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Sports
Drew Gladstone takes boys basketball head coaching job at Greenwich Country Day (CT)
TL;DR
Drew Gladstone has been appointed as the head coach for the boys basketball team at Greenwich Country Day School in Connecticut, starting in the 2026-27 season. He previously served as the associate head coach for the Northern Illinois men's basketball program.
Key points
- Drew Gladstone appointed head coach at Greenwich Country Day School
- Gladstone previously associate head coach at Northern Illinois
- Coaching role begins in the 2026-27 season
- Greenwich Country Day is part of NEPSAC
- School has played few games since joining NEPSAC
Mentioned in this story
Drew GladstoneGreenwich Country Day School
New England Preparatory School Athletic Council
(© Jerome Miron-Imagn Images)
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.
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.
Q&A
Who is Drew Gladstone and what is his coaching background?
Drew Gladstone is the newly appointed head coach for the boys basketball team at Greenwich Country Day School, having previously been the associate head coach at Northern Illinois.
When will Drew Gladstone start coaching at Greenwich Country Day School?
Drew Gladstone will begin his role as head coach for the boys basketball team in the 2026-27 season.
What is the history of Greenwich Country Day's basketball program?
Greenwich Country Day School joined the New England Preparatory School Athletic Council (NEPSAC) a few years ago and has played only a handful of games since then.
