Past Super Bowl Performances That Led to Big Contracts And Failed Expectations

Written By Martin Derbyshire on January 13, 2022 - Last Updated on June 8, 2022
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A big-time performance in the Super Bowl, a Super Bowl season, or even just a few games in a season that leads to a Super Bowl appearance can turn an otherwise mediocre NFL player into a bonafide star. If he happens to do it in a free agent year, he can turn that star power into dollars. Lots of ’em.

However, big NFL contracts come with big expectations. Don’t live up to ’em, and a player will quickly be considered a bust and put on this lucky list of seven one-hit wonders, players who had Super Bowl or Super Bowl season performances that led to fat free-agent contracts which didn’t quite work out as planned for the teams involved:

1. Larry Brown – Dallas Cowboys

The fact a cornerback won Super Bowl XXX MVP for the Dallas Cowboys in 1996 was a bit of a surprise. That it wasn’t Deion Sanders was a complete shock. Instead, Larry Brown benefitted from the Pittsburgh Steelers’ refusal to go after ‘Primetime.’ In the end, Brown got two interceptions and the Super Bowl XXX MVP trophy. Furthermore, a trip to Disney World and a massive five-year $12.5 million free-agent contract from the Oakland Raiders.

Brown started just one and played in only 12 games in two years with the Silver and Black. He was suspended for conduct detrimental to the team and ultimately waived. He tried again with the Minnesota Vikings and returned to the Cowboys, but injuries ensured Brown never had a better game than Super Bowl XXX. In fact, he only managed one career interception after the two he had in the Super Bowl.

2. Dexter Jackson – Tampa Bay Buccaneers

The fact a defensive player won Super Bowl XXXVII MVP for the Tampa Bay Buccaneers in 2003 was a bit of a surprise. It wasn’t defensive legends Warren Sapp, Derrick Brooks, or John Lynch that were a complete shock.

Instead, Jackson became the first player ever to record two interceptions in the first half of a Super Bowl, helping the Bucs go up 20–3 at the half. The Oakland Raiders never got close, and Jackson became only the second safety and the third DB to win Super Bowl MVP.

D-Jax signed a five-year and $14 million deal with the Arizona Cardinals in 2003. However, he was back in Tampa within a year, with the Cincinnati Bengals a year later, and finished his pro football career as a Florida Tusker in the United Football League.

3. Mark Rypien – Washington Redskins

The future was so bright for Mark Rypien he probably wore shades when he signed a big-at-the-time three-year and $9 million deal with the Washington Redskins heading into the 1992 season. He had just led the team to a 14-win regular season and a victory over the Buffalo Bills in Super Bowl XXVI, in which he threw for 292 yards and two touchdowns and was named Super Bowl MVP.

Unfortunately, Rypien never found that kind of success again. He did win 14 games again, but it took a decade to manage that many, rather than a single season.

The Redskins dumped him after a playoff loss in 1992, a knee injury in 1993, and a coaching change in 1994. After that, Rypien was a career backup, playing with the Cleveland Browns, the St. Louis Rams, and the Philadelphia Eagles, appearing infrequently and never winning more than three games in a season.

4. Desmond Howard – Green Bay Packers

Desmond Howard is one of the most recognizable names on this list. He won the Heisman Trophy as a senior at Michigan and Super Bowl XXXI MVP with the Green Bay Packers in 1996, thanks to a 99-yard kickoff return TD in the big game. No wonder the Oakland Raiders signed Howard to a four-year deal worth $6 million after the game.

After all, he was the only special teams player ever to win Super Bowl MVP.

The thing is, Howard was never more than a journeyman return specialist. He spent two seasons wearing the Silver and Black and scored just one TD for the team. Although, Howard did lead the NFL in kickoff returns (61) and kickoff return yards (1,381) in 1997.

Howard went back to the Packers in 1999 but was cut mid-season. He finished his NFL career in Detroit, scoring a TD in his Lions debut and making the Pro Bowl in 2001.

5. Neil O’Donnell – Pittsburgh Steelers

Neil O’Donnell didn’t win a Super Bowl or even play well in one. In fact, he was the QB that threw those two Super Bowl INTs to Larry Brown in 1996. However, O’Donnell did lead the Pittsburgh Steelers all the way to Super Bowl XXX and was attractive to a lot of teams as a free agent QB that summer.

He chose the big-market NY Jets, a five-year and $25 million contract, and all the impossible expectations that come with playing football in New York.

O’Donnell won just eight games over 20 starts in two seasons in NY before the Jets cut him. That included an 0–6 opening before a shoulder injury ended his first season with the team. O’Donnell signed another four-year and $17 million contract with the Cincinnati Bengals that came with fewer expectations, but he couldn’t live up to those either.

The Bengals finished 3–13 in his first year with the team, and O’Donnell was released. He did find some late-career success as Steve McNairs backup with the Tennessee Titans. O’Donnell made another Super Bowl, holding a clipboard in Super Bowl XXXIV with Tennessee, but the Titans lost, and O’Donnell ended his career ringless.

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6. Brock Osweiler – Denver Broncos

Brock Osweiler didn’t even play in the Super Bowl win that earned him an incredibly rich and decidedly undeserved free-agent contract. He was on the Denver Broncos team that won Super Bowl 50 and filled in admirably for a few games at QB for an injured Peyton Manning to end the regular season.

However, Manning took back his starting role in the postseason, and the Broncos’ defense took that team to a Super Bowl win, becoming one of the greatest Super Bowl moments in history.

Still, Osweiler signed a massive four-year and $72 million contract with $37 million guaranteed by the Houston Texans in the offseason. Osweiler was so bad as a Texan, throwing a franchise-record 16 interceptions, they traded him to Cleveland after one season and a Wild Card game win.

He was released before the next season and re-signed with the Broncos for the league minimum. Furthermore, leaving the Browns on the hook for the more than $15 million guarantees on that Texans contract. He won a few starts with the Broncos but never the starting job, ending his career as a backup with the Miami Dolphins.

7. Nate Odomes – Buffalo Bills

Nate Odomes was a big part of the Buffalo Bills record four straight Super Bowl appearances from 1990 to 1993. He led the NFL in INTs in the 1992-93 season and came off two consecutive All-Pro seasons. Buffalo lost every one of those Super Bowls, and Odomes did little to change that did not deter the Seattle Seahawks from signing him to a fouryear and $8.4 million deal that included a $2.2 million signing bonus.

Sadly, Odomes injured his knee in a charity basketball game in the offseason and missed his first season as a Seahawk. After rehab, he blew out the same knee in mini-camp and sat out the following season. Nate Odomes never played a snap for the Seahawks.

Photo by Jamie Lamor Thompson / Shutterstock.com
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Martin Derbyshire

Martin Derbyshire has more than ten years of experience reporting on the poker, online gambling, and land-based casino industries for a variety of publications including Bluff Magazine, PokerNews, and PokerListings. He has traveled extensively, attending tournaments and interviewing major players in the gambling world.

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