About 15 years ago, Charles Oakley and Michael Jordan went, with a handful of friends, to Churchill Downs in Louisville to see the Kentucky Derby. Jordan dressed like a gangster in a beige-and-white candy-striped suit, white shirt, gold tie, white shoes with thick soles. He carried a cigar, sometimes in his mouth, sometimes between the fingers of his right hand. He was talking preliminaries and odds when his crew happened on another crew, this one centered by John Salley and Dr. J and including the actor Chris Tucker and the comedian Dave Chappelle.

The groups met and mingled, admired, confronted. Salley wore a linen suit with a white shirt and a modest tie. He had one cigar in his hand and another tucked, with his sunglasses, in his breast pocket. He towered over everyone, in a Panama hat with a rust-colored band. Chris Tucker wore electric blue—suit, tie, shirt, belt. The toes of his shoes were pointy. Dr. J wore a fedora and a bolo tie. You’d have half expected them to break into song. The PA system announced the names of horses and trainers. Mint juleps went by in the crowd.