Four recent NFL free agent signings that were a gamble but ultimately paid off

The current free agency system in the NFL was introduced in the early 1990s and has enabled franchises to improve their rosters for the upcoming season while also giving the opportunity to players to earn lucrative contracts.

There have been a number of free agency signings in recent years that looked like a gamble when they were first announced but then became shrewd deals that led to drastic improvements on the field, and in some cases, success in the form of Super Bowl wins.

Tom Brady

The highest-profile free agency signing took place just 12 months ago when the Tampa Bay Buccaneers managed to snag the most decorated quarterback in NFL history, Tom Brady.

Reports that the Bucs could close the audacious signing came three days before the start of the free agency period, and on 20th March 2020, it was officially announced that Brady had joined on a two-year contract worth $50m upfront with a further $4.5m in incentives annually.

“When we looked at everybody that might be available at the quarterback position, obviously really never dreaming that Tom would be available, but if he was, he was going to be our number-one choice,” Bucs head coach Bruce Arians said.

At 42 years of age, Brady represented a gamble, especially away from the New England Patriots, where he had been for the previous 20 years.

However, it ended up being a fairytale first season for Brady and Tampa Bay as they squeezed through the regular season before embarking on an incredible postseason run that culminated with a Super Bowl LV victory over the much-fancied Kansas City Chiefs and rival QB Patrick Mahomes.

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Shaquil Barrett

The Buccaneers’ free agent game has been impressive recently, as also evidenced by the success of Shaquil Barrett. The 28-year-old linebacker initially joined on a cut-price, one-year deal worth $5m back in 2019, but his value soared after a memorable debut season that included a league-leading 19.5 sacks and 58 tackles.

Barrett appeared in more than three quarters of the Bucs’ defensive snaps during that season and earned a Pro Bowler spot. After stating his intention to remain in Tampa, Barrett earned $15.8m in 2020 as the Bucs became Super Bowl champions.

In March 2021, it was confirmed that Barrett had finally secured the long-term deal he wanted after signing for $72m over four years. After a risky move on paper two years ago, Barrett is now one of the most prolific pass rushers in the game.

Peyton Manning

Going a bit further back to 2012, Peyton Manning’s decision to move to the Denver Broncos on a five-year contract for $96m following a lengthy free agency tour that year drew some skepticism due to a neck injury.

However, like Brady, Manning dispelled any doubts in his first season after earning the NFL Comeback Player of the Year Award. After his fifth MVP and Super Bowl XLVIII appearance in 2013, Manning became the all-time leader in passing touchdowns in 2014 before winning Super Bowl 50 in the 2015/16 season as the Broncos cruised to a 24-10 win over the Carolina Panthers.

Malcolm Jenkins

After four years with the New Orleans Saints, Malcolm Jenkins became an unrestricted free agent in 2014 and eventually signed with the Philadelphia Eagles after putting pen to paper on a $16.25m contract.

While not as great a gamble as other free agents over the last decade, Jenkins still had to make a name for himself and did just that as he became one of the best safeties in NFL with a strong Eagles side that eventually won Super Bowl LII in 2018 with an epic 41-33 victory over Brady’s New England.

The Saints appeared to recognize the mistake they had made in letting Jenkins go as they brought him back to the franchise on a $32m, four-year contract in 2020.

With the NFL free agency period beginning again in March, there are sure to be more gambles on potential stars that could take teams to the next level and maybe even a Super Bowl in the future.

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