End Of An Era: All Of Bill Belichick’s Best and Worst Moments

Darren - January 12, 2024

End Of An Era: All Of Bill Belichick’s Best and Worst Moments

Darren - January 12, 2024

After 24 seasons of unparalleled success followed by a recent downturn, football legend Bill Belichick is no longer the coach of the New Patriots. Following an embarrassing 4-13 record in 2023, the legendary but controversial head coach mutually agreed with the team that it was time for a divorce. The writing was seemingly on the wall after the worst season of his career, and Patriots owner Robert Kraft appeared to be growing tired of losing. However, they also went through several years of regression in the post-Tom Brady era.

Nonetheless, the six-time Super Bowl-winning head coach will go down as one of the greatest – if not the outright greatest of all time. Early in his Pats runs, Belichick made phenomenal decisions and got the best out of Tom Brady. But he was also infamous for his repeated instances of cheating and made some truly horrendous draft picks as the Patriots’ de facto GM as well. His unique personality made him one of the NFL’s most compelling figures. So let’s remember his unique and polarizing career by looking back on Belichick’s greatest and worst moments right here.

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Quitting The Jets

One of the oddest moments of Belichick’s career saw him become the Jets interim head coach in 1997. They wanted to hire Bill Parcells but complications saw them turn to Belichick in the short term. However, he never coached a game because they finally agreed to a contract with Parcells.

Bill Belichick

Then Parcells quit in 1999 but he arranged for Belichick to replace him. They didn’t factor the Patriots entering the equation. New England made him a better offer and he quit the Jets on his first day. Belichick notoriously wrote on a napkin: “I resign as HC of the NYJ” in a legendary moment (via Fansided).

Julian Edelman

Julian Edelman

Everybody thinks of Tom Brady when it comes to Belichick’s best draft picks. He was a master of finding hidden gems like Brady and future Hall of Fame tight end Rob Gronkowski in later rounds. However, it’s fair to say that Edelman was another of his best finds. The wideout spent 12 seasons with the Patriots and became a three-time Super Bowl champion.

Julian Edelman
CBS Sports

He played for the unheralded Kent State before he entered the Draft in 2009. Edelman fell to the seventh round before Belichick finally took him off the board. It was a brilliant decision because he was one of the NFL’s most consistent receivers for over a decade. Astonishingly, he never made a single Pro Bowl appearance (via USA Today Sports).

The Boston Globe

Super Bowl LIII

Belichick won his final Super Bowl as Patriots head coach at Mercedes-Benz Stadium in Atlanta. The Patriots faced the Rams again as he came full circle. Remember, Belichick’s first Vince Lombardi Trophy as a head coach also came against this franchise. They won 13-3 in a tight victory that saw defense take center stage.

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CBS Sports

Meanwhile, Julian Edelman claimed the game’s MVP award. The win saw Belichick become the Super Bowl’s oldest winning coach while Tom Brady became the oldest winning quarterback. It was an amazing victory that was the end of a six-ring winning dynasty in Foxborough (via New England Patriots).

Bill Belichick
Sports Illustrated

The Cleveland Browns

It’s easy to forget that New England wasn’t Belichick’s first head coaching job. He cut his teeth in Cleveland after Art Modell hired him in 1991. Belichick built a big reputation for himself as a defensive coordinator in New York and became a hot property. But Cleveland was a volatile environment for any young coach.

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The Spun

He did bring them a playoff win in 1994 while he made the bold decision to cut QB Bernie Kosar. However, Modell wanted to move the franchise to Maryland. He fired Belichick after their final season in Ohio before they went to Baltimore. There was no love lost between them after Modell fired him on Valentine’s Day in 1996 (via NBC News).

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New Jersey

The Philly Special

This iconic trick play was one of the main reasons why Belichick missed out on another ring. The Patriots played the Eagles in his eighth Super Bowl appearance as a head coach. Nick Foles became the first player in the game’s history to throw and catch a pass for a touchdown (via The Ringer).

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CBS Sports

It was an incredible moment and he won the game’s MVP award too. Foles was only playing because their starter Carson Wentz suffered a torn ACL late in the regular season. He was the most unlikely hero ever and it convinced the Jaguars to give him a ridiculous contract that he never even came close to earning. For Belichick, it went down as one of his few defeats on the game’s biggest stage.


