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Dan Engelstad hopped in his beat-up red Volvo and drove 45 minutes from Bethesda, Maryland, to Prince George’s County in 2007. As a 22-year-old recent Saint Mary’s College of Maryland graduate, Engelstad was desperate to break into the coaching industry. So, he got creative.
He got word that then-Mount Saint Mary’s head coach Milan Brown would be recruiting at Dr. Henry A. Wise Jr. High School. Brown had an opening on his staff, which Engelstad expressed interest in. That wasn’t enough for him, so Engelstad showed up unannounced and immediately struck up a conversation with Brown.
The two discussed Engelstad’s possible role under Brown. He made it clear the pay wouldn’t be much — $5,000 to be exact, barely enough to be considered a part-time gig. It didn’t matter to Engelstad. Two weeks later, he was offered the job.
“He treated it like he was a kid in a candy store,” Brown said. “He didn’t care. I probably could have paid him nothing. He would’ve still done it. He was just hungry to coach.”
Engelstad’s actions initiated a snowball effect, which brought him to Syracuse 17 years later as an assistant coach. The 40-year-old built his coaching career from the ground up, totaling eight seasons as an assistant between Mount Saint Mary’s and Holy Cross. Then came a stint as Division III Southern Vermont’s head coach from 2013-18 before returning to the Mount as its head coach for six seasons.
To begin his career, Engelstad needed to work tirelessly with how little Brown offered him. He fit the bill.
Engelstad stuffed envelopes, emailed donors and developed detailed scouting reports — sometimes staying up until 6 a.m. The couch in his office acted as a second bed.
“There was always something to do, always something to be done,” Engelstad said. “I was fortunate to learn from some really good people and how the Division I basketball operation went.”
Still in playing shape from college, Brown used Engelstad as a scout team point guard. According to former MSM assistant Kevin Robinson Jr., Engelstad often challenged players by trash-talking them.
As a result, Players gravitated toward him. Whether it was getting a slice of pizza at the local restaurant, Rocky’s, talking to players in his office or conducting one-on-one workouts, Engelstad made himself available.
“That’s one of Dan’s greatest traits. As soon as you get to know Dan, you’re in his family, he’s gonna treat you as such … he just was relentless in the building of relationships,” Robinson said.
The work didn’t go unnoticed. After helping the Mountaineers to a Northeastern Conference title and NCAA Tournament appearance in 2008, he received two pay raises — joking they were “above minimum wage.” Engelstad impressed Brown enough that he asked him to join his staff when he became Holy Cross’ head coach in 2010.
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There, Engelstad gained more responsibility. His bread and butter came on the recruiting trail. In the offseason, he was on the road every day.
His strong ties to the DMV, where he grew up and went to college, helped him find diamonds in the rough. The biggest was Malcolm Miller, a forward from Gaithersburg, Maryland. Miller didn’t play for any major AAU team but captured the Patriot League Player of the Year in 2015. He later became an NBA Champion with the Toronto Raptors in 2019.
RJ Evans, who Engelstad built a close relationship with in Worcester, was another success story. Holy Cross cycled through two coaches in Evans’ first two seasons, so he leaned on Engelstad.
When the two worked out, Engelstad didn’t simply toss the ball to a stationary Evans in the corner. Instead, he simulated game action by dribbling up the court, initiating an offensive set. Engelstad wildly chased Evans’ rebounds, making him sweat more than Evans. After the workouts, they chatted about basketball and life in general.
“When (Dan’s) talking to you, he’s authentic,” Evans said. “At some point, sometimes the players are trying to figure out if this coach has an angle. Is he trying to do that? You never feel that way with coach Dan.”
Evans initially had no interest in coaching and worked in advertising following a short stint overseas. So, he reached out to Engelstad in 2015 to help him get a start in coaching.
Engelstad had connections to Texas head coach Shaka Smart, who he met through former Mount Saint Mary’s coach Jamion Christian. This helped Evans land a graduate assistant gig in Austin. Less than a decade later, Evans became the head coach at Northern Kentucky.
Engelstad always felt the need to go out of his way to help others. An enhanced way to do that was to become a head coach. After spending six years with Brown, Engelstad got the itch to lead his own program. He found an opening in 2010 at Southern Vermont, a 400-person Division III liberal arts school in Bennington, Vermont.
Its basketball team was putrid, winning one game the year before. Turning SVC around was a monumental task, until Engelstad did it with ease.
