ESPN - 25 Worst Contracts In NFL History (Includes Two Ex-Steelers)

ESPN has a two part article on the 25 worst contracts in NFL history

I was surprised that Mr. Woodley was not included

But two former Steelers made the list

Ranking the 25 worst contracts in NFL history

25. Mike Wallace, Miami, 2013

Initial reports: Five years, $60 million with $30 million guaranteed.

Actual payout by Miami: $27.1 million for two seasons.

In his first three pro seasons, Wallace grew to become one of the NFL's most imposing deep threats by averaging 18.7 yards per reception for Pittsburgh. He totaled 171 catches for 3,206 yards and 24 touchdowns during that span and was named to the Pro Bowl team in 2011. During his fourth year, he caught another eight touchdown passes, but his yards per reception dipped sharply to 13.1.

Perhaps that should have been an indication that Wallace's future production would be good -- but not great.

In two seasons with Miami, Wallace made 140 catches for 1,792 yards and 15 touchdowns. By comparison, the other top free-agent receiver in 2013, Wes Welker, signed a two-year deal for just $12 million with the Broncos and produced 122 receptions for 1,242 yards and 12 touchdowns.

Months after Wallace signed with Miami, his father told USA Today that the receiver had passed up a more lucrative deal from Minnesota. The Vikings wound up getting Wallace after all in March 2015, trading a fifth-round draft pick to the Dolphins for the player and a seventh-round pick. The deal allowed Miami to avoid a $3 million bonus Wallace was due.

24. Neil O'Donnell, N.Y. Jets, 1996

Initial reports: Five years, $25 million with $7 million guaranteed.

Actual payout by Jets: $10.8 million for two seasons.

After winning the 1995 AFC championship with the Steelers, O'Donnell was an attractive free agent for teams in need of a quarterback. The Jets, coming off a 3-13 record, were in the market and gave him a contract that was substantial in the days of a $40 million salary cap.

O'Donnell became the first quarterback not to return to his team after a Super Bowl season since the Vikings traded Joe Kapp to the Patriots* in 1970. Although the Jets also signed offensive tackle Jumbo Elliott and drafted wide receiver Keyshawn Johnson with the No. 1 overall pick, the ensuing season was a disaster. O'Donnell suffered an injured shoulder and torn calf muscle and went 0-6 with four touchdown passes and seven interceptions as the Jets went 1-15 overall.

Enter head coach Bill Parcells, who supplanted Rich Kotite for the 1997 season. O'Donnell's leash got shorter, and he was twice benched in favor of Glenn Foley. O'Donnell improved in '97, throwing 17 touchdown passes and seven interceptions. But Parcells didn't think he was getting enough production for the money from O'Donnell, who completed 56.3 percent of his throws with an 80.3 passer rating that season.

O'Donnell was cut in June 1998 when he refused to restructure his contract. The Jets then signed 34-year-old Vinny Testaverde to replace him and reached the AFC Championship Game that season. O'Donnell joined the Bengals for the '98 season and finished his career with five seasons in Tennessee as a backup.

http://espn.go.com/nfl/story/_/id/14047374/ranking-25-worst-contracts-nfl-history-part-1

http://espn.go.com/nfl/story/_/id/14047370/ranking-25-worst-contracts-nfl-history-part-2

Atlanta Dan wrote:

I was surprised that Mr. Woodley was not included

I'm not. Woodley was productive under his new contract until he decided his new role on the team was to out-eat Casey Hampton.

SteelersCanada wrote:

Atlanta Dan wrote:

I was surprised that Mr. Woodley was not included

I'm not. Woodley was productive under his new contract until he decided his new role on the team was to out-eat Casey Hampton.

Unfortunately that happened fairly early in the 6 year $61 million contract signed in 2011 that included a $13 million signing bonus.  

At the time a bonus of that size was seen as a cap friendly move

The new deal is front-loaded with bonus money, helping Pittsburgh to get some breathing room under the cap.

http://espn.go.com/nfl/story/_/id/6835818/lamarr-woodley-pittsburgh-steelers-lands-6-year-615m-deal

But in addition to sketchy productivity after Woodley injured his hamstring against New England in week 8 of the 2011 season, Woodley did not even make it to the 4th year of the contract

Which resulted in Mr. Woodley clocking in at #6 on this list SI.com published yesterday that I came across after my initial post

20 worst dead money deals in NFL

6. LaMarr Woodley, former Steelers linebacker

2015 Cap hit: $8.6 million

Woodley, once a core component of Pittsburgh’s Super Bowl XLIII championship team, represented the 15th-largest amount of dead money ($5.6 million) in the NFL when I did this exercise last year. The burden from Woodley’s old six-year, $61.5 million deal has only worsened in 2015.

Woodley tried to catch on with Oakland last year, but that resulted in an abysmal six-game stint with just five tackles from Woodley. Unlike the Steelers, however, the Raiders were smart enough not to guarantee Woodley any money for 2015..

http://www.si.com/nfl/2015/11/11/nfl-worst-dead-money-contracts-darrelle-revis-jimmy-graham

$14.2 million in dead money is quite a hit