Best and worst NFL free-agent contracts since 2020: Biggest deals ranked

This week marks the start of the NFL’s annual spending spree. The league’s two-day negotiating window opens Monday at noon ET, kicking off a wave of deals that will reshape rosters before free agency officially begins Wednesday.

Big names will move. Big money will be spent. And history suggests a lot of it won’t age well.

Every offseason brings massive contracts for the top unrestricted free agents, but the return on investment is wildly uneven. For every signing that helps push a contender over the top, several others quickly become cautionary tales. Below, we break down the five best and five worst big-ticket free-agent contracts since 2020.

Best big-ticket contracts since 2020

1. Sam Darnold, QB, Seattle Seahawks (2025)

Just last offseason, the Seattle Seahawks gambled by trading Geno Smith to the Las Vegas Raiders and signing Sam Darnold in free agency. Yes, Darnold was coming off a career year in which he won 14 games with the Minnesota Vikings, but there’s no question he flailed down the stretch, which left some teams hesitant to pursue him. 

The former No. 3 overall pick signed a three-year, $100.5 million deal with Seattle in free agency. That $33.5 million AAV came in lower than what some expected, but it was still the second-largest contract of the offseason. Darnold of course went on to become the first starting quarterback to win a Super Bowl after playing for five teams, and the first quarterback from that vaunted 2018 class that included Baker Mayfield, Josh Allen and Lamar Jackson to make the Super Bowl. 

Darnold’s individual statistics did not meet his 2024 season with the Vikings, but there’s no question he played a big part in Seattle’s surprising success this year. He became just the fifth quarterback to ever register multiple 14-win seasons, joining Tom Brady, Patrick Mahomes, Peyton Manning and Joe Montana. 

2. Trey Hendrickson, EDGE, Cincinnati Bengals (2021)

In 2021, Trey Hendrickson signed a four-year, $60 million contract with the Cincinnati Bengals. It was the sixth-largest contract of that offseason. The former third-round pick of the New Orleans Saints went from rotational pass rusher to starter, and upped his sack total from 4.5 to 13.5 in a contract year. The Bengals saw legitimate superstar potential in Hendrickson, and they were right.

In his first season with the Bengals, Hendrickson recorded 14 sacks as Cincinnati made the Super Bowl. He recorded 17.5 sacks in both 2023 and 2024, and picked up four straight Pro Bowl bids and his first All-Pro selection. Unfortunately, Hendrickson struggled to score that second contract from the Bengals — which became a major storyline in itself. But there’s no doubt he’s one of the best free-agent signings in recent memory. After all, Hendrickson owns the top three individual sack seasons in Bengals franchise history!

3. Joe Thuney, LG, Kansas City Chiefs (2021)

Following a disastrous performance from the offensive line in Super Bowl LV, the Kansas City Chiefs signed former Patriots offensive guard Joe Thuney to a five-year, $80 million deal. It was the third-largest contract handed out that offseason and smart move as the franchise looked to rebuild Patrick Mahomes’ protection. 

Thuney would go on to make three straight Pro Bowls and pick up three straight All-Pro selections as well, while winning Super Bowls LVII and LVIII with Kansas City. He allowed just four sacks in four seasons, and was an important member of one of the best offensive lines in the league. While Thuney was traded to the Chicago Bears last offseason, he’s still considered an elite protector. He even won the first-ever NFL Protector of the Year Award this season, beating out finalists such as Penei Sewell and former teammate Creed Humphrey. 

4. Trent Williams, LT, San Francisco 49ers (2021)

This was technically a re-signing, but it was the first contract the San Francisco 49ers actually gave Trent Williams. The star left tackle was traded to San Francisco during the 2020 NFL Draft but he was due for a massive extension in 2021. That came in the form of a six-year, $138.06 million deal that made Williams the highest-paid offensive lineman in the NFL. It was also the largest deal in free agency by over $55 million.

Williams went on to make three straight Pro Bowls and garner three straight First Team All-Pro selections as the 49ers made the NFC Championship game in all three of those years. Even at 37-years-old, Williams is still considered one of the best offensive tackles in the NFL.

5. Xavier McKinney, S, Green Bay Packers (2024)

In 2024, the Green Bay Packers signed former New York Giants safety Xavier McKinney to a four-year, $67 million deal. It was the sixth-largest contract of that offseason. McKinney responded to his payday by recording 88 tackles, one sack, 11 passes defensed and a career-high eight interceptions. Those numbers earned him his first Pro Bowl bid, and a First Team All-Pro selection as well.

