San Francisco 49ers Hall of Shame: Worst breakup and more

After celebrating the 49ers by highlighting their players who someday could be enshrined in the Pro Football Hall of Fame, we flip the script to give you San Francisco's Hall of Shame.

Worst draft pick: Jim Druckenmiller

The 49ers have had several legendary quarterbacks, but Druckenmiller is most certainly not one of them. San Francisco selected him in the first round (No. 26 overall) of the 1997 NFL Draft with the intention of grooming him to be the eventual successor to future Hall of Fame quarterback Steve Young. 

He never came close to achieving that goal.

Druckenmiller played in six games with the 49ers, throwing for only 239 yards, one touchdown and four interceptions over two seasons before being traded to the Miami Dolphins. He never played a game for the Dolphins. 

Along with being one of the worst quarterback draft busts in NFL history, Druckenmiller also had legal troubles off the field. (In 1999, he was acquited of rape.)

The 1997 quarterback class was one of the worst in NFL history, but Jake Plummer was taken just 16 picks after the 49ers selected Druckenmiller and ended up passing for nearly 30,000 yards in his career. 

Worst breakup: Terrell Owens

Owens was one of the best wide receivers in football, but by the 2003 season, it was becoming clear that his time with the 49ers was nearing an end. As a Niner, he clashed with coaches and made innuendos regarding San Francisco teammate Jeff Garcia in an interview with Playboy.  

Following the 2003 season, the Niners traded T.O. to the Ravens. Owens balked, an arbiter got involved and he eventually landed in Philadelphia in a trade. True to his antagnoistic nature, Owens had a bad breakup with the Eagles, too. 

Worst loss: 1991 NFC Championship Game, Jan. 20, 1991

The 49ers looked poised for a three-peat going into the 1991 postseason. Then, after an easy win over Washington in the second round, the top-seeded Niners hosted the New York Giants in the NFC title game. It was a brutal game in which nearly everything went wrong for San Francisco.

Defensive lineman Leonard Marshall knocked Niners QB Joe Montana out of the game with a devastating hit and normally sure-handed running back Roger Craig fumbled late in the fourth quarter as his team was trying to run out the clock. 

Craig's gaffe set the stage for a 42-yard field goal by Matt Bahr to win the game for New York, 15-13. The Giants went on to beat Buffalo in Super Bowl XXV. 

Worst trade: Defensive end Charles Haley to Dallas

From 1986 to 1991 with the Niners, Haley was one of the more disruptive defensive lineman in the NFL and a critical part of a defense that helped win two Super Bowls. During his first six seasons, he  recorded 63.5 sacks and played in three Pro Bowls.

Haley, however, clashed with the coaching staff and wore out his welcome to the point the 49ers traded him to the Dallas Cowboys for second- and third-round picks. 

Haley continued his dominance in Dallas and was one of the final pieces the Cowboys needed for their Super Bowl puzzle. He would go on to win three more Super Bowls with the Cowboys and earn election to the Pro Football Hall of Fame in 2015.