On May 5, 2023, during a three-hour event on Netflix called "The Greatest Roast of All Time," various participants used Tom Brady's divorce from Gisele Bundchen as a topic for humor. Among the roasters was Drew Bledsoe, Brady's former teammate, who continued making jokes about Bundchen even after the event. On a subsequent appearance on the "Up & Adams" show on May 13, 2024, Bledsoe shared a story from a skiing trip in Montana where he accidentally sprayed Bundchen with snow while attempting to do the same to Brady.
Bledsoe recounted that despite the awkward first meeting where he sprayed her with snow, Bundchen was gracious, giving him a big hug and expressing her respect for him, which she mentioned was often discussed in her house with Brady. Bledsoe and Brady, who were teammates, have evidently maintained a playful rapport, exemplified by Bledsoe’s anecdotes and jokes. The roast and the subsequent recounting show a light-hearted interaction trend, despite the sensitive subject of Brady and Bundchen's divorce after 16 years together, finalized in 2022.