During Netflix’s Roast of Tom Brady, a moment of tension unfolded when comedian Jeff Ross made a controversial joke about Robert Kraft, leading to a stern response from Brady himself. The incident has sparked discussions regarding the boundaries of humor in celebrity roasts and the personal connections that can influence reactions in such settings.

Jeff Ross’s joke referenced the 2019 accusations against Robert Kraft, owner of the New England Patriots, involving charges of soliciting prostitution, which were later dropped. Ross quipped that Brady had called Kraft the “best decision” the organization had ever made, adding a provocative “Would you like a massage?” This led to Brady confronting Ross onstage, warning him not to repeat such remarks, indicating the sensitivity of the subject due to Kraft’s mentor-like role in Brady’s life.

Following the roast, Ross addressed the situation on “The Rich Eisen Show,” downplaying any lasting tension between him and Brady. He suggested that Brady’s reaction was more about showing respect for Kraft, whom he views as a father figure, rather than genuine anger. Ross recalled that Kraft had appreciated the mention, viewing it as a form of acknowledgment rather than an insult.

This incident highlights the complex dynamics of celebrity roasts, where humor often treads a fine line between playful teasing and potentially hurtful comments. It raises questions about the limits of roast humor, especially concerning personal and legal issues that may be more sensitive for the subjects involved. The balance between ensuring a humorous evening and maintaining respect for individuals’ personal lives remains a delicate challenge for comedians and organizers of such events.