As a multi-positional guard-forward capable of operating offense as a primary ball handler, the 6-foot-5 Class of 2027 Dillon Callahan (Iona Prep, NY ‘27)was among the top underclassmen in the tri-state area during his two years at Iona Prep.

A skilled lefty buoyed by a vertically explosive style, Callahan turned in several double-doubles during his sophomore campaign. Including a 19-point, 14-rebound performance en route to a victory over Cardinal Hayes during the tail end of the 2024-25 season.

Callahan's ability to move fluidly and take advantage of seams was evident when he erupted for 31 points during a matchup against St. Francis Prep during the regular season. Callahan's awareness and know-how in making the right reads and authoring efficiency with his scoring were evident during the postseason. He scored a team-best 20 points during the Gaels' loss to Christ the King in the city quarterfinals.

Callahan heads to St. Thomas More in Connecticut as an enticing two-way threat with a wealth of experience playing in the CHSAA AA and in a hothouse, uber-competitive AAU environment. He brings positional size and versatility.

As a floor stretcher who can hit the outside shot with consistency, Callahan can be employed in a variety of roles. He's become a physical defensive threat, simultaneously utilizing his length and physicality in guarding the 1-4. With his handle and craftiness, Callahan has gained consistency with keeping defenders off kilter and evoking space creation.

The New York Rens product will play for an exalted figure in the coaching business in St. Thomas More boss Jere Quinn, who has nurtured high-end talent such as Andre Drummond, Eric Paschall, and, in recent times, Tyler Betsey. What remains to be seen is exactly what niche Callahan will adapt to at STM.

During his time at Iona Prep, he played off the ball and also orchestrated offense as a point forward while Johnny Keenan was sidelined during the second half of the season. With his offensive uniqueness and physicality on the blocks, Callahan differentiates himself with his knack for impacting the game in an array of ways. He's a notable riding prospect in a deep Class of 2027, which is generating significant buzz this off-season.