In Netflix’s live production of the ‘Greatest Roast of All Time’, Ross delivered a line that referenced when Brady introduced himself to Patriots owner Robert Kraft.
‘Tom became a Patriot, moved up to New England, and on the first day of training camp, that scrawny rookie famously walked into the owner Robert Kraft’s office and said, I’m the greatest decision your organization has ever made… would you like a massage,’ Ross joked.
It drew laughs from the room, but Brady appeared unimpressed by the joke and went up to Ross in the middle of his set.
‘Don’t say that s**t again,’ Brady said with a smile, while his hand poorly covered up the microphone.
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Tom Brady interrupted Jeff Ross’s roasting set after he took exception to a joke he said
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The joke involved a fake scenario where Brady asked Kraft if he wanted a massage
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That’s a reference to when Kraft was charged with soliciting a prostitute back in 2019
That joke, of course, was a reference to when Kraft was one of 25 people facing a misdemeanor charge for soliciting prostitution at a Florida day spa back in February 2019.
Kraft pled not guilty. Later, the charges were dropped in September of 2019 after a Florida appeals court ruled his constitutional rights were violated.
That’s because Kraft’s attorneys revealed hidden cameras were installed at the spa before Kraft visited under the guise of a response to a bomb threat.
‘I am truly sorry,’ Kraft said in a March 2019 statement about the case. ‘I know I have hurt and disappointed my family, my close friends, my co-workers, our fans and many others who rightfully hold me to a higher standard.
‘Throughout my life, I have always tried to do the right thing. The last thing I would ever want to do is disrespect another human being.
‘…As I move forward, I hope to continue to use the platform with which I have been blessed to help others and to try to make a difference. I expect to be judged not by my words, but by my actions. And through those actions, I hope to regain your confidence and respect.’
Social media reaction seemed to be in favor of Ross, with some saying that the incident felt like it would boil over into a sequel of when Will Smith slapped Chris Rock at the Oscars.
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Social media seemed to find the joke funny, but thought it could turn into a Will Smith moment
Ross was not the only person who roasted Brady. Several comedians – including Kevin Hart, Nikki Glaser, and Bert Kreischer – were on the dais.
So were a number of Brady’s former teammates – such as Drew Bledsoe, Randy Moss, Rob Gronkowski, and Julian Edelman.
Edelman also made a joke at Kraft’s expense. He said ‘I think the next time I see you all will be at Kraft’s funeral.’ When Kraft got the mic later, he retorted, ‘Julien, I’m not inviting you to my funeral.’
Among the many topics for jokes were Brady’s divorce from Gisele Bundchen, the Patriots’ multiple cheating scandals, his sexuality, and his looks.
Kim Kardashian, who was once rumored to be dating Brady, gave a toast at the roast.
‘I know there were some rumors of Tom and I dating and I’d never say if we did or not, I’d just release the tape,’ she opened, poking fun at her leaked sex tape with Ray J.
‘But I do know it would never work out,’ she went on. ‘An ex-athlete, high cheek bones, silky hair… you remind me too much of my stepdad now. Part of me thinks you’d want to undress me just to try on my clothes.’
WARNING: CONTAINS BAD LANGUAGE
Later in the evening, Bill Belichick made a surprise appearance after rumors suggested he wouldn’t show up.
‘I’m so honored to be here for the roast of Tom Brady on Netflix, not to be confused with the roast of Bill Belichick on the 10 part Apple doc,’ Belichick joked, in reference to the Apple documentary series ‘The Dynasty’.
After he arrived, Julian Edelman went into his set. ‘Remember when you used to yell at us, “Look a**holes, the f**king kids down at Foxborough High can make that f**king play. I’ve been waiting for this for so long: “Look a**hole [Belichick], Foxborough High’s the only job offer you f**kin’ had.’
At the end of Rob Gronkowski’s set, the former Patriots tight end joked that he never took a drink with Brady and Belichick – before the three all took a shot of alcohol together.
Then Gronkowski took his shot glass and spiked it on the stage – sending glass shards all over the place.