The NFL free agent market opened its doors back in 1993. Fast forward more than three decades later, and it remains a pivotal part of successful roster building.
Yes, you need to draft well and use the trade market accordingly, but efficient free-agent signings go a long way in sustaining a winner in today’s NFL.
Over the last half-decade, we’ve seen plenty of marquee free-agent signings that changed a franchise for the better. On the flip side, other recent signings turned out to be such wastes of money that teams continue to regret to this day.
With that, let’s dive into the five best NFL free agent signings from 2019 to 2023…as well as the five worst.
Best: Tom Brady
Like we were gonna start this list with anybody else…
After 20 years in New England, Tom Brady grew tired of Bill Belichick’s tight ship and announced that he was leaving the Patriots. Shortly after the free agent market opened, the GOAT signed a two-year deal worth $50 million in fully guaranteed money.
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Brady’s arrival in Tampa prompted old pal Rob Gronkowski to end his one-year retirement, so the Bucs acquired the other future Hall of Famer via trade with the Patriots to reunite the super duo.
All Brady and Gronk did in their first year with the Bucs was lead Tampa Bay to a Super Bowl 55 championship — in the Bucs’ home stadium of Raymond James Stadium no less! Brady’s Bucs outlasted three all-time greats in Drew Brees, Aaron Rodgers and Patrick Mahomes in the improbable Super Bowl title run.
After the Super Bowl triumph, Brady was awarded a one-year contract extension.
In 2021, Brady smashed the Bucs’ single-season passing records by throwing for 5,316 yards and 43 touchdowns — leading Tampa to its first NFC South division title in 14 years. Their quest for a repeat ended, however, with a heartbreaking loss to Matt Stafford and the eventual champion Los Angeles Rams.
The Bucs unexpectedly regressed big-time in 2022, but Brady’s efforts were enough to help Tampa finish 8-and-9 for a second straight NFC South division crown. Their season ended with a blowout loss to the Dallas Cowboys in the Wild Card Round.
Three playoff berths, two division titles and a Super Bowl 55 championship? That, folks, is how you spend money in free agency. All the Bucs had to do was pay the GOAT market value, and it changed the franchise forever.
Worst: Le'Veon Bell
The three-time Pro Bowl running back rejected a five-year contract extension with the Pittsburgh Steelers worth $70 million in the 2018 offseason, believing a better deal awaited him in 2019 free agency.
Bell wound up sitting out the entire 2018 season due to a contract dispute, which did absolutely nothing to improve his value. Nonetheless, the New York Jets got desperate and handed Bell a lucrative four-year deal worth $52.5 million.
Bell wound up being a mega bust in Gotham from the get-go. He had a career-low three rushing touchdowns and averaged a horrid 3.2 yards per carry — so don’t be fooled by his 1,250 yards from scrimmage. He was getting the ball a lot and hardly doing anything with it.
Bell got off to another awful start in 2020, appearing in just two games before being released in October. The defending Super Bowl champion Kansas City Chiefs took a flier on Bell, but he too proved ineffective there and proved that he was well past his playing prime.
His final season was split with the Bucs and Baltimore Ravens. Before he knew it, Bell was out of the NFL before his 30th birthday.
Probably should have just taken that $70 million from Pittsburgh, huh?
Best: Joe Thuney
The Chiefs’ second-string offensive line was man-handled by the Bucs’ front seven in their humiliating Super Bowl 55 loss. That ugly performance prompted GM Brett Veach to seek massive reinforcements ASAP.
Kansas City signed the former Patriots guard to a massive five-year deal worth $80 million. Throw in the trade for Orlando Brown Jr. and the draft selections of Creed Humphrey and Trey Smith, and now you had a complete and near-perfect o-line overhaul.
There’s a long history of former Patriots stars declining once they leave New England, but this wasn’t the case for Thuney. If anything, he just continued to get better and better in Kansas City.
Thuney shored up the interior of the Chiefs’ o-line. Per Pro Football Focus, he allowed just four total sacks in the regular season over his first three years with the club.
