Netflix’s “The Roast of Tom Brady” was a roaring success in 2024. Comedians, football stars, and celebrities were all joining in with jokes at Brady’s expense. Roast master and comedian Jeff Ross, who has done a number of roasts, played a big role in organizing the event.
Ross appeared to get on the wrong side of Brady, though, after a joke about New England Patriots owner Robert Kraft. Ross talked about it during a recent appearance on “The Howard Stern Show” where Ross spoke with Stern about the awkward exchange.

Jeff Ross Addresses Awkward On-Air Moment With Tom Brady in 2024
Entering the Brady roast, there appeared to be a no-holds-barred attitude about any subjects. Brady’s divorce from Gisele Bündchen was brought up on several occasions. Ross found out, though, pretty quickly that there was one line not to cross seconds after bounding gleefully over it.
After referencing Kraft’s 2019 run-in with the law for allegedly soliciting sex in a massage parlor, for which the owner was later cleared, Ross was reprimanded by Brady. The quarterback hastily rose from his seat and could be heard muttering, “Don’t say that s*** again.”
Opinions have been split on the seriousness of Brady’s message, but Ross claims that it was more of an anxious warning than an aggressive one.
“I think Tom was checking me the way a lawyer objects on behalf of a client even when they know it’s kind of bulls***,” Ross told Stern. “I just shrugged it off and kept going.”
Comedians Were Warned Not To Make Kraft Jokes
Ross’ dismissal of Brady’s intervention was likely because he expected it. According to fellow comedian Andrew Schulz, in the event’s aftermath, Netflix made a point of outlawing jokes about Kraft’s 2019 controversy.
“When Tom checked Jeff Ross, I think that was 100% real,” Schulz said during an episode of his “Flagrant” podcast. “The reason why I think it’s real is because [Netflix] told us no jokes about happy endings with Bob Kraft.”
Others who attended the event have claimed that Kraft’s attendance was kept a secret to avoid comedians writing jokes about him. It’s possible that both Netflix and Brady were concerned about potential legal ramifications of crossing the line, given that Kraft was cleared of the crime.
It’s also possible that Brady felt responsible for protecting his former boss from those kinds of jokes out of respect for him and his family. Whatever the reasons, though, it was clear that Brady wanted to put that fire out immediately and was willing to cause a minor scene to do so.