The Giants Victories

It’s easy to forget that Belichick was already a two-time Super Bowl-winning coach before he joined the Patriots. He was a brilliant defensive coordinator for the New York Giants before he became a head coach. Bill Parcells hired him in 1985 and turned Lawrence Taylor into one of the league’s best players.

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Meanwhile, they achieved glory in 1986 and 1990 with two Super Bowl victories. The second saw them win as underdogs against the Bills as Belichick pulled off a defensive masterclass. This remains one of the most famous game plans ever for its innovative use of overloading defensive backs (via Giants).

New England Patriots

Super Bowl XXXVIII

The Patriots enjoyed better luck against the Carolina Panthers when the Brady and Belichick dream team claimed their second title in 2004. They defeated the Panthers by a narrow margin of 32-29. Tom Brady won the game’s MVP award as the franchise edged its way toward a dynasty.

Sports Illustrated

Most people remember this game for the halftime show because of Janet Jackson’s ‘wardrobe malfunction’. But it was another day when Belichick’s well-oiled machine did the job they wanted to do. There were two scoreless quarters but this didn’t bother the defensive maestro who got his team over the line (via

Eli Manning

The Curse of Eli

The New York Giants and their quarterback Eli Manning came back to haunt Belichick twice. New England’s most painful moment came in Super Bowl XLII in a tight defensive battle. The Patriots were heavy favorites after an amazing, unbeaten 2007 season that saw them go 16-0 (via SBNation).

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However, David Tyree’s iconic helmet catch saw the Giants win the game. He crushed New England’s dream of a perfect season in one satisfying moment. ‘Big Blue’ beat the Patriots again in 2011 in another painful defeat. Eli Manning had the edge when it counted against Belichick and Tom Brady.

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Drafting Tom Brady

Very few football fans outside of the most hardcore knew Tom Brady when Belichick threw him into the fray as a replacement for the injured Drew Bledsoe in 2001. The former Michigan quarterback with the unimpressive physique arrived as the 199th overall pick the previous year. But it was the start of an incredible relationship that saw Brady and Belichick kickstart a dynasty.

Tom Brady
Tampa Bay Times

Brady was the perfect quarterback for Belichick’s system and developed into arguably the greatest NFL quarterback of all time. He remains the greatest NFL Draft steal ever. Brady was a three-time MVP and set more records than we can count. In the end, their bond broke down but they achieved glory together (via Newsweek).

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Ignoring the High Fives

Every NFL fan knows that Belichick is one of the most contrary men on the planet. He doesn’t care what people think about him and it’s almost comical. In 2018 he had an amazing moment that illustrates his overall attitude. Some children outstretched their hands for high-fives before their SNF game against the Lions.

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Belichick blanked them like they didn’t exist. It was a peak moment for the cantankerous head coach and his detractors hated him for it. However, his fans thought that it was hilarious and we’d be lying if we didn’t think it was funny too. Belichick made the NFL a more interesting place (via BroBible).

NBC Sports

Super Bowl XXXIX

The Patriots established their dynasty with a remarkable third Super Bowl win over the Philadelphia Eagles in Jacksonville. The 2004 season victory saw them become one of the NFL’s most-hated teams. It’s incredible to think that they went decades without winning the Vince Lombardi Trophy.

Philadelphia Eagles

However, they dominated the 2000s with Belichick at the helm. He became an almost unfireable figure after this because it was a period of total dominance. They defeated the Eagles 24-21 in the season finale but Philly got their revenge in 2018. This was a great moment for Belichick and his team (via The Philadelphia Eagles).

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Sports Illustrated

The Holey Shirt

Belichick found that one of the benefits of being the best in the business was that he could do whatever he wanted. Many people don Armani suits and Rolexes when they make it but he went in the opposite direction. In 2020, he rocked up to a press conference in a homeless man’s outfit (via Sports Illustrated).

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The New Yorker

Everybody knows that he loves sweatshirts with cut-off sleeves. But he wore one with many holes in it like somebody stubbed a cigarette on it. Meanwhile, his hair was messy and he had the facial expression of a man who wanted to be anywhere else. It was peak Belichick and a reason why he’s one of a kind.

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New York Post

Mac Jones

Belichick achieved many Draft masterstrokes in the early years of his New England tenure. But for all those hits, there were just as many (if not more) misses in the latter part of his run. Many fans thought that he pulled another rabbit out of the hat when Mac Jones fell into his lap in 2021. However, they jumped the gun because the former Crimson Tide starter wasn’t in the same mold. He had a similar physical appearance to Tom Brady and a decent record in Alabama (via

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Sky Sports

Jones also landed in a decent situation and had a promising rookie season. However, everything went downhill over the next couple of years. Finally, in 2023, Belichick benched him multiple times in favor of backup Bailey Zappe as the Patriots went 4-13. It was a disaster for the franchise and one of the reasons why Belichick lost his job.


