The Raiders were in the market for a new head coach back in 1998. Joe Bugel was let go after one 4-12 season, and owner Al Davis interviewed several candidates to run his team and help return it to prominence.
Davis was the final say and sole decision-maker on these matters, but he asked his CEO, Amy Trask, for her opinion on the candidates available.
“That was the one coaching search in which Al ever involved me,” Trask said in a Jan. 2019 episode of the Raiders Talk podcast. “I met with the candidates, and he asked me after I had met each one who I recommended he hire. Without any hesitation whatsoever, I said Bill Belichick.”
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Davis didn’t end up going with Belichick, but still ended up making a great hire. Jon Gruden was the guy, and the young offensive wizard helped take a downtrodden group to .500 twice before vaulting it into the AFC’s upper echelon.
Gruden took the Raiders to the AFC title game following the 2000 season and got jobbed by the Tuck Rule in a 2001 divisional-round loss to the New England Patriots and their second-year coach -- Bill Belichick.
Though Trask was thrilled with the Gruden hire and his subsequent contributions to the organization, the Patriots dynasty proved that she made a great recommendation.
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Belichick wasn’t ever a frontrunner for the Raiders gig. He was a defensive specialist and Davis has a long history of hiring offensive minds dating back to Tom Flores. The Raiders' defense, however, largely remained under Davis’ purview.
Belichick has great reverence for Davis and remembered his interview with the Raiders legend fondly in an interview before the Raiders and Patriots played in 2011.
"He's a great mind," Belichick said, via NFL.com. "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 'Xs' and 'Os' and strategy and use of personnel and acquisition of -- all the things really that a coach would talk about, that's really what he talked about. That made it pretty unique."
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Belichick, who was the Jets defensive coordinator at the time of his interview with the Raiders, said he knew during the interview he wasn’t going to be a top candidate, but he still enjoyed the conversation with a brilliant, detailed football mind.
"You know, it was good because we talked a lot about football and (Davis is) very, very knowledgeable about the game, personnel, schemes, adjustments and so forth," Belichick said. "He was asking a lot of questions about what [the Jets] did defensively.
"You kind of don't want to give too much information there because you know, he's running the [Raiders] defense. He wasn't really too interested in talking about offensive football."
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