Jack Castleberry is where he always wanted to be. He just isn’t sure how he got here.
“Nobody should take this path,” the new head coach at Fairleigh Dickinson. “My path doesn’t make sense. It’s been chaos.”
Today, Castleberry, 39, leads a program for the first time, a Cinderella that is months removed from pulling one of the biggest upsets in NCAA Tournament history.
A decade ago, the coach gave up the game.
After seven seasons as an assistant coach, Castleberry’s frustrations with the business led him to a two-year detour as a financial planner. Getting his foot back in the door required him to accept an entry-level coaching position while moonlighting as an Uber driver.
In 2022, Castleberry worked at three different schools. After his staff at The Citadel was not retained, he became an assistant at Queens University in Charlotte. The following spring, he was promoted to succeed Iona-bound Tobin Anderson as head coach of the tournament darling from northern New Jersey.
“It’s never the way you think you’re gonna get here,” Castleberry said. “There’s probably thousands of guys that have been just as deserving or more deserving to have the opportunity, but so much of this business is just right place, right time. There’s guys that are probably better at this that didn’t get their shot. I’m just one of the guys that was lucky enough to get the opportunity.
“Now let’s see if you can actually coach.”
He saw behind the curtain and he glimpsed his future.
Growing up in Virginia, Castleberry’s father, John, was a local TV sports anchor who also served as the play-by-play announcer for Old Dominion basketball (and the Mets’ Triple-A affiliate in Norfolk).
Castleberry felt like a member of Jeff Capel’s teams. He wore a Monarchs jumpsuit to school. He went to practices. He went on road trips to Alaska and Puerto Rico and Wyoming. He sat on press row, keeping game stats for his dad.
“I mean, how could you not love it?” Castleberry said. “I’m thinking, ‘How do you get to do this for a long time?’”
He was a preferred walk-on at VMI, and earned a scholarship and a starting spot as an upperclassman. A 6-foot-3 guard, Castleberry averaged 1.5 points for the highest-scoring team in the nation, contributing with toughness and selflessness as team captain and the winner of the “Spirit of VMI” award for his leadership and hustle.
After one season as an assistant coach at UT-Martin (2007-08), Castleberry returned to VMI as an assistant under Duggar Baucom. He spent four years there, but he was unable to ascend to the senior staff, prompting him to join Siena’s women’s team for two seasons.
“There’s guys that are probably better at this that didn’t get their shot. I’m just one of the guys that was lucky enough to get the opportunity. Now let’s see if you can actually coach.”
First-year FDU men’s basketball coach Jack Castleberry
The career couldn’t match the dream. So, Castleberry took up a friend’s offer for a more stable and lucrative position as a financial planner in Philadelphia.
“I’m 30 years old, I haven’t had the career path I thought I was gonna have, I want to get married, have a family,” Castleberry recalled thinking. “‘Is [coaching] what’s in my best interest, or am I chasing a pipe dream?’”
Leaving the game allowed him to fall in love with it again.
When Castleberry was done helping clients with their 401(k)s, he was hustling to volunteer as a coach at suburban Philly’s Cardinal O’Hara High School. He was spending Saturdays scouting AAU games. He asked Baucom to tell him about any openings on his staff at The Citadel.
The 32-year-old — who was months from his wedding date — was offered the position of director of basketball operations, which paid roughly $20,000 per year and would take them 670 miles from Philadelphia, where his then-fiancée, Kara, is from.
“Her reaction? It wasn’t great, and I don’t blame her. But she’s incredible and she jumped on board,” said Castleberry, now the father of two young girls. “I’m like, ‘Hey, I’m not gonna forgive myself if I don’t give this one more shot.’
“I got out of coaching because I lost track of why I coached. I started to let it be about the money or the level or, to some degree, my ego. Maybe I fell out of love with the dream or wasn’t willing to do what I thought I needed to do. Getting out of coaching helped me realize why I coach to begin with. When I came back, taking the [Citadel] job for 20 grand, I couldn’t have been more thrilled. I had another shot. It’ll never be lost on me how lucky I am to be here.”
While working at The Citadel, Castleberry took a second job, driving his Ford Fusion for Uber.
“It was mostly just a bunch of drunk people in the back of your car,” Castleberry said. “I would do it a lot at night because Charleston’s a big going-out city. I’d drive Uber until 1, 2 a.m., try to get the surges and go home. After a while, I was like, ‘I can’t keep doing this. It’s too chaotic.’”
Castleberry would become associate head coach, and the program achieved its first winning campaign in 13 years. Then Duggar was fired in 2022. Castleberry joined Queens University, but left six weeks later when Tobin Anderson asked his old friend (from their shared time at Siena) to help him rebuild a Fairleigh Dickinson program that went 4-22 the previous season.
“He’s the only guy I called,” Anderson said. “He’s a basketball junkie. He’s got great passion. And he’s genuinely a good person. He coaches for the right reasons. He cares about the guys and that goes a long way.”
Castleberry received ribbing for the “5,000 calories he eats within 20 minutes of games.” His well-organized desk was a sitting duck for pranks. And his presence helped the Knights win 21 games, matching the biggest single-season turnaround in Division I history.
They reached the NCAA Tournament (Merrimack won the Northeast Conference, but was ineligible for the Big Dance) and demolished Texas Southern in the First Four. Then, the smallest team in the nation took down 7-foot-4 National Player of the Year Zach Edey and top-seeded Purdue.
Two days after nearly upsetting eventual Final Four participant Florida Atlantic, Anderson took Rick Pitino’s place at Iona.
And FDU immediately named its replacement.
“I’m certainly not trying to change a whole lot,” Castleberry said. “If it ain’t broke, don’t fix it. If I try to change a bunch of things and it didn’t work out, I’d look like the biggest idiot in college basketball. Tobin laid such a good blueprint for what we’re trying to accomplish here.
“We accomplished this great thing in the NCAA Tournament, but we didn’t win our conference championship. Everyone who was eligible to come back decided to come back. It’s been pretty easy to get them motivated in the offseason.”
The school is all-in.
The Knights signed their first local TV deal with YES Network to broadcast multiple games. The program has been rebranded as FDU — think, TCU instead of Texas Christian — and a new logo sits at the center of the Rothman Center’s redesigned court.
The basketball team has a newly renovated locker room with a film room/players lounge replacing a communal shower where the team watched tape on a projector — that sat atop a Gatorade cooler and a shoe box — to prepare for March Madness.
“Our big challenge is the school has really put a lot into our program now, but we can’t lose the grittiness and toughness of the team watching film with the showerheads,” Castleberry said. “One of the pictures we’re putting in that lounge area, right in the middle, is the shower setup we had last year. Yeah, this is nice, but don’t ever forget where you came from.”
The Knights’ top two scorers were graduate students (Demetre Roberts, Grant Singleton), but the rest of the core returned. All of Anderson’s assistants followed him to Iona — except one.
“He’s putting his own twist on it,” sophomore Jo’el Emanuel said. “He does a great job balancing being the leader, making sure people respect you, but he also values the relationship with each of his players.”
On Monday, Castleberry’s players screamed with joy and dumped a water cooler over his head in celebration of the Knights’ season-opening win at Buffalo.
About 20 minutes earlier, Anderson lost his first game with Iona, when a game-winning 3-pointer rimmed out at the buzzer. In the visitors’ locker room at Charleston, the former FDU coaches took out their phones and voiced the same thought:
“How’s Jack doing?”