Ranking Bill Belichick's Worst Trades Since Taking Over the Patriots

The New England Patriots have the reputation of an organization that, for better or worse, isn't afraid to make trades. Since becoming the head coach back in 2000, Bill Belichick has been the mastermind of such transactions. While the six-time Super Bowl champ has pulled off some glaring victories in these deals -- look no further than him acquiring Hall of Fame wide receiver Randy Moss for a fourth-round draft pick -- he's also authorized a slew of trades that have not panned out.

With that mind mind, let's shed some light on some of Belichick's worst trades as the de facto general manager of the Patriots.

7. Trading Away Chandler Jones (2016)

The Patriots stunned the NFL in the 2016 offseason when they traded away breakout defensive end Chandler Jones to the Arizona Cardinals for offensive guard Jonathan Cooper and a second-round pick. Let's start by saying that Cooper, a former No. 7 overall pick, was released by New England before he ever appeared in a game for the team, and that acquired pick was ultimately traded. Jones, on the other hand, has established himself as one of the league's most formidable pass rushers. He's been named an All-Pro twice in his four seasons with Arizona, and is fresh off his best campaign as a pro, during which he accumulated 19 sacks, 26 QB hits, five pass deflections, and an NFL-leading eight forced fumbles. Consider the mic dropped.

6. Trading for WR Brandin Cooks (2017)

Looking to add speed on the perimeter in the 2017 offseason, the Patriots acquired wideout Brandin Cooks and a fourth-round pick from the New Orleans Saints in exchange for a first- and third-round selection. Though Cooks was productive with New England -- he produced 65 receptions for 1,065 yards and seven touchdowns -- he spent just one year with the franchise. The Saints, meanwhile, used that first-rounder on offensive tackle Ryan Ramczyk, who was named an All-Pro in 2019 and has played 99% of the offensive snaps since his rookie year. To add insult to injury, the Patriots forfeited the pick they acquired due to Deflategate.

5. Trading for Trent Brown (2018)

In April of 2018, the Patriots struck a deal with the San Francisco 49ers that sent offensive lineman Trent Brown and a fifth-round pick to Foxborough for a third-rounder. At the time, it seemed like New England was acquiring a player who would anchor its OL for the foreseeable future. However, Brown only spent one season with the franchise before the Pats let him walk in free agency. The 49ers, meanwhile, used the acquired selection on safety Tarvarius Moore, who is poised to make a big jump in Year 3 after a solid sophomore campaign.

4. Trading for DE Michael Bennett (2019)

The Patriots unloaded a fifth-round pick to the Philadelphia Eagles for defensive end Michael Bennett (and a seventh-rounder) last March with the hope that he would bolster their front seven. However, the three-time Pro Bowler appeared in just six games for New England before the franchise dealt him to the Dallas Cowboys midseason. In that limited stint, Bennett registered 2.5 sacks and four QB hits. To put the cherry on top of the failed trade, he was also suspended one game for "conduct detrimental to the team."

3. Trading Away Jacob Hollister (2016)

Not only did the Patriots trade away promising tight end Jacob Hollister to the Seattle Seahawks, but they did so not long after Rob Gronkowski announced his retirement from the NFL. After starter Will Dissly suffered a torn Achilles in Week 6, Hollister emerged as a reliable target for quarterback Russell Wilson. In his first season with Seattle (11 games), the 26-year-old pass catcher compiled 41 receptions for 349 yards and three touchdowns. You have to think that Hollister is locked in as a starter on the Seahawks offense moving forward. Ironically enough, the 2020 seventh-rounder that New England acquired was featured in the trade that sent Gronk to Tampa Bay.

2. Trading Away QB Jimmy Garoppolo (2017)

Boy, does trading away Jimmy Garoppolo look bad now, or what? In 2017, the Patriots put all of their faith in the hope that Tom Brady would be their starting quarterback for the remainder of his career. Of course, the 42-year-old left for the Buccaneers in free agency this offseason, leaving New England with uncertainty at the QB position for the first time in over 20 years. The franchise traded its acquired second-rounder for more assets that eventually turned into Yodny Cajuste, Christian Sam, Damien Harris, Duke Dawson, Jarrett Stidham and Joejuan Williams -- none of whom have had any real impact on the team. As we know, Garoppolo helped lead the San Francisco 49ers to the NFC's No. 1 seed and a Super Bowl appearance in 2020 in his first full season as the starter.

1. Trading for WR Mohamed Sanu (2019)

Desperate to equip quarterback Tom Brady with adequate wide receiver play, the Patriots coughed up a second-round selection for Atlanta Falcons pass catcher Mohamed Sanu in October of last year. The 30-year-old vet appeared in eight games (six starts) for New England and he shortly proved that he wasn't worthy of a second-rounder. Sanu logged just 27 receptions on 46 targets for 207 yards and one touchdown. Atlanta ended up flipping the acquired pick (No. 55 overall) to the Baltimore Ravens for tight end Hayden Hurst. At that spot, the Ravens drafted Ohio State running back JK Dobbins, a player that figures to make an immediate impact. From all angles, the Patriots have come out as huge losers in this deal.