Ranking all NFL HC trades made in the past 25 years

Miami Dolphins v Las Vegas Raiders
Las Vegas Raiders HC Jon Gruden

Each NFL offseason almost always features several head coaching changes. When the head coach fails to meet certain expectations from the team that hired them, they are often fired from their position.

This usually leads to each team having a head coaching vacancy to explore all of the available options. They have the opportunity to sign coaches that are free agents or promote an assistant or coordinator from any team to become their head coach.

While it's a rare occurrence, it's also perfectly within the rules for NFL teams to acquire a head coach via trade. It creates more of a risk to surrender assets when acquiring a head coach, but if an organization believes it will significantly upgrade its chances of success, it could definitely be worth the payoff. These trades usually include draft picks and sometimes include cash.

The 2023 NFL offseason could potentially see another one of these types of trades. Sean Payton retired from his position as the head coach of the New Orleans Saints following the 2021 season, but is rumored to be interested in making a return in 2023. It's also believed he is more interested in joining a new team, but is still under contract with the Saints.

Any team looking to add Payton as their head coach will likely need to trade assets to the Saints in order to acquire him. Over the last 25 years, just four NFL head coaches have been traded to a new team. Here's how each of the four trades ranks according to what the new team gave up to acquire them relative to their eventual success.

#4 - Bill Parcells

Bill Parcells
Bill Parcells

Bill Parcells is widely considered one of the greatest head coaches in NFL history. He helped the New York Giants win two Super Bowl rings, while twice being named the Coach of the Year. Following his legendary run with the Giants, he also helped the New England Patriots reach a Super Bowl.


Parcells was acquired by the New York Jets via trade with the Patriots in 1997 for first, second, third, and fourth-round draft picks. He never had a losing season with the Jets but lasted just three years with the team. The lack of longevity makes surrendering so much draft capital a losing deal for the Jets.

#3 - Mike Holmgren

Mike Holmgren
Mike Holmgren

Mike Holmgren began his head coaching career with the Green Bay Packers. He helped the franchise appear in two Super Bowls while winning a ring in one of them. He was then traded to the Seattle Seahawks prior to the start of the 1999 NFL season.

The Seahawks surrendered just a second-round draft pick to acquire Holmgren. He helped them reach the NFL Playoffs for five consecutive seasons, while also appearing in a Super Bowl. The Seahawks didn't have to give up much for a head coach that helped them remain contenders during his decade in the position.

#2 - Jon Gruden

Jon Gruden
Jon Gruden

Jon Gruden spent the first four years of his career with the Oakland Raiders. He was then traded to the Tampa Bay Buccaneers for a massive haul. The Buccaneers gave up two first-round picks, two second-round picks, and $8 million in cash to acquire the young star head coach.

Their investment paid off immediately as the Buccaneers won a Super Bowl ring in Gruden's first year in his new position. He helped them reach the NFL Playoffs twice more in his seven years with the team. He left in 2008 and spent 10 years away from coaching before returning as the head coach of the Las Vegas Raiders.

#1 - Bill Belichick

Bill Belichick
Bill Belichick

Bill Belichick is one of the most successful head coaches in NFL history. This is demonstrated by his six Super Bowl rings and nine conference championships -- the most by any NFL head coach ever. This has all been achieved with the New England Patriots, but not before being acquired via trade from the New York Jets.


Belichick spent five years as the head coach of the Cleveland Browns. He then spent one day as the head coach of the Jets in 2000 before resigning from his position and eventually being traded to the Patriots. The Jets acquired a first, fourth, and seventh-round draft pick. Nonetheless, when Belichick arrived in New England, the rest was history.

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Edited by Nicolaas Ackermann
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