seven times out of ten. It’s something that, as a baseball player, you need to be able to quickly forget after something bad happens.”
Not only would he forget those mistakes and move on, but he also welcomed any potential failure as a learning opportunity. When going into tournaments, he would long for the toughest opponents to pitch against. While some, including his father, might’ve wanted him to go up against lesser competition to put up gaudy numbers, his own mindset was different.
He wasn’t built to take the path of least resistance.
That relentless determination was needed in 2019 when he knew something was wrong with his elbow. Even after visiting doctor after doctor, none of the six doctors he consulted could pinpoint the exact issue.
Until Boston Flannery found Dr. Christopher Ahmad, the team physician for the New York Yankees. After one test, without even seeing an MRI or an X-ray, Dr. Ahmad identified the problem right away. The injury was called osteochondritis dissecans (OCD), and it was a rare condition involving crushed bones in the elbow. It was almost strictly a baseball-related injury.
After surgery, Flannery was determined to get back on the mound. And three months later, he was throwing again. He even had the date of the surgery tattooed on his right arm, serving as a perpetual reminder of the perseverance he needed to push past any obstacle.
Another one of those obstacles reared its head in Flannery’s sophomore year.
It came not in physical form, like his elbow surgery, but in mental. “I forgot how to play baseball,” described Flannery. “I was playing shortstop and… I feel like I couldn’t make a throw over to first. I had the yips, and it was bad.”
But after the worst season of his life, Boston Flannery did what he does every time he met a mountain of difficulty. “He was able to forget about it,” Boston’s dad remembered. “And then his junior year, he really blossomed.”
And he was ready to take the next step in his player development.
Flannery transferred to Brunswick School, a private school in Connecticut. They had offered him a full scholarship, and for Boston, the opportunity to attend an academically-driven school with a top-notch sports program would be vital for his growth.
Around this time, Flannery also made the transition to becoming a pitcher. While he had done some pitching in the past, he described himself more as a “thrower” – someone who just got on the mound and threw as hard as he could. In fact, even back in Little League, he would pitch because of his natural strength and because he could throw harder than everyone else on the team.
But fine-tuning that craft, developing his pitches, and getting his velocity up helped transform him from a “thrower” to a “pitcher.” A key figure in that transformation was Boston’s trainer, Dr. Nicholas Serio.
Serio, the president of Velo University, has trained with Flannery since 2021. And he saw immediately that Boston’s arm talent was there, even if Flannery, himself, hadn’t thought of himself as a pitcher yet.
“Oh, you’re a pitcher,” Serio told him bluntly. “You just haven't accepted it yet.”
Serio was introduced to Flannery’s innate hunger to be the best early on. At Serio’s facility, they did a weight sled activity with a group of athletes he was training. Athletes would keep adding more weight to the sled and pushing it – continuing to add weight until there was only one athlete standing – the “alpha.”
Serio looked on as the activity humbled Flannery. For most of his life, he’d been the top athlete in whatever team or group he’d been around. But here, in Serio’s facility of top-level baseball players, Flannery was just one of the rest. After facing the reality of where he was truly at, there was a choice to make: shy away from the moment, leave, and train elsewhere…
Or fight his way to becoming the alpha, himself.
Dr. Serio knew which path Boston Flannery took as soon as the competition ended. “The session ended half an hour after he had to tap out,” Serio recalled. But instead of recuperating or reflecting on the competition, Flannery had gone off on his own when Dr. Serio finally found him.
“I found him lifting in the weight room, when everyone else was dead. There’s nobody else lifting. From that moment on, he was on a direct quest to be the alpha.”
In that winter, Flannery was around the middle of the pack among a group that included several future college baseball players. Two years later, riding that same attitude from the sled activity, Flannery has pushed past everyone in terms of work ethic.
But he does it without forgetting his roots in his community and his dedication to his teammates.
“He’s a community-first kid,” described Flannery’s coach at Brunswick, Johnny Montanez. “He loves his teammates… Boston’s as good as they come.”
To gain insight into Flannery’s others-first mentality, one would just have to look at how he's treated his teammates. In late 2022, an unexpected tragedy hit when Brunswick’s pitching coach, Tom Daley, passed away suddenly. It hit the community, and the baseball team, hard.
But it was Flannery who called the team meeting, encouraging his teammates that their coaches and their community were there to support them.
It’s also no surprise that throughout the year, Flannery had taken junior varsity players under his wing to work out with them and walk alongside them in their journeys. And it was no surprise that he was named one of the varsity team captains for the 2023 season.
His growth as a leader came partly from Coach Daley, who would tell Flannery feedback that he needed to hear, rather than empty praise he might’ve wanted to hear. It’s a quality of Coach Daley’s that Flannery is forever grateful for – and a quality that he, himself, tries to emulate.
Once, Boston Flannery had a teammate who was being selfish, and it was hurting the team. So, channeling his inner Coach Daley, Flannery pulled his teammate aside and helped him understand the big picture, even when it was tough to hear.
