5 most disappointing trades in 49ers franchise history

Charles Haley #94 of the San Francisco 49ers Mandatory Credit: Tom Hauck /Allsport
Charles Haley #94 of the San Francisco 49ers Mandatory Credit: Tom Hauck /Allsport /
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DeForest Buckner, Indianapolis Colts
Indianapolis Colts defensive tackle DeForest Buckner (99) waves at fans after defeating the San Francisco 49ers Mandatory Credit: Stan Szeto-USA TODAY Sports /

While the 49ers have certainly won their fair share of trades over the years, there have been some blunders and utter disappointments.

Fortune can favor the bold when it comes to executing some sort of blockbuster trade. And even for a rebuilding team looking to head into a new direction, trading off star players can help spark a franchise’s turnaround.

The San Francisco 49ers are no strangers to blockbuster trades over the years. Decades ago, they sent off their best quarterback in franchise history, Joe Montana, to the Kansas City Chiefs to make room for another up-and-coming Hall of Famer, Steve Young. While it was a shocker of a move at the time, it proved to be the right call.

In more recent years, the Niners took advantage by trading for quarterback Jimmy Garoppolo, who at least helped take the franchise to a Super Bowl two seasons after being acquired.

Yes, there are some great trades in San Francisco history. And there were some massive busts as far as trades go, too.

For this exercise, however, let’s focus on the five trades that were utterly the most disappointing,

Starting off with one 49er fans won’t soon forget.

No. 5: 49ers ship off Pro Bowler DeForest Buckner to Colts

It might be one of those “where were you?” moments, when reports started flowing in the Niners were shipping off their 2016 first-round NFL Draft pick, Pro Bowl defensive tackle DeForest Buckner, to the Indianapolis Colts in exchange for a 2020 first-round pick that was eventually used to land his replacement, defensive tackle Javon Kinlaw.

San Francisco had just extended Buckner’s linemate, Arik Armstead, yet couldn’t find a way to extend Buckner, easily the better player and more-respected locker-room leader.

In the wake of the blockbuster, Kinlaw has yet to come anywhere close to filling Buckner’s shoes, both in terms of his on-field play and presence within the locker room. And while the 49ers defensive line has remained a strength, Buckner’s absence continues to be felt to this day.

Things didn’t get easier either when Buckner told Bay Area reporters the Niners wouldn’t even meet him in the middle of contract negotiations, further souring the deal that sent him to Indy.

San Francisco’s general manager, John Lynch, repeatedly admitted it was one of the toughest decisions he’s had to make in his position.

And the tough nature of that call is still being felt by 49ers fans everywhere.