WINCHESTER, Mass. — Just north of Boston, inside Middlesex County, one of the most slept-on teams in the state is starting to make some noise.
Winchester took one big step closer to claiming a Middlesex League title with a 63-55 victory over Arlington on Friday night inside a fully packed, raucous home gymnasium, one of the best environments I’ve seen in MIAA this winter. The Red & Black led by 10 at halftime before the Spy Ponders went on a 13-1 run out of halftime, but behind sophomore Jack Charchaflian and senior Alex Casey, they regrouped and made enough plays to squeeze out the win.
After falling to Arlington (11-4) on an overtime buzzer-beater on Dec. 20, Winchester (13-1) has now reeled off 12 consecutive victories after taking Friday’s rematch. And with a 10-1 mark in the Middlesex, they now hold a two-game lead over Arlington in the Liberty Division. At No. 7 in the MIAA’s latest Division 1 power rankings, Winchester is looking dangerous as the calendar turns to February.
“It’s huge for us,” Winchester head coach John Fleming said. “The Middlesex League is super tough, I think, kind of underrated. But to beat a team like Arlington who beat us early in the year is great for us. We still have a long way to go in the regular season, both in the Middlesex League and a couple tough ones to finish. But it gives us a chance, it gives us an opportunity to have some really competitive games down the stretch.”
Let’s dive into some standouts and takeaways from Friday’s game.
Alex Casey, Winchester
Class of 2025, 6-1 wing
Winchester’s senior captain picked up his third foul in the opening minute of the third quarter and took a seat as Arlington took advantage with its run to take the lead. But he had the last word. With the game knotted at 45, Casey drilled a straightaway buzzer-beating 3-pointer to end the third. Then, with the game hanging in the balance late in the fourth, he hit a corner triple that put Winchester up eight with 2:26 remaining. Casey finished with 16 points on four 3-pointers, none bigger than those two.
“We didn't have much offensively in the third quarter. And then to have that, it was like OK now we have a burst of energy going into the fourth, just because every hoop was so tough to get on both sides,” Fleming said.
“For Alex, as a senior, to really take on that leadership role and to hit big shots like that, there were a couple of them down in the second half where we just needed it, because their defense was so tough, to come off a screen in transition and then hit one was huge. He’s been terrific.
Jack Charchaflian, Winchester
Class of 2027, 6-0 guard
Charchaflian finished with a team-high 19 points, including 10 in the second half, as he continued his stellar sophomore campaign. When Arlington took the lead in the third, he was responsible for steadying the tide for Winchester with some tough, impressive takes to the rim. Charchaflian committed a few turnovers late, but he showed enough poise to overcome it. He’s confident as Winchester’s primary ball-handler, can use both hands and consistently makes the right reads.
A year after being named a Middlesex League All-Star as a freshman, Charchaflian has taken another step as he leads the Red & Black in scoring and assists while shooting 44 percent from deep.
“To have that continued growth, the sky’s the limit there in terms of what he’s eventually going to be able to do,” Fleming said. “I think he probably wishes he made a couple plays down the stretch, but he did enough to give us the win ultimately.”
Dawson English, Winchester
Class of 2026, 6-0 guard
The junior guard scored eight of his 10 points in the first half as he pushed Winchester ahead to its early advantage, and he was particularly effective inside. In the waning seconds of the first quarter, English followed a miss with a reverse putback layup at the buzzer to give the Red & Black a six-point lead. A few moments later, he weaved through defenders in transition with some impressive crossover dribbling to get two at the cup.
James Dingman, Arlington
Class of 2025, 6-3 guard
The Arlington co-captain finished with a game-high 24 points, and nearly willed the Spy Ponders to a comeback victory. He finished a strong three-point play in transition and flexed his muscles as he brought Arlington within one early in the third, and went on to make seven free throws in the second half as he made several plays down the stretch, including a huge 3-pointer that kept them in it in the fourth. Dingman’s pull-up jumper game was impressive, with a high-arcing, confident release that’s impossible to defend and drew a handful of fouls.
Leftover thoughts…
1. Though Winchester led by 10 at halftime, Fleming never expected a runaway victory. The Red & Black briefly lost the lead, but their response was an impressive display of poise.
“It was just about trying to keep our composure a little bit,” Fleming said. “We know they’re a really good team, they’re going to make plays and (for us, it was) to stay together. … Defensively, they’re the best team that we’ve played. Offensively, they make plays. We made just enough plays down the stretch.”
2. Winchester’s overtime loss at the buzzer to Arlington on Dec. 20 was brutal, but certainly not the end of the world. Fleming and his group knew there was no reason to hang their head and there would be a rematch coming. Twelve straight wins later, including a victory in the rematch, and that loss is far in the rearview mirror.
“Those are state tournament level games, so to lose the way that we did, in overtime at the buzzer, was tough,” Fleming said. “But you learn from that, you learn from a loss, sometimes more than a win. For us, we knew we lost a very competitive game that could have gone either way, and we were on the short end. But we knew we’d have an opportunity to compete with them again, and we found that opportunity and seized it at the end.”
3. I was really impressed with the unselfish brand of basketball that Winchester plays with. The ball is always moving, and the Red & Black are always making the extra pass. Charchaflian, though he takes his opportunities to create for himself when it’s there, sets the tone for that. It’s a fun offense to watch.
“For Jack to have the poise, because they're running guys at him, have some patience and then find some space eventually to make some plays and then be willing to make the pass, is huge,” Fleming said. “And we talk about that a lot, because he can do a lot with the ball in his hands, but those kick-outs, those extra passes, that’s what opens up an offense.”