Thuney’s rock-solid pass-blocking held up Mahomes against the ferocious Philadelphia Eagles’ and San Francisco 49ers’ pass-rush units in Super Bowl 57 and 58, respectively. Without Thuney’s efforts, those Chiefs probably don’t win back-to-back Super Bowls.
Thuney got paid and became a four-time Super Bowl champion in Kansas City. If that’s not an all-time great free agent signing, what is?
Worst: Landon Collins
Collins emerged as one of the NFL’s elite defensive backs during his four-year run with the New York Giants. He was named to three straight Pro Bowls and earned First-team all-pro honors in his sophomore year.
After the Giants decided not to extend Collins, he signed a massive six-year contract with the NFC East rival Washington club worth $84 million.
That contract felt like a giant mistake from the get-go, especially with seeing how other top safeties like Earl Thomas, Adrian Amos (AY-MISS), Tyrann Mathieu and Eric Weddle signed for far less money and term.
A renowned ball-hawker in New York, Collins totaled just three interceptions and seven pass defenses over his three seasons in Washington. And per Pro Football Focus, Collins’ highest grade in DC was a “meh” 60.0, which he garnered in the 2020 season.
Collins was released by the Commanders three years into the $84 million deal. A one-year return to the Giants in 2022 did nothing to revive Collins’ career, and he was out of the NFL for good by 2023.
Best: Jack Conklin
In a desperate effort to rebuild their atrocious offensive line, the Cleveland Browns signed ex-Tennessee Titans star offensive tackle Jack Conklin to a three-year deal worth $42 million.
The Browns completed the overhaul on the offensive line by using their first-round pick on Jedrick Wills. Fast forward to 2024, however, and it’s clear that Conklin was the most impactful addition of them all.
Conklin has remained one of football’s premier offensive tackles since coming over to Cleveland. He has been a top-tier run-blocker for Nick Chubb and Jerome Ford, and Conklin has allowed no more than two sacks in a season for the Browns, per PFF.
Most importantly, Conklin helped Cleveland end an 18-year playoff drought in 2020 — and to their first postseason W since 1994. His efforts guided the Browns to another playoff berth in 2023.
Late in the 2023 campaign, Conklin was awarded a massive four-year contract extension worth $60 million — a nice juicy reminder that the Browns hit the jackpot when they handed him $42 million in 2020!
Worst: Trey Flowers
Former Detroit Lions GM Bob Quinn and head coach Matt Patricia had a strange obsession with bringing in former New England Patriots players, hoping those guys would help develop a championship culture in Motown.
Those two single-handedly destroyed the Lions before the arrivals of Dan Campbell and Brad Holmes, before the latter two had to build it back up. One of the biggest swing-and-miss moves by the old regime? The signing of ex-Patriots star Trey Flowers.
After winning his second Super Bowl ring with New England, Flowers signed a giant five-year, $90 million deal with the Lions. That was a giant overpay for a non-Pro Bowler who never topped 7.5 sacks in a season, and the Lions learned this quickly.
Flowers was limited to 29 games over his three years with the Lions, compiling just 10.5 total sacks and five forced fumbles. The Lions’ defense never finished higher than 26th in scoring D during Flowers’ three-year run.
The Lions released Flowers in the 2022 offseason.
Best: Trey Hendrickson
Hendrickson broke out in the 2020 season with the New Orleans Saints, in his contract year no less. He racked up 13.5 sacks on the Saints’ star-studded defense, though it felt like a mirage considering he had 6.5 combined sacks over the previous three years.
Nonetheless, the Cincinnati Bengals took the risk and signed Hendrickson to a four-year contract worth $60 million in the 2021 offseason. This contract was widely panned at the time, but Hendrickson and the Bengals wound up getting the last laugh.
Proving he was no one-hit wonder, Hendrickson actually set new career-highs in sacks with 14 and in forced fumbles with three. He earned his first Pro Bowl nod and helped the Bengals to an unexpected Super Bowl 56 appearance, where they narrowly fell to the Los Angeles Rams.
