In 2008, Terrell Owens was coming off a Pro Bowl season and was one of the league’s best, and most controversial, players. On June 2nd 2008, The Cowboys rewarded Owens’ stellar play with a 4-year, $34MM extension, giving him a substantial raise from his previous $7MM annual salary.
Perhaps no player in the history of the league has had as much contract drama as Owens, who famously complained loudly and often about his compensation during his time with the Eagles, which eventually led to his release. Owens signed a seven-year deal with the Eagles, and only ended up playing two seasons for them. His extension from the Cowboys followed a similar pattern. Despite a solid 2008 season in which he racked up 1,052 yards and 10 touchdowns, the Cowboys decided he was simply too much of a headache and released him one-year into his new four-year deal. Owens was reportedly blindsided by his release, saying publicly that owner Jerry Jones had assured him his roster spot was safe.
Owens’ contracts were always a big deal during his playing days, and often overshadowed his on-field production. After being a notable snub from the Pro Football Hall of Fame’s 2017 class, Owens was recently announced as a member of the 2018 class, and will be enshrined in Canton this August. Owens has also repeatedly stated he’s still not giving up hope of an NFL comeback, recently saying he’d like to play for Andy Reid and the Chiefs.
Owens’ 2008 deal was the last multi-year contract he would ever get in the NFL, settling for a few one-year deals with three different teams after his release before eventually finding himself out of the league altogether. Still performing at a high level in 2008, not many would’ve guessed at the time that it would be the last big payday in Owens’ illustrious career.