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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Charles Haley, Steve Young, Dallas Cowboys, San Francisco 49ers
Charles Haley #94 of the Dallas Cowboys tackles Steve Young #8 of the San Francisco 49ers during the NFC Conference Championship game (Photo by Focus on Sport/Getty Images) /

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.

Read More: 30 greatest 49ers players in franchise history

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.

dark. Next. 10 most painful playoff losses in 49ers history