Jim Gray Gets Weirdly Snippy When Asked About His Friendships With Tom Brady And Oprah

Photo: Ethan Miller (Getty Images)

Career access merchant Jim Gray has made his name lobbing softballs to famous people, and he would prefer to have those same softballs tossed in his direction, thank you very much. In a Super Bowl week interview with Boston radio station 98.5 The Sports Hub’s Toucher and Rich, Gray had barely settled in before co-host Rich Shertenlieb (the guy in the hat) asked him about his background appearance on Tom Brady’s fluffy interview with Oprah Winfrey that aired last June.

That line of questioning gradually made Gray weirdly shady about his friendships with both Brady and Winfrey, explaining away his coincidental existence in the interview as simply being a prelude to a dinner put on by one of the most famous people in the world:

The interview lasted about three minutes before other host Fred Toettcher criticized Gray’s defensiveness and told him to leave. It’s a cringe-worthy look into a reporter whose livelihood is based on protecting the secrets of the rich and famous. While Gray might not have found the conversation riveting, it is newsworthy that he would randomly be in the vicinity of a PR-heavy fluff piece without being the one asking questions.

The audio of the interview was released last week, but the video makes for a fascinating watch. Here’s a partial transcript:

RICH SHERTENLEIB: It seemed kind of strange that behind the camera, it was Gisele, one of the producers, and you were there for the taping of the Oprah interview. So what was the story being part of that Oprah thing?

JIM GRAY: I was invited to dinner by Oprah, so I came to dinner.

FRED TOETTCHER: You know her like that?

GRAY: Should that be surprising? I’m sure you have friends. I was invited to dinner, so I went to dinner.

TOETTCHER: Yeah, but I’m not friends with Oprah.

Gray tried to say that he has friends and it should be normal and irrelevant that he had dinner with them. That raised a pretty good point from Toettcher, though: If Gray was just invited to dinner by Oprah—already a pretty wild thing to happen in this universe—why did he get there in time to cameo on the interview?

Gray’s response was not illuminating:

SHERTENLIEB: But that wasn’t dinner, that was a taping of the show.

GRAY: Well, it happened right before dinner.

SHERTENLIEB: At Tom Brady’s house?


SHERTENLIEB: Was that filmed at Tom Brady’s house?


SHERTENLIEB: So where was it filmed?

GRAY: Where Oprah films her stuff. I live in Los Angeles.

SHERTENLIEB: Okay, and that’s where you guys were having dinner?

GRAY: …Right by there, yes.

It’s at this point that Gray called the question stupid, which prompted Toettcher to kick him off the show for being an uncooperative dick. The best part of the whole clip happened at the 4:55 mark, as co-host Jon Wallach read off the headlines of the day while Gray and the other hosts continued to argue. If only there were audio of that, too.

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