2025-26 Deerfield Academy is Loaded with College Prospects
Deerfield Academy is an independent college-preparatory boarding school in Deerfield, MA. Founded in 1797, it is one of the oldest secondary schools in the United States. The Academy has maintained an outstanding academic reputation, described as an “elite boarding school” by the New York Times.
The Boys Basketball Program is a college basketball feeder program, where it competes in the highly competitive New England Prep School Athletic Council (NEPSAC) Class A division. Players in recent years have gone on to play at schools including Harvard, Middlebury, Bowdoin, Rochester, St. Lawrence and several others.
The team's 2025-26 game schedule and results will be found here.
The team is coached by Connor Merrill. Prior to joining Deerfield in 2022, Coach Merrill spent the previous six years coaching at the collegiate level, including four years as the top assistant at Middlebury College and two years as graduate assistant at Springfield College. His first stop in his coaching career was as an assistant coach at his alma mater, Vermont Academy, where he was able to coach current NBA player, Bruce Brown. Coach Merrill played fours years of basketball at Skidmore College, where he was an all-league player and helped the Thoroughbreds to two Liberty League championships and two NCAA Tournament appearances. His 2025-26 roster is stocked with college prospects as profiled below.
Jonathan Ocasio (2026) 6’0 guard - combo guard from Lawrence, MA. Lethal 3-level scorer who can fill it up quickly. Shoots it with range from deep, operates in the mid-range very effectively, and uses his burst and change of speed to get to the rim. Physical and tough-minded player who is a great leader and gets others involved. Poised for a strong fall and winter season. Video highlights
Harrison Miles (2026) 6’6 small forward - Mileswho can make shots at a high clip. Attacks off the bounce 2-3 dribbles, and has a great touch around the basket and in the mid-range. Wide shoulders and his frame continues to fill out. Receiving high academic interest. Plays AAU with BCRI-HGSL. 4.1 gpa Video highlights
Liam Simpson (2026) 6’7 small forward - 2024-25 Gatorade Rhode Island Player of the Year. An incoming post-grad from LaSalle Academy (RI) where he averaged 12 ppg and 15 rpg, while leading LaSalle to both a Division 1 and Open State Tournament championship. He is an elite rebounder of the basketball with a great feel and IQ for the game. Can guard multiple positions and has a rapidly developing skill set. Plays AAU with Basketball Club of Rhode Island-HGSL circuit. 4.0 gpa Video highlights
Andrew Rivera -(2026) 6’3 guard - An incoming post-grad from Milford, MA who averaged 18 ppg, 7 rpg, and 7 apg this past winter. Holds D1football offers. Skilled and tough combo guard who can score the ball in a variety of ways and is a great facilitator. Video highlights
Jameson Stockwell (2026) 6’4 guard - An incoming post-grad from New Hartford, NY. Skilled and athletic 3-level scoring combo guard. Consistently plays above the rim, and can make shots from deep and operate in the midrange. Very good at getting downhill. Plays AAU with Hoop Roots-HGSL circuit. 4.0 gpa 1380 SAT Video highlights
Elijah Webb (2026) 6’9 stretch forward - Webb can play inside-out. Quick and high release on his jumper which allows him to get shots off efficiently. High IQ and is someone you can run offense through. Rapidly developing skill set and body. High ceiling to what is already a strong skill set. Plays AAU with Middlesex Magic-HGSL. 4.0 gpa Video highlights
Teddy Cyr (2027) 5’9 point guard - Cyr is a lefty guard who is tough as nails and plays with an edge. Fearless competitor who had a great sophomore campaign this winter. Very good at getting downhill to his left hand and seeking out and finishing through contact. Deep range on his shot as well. He also plays soccer. Plays AAU with Middlesex Magic-HGSL. High gpa Video highlights
Zeke Williams (2028) 6’3 guard - An incoming repeat sophomore from Madison, CT. Sharpshooter who can really fill it up from deep. Quick release both off the catch and bounce. Good feel and IQ for the game as well. Plays AAU with Rens United-EYCL. Video highlights RTB profile
Bear Donovan (2029) 6'1 guard - An incoming repeat 9th grader from Indian Mountain School (MA), Donovan is a shooter with deep range and a quick release. Tough and hard-nosed combo guard. Plays AAU with Pick Enroll. Video highlights
To accommodate college scout visits, Deerfield holds a schedule of Fall Open runs, the details of which can be found here.