Origin: Mario Andretti's first Indy 500 win
Teams/people involved: The Andretti racing family
Year started: 1969
Racing-wise, 1969 was a good year for Mario Andretti, as the young racing legend managed to snag his first Indianapolis 500 title. However, it would end up being the only Indy win of his career. And not just for himself, but for his entire racing lineage. While the subsequent Andrettis (Michael, Jeff, Marco) all managed to have respectable racing careers, none were able to repeat the feat of their original racing ancestor. For whatever reason, bad luck often derailed any of Mario's efforts to win the title again, while his son Michael Andretti is essentially the Karl Malone of the Indianapolis 500, having completed and led the most laps out of any driver who never won the race.
The most heart-breaking of these losses had to occur in 2006, when Michael and his son Marco were both leading in the final laps of the race, only to be overtaken by Sam Hornish Jr., leaving the son-father duo to finish in second and third place, respectively. It was the only time in the history of the race that the winner has taken the lead in the final lap. Does it get much more heartbreaking than that?