VIDEO: Tom Brady CONFRONTS Jeff Ross Over Nasty Robert Kraft Joke During Awkward Moment At His Netflix Roast

Tom Brady and Jeff Ross during roastTom Brady and Jeff Ross (Photo via MLFootball/Twitter)
NFL star Tom Brady is no stranger to high-pressure situations—he holds a record seven Super Bowl victories—but he has never encountered anything like this.

The seven-time Super Bowl winner is currently being roasted on Netflix on Sunday night in what the streaming company is calling “The Greatest Roast of All-Time.”

The difference between this roast and other roasts is that it will be airing live and uncensored, and it did not take long for things to get out of hand.

Legendary roaster Jeff Ross was one of the first to get his chance to roast Tom Brady, but one joke he sent out really irked the legendary quarterback.

At one point, Ross brought up owner Robert Kraft and yelled out, “Would you like a massage?”

The fans laughed, but Brady quickly turned to him, then got up and told him never to say that again.

 

Brady will become the target of several jokes and insults from his former teammates because he is accustomed to earning high acclaim and admiration from his colleagues. Randy Moss, the Pro Football Hall of Famer, Drew Bledsoe, the former backup quarterback, and Rob Gronkowski, who will play for FOX Sports with Brady when he joins the network in 2024, are all part of this group.

Tom Brady Set To Enter World of Broadcasting In 2024

Tom Brady (Photo by Beatriz Velasco/Getty Images)
With another NFL season approaching, the networks that broadcast the country’s most popular sport are set to make big changes.

FOX Sports is set to start paying the greatest quarterback of all time over the course of ten years.

It was a few years ago when Tom Brady inked a ten-year, $375 million deal to become the No. 1 color commentator for FOX’s NFL coverage, via The New York Post.

Jeff Ross reacts to Tom Brady confronting him over Robert Kraft joke

From Nikki Glaser’s perspective, Brady’s frustration during his Netflix roast seemed “real.” But Ross clarified what the tone was during the exchange.

 / Source: TODAY
By Ariana Brockington and Lindsay Lowe

Jeff Ross is clarifying what really happened between him and Tom Brady when the quarterback briefly confronted the comedian during his live Netflix roast on May 5.

Some viewers, including fellow comic Nikki Glaser who also attended the roast, thought the retired NFL player was genuinely upset after Ross made a quip about New England Patriots owner Robert Kraft. But Ross revealed that wasn’t the case.

“Come on, come on, no way, no way,” Ross replied when asked on “The Rich Eisen Show” May 6 if Brady was actually angry.

He continued, “He was having fun. You know, it’s like that’s his dad. Robert Kraft is like a father figure to him. He was just showing his love for Robert Kraft.”

According to Ross, Kraft wasn’t offended by the joke either.

“And Robert Kraft loved it. We had a great talk afterwards. He was so happy that I gave him a shoutout and a salute. It was beautiful,” he said.

During Ross’s set on May 5, Brady stood up, approached the comic and whispered in his ear, “Don’t say that s–- again,” after Ross referenced a 2019 controversy involving the Patriots CEO.

Ross replied, “OK, OK,” and finished the rest of his routine.

Although Ross minimized the moment in his interview on “The Rich Eisen Show,” Glaser had a different perspective when commenting on the awkward confrontation. She was watching from the stage when Brady interrupted Ross.

In an interview May 6 with Howard Stern, Glaser said she thought Brady’s reaction in the moment was authentic.

“I believe that was for real,” she said.

She added that she was surprised to see Kraft at the roast since the 82-year-old mogul was “kind of like a dad figure to Tom.” She said she felt Kraft may not have wanted to sit through all the below-the-belt jokes about the retired quarterback.

“So yeah, I was surprised when Jeff made that joke, but I do think that Tom was actually looking out for him (Kraft),” Glaser said.

She also said Ross seemed concerned afterward that he had gone too far with the joke.

“Afterwards he was a little like, ‘Was that too … ?’ He was a little bit worried,” Glaser told Stern, speaking about Ross. “I mean, we have consciences about these things. Afterwards, we go, ‘Did that really hurt his feelings?’

“You know, he had to do it performatively for Robert, I’m sure,” she continued, apparently referring to Brady’s reaction. “But I’m sure it was not an issue that Jeff is going to hear about today or anything like that.”

During the live roast, Brady sat onstage at the Kia Forum in Los Angeles as multiple celebrities, like Glaser and Ross, took the stage and joked about his NFL career and personal life.

In the lead-in to the joke that appeared to rub Brady the wrong way, Ross mentioned that Brady was famously drafted as the 199th overall pick before going on to have a legendary career, winning seven Super Bowl rings.

The comic joked that after Brady was selected he entered Kraft’s office and said, “‘I’m the best decision your organization has ever made.’”

While the audience applauded, Ross continued, “‘Would you like a massage?’”

That’s when Brady arose from his seat next to the lectern and audibly whispered to Ross. At the time, it was unclear if Brady’s response was scripted into the set.

The massage joke appeared to refer to 2019 headlines involving Kraft, who he was charged as part a human trafficking investigation involving a massage parlor in Jupiter, Florida. The Patriots CEO pleaded not guilty to two counts of soliciting a prostitute and released a statement at the time.

“I am truly sorry. 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,” he said in March 2019, as NBC News reported.

He added, “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.”

In September 2020, Florida prosecutors dropped the solicitation charges, NBC News reported.

Still, Ross’s innuendo prompted Brady to confront the comic on stage. Viewers reacted to the uncomfortable interaction on X.

NFL reporter Ari Meirov wrote that it “Felt like a near Will Smith moment.”

One X user complimented Ross for his response.

“Jeff handled it like a pro. Tom, come on,” he said.

Another asked, “Out of all of the jokes about his kids, Gisele etc.. this is where the line is crossed for Tom?”

Other comedians, like host Kevin Hart and Glaser, repeatedly poked fun at Brady’s 2022 divorce from Gisele Bündchen throughout the evening. The former athlete simply chuckled or took a sip of his drink.