A landmark event took place in the NFL on Tuesday; a head coach trade. With the New Orleans Saints trading Sean Payton to the Denver Broncos, the head coach joins an exclusive club of coaches to be traded. Only a handful of coach trades have occurred throughout NFL history, and they usually leave a huge mark on the league, as Broncos fans are hoping Payton can do for them.

Today, we're going to rank the five biggest coaching trades in NFL history. It's important to note that we're ranking these trades based on the compensation received for each coach, not on their overall impact on the league. This gives us a concrete, mathematical way of ranking each deal (and besides, the Payton trade just happened, so it's impossible to judge its impact). Additionally, we wanted to point out the few trades that just missed out on the list.

  • 2006: Herm Edwards to the Chiefs: The New York Jets sent Herm Edwards, who had been their head coach for five seasons, to the Kansas City Chiefs in exchange for a 2006 fourth-round pick. In three seasons with Kansas City, Edwards compiled a 15-33 record with one playoff appearance in 2006.
  • 2019: Bruce Arians to the Buccaneers: After Arians retired following the 2017 season, the Arizona Cardinals sent him along with a 2019 seventh-round pick to the Tampa Bay Buccaneers in exchange for a 2019 sixth-round pick. Arians racked up a 31-18 record in three seasons with Tampa Bay, including a win in Super Bowl 55.
  • 1970: Don Shula to the Dolphins: Technically this one isn't a trade, but it's still worth mentioning. The Miami Dolphins poached Don Shula away from the Baltimore Colts in 1970, but the league found them guilty of tampering. As punishment, the Colts received the Dolphins' first-round pick in 1971. Shula then became a legend in Miami, with a 257-133-2 record, two Super Bowls and a perfect season in 1972 in his 26-year tenure.

With those honorable mentions out of the way, here are the five biggest head coach trades in NFL history.

5. 1999: Mike Holmgren to the Seahawks

  • Seahawks receive: Mike Holmgren
  • Packers receive: 1999 second-round pick

In the late 90s, Mike Holmgren had earned a reputation as one of the best head coaches in football. With a 75-37 record and a Super Bowl 31 win in six seasons with the Green Bay Packers, it's easy to see why. Holmgren also received credit for developing Brett Favre into a Hall of Fame quarterback after his rough start.

At this time, the Seattle Seahawks hadn't made the playoffs in a decade. Desperate to break the skid, they offered Holmgren an eight-year contract worth $4 million annually (a lot at the time). However, because he was still under contract with the Packers, the Seahawks had to give up draft compensation.

Although he never reached the heights of his time in Green Bay, Holmgren still had a successful tenure in Seattle. In 10 seasons, he finished with an 86-74 record, including five division titles and a Super Bowl 40 appearance. Meanwhile, Ray Rhodes, Holmgren's successor in Green Bay, only lasted one season after going 8-8.

4. 2000: Bill Belichick to the Patriots

  • Patriots receive: Bill Belichick, 2001 fifth-round pick, 2001 seventh-round pick
  • Jets receive: 2000 first-round pick, 2001 fourth-round pick, 2001 seventh-round pick

In terms of impact on the NFL, this trade is undoubtedly at the top of the list. Many see Belichick as the greatest NFL coach ever, and it's hard to argue against that with his six rings. Before he built his dynasty in New England, though, he was a member of the rival New York Jets.

However, his time with the Jets was very short and bizarre. Bill Parcels (who we'll get to later) resigned as New York's head coach following the 1999 season, and told management he wanted Belichick to succeed him. Instead, after only one day on the job, Belichick announced his resignation in what should have been his introductory press conference. Soon after, he joined the Patriots just after they had fired Pete Carroll. However, they had to give up a first-round pick and more to hire him.

After that, the rest is history. Through 23 seasons in New England, Belichick has a 262-108 record, 17 AFC East titles, and six Super Bowl titles. With Belichick off to the Patriots, the Jets instead hired Al Groh, who went 9-7 in his only season in New York.

