After five successful seasons as an associate head coach with the Northern Illinois men's basketball program, Drew Gladstone is making a highly anticipated return to the prep ranks. He has been named the new head coach of the Greenwich Country Day School (CT) boys basketball team, taking the helm for the 2026-27 season.

This move marks a homecoming of sorts for Gladstone, who is no stranger to the competitive New England Preparatory School Athletic Council (NEPSAC) landscape. He previously led the program at St. Luke's School in New Canaan, CT, where he built a powerhouse. During his tenure, Gladstone posted an impressive 64-12 overall record, capturing two Fairchester League Championships and two New England Championships. His outstanding work earned him the New England Class C Coach of the Year award twice.

Following his success at St. Luke's, Gladstone spent four seasons with the Indiana University men's basketball program as a Team and Recruitment Analyst before heading to Northern Illinois. Now, he faces an exciting new challenge: building a program at Greenwich Country Day, which joined the NEPSAC just a few years ago and is still in its early stages of competition.

The Tigers may be a young program, but they boast a rich basketball pedigree. The school is the alma mater of Cleveland Cavaliers star shooting guard Donovan Mitchell, who donated $12 million to fund the Donovan Mitchell Family Athletic Center, which opened just a couple of years ago. With that kind of foundation and a proven winner like Gladstone at the helm, the future looks bright for Greenwich Country Day basketball.