His first call was to Antoine White, a junior college dropout who played at Walt Whitman High School a year after Engelstad. The two competed against each other in open gyms during the summer and maintained a strong relationship. Engelstad heard White wanted to coach in college. First, he needed to get his degree.
As a result, Engelstad reached out to White. During a 45-minute phone call, Engelstad convinced White to be his first recruit. He was 230 pounds and 24 years old. White was exactly the type of player Engelstad was looking for — one that needed a second chance.
“It was the right phone call at the right time for me,” White said. “I’m glad he made that call because that phone call changed my life.”
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White, now the women’s coach at Mount Saint Mary’s, was one of many players who needed another shot. Engelstad took players from the DMV who didn’t have the grades to make it at the D-I level or came from rough backgrounds. He wanted to guide them on the right track.
Players flocked to Engelstad. It didn’t matter that Burlington’s climate was cold and gloomy for most of the year. Nobody cared if the gym floor needed to be mopped every day to gain traction or how bad the gym’s acoustics were.
“They were locked in,” Sharief Hashim, who joined Engelstad’s coaching staff during his second season, said. “Everything aligned where we were able to just do some positive things and it was because Dan had the right coach style.”
Engelstad used his talent accordingly, initiating a Smart-esque VCU press. They trapped everywhere, unleashing relentless pressure for 40 minutes straight. Engelstad’s teams were 11 players deep, keeping everyone fresh.
It translated to instant success. In Engelstad’s first game, Southern Vermont took down national powerhouse Williams College, led by future NBA forward Duncan Robinson.
SVC won 16 games that year after just three in the previous two seasons. It then accumulated 49 wins from 2014-16, going 32-0 in the New England Collegiate Conference and clinching a spot in the 2015 D-III NCAA Tournament.
Engelstad’s 104-34 record, four straight NECC regular-season titles and two conference tournament victories (2015, 2018) changed the standard at Southern Vermont.
“We won some championships. We had some tough heartbreak losses. But everyone that was part of that (team) still stay in close contact and talk about the relationships,” Engelstad said of SVC.
His success garnered attention from a familiar face.
Christian took the Siena head coaching job in 2018, which left a vacancy at Mount Saint Mary’s. Due to Engelstad’s previous time there, he was targeted for the opening. Though it was tough to leave Southern Vermont, Engelstad knew D-I jobs didn’t magically appear.
“The Mount was probably the one job that I could have gotten at that point, from the Division III level,” Engelstad said. “I’d been there and cultivated a lot of really great relationships within that department.”
Engelstad carried the same principles back to The Mount. He recruited the DMV well, prioritizing lengthy wings who could defend hard. He didn’t garner the same success as SVC, posting a 72-109 record in six seasons.
Syracuse assistant coach Dan Engelstad had numerous stops in his 17-year coaching career, ranging from Mount Saint Mary’s, Holy Cross and Southern Vermont. Aaron Hammer | Staff Photographer
His biggest success came in 2021, helping MSM to the NCAA Tournament. The Mountaineers defeated top-seeded Wagner in the Northeastern Conference semifinals before dispatching No. 2 seed Bryant in the finals. The Mountaineers later fell to Texas Southern in the First Four.
After one more season in the NEC, Engelstad helped Mount Saint Mary’s transition to the Metro Atlantic Athletic Conference. Then, two years later, a Power Five opportunity opened for the first time when former SU assistant Gerry McNamara left for Siena this offseason.
Syracuse head coach Adrian Autry and Engelstad’s relationship goes back 20 years. In Engelstad’s first stint at MSM, he recruited Raven Barber, who played at Paul VI High School (Virginia), where Autry spent time as an assistant.
Despite being an assistant coach, SU’s rich history was something Engelstad couldn’t pass up. Now, he looks out his window at the banners scaling the walls of the Carmelo K. Anthony Center. It serves as a constant reminder of where he wants Syracuse to be and how far he’s come.
Two decades ago, just the thought of having an office seemed unfathomable. When Engelstad started coaching, he barely made enough to get by. He did obscure things nobody else wanted to, allowing him to foster strong relationships.
It all culminated in an unorthodox climb to the top, which Engelstad only has himself to thank.
“One of the smartest things I ever did was hop in that car and go sit down and talk with Milan,” Engelstad said. “It’s amazing where the coaching journey has taken me.”
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