3. 2023: Sean Payton to the Broncos

  • Broncos receive: Sean Payton, 2024 third-round pick
  • Saints receive: 2023 first-round pick, 2024 second-round pick

Sean Payton arrived in New Orleans in 2006, the same year they signed Drew Brees in free agency. The two turned the Saints into a contender overnight, eventually winning Super Bowl 44 in the 2009 season. Payton coached the Saints for 15 seasons, going 152-89, winning six NFC South titles and the aforementioned Super Bowl. The Bountygate scandal clouded his career for a while, but he is still the most successful coach in team history by a wide margin.

Payton resigned from his position following the 2021 season, one year after Brees retired, and became an analyst with FOX. However, he continually teased a return to coaching, and interviewed with multiple teams this offseason. On Tuesday, the Broncos made the move official by acquiring him from the Saints for a first- and second-round pick.

Now, Sean Payton will have the tough task of turning around a Broncos team that just went 5-12, as well as reviving Russell Wilson's career. On the other side, the Saints recoup some of the draft assets they traded away to the Eagles last offseason. Time will tell how this trade works out, but it is certainly a blockbuster, as Sean Payton was one of the most sought-after coaches in recent memory.

2. 1997: Bill Parcels to the Jets

  • Jets receive: Bill Parcels
  • Patriots receive: 1997 third-round pick, 1997 fourth-round pick, 1998 second-round pick, 1999 first-round pick, $300,000

See, told you we'd come back to Bill Parcels. By 1997, the head coach had built up an astounding resume, including two Super Bowls with the Giants. In fact, he had just led the Patriots to Super Bowl 31, where they lost to Holmgren's Packers. However, he left New England after a dispute with Robert Kraft, and the Jets saw an opportunity.

As is often the case in these situations, Parcells was still under contract with the Patriots, so the Jets couldn't hire him outright. Ironically, they instead hired Belichick to be their head coach, then hired Parcells as an “advisor.” Needless to say, the Patriots were furious and threatened legal action against Parcells and the team. Eventually, the league worked out a deal that awarded New England a haul of draft picks in exchange for releasing Parcells from his contract.

After going 4-28 the previous two seasons, Parcells went 29-19 with an AFC Championship Game appearance in three seasons under Parcells. He retired after the 1999 season (see above), but later returned to coach the Cowboys from 2003-2006. Meanwhile, the Patriots went 27-21 with two playoff appearances in three seasons under Carroll. Think of this trade as the A New Hope to the Belichick trade's Empire Strikes Back.

1. 2002: Jon Gruden to the Buccaneers

  • Buccaneers receive: Jon Gruden
  • Raiders receive: 2002 first-round pick, 2002 second-round pick, 2003 first-round pick, 2004 second-round pick, $8 million

Maybe not in terms of impact, but in terms of draft compensation, this trade is by far the biggest involving a head coach. Gruden had emerged as a strong coach by 2002, off the heels of two straight AFC West titles. On the other hand, Tampa Bay had been a strong team throughout the late 90s and early 2000s, but couldn't get over the hump in the postseason. After a Wild Card loss to the Eagles in 2001, the Buccaneers fired Tony Dungy despite his 54-42 record over six seasons.

Tampa Bay interviewed a variety of coaches, including Parcells, but came up fruitless. Needing a big splash, the Buccaneers traded a haul to the Raiders to acquire Gruden. The move paid immediate dividends, though, as they won Super Bowl 37 against none other than the Raiders in Gruden's first year.

After that, though, both teams began to trend downward. Gruden went just 45-51 in the rest of his Buccaneers tenure before the team fired him in 2008. He then became an analyst on Monday Night Football, returned to the Raiders, and then resigned following controversial leaked emails in 2021. The Buccaneers also removed Gruden from their Ring of Honor following the scandal. On the other hand, the Raiders didn't make the playoffs again until 2016, and still have not won a playoff game since their Super Bowl appearance in 2002.