
28. Terrell Owens
Yes, Owens made life a nightmare for his quarterbacks. Nonetheless, he was a brilliant player. He was electrifying for the Niners before his move to the Eagles. However, that trade was very complicated. It almost went to an arbitrator because of the fallout between the franchise and the player. In the end, it didn’t go that far. But this was a toxic situation for everybody.

San Francisco agreed on a trade with Baltimore in exchange for a second-round pick. Owens shut this down because he wanted to move to Philadelphia. Finally, the wideout achieved his move. The 49ers received Brandon Whiting and a fifth-round pick in a three-team trade. This was a blockbuster deal because of Owens’ profile. But San Francisco came off as the biggest loser (via Philadelphia Inquirer).