The history of NFL free agency has led to countless “what ifs” that continue to be discussed among football fans and analysts to this day.
What if a certain superstar player didn’t sign with Team X? What if he ended up going to Team Y instead? Well, history would have been a lot better — and different — for all football fans.
With that said, let’s dive into 10 recent NFL free-agent signings that we wish would have happened.
Tom Brady To Miami Dolphins (2020)
You’ll recall that the Dolphins were punished heavily by the NFL for violating the league’s tampering rules. An investigation found that they spoke to then-New Orleans Saints head coach Sean Payton and then-New England Patriots QB Tom Brady while both were under contract with their teams.
Clearly, the Dolphins badly wanted Brady — somehow being alert in advance that he was orchestrating his exit from New England. But of course, he wound up signing with the Tampa Bay Buccaneers on a two-year pact worth $50 million.
Brady obviously regrets Zilch after winning his seventh ring with Tampa….but the Bucs were never the most exciting team for your average Joe. From an entertainment standpoint, WHAT IF Brady instead signed with Miami?
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He’d be sticking it to Bill Belichick and the Patriots by joining the rival team. We would have seen Brady vs. Belichick TWICE a year, instead of only once back in 2021.
Miami had four straight winning seasons from 2020 to 2023, but they didn’t have a single playoff win. Think some GOAT and all could have changed that?
As Tampa Bay did, the Dolphins would have wasted no time stockpiling superstar weapons around Brady. His arrival means Rob Gronkowski is coming to South Beach, too. And did we mention it’d be Brady vs. the Pats twice a year?
Damn, that would have been a sight to see.
Von Miller To Dallas Cowboys (2022)
After winning his second Super Bowl ring with the Los Angeles Rams as a trade rental in the 2021 offseason, the perennial Pro Bowler cashed in one more time by signing a mammoth six-year deal worth $120 million.
With the benefit of hindsight, we now know this contract hasn’t worked out as hoped for either side. Injuries limited Miller to 23 total games over his first two years with the Bills. He had zero sacks in the 2023 season, and the Bills have yet to get over the Super Bowl hump despite his arrival.
In the 2022 offseason, Miller stated that the Dallas Cowboys offered him a five-year worth $70 million. He was keen on playing for Dallas, but the future Hall of Famer couldn’t turn down more money from Buffalo.
Love or hate the Cowboys all you want, but a Von Miller-Micah Parsons pass-rushing duo would be must-watch TV….not to mention that they’d also have DeMarcus Lawrence and Trevon Diggs anchoring the defense.
Miller to Dallas would have made for a fun homecoming story, too.
Kirk Cousins To New York Jets (2018)
In the 2018 offseason, the Minnesota Vikings gave Kirk Cousins a three-year contract worth a fully guaranteed $84 million. That’s how bad the reigning NFC runner-ups wanted the ex-Washington star.
But there’s one team that wanted Cousins just a little more than the Vikings: The New York Jets, who offered “Captain Kirk” a three-year deal worth a fully guaranteed $90 million.
Cousins took less to join a Minny team that seemed significantly closer to Super Bowl contention. Though he put up superb stats over his six years with the Vikings, the Cousins era largely was largely underwhelming for all parties.
Minnesota only went to the postseason twice with Cousins, and they won just a single playoff game. It didn’t help Cousins that the defense around him was awful and that former head coach Mike Zimmer quickly soured on him.
So looking back, we ask this: What if the Jets came away with Cousins instead of the Vikings?
Landing Cousins means the Jets don’t waste first-round picks on Sam Darnold and later Zach Wilson. His arrival makes this big-market team somewhat watchable again – and there could have been worse than some Kirk Cousins vs. Tom Brady and Josh Allen duos in the AFC East.
No guarantee that Cousins lives up to the hype in Gotham. But maybe Minny remains a Super Bowl contender with Keenum, who fits their offense nicely. Maybe Darnold and Wilson — two highly-touted QB prospects — hit their ceilings elsewhere instead of being ruined by the Jets.
And maybe Aaron Rodgers doesn’t end up getting traded to the circus team in 2023. Maybe he lands with another club that would have put him in a better position to win that second Super Bowl.
