The 10 Best Trades In NFL History (Where Both Sides Won)

In the NFL, championship teams are built through the draft. While free agency is important, due to the salary cap, teams that are contending tend to get the most value through drafting, especially since rookie contracts are notoriously cheap since 2010.

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However, that's not entirely the case, as several teams have gotten over the hump thanks to some big trades. While most trades tend to have one team coming out on top, sometimes both teams end up winning. Throughout NFL history, there have been several trades where both franchises came away as winners.

10 Rob Gronkowski To Tampa Bay Buccaneers

As the story goes, Rob Gronkowski retired following the 2018 season with the New England Patriots due to injuries. In 2020, he shockingly came out of retirement to join Tom Brady in his first season with the Tampa Bay Buccaneers in the NFC.

This trade worked out well for both sides, as Brady and Gronkowski won yet another championship. Meanwhile, the Patriots got a fourth-round pick for a retired player that wasn't contributing to their rebuild.

9 Champ Bailey And Clinton Portis Swap Teams

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In 2004, future Hall of Famer Champ Bailey was unhappy in Washington and wanted out. As a result, he, along with a draft pick, headed to the Denver Broncos in return for All-Pro running back Clinton Portis.

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While this trade seems a bit lopsided on the surface, it mostly worked out for both squads. The Broncos got a decade of fantastic play on defense from Bailey, while Washington got several pro bowl seasons from Portis during his seven-year stint.

8 Brock Osweiler To Cleveland Browns

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Yes, one of the worst contracts in NFL history turned into a win-win trade. In 2017, Brock Osweiler, who had a monster contract, was coming off a horrendous season. As a result, the Houston Texans had to get creative to get rid of the quarterback.

He was then sent, along with a draft pick, to the Cleveland Browns, who were rebuilding and had the cap space. That draft pick later turned out to be Nick Chubb. As far as the Texans go, they wound up drafting Deshaun Watson to replace him.

7 Jared Allen To Minnesota Vikings

Jared Allen was an All-Pro who appeared to just be hitting his stride in 2008. As a member of the Kansas City Chiefs, the defensive end was unhappy with being franchise tagged, while the team was upset with his recent DUI.

In turn, he was traded to the Vikings, who were happy to get several years of defensive excellence from Allen. The Chiefs received a first-round pick, as well as two third-round picks. Two of those picks turned out to be Pro Bowl lineman Branden Albert, and All-Pro running back Jamaal Charles.

6 10th Overall Draft Pick (Patrick Mahomes) To Kansas City Chiefs

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As the story goes, the Kansas City Chiefs were stuck in purgatory with Alex Smith in 2017. Shockingly, the team traded up from 27 to 10 in order to draft a boom or bust prospect in Patrick Mahomes.

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Trading up worked out for the Chiefs and Mahomes, as he's currently one of the best players in the league. However, the Buffalo Bills, who switched spots with Kansas City, took Tre'Davious White at 27th overall. He's currently one of the best cornerbacks in the league.

5 Emmanuel Sanders To San Francisco 49ers

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Emmanuel Sanders was wasting away as a member of the Denver Broncos in 2019. The team was in rebuilding, and the wideout was closing out his career. Both sides weren't happy with the situation, so they dealt Sanders to the San Francisco 49ers.

The deal worked out, as the 49ers made the Super Bowl thanks to Sanders' contributions. Meanwhile, the Broncos got two draft picks and were able to build for the future.

4 Eli Manning And Philip Rivers Swap Teams

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Eli Manning really, really, really didn't want to be a member of the Chargers. So much so, that prior to the 2004 NFL draft, he informed the team that if they drafted him first overall, he would refuse to play for them. Manning kept his word.

As a result, the team sent Manning to the New York Giants in exchange for the newly drafted Philip Rivers, and two draft picks (which turned out to be Nate Kaeding and Shawne Merriman). Both players fit perfectly on their new squads, and will likely make the Hall of Fame.

3 Khalil Mack To Chicago Bears

On paper, this trade looks terrible. Khalil Mack was one of the greatest defensive players in the league in 2018 and wanted to be paid as such. However, the Las Vegas Raiders disagreed with how much he should make and sent him to the Bears.

Mack continued to dominate for the Bears, putting in several great years of work on defense. Meanwhile, the Raiders, who received three draft picks, used one of them to select Pro Bowl running back Josh Jacobs.

2 Atlanta Falcons Trade Up For Michael Vick

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The 2001 NFL draft had some incredible prospects, but Michael Vick was at the top of everyone's draft boards. That includes the Los Angeles Chargers, who wanted the quarterback. However, the Atlanta Falcons offered them a trade they couldn't refuse, including a first-round swap, and a second and third-round pick.

The Falcons selected Vick and got several incredible seasons from him. Meanwhile, the Chargers used one of the picks to select LaDainian Tomlinson, and instead selected Drew Brees as their quarterback of the future.

1 Stefon Diggs Heads To Buffalo

Following the 2019 season as a member of the Minnesota Vikings, Stefon Diggs was unhappy. He felt the team was far away from contending, and he was in his prime. So, the team dealt him to the Buffalo Bills for a load of picks.

Diggs has thrived alongside Josh Allen in Buffalo, but things worked out for Minnesota as well. The following year, they selected Justin Jefferson in the first round, who has blossomed into arguably the best pass-catcher in football.