The Raiders Once Considered Hiring Bill Belichick? True Story, Says Amy Trask

(EDITOR’S NOTE: To access the Amy Trask interview log on to the following attachment: Ep 38: Amy Trask Joins to Talk Raiders, Al Davis, and Much More! | Spreaker)

Bill Belichick to the Raiders? Don’t laugh. It could’ve happened. And it would have … if former Raiders’ CEO Amy Trask had her way.

Rewind the videotape to January 1998. The then-Oakland Raiders had just fired their head coach, Joe Bugel, after a 4-12 season, and owner Al Davis was busy interviewing a battery of candidates, including Belichick – then the assistant head coach and defensive coordinator with the New York Jets.

But he didn’t choose him. He chose then-Philadelphia assistant Jon Gruden instead. And the rest you know.

What you might not, however, it that rumor had it that Trask recommended Belichick. So we asked if that was true when Trask – now an analyst for CBS Sports and the CBS Sports Network — appeared on the latest “Eye Test for Two” podcast.

“Not only is it true,” she said, “I am grinning ear to ear as you mention it. That was the only time in my entire career with the Raiders that Al involved me in a coaching search. It only happened that once. Never before and never after.

“He had me meet with each of the candidates, and after I did he asked me, ‘OK, who would you hire?’ I said, ‘Bill Belichick,’ and I said it without equivocation. And we talked a little bit about it. He went on to hire Jon Gruden, also a good choice. Jon did a terrific job, so this is not in any way to denigrate Jon. But I suggested that he hire Bill.”

Belichick went on to write history, winning six Super Bowls in New England. Gruden did a credible job, too, taking the Raiders to two consecutive AFC West titles and the 2000 conference championship game before leaving to win a Super Bowl in Tampa Bay. But the Raiders never forgot him, and he was re-hired in 2018.

So let’s go back to 1998 again. Gruden never had been a head coach. Belichick had. He coached the Cleveland Browns from 1991-95 and led them to the playoffs once. But he was fired in February 1996, after then-owner Art Modell announced he would move the franchise to Baltimore.

Now the question: What convinced Trask that he could be successful with the Raiders?

“How smart he is,” she said. “Just so, so intelligent. I don’t know how else I can state it, other than I was just ‘wowed’ not only by his football acumen and his football intelligence but his intelligence as a whole.”

That story was never revealed … until several years later. And then, Trask said, it was Davis who made it public after Belichick had been hired by New England and started winning Super Bowls.

“I thought that would remain between the two of us,” she said. “But quite a while later – I think at a press conference — he said, ‘Amy told me to hire Bill.’ And that was very, very meaningful to me … He didn’t have to tell people that, and I thought it was really gracious and generous that he did so.

“But what I loved even more (is that) from that point on … after I recommended Bill and Bill went on to have the success we’ve seen him have … most any time coaching issues came up, Al would say to me, ‘Kid, you know how to pick a coach.’ “