Sportsbooks infuriatingly usually refuse to allow parlaying two futures bets on one ticket. But In February 2014, at least one online bookmaker offered the novelty cross-sport prop, "Will both Peyton Manning and Tim Duncan retire as champions?" with decent odds of 20/1.
In Super Bowl 50, the Denver Broncos indeed sent Manning into the sunset as a champion. Unfortunately for bettors, Duncan's San Antonio Spurs went out in the first round of the NBA playoffs three months after the Broncos win.