Tom Brady and Bill Belichick were at the helm of the New England Patriots' two-decade run of NFL dominance, and hoisted six Vince Lombardi Trophies during their time together. 

But the coach and now-retired quarterback's relationship is often brought up during conversations about the Patriots dynasty. Brady was famously drafted in the sixth round in 2000 and went on to spend 20 seasons in New England. He left after the 2019 season and joined the Tampa Bay Buccaneers, where he won another Super Bowl.

Belichick was an assistant coach with the Patriots during the 1996 season and returned to New England as the franchise's head coach in the same year Brady was drafted.

Despite spending so many years together and reaching unprecedented levels of success, by all accounts the working relationship between Brady and Belichick was straightforwardly transactional. But longtime team owner Robert Kraft recently gave his account of how the relationship ultimately transpired.

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Robert Kraft, head coach Bill Belichick and Tom Brady celebrate with the Lamar Hunt Trophy after winning the AFC championship game at Gillette Stadium on Jan. 22, 2017, in Foxboro, Massachusetts.

Robert Kraft, head coach Bill Belichick and Tom Brady celebrate with the Lamar Hunt Trophy after winning the AFC championship game at Gillette Stadium on Jan. 22, 2017, in Foxboro, Massachusetts. (Getty Images)

During a recent appearance on the nationally syndicated radio program, "The Breakfast Club," Kraft recalled the moment Brady told him about his decision to leave New England.

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"I’ll never forget… I believe it was in the month of March (2020). He lived down the street from me. (Brady) came to my house and I opened the door. He started crying," Kraft said.

"And he hugged me and he said, ‘I’ve made a decision. I’m gonna leave the Patriots after 20 years.’ We normally would’ve franchised someone like that… but I kept my word to him. And it was one of the worst days – it’s like losing a child."

Robert Kraft and Bill Belichick

Robert Kraft and Bill Belichick after defeating the Pittsburgh Steelers in the AFC championship game at Gillette Stadium on Jan. 22, 2017. (Maddie Meyer/Getty Images)

Kraft noted that he informed Brady that he "wouldn't allow Bill or the team to franchise (tag) you," which suggested that Belichick may have wanted to place the designation on the quarterback to keep him contractually tied to the organization for one more season.

But Brady was given the autonomy to reach whatever decision he felt was best for him – and the NFL icon ultimately moved to Tampa Bay.

Tom Brady greets Robert Kraft

New England quarterback Tom Brady meets with Patriots owner Robert Kraft in Super Bowl LIII at Mercedes-Benz Stadium in Atlanta, Feb. 3, 2019. (John David Mercer-USA Today Sports)

Kraft said Brady was emotional when he was preparing to depart New England and hinted that the divide between the quarterback and the coach weighed heavy on Brady.

"He cried that whole time when he had to leave us. I understood it. He lived under an arrangement that was very difficult for him the last decade," Kraft said.

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Brady and Belichick never even had dinner together, Brady's father, Tom Brady Sr., said in 2017.

"They have never even gone out to lunch or dinner," Brady Sr. said. "That’s not what they do."

Earlier this year, Brady Sr. also suggested that Belichick's lack of interpersonal skills directly contributed to the Patriots' fall from grace. 

"Bill is tough," he told The Boston Globe. "He runs a military system. It’s a different generation. Bill is a great, great, great coach. But his interpersonal skills are horrible. That’s the bottom line."

Brady and Belichick did appear to mend fences in May when the coach took a few playful jabs at the former quarterback during the "The Roast of Tom Brady."

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