Charles Krupa/AP
Donald Trump and New England Patriots owner Robert Kraft prior to a game.
Mark Leibovich of the New York Times explored that relationship in a story for the New York Times, "The Uncomfortable Love Affair Between Donald Trump and the New England Patriots."
According to Leibovich, the relationship between Trump and the Patriots is so strong that it has spilled over into Trump's feeling towards NFL Commissioner Roger Goodell.
Leibovich met with Trump in the Fall of 2015, shortly after Kraft had conceded his fight with the NFL over Deflategate and accepted the punishment - a $1 million fine and the loss of a first- and fourth-round draft pick - handed down by Goodell.
Trump seemingly confirmed to Leibovich what had long been suspected, that Kraft only conceded to the NFL because he felt Goodell would reduce Brady's punishment.
"Bob said, 'I had a wink from the commissioner,'" Trump added, meaning that Kraft seemed to think that by standing down and not fighting the N.F.L., the league would reduce Brady's penalty on appeal.
Kraft was under pressure, Trump explained. "He choked, just like Romney choked. He said: 'You know what? They winked at me.'"
Trump told Leibovich that he criticized Kraft for making the deal, saying "I said, 'Bob when you make a deal, you should have gotten it all wrapped up.' Who ever heard of making a deal like that? Now you got this mess." Kraft should never have trusted Goodell, he said.
Trump then went all in on Goodell, calling him "a weak guy," "a dope," and "a stupid guy."
"The commissioner is a weak guy," Trump said. "When he made the Ray Rice deal, everybody said: You're stupid. You're weak. And it was such a weak deal. So now he's going overboard with their star, Brady ... The commissioner is a dope. He's a stupid guy."
Trump went on to explain that he tried to persuade Brady to sue the NFL for $500 million.
"I said, 'Tom.' - I gave him a lawyer. - I said: 'Here's what you do," Trump said. "Sue the N.F.L. for $500 million tomorrow. Sue 'em up in Boston, for everything. They'll come to the table.'"
According to Trump, Brady was torn but ultimately decided against it because just wanted to win another Super Bowl. Trump said that he told Brady he understood.