FORT MEADE, Fla. — Ninety minutes southwest of Orlando, among the two-lane country roads of central Florida, sits a small town where everybody knows everybody and football is king.



It’s a comfortable 65-degree day in late January when Phillies outfielder Andrew McCutchen, Fort Meade’s most famous native, pulls up behind an elementary school where a community festival is under way in an open field. McCutchen, dressed in all black except for his bright yellow sneakers, steps out of the car and is welcomed by his mother, Petrina, who wastes no time pulling him in for a hug. Minutes later, his dad, Lorenzo, stops by to say hello after speaking to a group of kids attending the event, which McCutchen’s parents established to raise awareness for Fort Meade, a city with a poverty rate of more than 17 percent, according to the U.S. Census Bureau. At one point, two young brothers dressed in black suits, backed by a band, take the stage and croon to the Jackson...