NFL Free Agency: 30 worst free agency signings this century

9. Worst NFL free agency signings this century: Antonio Bryant

Coming in at No. 9 is Antonio Bryant, a wide receiver who is an interesting case, as he could be on here for two different teams. Both the San Francisco 49ers and the Cincinnati Bengals overpaid for him, despite knowing he had a checkered past.

Bryant began his career with the Dallas Cowboys in 2002 and showed a lot of promise. As a rookie, he had 44 receptions for 733 yards and six touchdowns.

However, he started to grow agitated with the team after head coach Bill Parcells traded for Keyshawn Johnson Bryant’s targets declined largely because of that deal for Johnson. It all came to a boiling point that saw Bryant throw his jersey at Parcells. He was later traded to the Cleveland Browns.

Bryant had a great season for them in 2005. That’s when the 49ers came calling with a four-year, $14 million deal in the following offseason. Bryant lasted only one year with San Francisco, as the 49ers released him and he was later suspended for failed drug tests. While they didn’t get a good return on their investment, at least San Francisco did get 14 games out of him.

Bryant ended up with the Tampa Bay Buccaneers after not playing at all in 2007 and put up respectable numbers. That’s when the Cincinnati Bengals came into the picture and doubled the deal the 49ers previously gave him. Bryant and the Bengals agreed to a four-year, $28 million deal in 2010, but he never even made it to the regular season.

Knee problems ended his final campaign with the Buccaneers. They continued to be a problem with Cincinnati during training camp and the preseason. He ended up being released at the end of August, as their gamble on the enigmatic wideout was fruitless.