Sherwood is a skilled, physical, and versatile two-way player that can score from 3-levels, impacts the scoreboard playing on or off the ball, and can space the floor from beyond the arc. Sherwood had a strong showing at this year’s event with his personal best of 28 points, connecting on a pair of threes, coming in a win over Clovis North, as well as an average of 16 points per game to help Chaminade go undefeated and win its bracket over Whitney of Rocklin. Sherwood has solid handles, keeps the dribble alive to find openings to attack the defense, has the moves and length to get by his initial defender, using the crossover, hesitation, fade-away, wrap-behind, and toss-cross to get to his shot spot, gets good lift with body control and accuracy on the mid-range jumper off the bounce, has various moves to score in tight windows around the basket, using the spin-move, euro-step, and up-and-under lay-ups to score among height in the paint, moves well off the ball to get to the open spot, and is accurate with the 3-ball off the catch to space the floor. Sherwood crashes the boards on both ends, looks to push the pace of play up the court, has touch on the put-back off the miss, and draws fouls routinely with his ability to play through and absorb contact attacking the basket to put up points from the line.

Sherwood put together a strong freshman campaign in which he finished second on his team in scoring with 12.7 points per game and added 4.1 rebounds and 1.4 steals per game while helping the Eagles to a 21-7 overall record. The 6-foot-4 wing used his combination of physical and athletic tools to impact the game as a slasher and interior finisher through contact but also flashed signs of becoming a reliable perimeter shooter as he shot 33 percent from deep on 79 attempts.