The Loser won a contest

New Jersey, 1959. The Complete and Total Loser is a baby, about a year old. The disease that will warp his right leg won't manifest itself for another three years, and the Loser is an ordinary white baby with a cheerful, positive disposition, trusting of strangers, smiling, seldom crying.
It's summer and that's why the Loser is at the shore; he's not a native New Jerseyite. His parents -- his mother -- have entered the Loser is the annual baby parade at this little slice of beach they bake on each year, far from Philadelphia's industrial filth (things were still made in the city at the time). 
The Loser is dressed as a miniature lifeguard. Hat, tiny sunglasses, a singlet. White stuff on nose, whistle around neck. A highchair functions as a lifeguard stand.
He wins, more because of the costume than any innate ability or charm he shows during the competition, though remaining phlegmatic throughout probably nets him many points from the judges.
No one knows it yet, especially the Loser, for whom the event has been merely a place he's been, one that for all he knows he will be at daily for the rest of his life, but this is the only contest he will ever win, except for the three-legged race he'll triumph in eleven years later, but he had help in that from his best friend, Rip. 
Being a baby is the best for obvious reasons. Free room, board, healthcare. No obligations. Everyone smiles at you. You're urged to sleep whenever possible. You can relieve yourself effortlessly without consequence. Every day brings only more powers and awareness. All signs point up, and you and the nice people around you will never die.