One wrong decision and it can make even the most famous of coaches, players, and GMs a tale of the past. UNC’s head coach, Bill Belichick, is the GOAT of the NFL because of his Patriots’ move in 2000. But he could have also landed a “pressure cooker” NFL job, which could have easily altered his NFL trajectory, according to a $30 million former Raiders HC.

Gruden appeared on a February 14 interview and detailed how Belichick could have easily gotten the Raiders HC job instead of him in 1998. “You know, Bill Belichick had the job. He was going to get the head coaching job,” Jon Gruden said. “He called me, he says, hey, do you want this job? I said what are you talking about? He goes, do you want the Raider job? I go, yeah. I do. He goes, you can have it. I’m pulling my name out.”

Belichick and Gruden share a long-standing relationship as respected coaches, and Belichick has expressed admiration for Gruden several times. “Jon and I have never worked together, but I think considering that we’ve never worked together, I’m probably as close to him as any coach that there is in the league,” Belichick said in 2005.

Gruden became the Raiders’ head coach in 1998 and stayed there till the 2001 season. Under Gruden, the Raiders moved away from last place in the AFC West and posted consecutive 8-8 seasons. Finally, in the 2000 season, Gruden’s team finished with a 12-4 season and made the postseason again in 2001. Although Gruden switched camps to the Tampa Bay Buccaneers in 2002, 2,500 miles away in New York, Belichick was rewriting his NFL career.

Belichick came in as the New England Patriots’ assistant head coach and DC in 1996 after a failed five-year stint with the Browns. The 73-year-old was back to square one in his NFL career and eventually moved to the NY Jets in the same role for three years. Instead of accepting the Raiders’ job, Belichick persisted with the Giants and even became the head coach for one day, after Bill Parcells stepped down. The franchise was planning to introduce him as their next head coach. But Belichick pulled a U-turn.

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In what is considered one of the most stunning announcements in sports history, Belichick resigned from the job at his inaugural Jets press conference. “I resign as HC of the NYJ,” Belichick said and left the press conference room. Not many know the exact reason for Belichick’s abrupt resignation, and only theories are afloat. In hindsight, it has worked in favor of Belichick and the Patriots massively. In that sense, leaving the Raiders’ job also seemed like a predestined thing for Belichick. But in truth, though, the Raiders HC job was far from easy.

Belichick reaped the benefits of passing the Raiders’ “pressure cooker” job

Before Jon Gruden joined the Raiders, the head coaching job was considered the toughest in the country. Al Davis’s hands-on ownership style created problems for coaches, and he functioned as the de facto GM. The room for error was extremely narrow. The team saw abrupt firings and forced changes within short tenures.

Mike Shanahan’s firing four games into his second season in 1989 is evidence of that. Later, when Art Shell was promoted to head coach, he was fired despite winning the AFC Coach of the Year award in 1990. Even Davis later admitted the firing to be a “mistake.” That might be the biggest reason why Belichick passed on the Raiders job.

“When you’re working for Al Davis, there aren’t a lot of jokesters,” Gruden told. “There were a lot of people who said, ‘You want to ruin your career?’ ‘You go work for that guy.’ Because people have been fired and fired and fired. So there was a lot of pressure. It wasn’t a lot of joke-telling. This was not a real loose atmosphere.”

Upon looking back, passing on the Raiders job reaped dividends for Belichick. He won 6 Super Bowls as head coach with the Patriots and developed the greatest player the NFL has ever seen in Tom Brady. As for Jon Gruden, the first Raiders stint might not have created problems for him. But in his second one from 2018, he got entangled in a cobweb of controversy. The repercussions of which the head coach is still paying.