2010-11:Wiley Sherman skated in 23 games for the Hotchkiss School in Connecticut as a freshman. In what was a difficult season for the Bearcats (6-19), he had 4 assists. Sherman participated in USA Hockey's Select 16 Development Camp in June and was selected by Omaha in the fourth round (56th overall) of the 2011 USHL Futures Draft.
2011-12: Sherman committed to playing college hockey at Harvard in 2014-15 before returning to Hotchkiss for his sophomore season. He scored 2 goals with 5 assists in 24 games. Hotchkiss again missed the New England Prep School tournament, but finished the year on a positive note – winning three of its last five games and tying eventual NEPSIHA semifinalist Kent, 5-5. Sherman was selected by Saint John in the 13th round (236th overall) of the QMJHL Entry Draft.
2012-13: Sherman returned to Hotchkiss for his junior season and played for the Fairfield Blues midget AAA team. He scored 4 goals with 6 assists in 26 games for Hotchkiss and had 1 assist with 4 penalty minutes in four games with the Blues. Sherman was ranked 125th amongst North American skaters in Central Scouting's final rankings and was selected by Boston in the fifth round (150th overall) of the 2013 NHL Draft.
Sherman is a huge big-bodied defenseman that has a natural presence in the defensive zone.
"My size gives me an advantage," Sherman said of himself. "I have a little bit more time to react because I have such a long stick. I have a little bit [of a mean streak], but right now I am just trying to make right play. Hopefully as I start to get more comfortable that the physicality will come."
Sherman will play one more season of Prep School puck before joining Ted Donato and the Harvard Crimson in 2014-15.