Kenny Golladay To Baltimore Ravens (2021)
Golladay missed all but five games in his contract year in 2020, but the ex-Detroit Lions star was nonetheless about to get PAID. He had back-to-back 1,000-yard seasons in 2018 and 2019, leading the NFL with 11 touchdown receptions in the latter year.
There were several teams interested in Golladay, with ESPN’s Adam Schefter mentioning the Baltimore Ravens as one of those teams.
But as everybody knows, Golladay chased the money and signed a four-year deal with the New York Giants worth $72 million. Instead of playing with an MVP quarterback in Lamar Jackson, Golladay saw his career go into rapid decline.
Golladay lasted just two seasons with the Giants, compiling 43 receptions for 602 yards and one touchdown in 18 games before being released.
Now ask yourself this: What if Golladay joined the Ravens’ high-flying offense with Jackson and Mark Andrews? We’ll tell ya this: The former Pro Bowler wouldn’t have gone from zero to hero in the blink of an eye.
And maybe Golladay serves as the final piece to help the Ravens get over the top in the AFC once and for all. Hey, you Kansas City Chiefs haters would easily take a Ravens Super Bowl over a KC dynasty, right?
Le’Veon Bell To Green Bay Packers (2019)
In an all-time blunder, Bell rejected a five-year extension from the Pittsburgh Steelers in the 2018 offseason worth a reported $70 million. He sat out the entire year, believing a better deal awaited him in 2019 free agency.
Bell threw his career and Hall of Fame bid away by signing a four-year deal with the New York Jets worth $52.5 million. It was well-known among the football world that new Jets head coach Adam Gase was enraged over then-GM Mike Maccagnan handing out that much money to a player at a devaluing position.
Bell didn’t even last two seasons in New York before he was cut in the midst of the 2021 seasons. Brief stops with the Chiefs, Buccaneers and Ravens did nothing to revive the former All-Pro’s career, and he was out of the league before his 30th birthday.
After the 2019 trade deadline, Bell revealed that the Packers were among the teams that tried acquiring him. Which brings us to this: Why didn’t Green Bay just sign Bell in the first place?
Yes, yes, we know. Aaron Jones and Jamaal Williams wound up becoming a top-tier rushing tandem anyway. But when he was in his prime, Bell was in his own class of workhorse running backs — basically what Christian McCaffrey is in San Francisco.
The Packers failed time and time again to find more offensive weapons to help Rodgers and Davante Adams during A-Rod’s final years with the organization. Add the ex-Pittsburgh star to the mix, and you have a Rodgers-Adams-Bell trio that might be even better than the Bell-Antonio Brown-Ben Roethlisberger trio in Steel City.
At the very least, Bell signing with Green Bay would have been much better than whatever you want to call his stint in New York.
Chandler Jones To Buffalo Bills (2022)
Much like Le’Veon Bell, Jones’ career went down the drain once he signed with a team that couldn’t make the most of his all-world talents.
The four-time Pro Bowler reportedly thought about joining the powerhouse Buffalo Bills, but he instead joined the Las Vegas Raiders in 2022 free agency on a three-year deal worth $51 million.
So let’s pretend the Bills never sign Miller, and they end up with Jones instead. Miller goes on to shine with Dallas or somewhere else, while Jones continues his Hall of Fame-like run in Buffalo.
Jones, a proud member of the 100-sack club, might serve as the difference for Buffalo to get over the Chiefs and Cincinnati Bengals in the AFC. At least, he fares better in Buffalo than he did in Vegas, where Jones was released after just one year following off-the-field troubles.
If Jones arrived in Buffalo and continued his all-world play, the Bills could have totally won a Super Bowl by now. I mean, this team has lacked all-world pass-rushers for a while, and Jones could have been the difference.
Instead, Jones joining Vegas marked the unfortunate beginning of the end for an otherwise remarkable career.
Earl Thomas To San Francisco 49ers (2019)
The last remaining member of the Seahawks’ “Legion of Boom” suffered a fractured leg that ended his 2018 season abruptly. Thomas infamously flipped off the Seahawks sideline as he was carted away, a tragic end to his legendary career in the Pacific Northwest.
In 2019 free agency, the Baltimore Ravens handed Thomas a lucrative four-year deal worth $55 million. The ex-Seahawks safety looked like he was worth every penny in Baltimore, earning his seventh career Pro Bowl nod while helping the team to the league’s top record at 14-and-2.
