Belichick has run one of the tightest ships in all of sports, while the Raiders struggled mightily from 2003-09, bungling their personnel moves and failing badly on the field.
Yet the marriage nearly happened. Belichick interviewed for the head coaching vacancy in 1998, and he spent a couple days conversing with Raiders owner Al Davis, who wound up hiring Jon Gruden.
Belichick recalled the interview with Davis on Friday, and he remembered the experience fondly.
"It was good experience for me," Belichick said. "We had a good couple days of conversation. I told him when I got out there it really seemed like a waste of time because I felt pretty certain that he wouldn't hire a defensive coach, because he hasn't since Eddie Erdelatz in . It's a parade of offensive coaches out there. [Davis] is really a defensive coordinator and has been. It was good because we talked a lot about football, and he's very, very knowledgeable about the game, personnel, schemes, adjustments and so forth. He was asking a lot of questions about what we did defensively. You kind of don't want to give too much information there because you know he's running the defense. He wasn't really too interested in talking about offensive football — a little bit.
"He's a great mind. It was unlike any other interview I've ever had with an owner because he was so in-depth. His interview was so in-depth really about football, about X's and O's, and strategy, and use of personnel, and acquisition of [players]. All the things really that a coach would talk about, that's really what he talked about. That made it pretty unique. But he hired a good coach, Gruden. Which is again, in all honesty, the way that I expected it to go because that's been all the Oakland coaches from Art Shell to Mike White, Joe Bugel, [Mike] Shanahan, you know right down the line, Lane Kiffin, they're all offensive coaches. They have their own way of doing things, which is interesting, but certainly well thought-out and well planned. I'm not saying that in a negative way at all, they just have their own way of doing it. They've had a lot of success.
"It was a great experience for me to have those couple days of conversations with him and also some other members of his organization relative, again, to the overall way of doing things."