Tom Brady appeared on the Howard Stern Show Wednesday. Brady stuck to his gameplan and mostly gave Stern nothing compared to what he usually gets out of guests. One of the few times Stern got Brady to sweat a little was when he brought up Donald Trump. It wasn't anything political that tripped him up - Brady said that teammates knew him so there was never any real tension around his friendship with the president - but when Stern asked him about Ivanka Trump, it drew some nervous laughter from Brady.
Being Brady, he quickly recovered and acted like he didn't really know what Stern was talking about. Stern referred to some comments that Trump made nearly two decades ago about wanting Brady to date his daughter. Boston.com found at least some of the Trump-on-Stern comments and it wasn't quite how Howard remembered.
"“Tom Brady, the quarterback, is somebody that really likes Ivanka and he’s a great guy and I got to know him at the Miss Universe contest,” Trump said. Shortly after winning his first Super Bowl, Brady had served as a judge at the 2002 Miss U.S.A. beauty pageant, which Trump owned from 1996 to 2015. “And you’d be OK with him dating your daughter?” Stern asked. “I think he’s great,” Trump said. “He’s 25 years old. He’s Mr. All-American.” “Is he dating your daughter?” Stern asked. “Well, it could happen. I mean, he’d like to, and we’ll see,” Trump said, noting that Brady was “focused now on the football stuff.” "
This was right before Brady started dating Bridget Moynahan. As Stern recalls, Trump is the one who wanted Brady dating Ivanka. Since Trump is the one with quotes on the record, we can probably assume he put some words in Brady's mouth.