But the Ravens released Thomas ahead of the 2020 season after he punched teammate Chuck Clark during a practice. Thomas was already reportedly disliked in the locker room, and the Ravens’ “leadership council” convinced John Harbaugh to release the veteran stalwart.
Interestingly, Thomas was never signed by another NFL team again.
Which brings us to this: WHAT IF Thomas had stayed on the West Coast and joined the Seahawks’ archrivals in the San Francisco 49ers?
Consider this: Thomas would have added more juice to the Seahawks-49ers rivalry. Oh, and he would have reunited with old Legion of Boom teammate Richard Sherman — who had signed with San Fran in 2018 free agency.
And we’ll just go ahead and guess that Thomas would have played nicer in San Fran and wouldn’t have done something stupid to abruptly end his tenure in San Francisco. Not to mention that by joining the 49ers’ star-studded defense, Thomas could have potentially led the 49ers to a Super Bowl championship or two by now.
Thomas, Sherman, Fred Warner AND Nick Bosa on that defense? Wonder how Patrick Mahomes and company would have fared against those 49ers in Super Bowl 54.
Thomas and Sherman leaving Seattle to win another Super Bowl together in San Fran would have been Oscar-worthy stuff. Too bad we never got to see them try it out together.
Philip Rivers To Las Vegas Raiders (2020)
The Raiders had Derek Carr at the time, but the ex-Los Angeles Chargers star was once linked to the Bolts’ archrivals.
As 2020 free agency neared, NFL Network’s Ian Rapoport said the Raiders loomed as a possible destination for the eight-time Pro Bowler. Fast forward all these years later, and we’re officially upset that it never came to fruition.
Rivers signed a one-year deal with the Indianapolis Colts, while the Raiders got to endure three more years of mediocrity with Derek Carr. Yay.
Rivers had a stellar year in Indy and helped them to a playoff berth, but they were eliminated by Buffalo in the Divisional Round. Despite showing few signs of slowing down, Rivers announced his retirement after the loss.
But WHAT IF the Raiders traded Carr and signed Rivers after his 16-year run with the Bolts?
Rivers would be slinging it in an offense with Josh Jacobs, Hunter Renfrow and Darren Waller. Plus, he and Jon Gruden would have made for must-watch TV with their never-ending epic mic ’d-up soundbites.
Maybe Rivers LOVES Vegas so much that he continues his borderline Hall of Fame career instead of retiring while still at the top of his game? Hmm…
DeAndre Hopkins To Buffalo Bills (2023)
After his release from the Arizona Cardinals, DeAndre Hopkins mulled plenty of offers before surprisingly joining the Tennessee Titans on a two-year deal worth $26 million.
Good on D-Hop for being paid and having a vintage D-Hop season in 2023. But the Titans were awful anyway, and we still continue to dream of Hopkins joining forces with an elite quarterback like Josh Allen.
The Bills lost to the Chiefs in the 2023 AFC Divisional Round. Once again, the lack of a true No. 2 receiver to help Allen and Stefon Diggs led to the Bills’ postseason unraveling.
An Allen-Hopkins-Diggs trio gives us all can’t-miss highlight reels. And again, if you’re sick of Kansas City always winning, the Bills probably thwart their repeat with Hopkins in that offense.
J.J. Watt To Pittsburgh Steelers (2021)
With the Houston Texans in rebuilding mode, Watt was granted his release and became a highly sought-after free agent in 2021.
Watt surprised everybody by signing with a “meh” Arizona Cardinals team on a two-year deal worth $28 million. Unfortunately, injuries limited the three-time Defensive Player of the Year to seven games in 2021, essentially wasting Watt’s penultimate season.
He regained his star-like form in 2022, racking up 12.5 sacks and seven pass defenses on a lousy Arizona team. Watt then retired after the season, citing a wish to spend more time with his family.
Since the Cardinals wasted Watt’s last two seasons, we remain bitter and wish he joined younger brother TJ in Pittsburgh.
Imagine if the Watt Bros were wreaking havoc together on defense. And at least Pittsburgh was a playoff contender, so maybe their winning ways would have convinced him to play longer and chase a championship with TJ.
