Set in the hardscrabble section of Chicago, this song tells the story of Leroy Brown, the "baddest man in the whole damn town." He's big and dangerous, loved by the ladies and feared by the men. But one day he picks a battle he can't win, making a move on the wife of a guy who leaves him looking like a jigsaw puzzle with a some missing pieces.
The story is based on truth, but embellished. Jim's wife, Ingrid Croce, told Songfacts the story
Jim Croce joined the US National Guard in 1966, hoping it would keep him from getting sent to Vietnam. He married Ingrid that year, and hoped to continue his education and launch his music career. Unfortunately, Jim was sent for training less then two weeks after their wedding. As Ingrid explained, Jim had no interest in being a soldier and had the distinction of having to repeat basic training. But he did meet a guy who inspired one of his most famous songs. "Leroy Brown is a guy that he actually met," said Ingrid. "When he was in the service - The National Guard - this guy had gone AWOL. He was a guy that Jim kind of related to, he liked to sing with him. This guy had gone AWOL but he came back to get his paycheck, and he got caught. Jim just thought he was such a funny guy that he thought he'd include his name in the song, and it just worked. There really was a Leroy Brown, and sometimes having a name helps you to build a song around it."