He quit coaching. He drove Uber to make ends meet. Now he’s taking over college basketball’s reigning Cinderella at FDU

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.