Drew Gladstone takes boys basketball head coaching job at Greenwich Country Day (CT)
After five years as apart of the Northern Illinois men’s basketball program, associate head coach Drew Gladstone will be stepping back into the high school space for the 2026-27 season.
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The basketball program announced last week that Gladstone has been named the Tigers’ head coach. Greenwich (CT) Greenwich Country Day joined the New England Preparatory School Athletic Council (NEPSAC) just a few years ago and only has played a handful of games since that point.
This isn’t Gladstone’s first rodeo coaching in the NEPSAC as the Tigers’ new head coach previously had led New Canaan (CT) St. Luke’s School boys basketball program. Per Gladstone’s NIU bio, he owned an overall record of 64-12 along with winning two Fairchester League Championships, two New England Championships and twice named New England Class C Coach of the Year.
After his time with St. Luke’s, Gladstone left to join the Indiana men’s basketball program as the team’s Team and Recruitment Analyst where he spent four seasons with the team before joining the Huskies.
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Now Gladstone will be tasked with putting together a program that plays in one of the most competitive prep school leagues in the country. The Tigers is the alma mater for Cleveland Cavaliers’ star shooting guard Donovan Mitchell, who pledged $12 million to the school, helping fund the Donovan Mitchell Family Athletic Center, which opened just a couple years ago.
Greenwich Country Day finished the 2025-26 season with a 0-1 record and was an unranked team, according to the final Connecticut High School Boys Basketball Massey Rankings.
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