This past season, McKinney recorded 107 tackles, one sack, 10 passes defensed and two interceptions, which landed him Second Team All-Pro honors. He’s a playmaker that can do it all, whether it’s breaking up passes deep downfield or playing in the box.  

Worst big-ticket contracts since 2020

1. J.C. Jackson, CB, Los Angeles Chargers (2022)

After recording a whopping 17 combined interceptions in 2020 and 2021 for the Patriots, J.C. Jackson signed a five-year, $82.5 million deal with the Los Angeles Chargers in 2022. It was the second-largest contract handed out that offseason. 

Jackson would play in just seven (!!) games for the Chargers before being traded back to New England in a late-round pick swap. He made over $38 million for those seven games. Injuries played a part in this dramatic fall from grace, as Jackson had ankle surgery before even playing a down for L.A., then dislocated his knee in Week 7. Jackson’s last NFL snap came on Dec. 7, 2023.

2. Kenny Golladay, WR, New York Giants (2021)

The Giants signed former Detroit Lions wideout Kenny Golladay to a four-year, $72 million deal in 2021. It was the fourth-largest contract that offseason. Golladay put up back-to-back 1,000-yard seasons in 2018-19, and led the NFL in receiving touchdowns in 2019 with 11.

Even before he landed in the Big Apple, injuries had begun to take their toll on Golladay. A hip injury held him to five games played in his final season with Detroit in 2020, he suffered through a hamstring issue in the summer and then suffered a knee injury five games into his Giants career. Golladay finished his first season in New York with 37 catches for 521 yards and zero touchdowns. Things didn’t get any better in 2022, as Golladay caught just six (6) passes for 81 yards and one touchdowns in 12 games played. 

In all, Golladay caught 43 passes for 602 receiving yards and one touchdown in 26 games played with the Giants. That marked the end of his NFL career, but he did make over $40 million with the Giants. 

3. Christian Wilkins, DT, Las Vegas Raiders (2024)

The mystery of Christian Wilkins remains unsolved. In 2024, the Raiders signed the star defensive tackle to a four-year, $110 million deal that was the second-largest contract of the offseason. Wilkins played just five games before suffering a foot injury which landed him on injured reserve. Then, things got worse.

NFL Media reported the Raiders wanted Wilkins to get another procedure done on his foot that following offseason, which is something he refused to do. Wilkins instead wanted to rehab the injury, leading the franchise to release him with a “terminated vested veteran” designation. There was apparently more to the story of Wilkins’ release, as ESPN reported he “playfully” went to kiss an unnamed teammate on the top of his head in the locker room, and that teammate took offense to it. ESPN published an article reporting that a complaint was filed to the Raiders’ human resources department following the incident. 

There weren’t many more details reported about this situation, but Wilkins made $49.8 million for five games played. He did not play in 2025. 

4. Kirk Cousins, QB, Atlanta Falcons (2024)

Following six successful seasons with the Vikings, quarterback Kirk Cousins landed a four-year, $180 million deal from the Atlanta Falcons. It was the largest contract of the 2024 offseason. Not only did the Falcons sign Cousins to the largest free-agency deal that year, but they then used the No. 8 overall pick on another quarterback in Michael Penix Jr. After Cousins threw 18 touchdowns and a league-leading 16 interceptions through 14 games, he was benched for the rookie Penix — who did enough in the final three games of the season to earn the title of QB1. 

Cousins did go 5-3 as the starter this past season for the Falcons while throwing 10 touchdowns compared to five interceptions, but this was not the signing Terry Fontenot and Raheem Morris envisioned. Both were fired this offseason, while Cousins made over $90 million.

5. Derek Carr, QB, New Orleans Saints (2023)

After the Raiders released Derek Carr in 2023, the Saints decided to sign the veteran quarterback to a four-year, $150 million deal that was by far and away the largest contract of the offseason. No other free agent even reached $88 million in total value. 

Carr’s first season with the Saints was interesting. He started off the year 5-7, but ended on a tear — throwing 14 touchdowns compared to two interceptions while finishing the year 4-1. The following season, Carr went 5-5 for the Saints while suffering through several injuries. A fractured hand and concussion in Week 14 ended his year. Carr then retired the following offseason, citing a shoulder injury. He made $70 million from New Orleans for his 27 starts, and there are apparently teams out there that want to give him more money.