In the NFL, there are plenty of ways to upgrade your roster. The NFL Draft and free agency are the two most popular routes, but if you want to take a bit of a gamble, a trade can make or break your future.

Just ask the Dallas Cowboys, who received eight draft picks for Herschel Walker back in 1989. This trade fueled the Cowboys’ dynasty, as they used the picks to draft future Hall of Famer Emmitt Smith and Pro Bowlers Darren Woodson and Russell Maryland. For the Minnesota Vikings, Walker never rushed for more than 825 yards, and he was out of Minnesota by 1992.

Or ask the Cleveland Browns, who shipped three first-round picks, a third-rounder, and two fourth-rounders to the Houston Texans for Deshaun Watson. They mortgaged their future on a guy who has just over 3,000 yards and has thrown 19 touchdowns to 12 interceptions for them in four seasons.

The point I’m trying to make is, trades are risky. You never know what future draft picks will become, so shipping away a first or second could end up costing you big time.

But sometimes it doesn’t. There have been a handful of trades in NFL history that have panned out for both sides, most notably the trade between the Detroit Lions and Los Angeles Rams just a few years ago, which sent Matthew Stafford to LA in exchange for Jared Goff and two first-round picks.

Was the Goff/Stafford trade the most win-win trade in NFL history? That’s the question I’ve set out to answer today.

Matthew Stafford for Jared Goff and Picks

I’m not sure a trade gets more even than this. In January of 2021, almost five years ago, the Lions and Rams swapped quarterbacks, with the Rams sending Jared Goff two first-round picks plus more draft capital to the Lions in exchange for Matthew Stafford. The Rams got the quarterback they felt like they needed to win a Super Bowl, and the Lions received a solid signal caller and draft capital to help their rebuild.

There will be a crowd out there (mostly Rams fans) saying that they clearly won this trade because they got a Super Bowl (and maybe even two after this year) out of it. And while yes, they certainly did win in that aspect, you can’t understate what this trade did for the Lions.

Detroit, which hadn’t won a playoff game since 1991, reached the NFC Championship game in 2023 after finishing 12-5, their best regular-season record since 1991, when they went 12-4. They followed that up with the best regular season in franchise history in 2024, finishing 15-2 and earning a first-round bye, before falling to the red-hot Washington Commanders in the Divisional Round. So while they did not win a Super Bowl with Goff (at least not yet), this trade kick-started a new era of Lions football. And for Detroit fans, I think they would do this trade 100 times out of 100 if they knew it would lead to this result.

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On top of both franchises getting what they desperately needed, Goff and Stafford have posted nearly identical stats to each other since the trade five years ago. Just look at their stats since joining their respective teams, and tell me this isn’t about as even as it gets.

If the Rams win another Super Bowl with Stafford and the Lions never get one with Goff, sure, you can make the case that the Rams won this trade by a landslide. But again, the revitalization of one of the oldest franchises in the league has to count for something.

Stefon Diggs to Buffalo for Justin Jefferson

In 2020, the Minnesota Vikings traded their star receiver, Stefon Diggs, to the Buffalo Bills in exchange for a first-round pick and other draft capital. Diggs was coming off a 1,130-yard, six-touchdown season, but he was frustrated with his role and wanted out of Minnesota. Enter the Bills, who just lost in the Wild Card round for the second time in three years, and they desperately needed a dynamic wide receiver to pair with their young but highly talented quarterback, Josh Allen.

The Bills shipped off what would become the 22nd overall pick in the draft for Diggs’ talents. The trade instantly paid off for Buffalo. Diggs racked up 1,535 yards and eight touchdowns in his first season with the Bills, and helped lead them to the AFC Championship for the first time since 1993. Diggs played four seasons with the Bills, going over 1,200 yards and eight touchdowns in every one of them. Buffalo had one of the best offenses in the NFL during that span, and they reached the Division Round every year Diggs was there.

Minnesota didn’t come out of this trade half bad, either. That first-round pick they obtained for Diggs turned into Justin Jefferson, who has been one of the best receivers in the league since he stepped on the field and put up 1,400 yards as a rookie. He’s battled injuries this season, but Jefferson has totaled 1,400+ yards in every season he’s been healthy.

The Vikings haven’t had the same level of success as Buffalo, but they’ve found a future Hall of Fame receiver who can help them win games for over a decade.

It’s hard to say either team lost this trade. Sure, if Buffalo held onto their pick and selected Jefferson, maybe their offense is even more dynamic and they win a Super Bowl during that stretch. But if my mom had wheels, she’d be a bike, so playing the if game is pointless. I think it’s safe to say both sides are very happy with how this trade turned out.

Eli Manning for Philip Rivers

Another trade that worked out pretty well for both sides was the draft-night trade between the then-San Diego Chargers and the New York Giants. When Eli Manning, the No. 1 pick in the 2004 draft, refused to play for the Chargers, they traded him to the Giants in exchange for Philip Rivers, the No. 4 pick in the draft.

Manning played 16 years in the NFL, all for the Giants, and threw for 57,023 yards and 366 touchdowns, both of which rank 11th in NFL history. Manning also led the Giants on two magical Super Bowl runs, beating Tom Brady in both of them. The first came in 2007 against the undefeated Patriots, and it was the Giants’ first Super Bowl since 1990. The second came four years later in 2011, once again against the Patriots. Manning turned a 4-12 team to a Super Bowl team in just four years. I don’t think the Giants could’ve asked for much more.

Rivers played 17 years in the NFL before initially retiring after the 2020 season. As you know, he’s not back and playing for the Colts, but after this year, it appears his now 18-year career will be over. He’s thrown for 63,560 yards and 422 touchdowns, which rank seventh and sixth, respectively, and led the Chargers to the playoffs seven times, including an AFC Championship game appearance in 2007.

This is a lot like the Stafford-Goff debate. The Giants obviously won the trade because they got two Super Bowls out of Manning, but the Chargers turned a franchise that hadn’t won double-digit games in nine seasons into a consistent playoff team (at least in the early years) with Rivers.

Outside of this, when’s the last time we’ve seen two future Hall of Fame quarterbacks traded for each other? I’d dare to say never.

Michael Vick for LaDainian Tomlinson

Another pretty even trade occurred in 2001, when the Atlanta Falcons traded up from No. 5 with the Los Angeles Chargers for the No. 1 pick in the draft. The Falcons selected Michael Vick, one of the most dynamic quarterbacks in NFL history, while the Chargers collected some extra picks and selected LaDainian Tomlinson, arguably the most electric running back in NFL history.

For the Falcons, the trade never amounted to a Super Bowl, but Vick sure was fun to watch in Atlanta. He set records for rushing yards by a quarterback while also throwing for 2,300+ yards every season he was healthy. He even helped the Falcons reach the NFC Championship in 2004, but ultimately came up short against Philadelphia. His tenure in Atlanta ended in 2007 after he was arrested for dog fighting, but he would return to the NFL a few years later with the Eagles.

For the Chargers, they got the best offensive player in franchise history out of this trade. Tomlinson set, and still holds, the record for the most touchdowns in a single season with 31 (28 rushing, 3 receiving) in 2006. In nine years with the Chargers, Tomlinson racked up 12,490 rushing yards and 138 rushing touchdowns while adding 3,955 receiving yards and 15 receiving touchdowns.

Neither team ended up winning anything significant with these players, but they both were responsible for some of the most fun and explosive offenses their franchises have ever seen, so that’s a win in my book.