Who: Quebec
Olympics: Montreal 1976

Montreal incurred a stunning amount of debt from hosting the 1976 Summer Games: $1.5 billion. Today, it is almost a foregone conclusion that the host city will actually lose money. What sets apart Montreal’s debt, however, is how long it took them to pay it off. Montreal had debt from hosting the games for an astonishing 30 years until they finally paid it off in 2006.