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.
No. 4: 49ers give up on Hall of Famer Y.A. Tittle
We have to go back into the archives a bit to break down the No. 4 most disappointing trade in Niners history. And in some ways, it parallels San Francisco’s moving of Joe Montana to free up space for Steve Young to start.
But, while Montana enjoyed a few more productive years from the Chiefs, he was entering the twilight of his career. And Young became a superstar in his own right.
That can’t exactly be said of the 1961 trade of Hall of Fame quarterback Y.A. Tittle to the New York Giants, though, even though an up-and-coming quarterback, John Brodie, was waiting in the folds.
Brodie would go on to have his own success in relief of the then-35-year-old Tittle, who already head four Pro Bowl nods with the 49ers before being jettisoned to the G-Men. Yet Brodie’s success came nowhere close to that of Young, hence making this particular trade one of disappointment.
Tittle, already a star during his Niners days, effectively defined his career as a legendary quarterback after being traded to the Giants, netting three more Pro Bowls and two first-team All-Pro selections while boasting a league-leading and career-high 36 pass touchdowns in 1963.
In hindsight, San Francisco has to be disappointed it didn’t hold onto Tittle a bit longer to capitalize on how he finished his legendary career.
No. 3: 49ers botch the trade of Terrell Owens to Ravens
The next trade on this list isn’t necessarily a trade that was simply disappointing because of the nature of the deal or the caliber of player involved, although that’s certainly the case with the franchise’s second-best leading receiver of all time, Terrell Owens.
But the sheer disappointment stems from just how it all went down.
By 2003, Owens wanted off a crumbling 49ers franchise that was heading in a downward spiral fast. The Niners claimed Owens’ agent had missed the deadline to void the final years of his contract, hence making him a free agent for 2004, which subsequently resulted in San Francisco attempting a trade to the Baltimore Ravens for a second-round draft pick.
The NFLPA was brought in to hear grievances, but the 49ers, Ravens and Philadelphia Eagles, with whom Owens had already negotiated a new three-year contract, agreed to a new settlement.
Owens would join Philly, Baltimore would get its second-round pick back.
And the Niners would be left with the Eagles’ fifth-round pick and defensive end Brandon Whiting, who played only five games for San Francisco with zero sacks and just 11 tackles.
Hardly the return for one of the greatest wide receivers of all time.
No. 2: 49ers take a chance on Reuben Foster and get burned
A little more recent 49ers history here.
In the 2017 NFL Draft, the Niners already traded down from No. 2 overall one spot in a deal with the Chicago Bears to land defensive end Solomon Thomas. While that deal didn’t work out to the max for both teams, at least San Francisco used one of those picks on linebacker Fred Warner a year later.
So, in that sense, the 49ers still won that trade.
Yet there was plenty of sudden excitement later in Round 1 long after most fans were convinced the Niners were finished selecting. In order to jump ahead of the No. 32 overall-drafting New Orleans Saints, San Francisco moved back into the first round at No. 31 overall to grab a free-falling first-round player in Alabama linebacker Reuben Foster.
Foster, whose talents warranted top-10 consideration, nevertheless came with red flags surrounding his injury history and off-field character concerns.
Never mind, though. Foster would thrive with the 49ers, right? He’d be the latest in a long line of exceptional Niners linebackers.
In his rookie year, this looked to be the case. But heading into 2018, Foster was already dealing with off-field arrests and run-ins with the law, eventually leading to his dismissal from the team in November of that year.
Not even two years into his pro career, creating quite the disappointment among the San Francisco Faithful.
No. 1: 49ers turn Cowboys into Super Bowl champions with Charles Haley
There’s a reason why teams don’t trade their top players to chief rivals. Those moves can come back to haunt a franchise for a long, long time.
Yet that’s what the 49ers ultimately decided to do in 1992 by trading away All-Pro defensive end Charles Haley to the Dallas Cowboys, who were beginning to emerge as a serious threat to the Niners’ previous dominance of the NFC in the early 1990s.
If anything, Haley’s transition from San Francisco to Dallas tipped the balance of power within the conference over to the Cowboys’ favor.
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According to 49ers alumnus Dexter Carter, the final straw for Haley’s already tenuous career with the Niners was when the star pass-rusher crossed paths with wide receiver Jerry Rice, which ultimately left San Francisco little choice but to move on from Haley.
In return, the 49ers grabbed a second- and third-round draft pick from Dallas. But neither one of those picks mattered.
If anything, Haley would go on to thrive with the Cowboys, winning three Super Bowls with his new team and frequently tormenting his old one when these two squads would meet up in the playoffs.
Creating plenty of disappointing moments for Niners fans during the remainder of the decade.