Here's the joke that crossed line for Tom Brady at Netflix roast

Tom Brady in shades by a sign reading "The Greatest Roast of All Time: Tom Brady"

Published May 6, 2024 Updated May 7, 2024 8 AM PT

Tom Brady was a great sport Sunday night.

He endured jokes about his divorce, his business decisions, his love life, his multiple retirements, his former teammates, his ex-wife, his healthy lifestyle and much more — all with a smile on his face.

And that was just in the first 20 minutes of “The Roast of Tom Brady” at the Kia Forum that was streamed live on Netflix.

One gag, however, apparently crossed the line as far as Brady was concerned — and the seven-time Super Bowl champion wasn’t even the butt of that particular joke. The target was New England Patriots owner Robert Kraft, the man who signed Brady’s paychecks for the first 20 years of his 23-year NFL career.

After host Kevin Hart opened the show with a blistering monologue — “Why didn’t we go to the Crypto.com Arena downtown? Well, the reason why we didn’t go there is because we didn’t want to remind Tom’s fans of how much money he owes them” — comedian and celebrity roast staple Jeff Ross kept the hits coming. He talked about how Brady was drafted in the sixth round with the 199th pick of the 2000 NFL draft “when Bill Belichick’s dog stepped on the keyboard by accident.”

“So Tom became a Patriot,” Ross said, “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 best decision your organization has ever made. Would you like a massage?’”

The joke was a reference to Kraft being arrested in 2019 on charges of soliciting sex from a prostitute during an encounter at a Florida day spa. Kraft pleaded not guilty, and the charges were dropped the following year after his lawyers prevented video and audio footage from being used as evidence in court.

As the crowd laughed and Ross blew a kiss in Kraft’s direction, Brady could be seen shifting in his seat behind and to the right of the comedian. The camera cut to a close shot of Ross, who said “I love Robert Kraft.”

Brady then approached Ross. The NFL’s all-time leader in passing yards and touchdown passes had a bit of a smile on his face, but his tone was dead serious when he leaned in and said to Ross, “Don’t say that s— again.”

As Brady returned to his seat, Ross laughed, put his hands up and said, “OK, OK!” He pointed in Kraft’s direction and said, “He’s having fun, look at him.” As Ross added some sincere words of praise and a salute for Kraft, the Patriots owner was shown smiling in the crowd.

Brady didn’t appear to hold a grudge and could be seen laughing during the rest of Ross’ set. The two men embraced and spoke after Ross’ performance — a scene Hart mocked by implying Ross was kissing up to the GOAT. “I heard you over there,” Hart said. “‘Tom, you all right? Yeah? Your hair’s so straight.’”

Brady absorbed many more barbs throughout the evening without feeling the need to step in again.

The next day, Ross appeared on “The Rich Eisen Show” and insisted that Brady wasn’t really angry in that moment.

“He’s having fun,” Ross said of Brady. “It’s like that’s his dad, you know? Robert Kraft is like a father figure to him. He was just showing his love for Robert Kraft. And Robert Kraft loved it. We had a great talk afterward, and he was so happy that I gave him a shoutout and a salute. It was beautiful.”

Former Patriots quarterback Drew Bledsoe, who also took part in the roast, called Brady’s reaction to Ross’ quip about Kraft “an authentic moment.”

“We’re sitting up there on the stage, so I can see the teleprompter, I can see what’s scripted and what’s not. And that was not scripted,” Bledsoe said Monday on “The Dan Le Batard Show with Stugotz” podcast. “That was Tom genuinely coming to his defense.”

Many others came out to take their best shots at Brady and often one another.

Kim Kardashian recovered from being booed for about 15 seconds upon taking the podium to receiving big laughs and applause for some of her quips.

“Honestly, it’s hard for me to watch people roast you, but I think enough of my family members have helped defend former football players,” said the daughter of Robert Kardashian, who was a member of O.J. Simpson’s legal team during the former USC and NFL star’s murder trial in the 1990s.

She also got a big laugh from Brady when she told him, “I think it’s so great the way you’re showing everyone that even after winning seven Super Bowls, you can still have a midlife crisis.”

Belichick and several of Brady’s former teammates — including Rob Gronkowski, Julian Edelman, Randy Moss and Bledsoe, whom Brady famously replaced as the Patriots’ starting quarterback in 2001 — all had their turns at the podium, as did his former on-field rival Peyton Manning.

“Honestly, it is great to be here with a bunch of people sitting around talking smack about Tom Brady,” Manning said. “Or as we call that in the Manning family: Thanksgiving.”

Peyton’s brother Eli Manning, who led the New York Giants to two Super Bowl wins over Brady and the Patriots, was not present for the show but offered a jab of his own on X the next morning.

“I thought about attending the Roast of Tom Brady last night,” Manning wrote, “but I did not want to Roast him for a 3rd time!!”

Others who joined in the roast Sunday included stand-up comic Nikki Glaser, UFC president Dana White and actor Will Ferrell in character as Ron Burgundy from the “Anchorman” movies.

As is custom at these events, Brady got his chance at the podium — and he didn’t hold back. He said to Belichick, “I’ve been out of the game for a minute, so I’m curious, how many Super Bowl rings have you won since I left? Maybe it’s not just the guy on the sideline. When I go to the Indy 500, I don’t ask the winning driver, ‘Hey, who gassed up your car?’”

He even (jokingly) admitted to Deflategate. “The NFL spent $20 million and found that it was ‘more probable than not’ that I was ‘generally aware’ that someone may have deflated my footballs. You should’ve just given me the $20 million and I would’ve told you I f— did it.”

Brady was also one of several speakers who made jokes at the expense of Aaron Hernandez, the former Patriots tight end who hanged himself in a prison cell in 2017 while serving a life sentence for first-degree murder. Hernandez, whose death was ruled a suicide, was later determined to have had CTE and early brain atrophy.

TMZ reports that Hernandez’s former fiancee, Shayanna Jenkins Hernandez, the mother of their 11-year-old daughter, thinks those jokes went too far.

“It’s sad that I’m trying to raise my children in such a cruel world,” she told the website.