Jim Druckenmiller
NFL teams rarely experience two back-to-back Hall of Fame quarterbacks. The Niners achieved this with Joe Montana and Steve Young. Meanwhile, the Packers are replicating this feat with Brett Favre and Aaron Rodgers. But imagine being a mediocre player who ends this incredible run of good luck (via Washington Post).

Sadly, Druckenmiller found himself in this position in 1997. San Francisco said they’d groom him as Young’s successor and this raised expectations through the roof. But he failed to impress and repeatedly threw the ball to opposing teams. This crushed the Niners fanbase as the franchise fell into a miserable malaise.