No. 8: 49ers trade away their GOAT quarterback, Joe Montana
From a logical perspective, it made sense for San Francisco to trade Hall of Fame quarterback Joe Montana to the Kansas City Chiefs in 1993. The 49ers already had his heir apparent in place, Steve Young, and it’s only the nature of the business to get both younger and cheaper. It’s called roster turnover.
Perhaps that’s why Montana being dealt to Kansas City shouldn’t rank any higher on this list. It wasn’t a bad deal in itself. The Niners acquired safety David Whitmore and a first-round NFL Draft pick in return, and that pick would later be used as part of a package to land an eventual San Francisco stalwart, defensive tackle Dana Stubblefield.
If anything, though, the Montana trade was made infamous because it signaled the end of the franchise’s dynasty years of the 1980s and early 1990s.
Although transitioning to Young worked out pretty well.
Yet the 49ers surely thought Montana was nearing the end when they executed the deal, and Montana’s rift with Young at the time wasn’t exactly pretty. At least for Montana, he had two successful years in Kansas City to round out his Hall of Fame career.
But it doesn’t mean this trade was easy to swallow for the fanbase, neither then nor now.