When Tommy Messinger first saw him, he knew he had to have him. The 6-foot-4-inch wing playing for SOH Elite at an Under Armour event in Atlanta made an immediate impression on the then-Hargrave Military Academy Head Coach
“He banged a 3, dunked on somebody, then blocked three consecutive shots, and I was like ‘Who the heck is this kid,’” Messinger said. “It wasn’t in the book.”
After the game, he did some digging, and he learned that the player was De’Shayne Montgomery.
A little over a year later, the unheralded Floridian is now starring as a true freshman for Dan Engelstad at Mount St. Mary’s. In an 80-48 win over Siena, Montgomery scored 27 points, the most by a Mountaineers freshman since Shivaughn Wiggins scored 28 against FDU on March 2, 2013.
“He had a pop to his game,” Engelstad, who was also at that event in Atlanta, said, “We don’t have anybody that can do some of the things he can do. You saw him play with spirit, and he had this way of competing.”
Montgomery’s talent rarely goes unnoticed, but playing AAU ball off the circuit and high school ball for a school that didn’t do a good job of recording games did not do him any favors. In fact, that tournament in Atlanta was Montgomery’s first with SOH Elite, and it came after his high school graduation.
His high school career with Somerset Prep in Fort Lauderdale was very successful, as he scored 19 points per game in his senior year to go along with six rebounds, five assists, three steals, and two blocks, but there wasn’t much interest. That all changed when he first suited up for SOH Elite in July of 2022.
Montgomery, who grew up playing soccer thanks to the German influence of his mother, didn’t take to basketball until ninth grade. He credits a neighbor as the one who introduced him to the game.
“I met this one kid who moved on my street and I started playing basketball with him outside, and ever since then, I fell in love with basketball,” he said.
After attending a summer camp run by Ralph Mata, the head of the SOH Elite program, Montgomery went back to his stomping grounds to hone his craft. By his junior year of high school, he was back on Mata’s radar thanks to a mutual friend.
In his senior year — still with no offers — Montgomery’s Somerset Prep team defeated Mata’s Miami Country Day in the regional tournament, prompting an invite to join the SOH Elite program in the summer. From there, the offers started rolling in as coaches took notice.
“His first week playing with us, he had three offers,” Mata said. “He was just never in front of the right people.”
Among the “right people” was Engelstad, who was floored by Montgomery’s talent.
“He’s got a natural feel, but he does some things that you just can’t coach.” he said. “His ability to get into passing lanes, make plays in transition, and finish at the rim is unique.”
“We tried hard to get him to the Mount [for the 22-23 season],” Engelstad added, but the Montgomery family believed that a post-graduate year would best serve De’Shayne.
“My dad told me how I need to develop my game some more since I started so late,” Montgomery said. “I don’t have to ‘waste’ a year of college eligibility.”
Even with the heavy courtship of Messinger, Montgomery had his reservations about starting at Hargrave.
“I didn’t know anything about the school at all,” he said. “At first, I didn’t want to go because it was a military school.”
“There’s a lot of uncertainty when you first get to Hargrave,” Messenger said. “About finding your way personally, navigating the military structure, and being around more talented players”
However, the same pitch that has been used for years by Hargrave coaches such as Kevin Keatts and A.W. Hamilton, that the school allows for players to develop with limited distraction, ended up bringing Montgomery to campus.
Montgomery believes that taking a post-grad year helped him develop in a way that a year in college wouldn’t, and will benefit him in the long run as he pursues his dream of playing basketball professionally. Thanks to individual workout sessions with Hargrave assistant Kasey Bryant, Montgomery improved his ball handling and shooting.
Bryant ran Montgomery through drills such as dribbling through cones, catch and shoots, shooting off screens and handoffs, and much more.
“At Hargrave, they focus on you individually,” Montgomery said, “It helps you get better at what you need to do so you can take that extra step before college.”
“[Montgomery and I] would always go in and work out,” Montgomery’s Hargrave teammate Kailon Nicholls, now at Duquesne, said. “The coaches were always willing to sacrifice their time to work on whatever we needed to work on.”
Nicholls was Montgomery’s workout partner, and throughout the year, he observed plenty of growth in his game thanks to his ability to soak in information.
“He’s not the type to kind of brush off what you tell him,” Nicholls said. “He was always willing to learn.”
Montgomery continued to make positive impressions on his coaches. Engelstad stayed in contact with him, but at this point, he was far from the only coach interested.
“He had a lot of high-major interest early on,” Messinger said. “And a lot of [smaller] schools that came to watch us play didn’t want to waste their time on him when they heard who was interested.”
However, the high-major interest began to fizzle out as the year went on. With many programs using the transfer portal instead of the prep ranks, Montgomery was never officially offered by any of the high-major programs.
This was excellent news for Engelstad, who had become even more enamored with bringing Montgomery to the program after seeing him succeed at Hargrave.
“If you go to Hargrave, you love basketball,” Engelstad said, “It’s in the middle of nowhere, it’s the limit of distraction, and it’s a factory. Guys get better and they’re pushed to get mentally stronger.”
While Mount St. Mary’s was never out of the picture, it became an increasingly larger part of the picture when the high-major interest went away.
“I worked hard to get him on an official visit,” Engelstad said. “We have something really great to offer at Mount St. Mary’s, and we want to roll our sleeves up and fight against anybody.”
Montgomery didn’t commit on his official visit to the Mount, but Engelstad still felt confident, and he was rewarded soon after. From the airport of another official visit, Montgomery called Engelstad and told him the good news.
“I thought there was no other coach that wanted to coach De’Shayne as much as I did,” Engelstad said of his pursuit.
So far, it has paid massive dividends.
Through his first 12 college games, Montgomery is averaging 13.5 points and 3.7 rebounds per game, and that’s not even close to the most impressive part. Thanks to his soccer instincts and 6-foot-10 wingspan, he’s the only freshman in Division I basketball with a block rate of 4% or higher, and a steal rate of 5% or higher.
Hargrave has a rich tradition, sending many coaches, including Kevin Keatts and A.W. Hamilton, to the next level. Even Messinger has used his success at Hargrave to get a college coaching job, working on Grant Billmeier’s staff at NJIT. The program has sent 26 players to the NBA, and Montgomery is hoping to be the 27th.
His current coach absolutely thinks he can get there.
“He has a future in the highest level of basketball,” he said.