Those aspirations never materialized. Mr. Giuliani was passed over for both jobs — not once, but twice for each position.
Still, Mr. Giuliani has never wavered in his support for his fellow New Yorker. And when Mr. Trump was seeking a new lawyer — a high-wattage TV combatant who would not wilt under the pressures of the news media or legal adversaries — Mr. Giuliani seemed a natural pick.
But Mr. Giuliani has historically been something of a loose cannon who is not used to having his words carefully managed. (Just ask his campaign handlers from 2008, who were constantly frustrated by his freestyling ways.)
So it may have surprised nobody when Mr. Giuliani’s comments on Wednesday night on Fox News set off a frenzy on Twitter. Almost instantly, people were reposting video of Mr. Trump on Air Force One last month saying he knew nothing about the payments.
Asked about his remarks after finishing the Fox News interview, Mr. Giuliani said that what might have seemed to some viewers — including, perhaps, Mr. Hannity — like a slip of the tongue, was actually a planned disclosure.
“That removes the campaign finance violation, and we have all the documentary proof for it,” Mr. Giuliani said, explaining that the president and his other lawyers were well aware of what Mr. Giuliani intended to say on the program. He insisted he had spoken with the president before and after the interview on Fox News. Mr. Giuliani also dismissed the social media furor. There was no cause for concern.
But it may take some time to determine if he was correct.
Late Wednesday night, Common Cause, a government watchdog group, said Mr. Giuliani’s remarks bolstered its lawsuit accusing the president and his campaign of breaking the law by failing to disclose a contribution to his campaign.
“Giuliani seemingly thought he was doing President Trump a favor — but instead made Trump’s legal problems much, much worse,” said Paul S. Ryan, the group’s vice president for policy and litigation.
Whether or not that proves true, Mr. Giuliani is likely to have an opinion about it. And a combative one, at that.