Giuliani told Elite Daily's Alexandra Svokos: "[Trump] was too reserved, and he was too gentlemanly at the end to say what I would have said about Hillary Clinton's attack on him about not being a feminist."
Giuliani continued: "Well, I'm not sure I should tell you what I would have said. But I sure would’ve talked about what she did to Monica Lewinsky — what that woman standing there did to Monica Lewinsky, trying to paint her as an insane young woman when, in fact, Monica Lewinsky was an intern. ... And after being married to Bill Clinton for 20 years, if you didn’t know the moment Monica Lewinsky said that Bill Clinton violated her, that she was telling the truth, then you’re too stupid to be president."
Giuliani added to the New York Times of Trump's failure to press the issue on Clinton and women: "That’s what he wanted to say, but he didn’t say it, and as his friend, I’m going to say it for him. She’s a total phony."
Giuliani, of course, isn't standing on particularly firm ground here. Back when his marriage to Donna Hanover fell apart in 2000, Hanover cited Giuliani's relationship with a staffer just hours after Giuliani suddenly announced their separation. From the Times back then:
Three hours later, Ms. Hanover appeared outside Gracie Mansion and, with a wavering voice and tears in her eyes, said: ''Today's turn of events brings me great sadness. I had hoped to keep this marriage together. For several years, it was difficult to participate in Rudy's public life because of his relationship with one staff member.''Joannie Danielides, Ms. Hanover's press secretary, said Ms. Hanover was referring to Cristyne Lategano-Nicholas, Mr. Giuliani's former communications director who is now president of NYC and Company, the city's tourism bureau. Friends of Ms. Hanover's said yesterday that she had described the relationship between her husband and Ms. Lategano-Nicholas as intimate while Ms. Lategano-Nicholas worked at City Hall. The mayor has denied having had a romantic relationship with Ms. Lategano-Nicholas, who left City Hall last May and married Nicholas Nicholas, a sports writer, in February.
Apart from the allegation made by Hanover, Giuliani was also having an affair at the time with Judith Nathan, who later become his wife. It was later reported by Politico's Ben Smith, during Giuliani's 2007 presidential run, that Giuliani had been billing "obscure city agencies for tens of thousands of dollars in security expenses amassed during the time when he was beginning an extramarital relationship with future wife Judith Nathan in the Hamptons."
This is merely the latest example of top Trump advisers and supporters broaching a topic that Trump himself hasn't yet embraced for a whole host of reasons — not least of which are his own indiscretions.
Trump national spokeswoman Katrina Pierson back in April threatened to bring it up if Clinton accused Trump of being a sexist: "If Hillary Clinton or her team wants to go after Donald Trump as a sexist, then he will absolutely bring up that topic."
A month later, senior Trump adviser Barry Bennett told Fox News that it would be part of an "education process" for younger voters. "We now have 30 or 40 million new voters who didn’t participate in the Clinton presidency years, so I mean, they don’t know this stuff," he said. That same week, top Trump media supporter Sean Hannity interviewed three Bill Clinton accusers — Juanita Broaddrick, Kathleen Wiley and Paula Jones — on his radio show, and Trump released an ominous video featuring the words of Bill Clinton's accusers.
But apart from that and a tweet this weekend about potentially inviting Gennifer Flowers to the debate, Trump hasn't totally pressed the issue.
It's not clear whether Giuliani is freelancing here or simply trying to inject a topic into the debate without having Trump himself talk about it. It's certainly not the first questionable decision or strange claim Giuliani has made as a Trump surrogate, and Giuliani isn't the first surrogate to lean toward making this an issue.
But it does reinforce the liabilities Trump faces if he is to go down this road — or perhaps, as it seems increasingly likely, when he goes down this road.