Massachusetts Showday: Milton Academy Underclassman Standouts Skill Analysis
The Milton Academy program had many talented prospects participating in their annual spring showcase held May 14, 2026. In this report, I will highlight five underclassman players that caught my attention during the live evaluation event held May 12, 2026 and include a short skill analysis while also listing the players who earned verbal offers after the event concluded.
Massachusetts Showday: Milton Academy Standouts Skill Analysis
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Hudson Garrity
New England
2030
5’11”
180
QB
Archbishop Williams High School transferring to Milton Academy in the Fall of 2026
Player Performance Report:
Hudson Garrity impressed at the Evaluation Showcase, showcasing his potential as the cornerstone of Milton Academy’s football program. At 6’0″ and 188 lbs, Garrity displayed exceptional proficiency in connecting with receivers, demonstrating an ability to throw them open and effectively execute back shoulder throws. His mechanics were polished, marked by a quick release that allows him to get the ball out efficiently under pressure.
Notably, Garrity’s commitment to strength training is evident, as his improved physicality translates into better overall performance on the field. His presence during drills highlighted a blend of skill and athleticism that will serve him well as he transitions into his new role. As he approaches the fall season, Garrity is shaping up to be a standout player worth following closely.
Osiris Niven
Massachusetts
2028
6’2″
235
Edge
Milton Academy
Player Performance Report:
At the Milton Academy Evaluation Showcase on May 12, 2026, Osiris Niven showcased his standout abilities as a top edge rusher. His body control and leverage are impressive, allowing him to effectively navigate the line of scrimmage and capitalize on opportunities as both a pass rusher and run defender. Osiris consistently tracks the ball and closes in with purpose, demonstrating a high football IQ. His relentless effort and high motor were evident throughout the event, maintaining intensity during drills and scrimmages. Notably, his commitment to strength training has sculpted his already lean frame, making him a more formidable presence on the field. Osiris has developed significantly since the 2025 season, positioning himself as a top prospect for college coaches to consider moving forward. Osiris earned a verbal offer from Army after the event concluded.
Benjamin Allen
Massachusetts
2028
6’2
190
WR
Milton Academy
Player Performance Report:
At the Evaluation Showcase held at Milton Academy on May 12, 2026, Benjamin Allen showcased his impressive skill set as a wide receiver. Standing at 6’2″ and weighing 190 pounds, he demonstrated soft hands, consistently plucking the ball from the air with confidence and precision. His route release was effective, allowing him to create separation from defenders. Allen displayed strong body control and an impressive catch radius, which should attract further attention from college programs. His verbal offer from the University of Rhode Island, reported via Twitter in January, speaks to his potential. Allen’s performance underscores his status as a rising prospect in Massachusetts, and he will likely be a key player to watch in the coming seasons.
Blake Nelson
Massachusetts
2028
6’1
190
WR/LB
Milton Academy
Player Performance Report:
Blake Nelson, a 2027 recruit transferring from Archbishop Williams High School to Milton Academy, showcased impressive skills at the showcase. Standing 6’1″ and weighing 190 lbs, his frame immediately stands out. Throughout the event, Nelson demonstrated exceptional athleticism with fluid movements and quick acceleration after the catch, allowing him to gain yards effectively.
His hands proved to be both soft and reliable, consistently securing passes even in congested scenarios. Notably physical in his playing style, he displayed an ability to battle through defenders, which complements his impressive junior season stats of 850 yards, 56 receptions, and 10 touchdowns. With his combination of size, speed, and skill, Nelson is poised to make an impactful transition to Milton Academy this fall, drawing attention from college coaches in attendance.
Jordan Toribio
Massachusetts
2028
5’10
170
Rb/Db
Milton Academy
Player Performance Report:
Attending the Evaluation Showcase at Milton Academy on May 12, 2026, Jordan Toribio showcased a dynamic skill set that caught the attention of college coaches. At 5’10” and 170 pounds, his athletic frame complements his playing style perfectly. Known for his quick hips and fast feet, Jordan exhibited impressive burst, allowing him to break into the open field effectively.
Throughout the event, he demonstrated excellent field vision and the ability to navigate through traffic, consistently getting downhill with authority. His explosive jump cuts made him difficult to tackle in one-on-one situations, particularly in open space. Additionally, his proficiency in blocking and receiving adds versatility to his game, though his strongest attribute remains his ability to run with the ball. Overall, Jordan’s performance solidified his status as a standout prospect for college recruitment.
Edward Skeffington
Massachusetts
2028
6’2
280
DL/OL
Milton Academy
Player Performance Report:
At the Evaluation Showcase held at Milton Academy on May 12, 2026, Edward Skeffington emerged as a top performer among defensive linemen. With a solid build of 6’2″ and 280 lbs, his physicality was evident in one-on-one drills. Skeffington displayed impressive first-step quickness, consistently gaining the upper hand on offensive linemen. His intensity and relentless motor set him apart, as he can maintain pressure on quarterbacks and effectively disrupted plays in the backfield. Additionally, his ability to leverage his strength while demonstrating agility showcased a strong combination of skills. College coaches took note of his high football IQ and work ethic, making him a promising prospect for collegiate programs. Overall, Skeffington’s performance at the showcase solidified his status as a standout defensive lineman with significant potential.
Shamus Devine
Massachusetts
2029
6’4
206
TE/WR
Milton Academy
Player Performance Report:
Attending the Evaluation Showcase at Milton Academy on May 12, 2026, Shamus Devine showcased an impressive 6’4″, 206-pound frame that immediately stood out among peers. His athletic fluidity in movement was notable, demonstrating agility and quickness that will keep defenders on their toes. Devine’s ability to consistently pluck the ball out of the air and execute back shoulder catches with ease underscores his advanced hand-eye coordination and ball skills. Throughout the event, he displayed a strong presence, proving to be a reliable target in drills and scrimmages. With ongoing developmental focus, Devine is a promising prospect to monitor closely as he progresses in his career. College coaches should take note of his potential, making him a player to watch in the coming years.
Notable Top Performers & Offers Earned After Event
| Matt Eliason | 2027 | Milton Academy | Univ of Albany 5/6/26, UNH 5/12/26 |
| Osiris Niven | 2028 | Milton Academy | Army 5/12/26 |
