When “Roastmaster General” Jeff Ross got onstage at Tom Brady’s Netflix roast and told a joke about New England Patriots owner Robert Kraft getting caught in a prostitution sting, he was crossing a line he’d been explicitly warned about, according to another comic at the event.
The crack about Kraft’s apparent penchant for massages seemingly got the G.O.A.T.’s goat, with Brady rising from his seat and crossing the stage to warn Ross not to “say that shit again.”
Earlier this week, Ross insisted that Brady was just “having fun.” But now comedian Andrew Schulz is wading into the fray to say that no, the future Hall of Famer actually was pissed off.
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“When Tom checked Jeff Ross, I think that was 100 percent real,” Schulz said on Wednesday’s episode of his Flagrant podcast.
“I’ll tell y’all something,” he continued. “The reason why I think it was real is they told us, ‘No jokes about happy endings with Bob Kraft.’”
Schulz said that he’d prepared a “happy ending” joke of his own, name-checking Kraft and Patriots wide receiver Randy Moss, but organizers “were like, ‘Tom asked us not to do anything with the massage shit.’
“I was like, ‘Alright, cool,’” Schulz said. “[Kraft]’s coming here for this thing. He’s not getting roasted.”
But Schulz observed that Ross, the first comic of the evening, was prepared “to shut the whole thing down” with his Kraft quip.
“That’s an alpha-ass move right there,” he added.
In a set that pulled no punches, Ross turned his sights on Kraft to reference that time in 2019 he was charged with two misdemeanor counts of soliciting prostitution after being arrested at a Florida day spa in 2019. (The charges were dropped the next year.)
“So Tom became a Patriot and moved up to New England,” Ross said, “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 best decision your organization has ever made. Would you like a massage?’”
After Brady confronted him, though, Ross appeared to wilt slightly. “OK, OK. He’s having fun, look at him,” he said. “I love what you do for the Jews, Robert Kraft. You’re incredible.”
On The Rich Eisen Show on Monday, Ross said that Brady was “just showing his love” for Kraft, who “loved” the jab.
“He was so happy that I gave him a shoutout and a salute,” the comedian added. “It was beautiful.”
But it’s just as possible that Kraft was too distracted by a painfully awkward backstage encounter with former Patriots head coach Bill Belichick that had occurred just before the broadcast kicked off, according to Drew Bledsoe.
Bledsoe, himself a former Patriots quarterback, recalled on Julian Edelman’s Games with Names podcast this week that Belichick had been “holding court” in the green room, “talking war stories,” when Kraft walked in.
“As he’s in the middle of the story, Kraft walks in, and so you guys all go over to say hi to Kraft,” Bledsoe said.
“The tension in that room, though, could cut fucking glass,” Edelman agreed.
Belichick’s departure from the Patriots in January was overshadowed by reports about the alleged acrimony with Kraft that had led to his exit, which came after 24 seasons with the team.
But the two men were all smiles in front of the camera, even doing a shot together onstage at one point. “I want to say this is the greatest coach in the history of the game,” Kraft said, “that did what no one else has done. And having Tom Brady and him was the greatest honor the good Lord gave me.”