Hendrickson remained in beast mode during the 2021 postseason run, racking up 3.5 sacks and a forced fumble in four postseason games.
Though injuries limited him to eight games in 2022, Hendrickson earned his second Pro Bowl selection after posting eight sacks and a trio of forced fumbles. Cincy returned to the AFC Championship Game, narrowly falling to Patrick Mahomes’ Chiefs.
Cincinnati handed their star pass-rusher a one-year extension in the 2023 offseason. How did he respond? By turning in ANOTHER career year, racking up 17.5 sacks for a third straight Pro Bowl nod.
It’s a good thing Bengals owner Mike Brown decided to start spending money in free agency, huh? Sure hit a grand slam with the Hendrickson signing!
Worst: Kenny Golladay
Looking to bolster the receiving corps around young quarterback Daniel Jones, the Giants handed former Lions star wideout Kenny Golladay a giant four-year deal worth $72 million in the 2021 offseason.
Golladay was a two-time 1,000-yard wideout in Detroit who led the NFL with 11 receiving touchdowns in 2019. So what could go wrong? Surely he’d give “Danny Dimes” that game-changing target he needed to break out…right?
Golladay had an awfully disappointing first year in the Meadowlands, tallying just 37 receptions for 521 yards and zero touchdowns. He was limited to 12 games the following year, finishing with just six catches for 81 yards and a single touchdown.
New York released Golladay after just two seasons, taking on a hefty $14.7 million dead money hit for 2023. Making matters worse for Golladay? No team bothered to pick him up and give the veteran wideout another chance after a miserable two-year stint with the G-Men.
Best: Tyrann Mathieu
While Tyrann Mathieu has proven to be a great pickup by the Saints, we’d like to clarify that we’re speaking on the Chiefs’ 2019 signing of “Honey Badger”.
Kansas City rebuilt its defense in the 2019 offseason, hiring Steve Spagnuolo to replace Bob Sutton as the DC. Mathieu and Frank Clark were brought in to rebuild the defense, while the team bid farewell to veterans Eric Berry, Justin Houston and Dee Ford.
After a one-year stint with the Houston Texans, Mathieu signed a three-year deal with the Chiefs worth $42 million. And he proved to be worth every single penny.
Over his three seasons with the Chiefs, Mathieu earned two First-team all-pro nods and a pair of Pro Bowl selections. The do-it-all safety had 13 interceptions, 27 pass defenses, four fumble recoveries and three sacks with Kansas City.
He won a Super Bowl 54 ring in his first year with the team and helped them back to the big game one year later. In his three years there, Kansas City won at least 12 games each season and never once failed to make the AFC Championship Game.
Many were baffled by the Chiefs’ decision to not extend Mathieu once his contract ran up, but they won back-to-back Super Bowls anyway. Mathieu, meanwhile, has remained a top-tier safety in the Big Easy, so it wasn’t the worst divorce by any means.
Worst: J.C. Jackson
The Chargers made two big moves on the defensive side of the ball in the 2022 offseason. The first one was signing ex-Patriots cornerback JC Jackson to a five-year contract worth $82.5 million.
The second big move was trading for superstar edge-rusher Khalil Mack via the Chicago Bears. Guess which one panned out, and guess which one was an all-time flop?
The Chargers ignorantly thought they would help Jackson remain a superstar when he was clearly a product of Bill Belichick’s elite defensive system.
As a Patriot, Jackson flourished as a ball-hawker with 25 interceptions and 53 pass breakups, winning a Super Bowl 53 ring in his 2018 rookie year. But Belichick wisely knew that Jackson was replaceable, so he was happy to let the undrafted product price himself out of New England.
Jackson was limited to six games in 2022, having suffered a ruptured Patellar Tendon that abruptly ended his year. Before the injury, Jackson had been benched once and had a laughably sad 28.7 grade at PFF for the year.
Jackson appeared in two games for the Bolts in 2023 before getting traded back to New England, all but ending the $82.5 million headache once and for all.
