
Clinton native Keith Chesley was recently hired as an assistant coach for the Mount St. Mary’s men’s basketball team, a Division I program in Emmitsburg, Maryland. Chesley most recently worked at Virginia Military Institute. Photo courtesy of Army West Point Athletics and Virginia Military Institute Athletics
Keith Chesley has a full summer ahead.
“I was in Connecticut recruiting two weekends ago, I’ve already been in (Philadelphia) and New Jersey recruiting this summer,” Chesley said. “I’ve spent a lot of time in my career recruiting in Florida and Georgia, so I spent a weekend recruiting in Florida as well. This coming Wednesday, I’m heading down to Atlanta to recruit down there. I’ll be back in Philly (after Atlanta), I think we have two more recruiting periods after that. I’ll be moving all over the place.”
It’s just the typical week in the life of a Division I assistant basketball coach, one that Chesley — a Clinton native and former standout at Lawrence High School and the University of Maine at Augusta — knows well. This season will mark Chesley’s ninth in the D-I ranks, but it’ll be his first with his new program, Mount St. Mary’s University in Emmitsburg, Maryland, a member of the Metro Atlantic Athletic Conference. Chesley was hired by the school in May, and will work under first-year head coach Donny Lind.
“I’m really excited,” Chesley said. “It’s a great place, full of great people. I’m working with people that I love and care about. Every step in my career has been a blessing and this is no different. I’m really excited to get to work. (The team) has already been here for three weeks now (for summer workouts). It’s been a ton of fun.”
Chesley spent the past two seasons as an assistant coach and defensive coordinator at Virginia Military Institute. The Keydets had a 4-28 record last season, but were 37th in the nation in defensive rebounds, averaging 27 per game. Chesley will have the same role at Mount St. Mary’s.

Keith Chesley Photo provided by Virginia Military Institute
“I’ve learned a lot,” Chesley said. “I’ve been to so many places and seen and taught and been involved in a ton of schemes and a lot of different styles of defense. I’ve done full-court press, I’ve done traps, I’ve done zones. I’ve been with teams that try to keep it to one side of the floor, trying to push the middle, trying to push the baseline. I think the biggest thing I’ve learned is that you have to be willing to be flexible, to be willing to do what fits your team and your personnel. That’s the most important part of it. If your guys aren’t bought into it and don’t believe in it and it’s not something they’re good at, and it doesn’t play to their strengths, they are going to struggle with it no matter what.”
Chesley started his coaching career as a graduate assistant at Florida State in 2016. His previous stops also include Stetson University, Georgia Southern, James Madison and Army West Point.
Chesley was hired at VMI in 2022 and got to know and coach against Lind, who was an assistant at UNC-Greensboro, a fellow conference opponent. Chesley and Lind met each other through a mutual friend four years ago.
“Right away, I was impressed by (Chesley’s) professionalism and attention to detail,” said Lind, who served as an assistant coach at Mount St. Mary’s from 2013-2016 and was a video coordinator at Virginia Commonwealth University from 2010-2013 under then-head coach Shaka Smart, now at Marquette University. “The No. 1 reason I hired Keith is because he fit the profile of someone I was looking for. Someone who recruited really good players to really hard jobs. Having worked at Army and VMI, I knew he had really difficult jobs and was able to evaluate really good players and get them there and help them to successful careers. The work ethic that it takes to do that, and the relationship-building that it takes to do that, those are the things that really stood out to me and made it easy to get on him pretty quick.”
Mount St. Mary’s has a strong basketball history, reaching the Division II national tournament 14 times from 1957-1987, winning a Division II national title in 1962 under head coach Jim Phelan, who had an 830-524 record during his 49 years (1953-2003) leading the Mountaineers. Phelan is in the National Collegiate Basketball Hall of Fame. In its time as a D-I program, the Mountaineers have reached the NCAA Tournament six times, the latest in 2021.
Last season, the Mountaineers went 13-19 (9-11 MAAC). Mount St. Mary’s lost leading scorer Dakota Leffew (17.6 ppg) to graduation and MAAC rookie of the year De’Shayne Montgomery (13.2 ppg), who transferred to Georgia.
“I’m excited about the group, I think we have a chance to be really good,” Chesley said. “We have a couple older guys that have been veteran leaders that have been around a little bit. We have a good mix of those guys with the young guys. Hopefully, as we build the culture to where we want it to be, we can bring those guys along, continue to learn and grow.”
“I’m a high-energy, relentless person and I want a team that embodies that,” added Lind. “I firmly believe that you can choose to have fun in pretty much any situation and see the bright side in whatever (situation) you’re in. I want to have a team that enjoys being with each other every day, that enjoys the hot days in the summer (at practice) and finds the purpose or finds the joy in going to study hall, going to the weight room.”
The Mount St. Mary’s position is the continuation of a dream for Chesley, who scored 2,119 points during his career at UMA, which ended in 2015. Chesley credits his wife, Jamie, a former Richmond High School and UMA standout, for supporting his career. The couple were inducted into the UMA Hall of Fame in 2022.
“You have to love it, or it’s not going to work out for you,” Chesley said. “You have to be driven. It’s a very, very challenging profession. I spend a lot of time away from my family and my wife. She’s a rock star. She crushes it, and I wouldn’t be able to do it without her. I’m very lucky, but it (can be) difficult. But I do love it. I’m trying to make a difference every day in someone’s life and that’s the mindset I take every day and I’m going to try to do it for as long as I can.”
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