Middleton, a wing out of the St. George’s School in Rhode Island, checks in at #16 among the small forwards and #99 overall in this update. A 6’5″ wing that plays with great athleticism, he impresses as a finisher around the rim and also shows the ability to get to his spots with limited bounces. He does a nice job of getting square to the basket off the catch and elevates nicely into his jumper. On the other end of the floor, he’s a big-time playmaker in passing lanes and has the ability to be an elite, multi-positional defender down the line. He’ll run on the travel circuit with Crown Basketball.

Blending in nicely with his new surroundings at St. George’s, Middleton made a clear case for inclusion in the next rankings with his steady complementary play on the wing in a Sunday win over Albany Academy (NY). The Hackley School (NY) transfer stands out immediately with a chiseled frame and enveloping length. He plays a clean game in support of the talent alongside him, contributing as a floor-spacer, defender, transition athlete, and opportunistic rim attacker. Middleton is continuously emerging as a clear scholarship-level talent with the physical tools and translatable skillset to garner D1 attention heading into the grassroots season.

Middleton impressed with his two-way versatility against Albany Academy (NY). His length was seen frequently on the defensive end of the floor by rebounding, forcing turnovers and altering shots. He was very efficient with his shot selection and was able to connect on two three pointers. He plays with an aggressive motor. Middleton finished with 11 points. He also made a few trips to the charity stripe and made the most of his chances from there. He is just starting to scratch the surface as a prospect and should be on the big board of low to mid major programs throughout the Northeast.

Middleton has a freakishly intriguing skillset and might have the most potential of anyone on the 2027 watch list. The 6-foot-4 wing gets minutes on an incredibly talented St. George’s team, and he plays his role well; he runs the floor for transition dunks and layups, he cuts to the rim to open up space, and he defends his behind off by using his athleticism and length. If he were on a different team, he’d probably be able to showcase more of his on-ball capabilities, but this year is proving he can play a role. When the junior gets the chance to make more plays offensively—whether it be during this prep season, the upcoming season, or next prep school season—watch out for some incredible development.