Caldarella, a senior guard out of Cheshire Academy in Connecticut, has taken full advantage of his year in the NEPSAC and proven to be one of the most efficient offensive performers around. Few teams have played better as a collective unit this winter than Cheshire Academy, who sits in 4th place in the league at 10-4 and has gotten terrific play on both ends of the floor from Caldarella. A high IQ decision maker, Caldarella is as solid as it gets on the offensive end of the floor. He can play on or off the ball, directs offensive in the half-court, and does a nice job of moving in space without the ball in his hands. He’s a high level shooter from the perimeter, finishes with touch over size in the paint, and does a good job of playing within a team’s scheme on the defensive end of the floor. Caldarella will continue his career in the fall at the United States Air Force Academy.

Caldarella did a nice job running the show and finding others for scoring chances. He even showed that he can put the ball in the bucket. Caldarella was a threat from behind the arc and can play on or off the basketball.

I love the way the ball comes out of his hands quick finding his teammates. Shot the ball well from deep in rhythm, quick release, no dip 3 player. Defensively made Winchendon’s players alter their shots, making easy shots look difficult. Continuing with his defense forced turnovers or inaccurate passes without getting his hands on the ball. Out hustled opposing players to 50/50 balls and rebounds. Air Force commit is a must watch!

Caldarella, a guard out of Cheshire Academy, continues to stand out with his ability to consistently make the right play. At 6’3″, the Air Force commit has good size for a combo guard and shows a high level understanding of how to create good scoring looks for himself and his teammates. He plays at his own pace, does a nice job of changing speeds as a driver, and continues to knock down threes at a high clip. He’s a tough perimeter defender that does a good job of playing in rotation and has the ability to guard up and down a position.

+30 (#113 to #83)

Caldarella rises in the rankings after a big time AAU season for BCRI in which he was one of their most impressive players. The 6-foot-3 guard initially burst onto the scene because of his three point shooting ability, but he has a lot more to his game the more you watch. Like all BCRI players, he moves well without the ball and is incredibly unselfish, but he can also create for himself and others out of the pick and roll if he really needs to. He has solid positional size and despite not being a freak athlete, he has above average strength and the fundamentals to make up for it. He’s a high D3 player or perhaps even a low scholarship player in my book, and he should get lots of looks on a great Cheshire team this season.

Caldarella offensive skillset was on full display. He was able to find teammates with his passing and get them the ball in the right spots on the floor to convert scoring chances. He does a nice job driving baseline on the attack. Caldarella converted several shots from behind the three point line and shouldn’t be left open. Caldarella should be a priority for small college coaches in need of a guard.

Caldarella is an excellent passer who truly understands how to play the game. He’s always thinking multiple passes ahead and is supremely aware of his team’s spacing and cutting, and he does a good job manipulating the defense with his eyes. Once he gets the ball, he’s a knock down three-point shooter and has some solid ball-handling ability as well. I would be surprised if Caldarella doesn’t have a nice season at Cheshire Academy next year (where he’ll reclass to 2026) and find his way onto a D3 roster once the time comes. Really high IQ and skilled basketball player who could even potentially get scholarship looks if he gets more athletic and stronger.

Caldarella, a standout in Rhode Island at Bishop Hendricken, had multiple games of 20+ points as a junior last season. An impressive shot maker, Caldarella does a great job of moving without the basketball and exploding into his jumper on the perimeter. He’s continued to expand his off the dribble game and proved capable of being a crafty rim finisher this summer. He does a great job of spacing the floor and running off screens, quickly gets his body squared to the rim, and has a clean, quick release. He’s a willing ball mover that isn’t afraid to turn down good shots to hunt great shots later in the clock. Bishop Hendricken has a chance to make a deep run in the state tournament this winter, and if they do, Caldarella and his ability to score the basketball will be a big reason why.