Those traits have helped mature Flannery into a strong leadership role. But these days, one’s influence isn’t limited to the field.
Boston Flannery’s impact extends to social media, where he has 29,000 followers on Instagram and almost 60,000 followers on TikTok. His most-watched TikTok video is of him with Max Clark, one of the top-ranked high school players in the nation. Both Flannery and Clark played together on the Indiana Bulls’ travel team.
In January 2022, Flannery also did content with Momentum, a sports media company founded by Cy Young Award winner Trevor Bauer. In a viral clip that has reached 2.2 million views on TikTok, Flannery struck out Eric Sim, a former minor league baseball player.
“That was truly awesome,” Flannery said with a smile. “It was something that changed my life a little bit, because it was my first time pitching against professional hitters.”
And after performing well against them in the video, he became a more recognizable face in public. “I’d have people come up to me,” Flannery explained, “and be like, ‘I saw you in the Eric Sim video.”
While that was his first time facing pro hitters formally, it’s not the first time he’s worked with one. During quarantine, Flannery kept his skills sharp by working out with Justyn-Henry Malloy. A third basemen for the Atlanta Braves’ minor league system at the time, Malloy is on the Detroit Tigers’ Double-A team as of January 2023. Flannery credited Malloy for teaching him how to train the right way and for providing another solid example of how to be a leader to those around him.
If Flannery is going to follow Malloy’s footsteps and get to the Majors, he’s going to need the mental fortitude and perseverance that’s carried him this far.
In fact, Dr. Serio believed it’s not just one of the traits separating players at this level; it’s the only thing. “That’s the only delineating factor. They’re all equal when it comes to talent at a certain point,” explained Serio. “The only people who make it are those who can manage their mental landscape.”
For Flannery, his mental landscape is filled with a hunger to be the best. But as Dr. Serio has witnessed with many players, that’s easy to say; it’s another thing entirely to put in the hours of work and sweat no one else will see.
Not only did Flannery put in the work, but he also answered the bell again and again.
As Keith Flannery noted, his son wanted to face the toughest competition. He wanted the pressure, the shining lights, the big moment.
In one tournament in Jupiter, Florida, Boston’s father recalled there being 30 scouts, all with radar guns pointed at Boston. 60 golf carts with MLB or college scouts filled the parking lot. And, true to his nature, Flannery absorbed the moment, trusted his work ethic, and came through. He kept his pitches tight throughout the day, impressively throwing between 92 and 94 miles an hour.
Coach Montanez reaffirmed Boston’s love for the big moment. In April 2022, Brunswick was up against Citius Baseball Academy, a powerhouse that has produced multiple pro players. Brunswick was down two runs in the bottom of the seventh. And Citius intentionally walked Adonys Guzman – another Brunswick star – to load the bases.
With the game on the line, Boston Flannery walked up to the plate. With two outs and a two-two count, the Brunswick Bruins were down to their last strike.
Until Flannery launched a walk-off grand slam over the left field fence to take down Citius six to two.
The ability to zone everything out, and deliver, was seen again two weeks later. Coach Montanez called on Flannery to start a game against a team they were battling for the one-seed.
Flannery responded by throwing a complete game shutout with 17 strikeouts.
Not even physical pain could get in the way of his singular drive to push himself, and his team, to the next level. Once, Flannery was at a USA Baseball tournament with 12 of the top travel teams in the nation. His eyes were on Canes National, one of the premier travel teams for Boston’s age group.
But in the first game of the tournament, Flannery badly rolled his ankle. He had to be taken out of the game as his swollen ankle only ballooned even more. The game against Canes National was in three days, and Flannery’s father believed there was little to no chance of his son being ready in time.
But thanks to an ankle brace, high-top cleats, and high pain tolerance, Boston Flannery went out on the mound to pitch against Canes. His dad knew the ankle was bothering him, but Boston didn’t show it. Battling both the pain and Canes, he pitched a strong game to lead his team to a win.
With his mindset of relentless determination, it's no wonder that Flannery has lofty hopes for his future.
Since early on, his goal for himself has been clear: get to the MLB, and have a 10-year pitching career. That, alone, is a tough feat to accomplish – especially when long-term consistency for a pitcher is so difficult to maintain.
But there’s more.
Flannery’s master plan for himself includes winning not one, but two Cy Young awards. While only the best of the best ever win the award, it’s no surprise to anyone who knows Boston that his eyes are set on being the best.
Because it’s his mental toughness and grit that has pushed him to work harder and overtake others who used to be ahead of him.
It’s his leadership that has carried his team and community through any circumstance, even the most difficult ones, unafraid to say what needed to be said.
And maybe most of all, it’s his compassion and his heart that’s the driving force behind it all.
With his senior season at Brunswick and his college career at UNC ahead of him, Boston Flannery is armed and prepared to face whatever challenges may lie ahead.
Even if it’s a home run hit off him, just as he was trying to get acclimated to a new school and a new team.
But he just smirked, got back on the mound, and threw the next pitch.
Strike one.
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