Belichick’s Draft Dog

Yes, Belichick was grumpier than The Grinch but he also had a sense of humor. It didn’t emerge often but he provided some fun moments. One of the best unexpectedly arrived during the 2020 Draft. Whenever the camera switched to the Patriots’ war room they saw Belichick’s dog Nike.

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CBS Sports

Nike perched perfectly on Belichick’s seat in front of a computer. It was amazing and instantly he became a viral sensation. Some fans also thought that it was one of the most entertaining moments of his career. It was nice to show that Belichick is human too even if it’s rarely seen (via CBS Sports).

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The Providence Journal

The Cowboys Loss

Belichick’s final season in Foxborough saw him post some of the worst statistics of his career. This included a horrible defeat to the Dallas Cowboys. They inflicted a 38-3 blowout loss to seal Belichick’s heaviest defeat. It was a painful moment for the veteran head coach and his team (via ESPN).

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However, he made many mistakes that year including appointing Matt Patricia as offensive coordinator. Furthermore, Mac Jones didn’t justify his faith in the quarterback position. In the end, it was almost a relief when he stepped away by mutual consent from the franchise.

Pete Carroll

Super Bowl XLIX

Pete Carroll and the Seahawks had an opportunity to kickstart another dynasty in 2014. The Legion of Boom faced the Patriots and had a golden opportunity to seal victory in the game’s dying moments. Malcolm Butler pulled off a shocking interception to seal the win for New England.

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Seattle passed the ball on the goal line instead of running it with Marshawn Lynch and stunned the world in the process. It didn’t matter what statistics Carroll threw out to support his decision. They should have given it to Lynch but they didn’t and they paid the price. Belichick laughed all the way home to Boston (via CBS News).

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The New York Times


‘Belicheat’ emerged from the shadows for the second time after the AFC Championship game in 2015. The Indianapolis Colts alleged that Tom Brady used underinflated balls to gain a tactical advantage. Most people agree that there’s no way Belichick didn’t know about it. However, he shrugged and compared himself to the Mona Lisa (via Time).

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Then he threw Brady under the bus in a moment that saw relations cool between the two men. Brady received a four-game suspension but rebounded to win the MVP. Meanwhile, it burgeoned Belichick’s reputation as one of the NFL’s most cynical masters of the dark arts.

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The Ringer

Super Bowl LI

This game remains one of Belichick’s most glorious moments because the result was insane. Nobody gave the Patriots a hope of achieving victory after the Falcons took a 28-3 lead. It should have been insurmountable but then Atlanta had a meltdown. It was one of the most dramatic comebacks ever.

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The Patriots scored touchdown after touchdown as the Falcons wilted in front of them. Finally, they won 34-28 to complete the victory and win Belichick’s fifth Super Bowl as a head coach. Meanwhile, the Falcons never recovered from this defeat and went into disarray over the following seasons (via The Ringer).

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CBS Sports

Super Bowl XXXVI

Belichick won his first Super Bowl as a head coach in 2001. It was an amazing season because nobody gave them hope. They lost their starting quarterback Drew Bledsoe to injury for the season. This saw them throw the unproven Tom Brady into the fray. New England annoyed their rivals along the way including the Raiders in the infamous ‘Tuck Rule Game.’

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Finally, they faced ‘The Greatest Show on Turf’ in the St. Louis Rams. Kurt Warner’s men entered the game as betting favorites but Belichick pulled off another outstanding defensive masterclass. The Rams only put up 17 points as the Patriots won their first Super Bowl in franchise history (via CBS).



Many people will always think of ‘Spygate’ when they hear Belichick’s name. The Patriots and their head coach earned notoriety in 2007 after the Jets accused them of cheating. Coach Eric Mangini said that they were videotaping the Gang Green’s defensive signals. Belichick apologized but said that he believed he was following the rules.

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However, the NFL didn’t think so as they fined him $500,000. Meanwhile, Mangini coined the brilliant moniker ‘Belicheat’ and it became synonymous with the Patriots coach. New England also lost a first-round draft pick for their troubles after the NFL found them guilty (via