Jeff Ross Was ‘Worried’ About Tom Brady’s Reaction to His Robert Kraft Joke

Jeff Ross wasn’t sure how Tom Brady was going to handle his Robert Kraft joke during the athlete’s roast.

“I don’t think Jeff would — I hope he wouldn’t mind me saying — like, afterward, he was a little like … he was a little bit worried,” Nikki Glaser said during a Monday, May 6, appearance on The Howard Stern Show. “We have consciences about these things. You know, afterward, we go, ‘Did that really hurt his feelings?’ And I go, ‘You know, [Tom] had to do it performatively for Robert, I’m sure.’ But I’m sure it was not an issue that Jeff was going to hear about today or anything like that.”

During The Roast of Tom Brady, which premiered live on Netflix on Sunday, May 5, Ross, 58, took a dig at Kraft, 82, and his infamous massage scandal.

“Tom became a Patriot and moved up to New England, and on the first day of training camp,” Ross teased, “that scrawny rookie famously walked into the owner Robert Kraft’s office and said, ‘I’m the best decision your organization has ever made. Would you like a massage?’”

Ross then blew a kiss to the Patriots owner in the audience and pointed at him before saying, “I Love Robert Kraft.” After making the joke, Brady, 46, approached Ross and whispered to him, “Don’t say that s–t again.”

While there was seemingly tension between the pair, Glaser shared on Monday that she thought Ross handled the situation “perfectly.”

“Jeff worked with Tom closely on this and is a big reason Tom even did it because they formed a friendship and he was able to coach him through it and really encourage him,” she recalled. “So I think Jeff really did feel bad after that moment. I don’t know what made him decide to do that joke.”

Glaser shared that she also thought about making a massage joke but ultimately decided against it once there were rumblings that Kraft would possibly be in attendance for the special.

“I didn’t know [he was] gonna be there until I was there. And I knew everyone else,” she said. “I was like, ‘Oh, my God Robert Kraft’s here.’ Because I think there was a vibe that Robert Kraft is kind of, like, a dad figure to Tom. He doesn’t want to sit there and listen [to] all these jokes about him, so maybe he wouldn’t show.”

Brady played most of his NFL career with the New England Patriots. During his 20 seasons in New England, the team played in nine Super Bowls and won six of them. After two decades with the Patriots, Brady left the organization to sign with the Tampa Bay Buccaneers where he earned another Super Bowl ring. In February 2023, Brady retired from the sport for good.

The Roast of Tom Brady is now streaming on Netflix.