Jim Gray doesn’t like to be asked about his celebrity connections

This interview is from last Friday, but Boston sports radio show Toucher and Rich just posted video of it today, so we can all enjoy the sight of Jim Gray growing more and more annoyed by the very reasonable question of how the hell he’s friends with Oprah.

That line of questioning stems from a brief and very puzzling shot of Gray during Tom Brady’s interview with Oprah last summer:

Sitting behind Gisele, wearing weird headphones, during Tom Brady's interview with Oprah? Why, that's Jim Gray, of course. pic.twitter.com/AlwPrA6rfq

— Michael Hurley (@michaelFhurley) June 14, 2018

Credit Toucher and Rich hosts Fred Toettcher and Rich Shertenlieb for bringing this up, because it’s hard to imagine a more intriguing Jim Gray-related line of questioning. Gray, though, had zero interest in talking about it. Here’s video (via Twitch), and it’s crazy how quickly things jump the rails.

For everyone who has been asking…we had not posted this yet. Here is our interview gone wrong with JIM GRAY. #TomKnowsOprah #OprahKnowsTomhttps://t.co/5YwlSFsUpJ

— Toucher & Hardy (@toucherandhardy) February 8, 2019

Rich isn’t disrespectful in his questioning at all, here, he just comes across as genuinely curious as to what the fuck Jim Gray was doing chilling with Giselle at an Oprah interview with Tom Brady. An understandable curiosity! Gray, though, has zero interest in talking about it.

“What was the story with you being part of that Oprah thing?”

“I was invited to dinner by Oprah, so I came to dinner.”

“You know her like that, really?”

“Should that be surprising? I’m sure you have friends.”

“I’m not friends with Oprah.”

From there, it got even weirder, as Gray responded to another reasonable point from Toettcher (that Tom Brady and Oprah are incredibly famous people, while Jim Gray is more “longtime local car dealer” famous, so it’s weird that he’d just happen to be there) by listing all the ways in which his social circle is entwined with Oprah and Tom:

“Tom knows Oprah, Oprah knows Tom, I know Oprah, Oprah knows my wife, Tom knows my wife, Tom knows Stedman, I know Stedman…" pic.twitter.com/Izer7XFlWh

— Toucher & Hardy (@toucherandhardy) February 8, 2019

But it’s Toettcher’s decision to just send Gray packing that really makes the whole interview. That and the return from break, which features third man Jon Wallach gamely reading news updates while Gray is still standing near the table having words with the two hosts, before slinking off, but not before one last menacing look back while walking through a tiny indoor gate.

Now that is good radio.

[Toucher and Rich]