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(CNN) —  

For the last three years, Rudy Giuliani seemed to roam the world with impunity as a kind of rogue ambassador to President Donald Trump, swatting aside concerns from US national security aides and diplomats as he carried out the President’s bidding.

But new reporting suggests that the man once hailed as “America’s mayor” was simultaneously pursuing his own fortune, and his apparent self-dealing is now under such intense scrutiny that even the President is seeking distance from his personal lawyer.

Wednesday marked a terrible day for the former New York mayor when scrutiny on him intensified with new reports on his business dealings from The New York Times and The Washington Post.

The stories paint a portrait of a man who traded on his close relationship with the President as he explored lucrative deals in Ukraine that would enhance the influence of his firm, Giuliani Partners, and his personal wealth.

The unflattering revelations come at a time when lawmakers are investigating the motives behind Giuliani’s efforts to oust former Ukraine Ambassador Marie Yovanovitch – whether they were at the behest of Trump or Ukrainian officials who wanted her out. CNN has also reported that federal prosecutors are examining Giuliani’s business arrangements as part of a broader probe of his business associates in an investigation that could include criminal charges ranging from conspiracy, obstruction of justice, campaign finance violations and money laundering.

Giuliani’s ties

Federal prosecutors in New York are looking into the ties of Giuliani and his associates had to Ukraine’s state-run oil-and-gas company. And on Wednesday, CNN’s KFile reported that Giuliani has given inconsistent answers about his connections to a Ukrainian oligarch who he previously said he had “nothing to do with.”

The tightening legal vise around Giuliani apparently led Trump to tell conservative radio host Bill O’Reilly on Tuesday night that he had no idea what the former New York Mayor was actually doing in Ukraine, as that conduct continues to get white hot scrutiny in the House impeachment inquiry.

In a pattern reminiscent of the way Trump dealt with his previous personal attorney Michael Cohen – who is currently serving a three-year prison sentence – the President suggested he was in the dark about Giuliani’s agenda in Ukraine, despite weeks of impeachment testimony establishing the opposite.

When asked by repeatedly by O’Reilly Tuesday whether he directed Giuliani to go to Ukraine or to put heat on that country, Trump said: “No.”

“No, I didn’t direct him, but he’s a warrior, Rudy’s a warrior,” Trump added. “Rudy went. He possibly saw something. But you have to understand, Rudy (has) other people that he represents.” He also noted that Giuliani had involvements in Ukraine over many years.

It strained credulity to think that Giuliani would have any client more important than the President, but Trump’s claim directly contradicts his statements to Ukrainian President Volodymyr Zelensky in their July 25 phone call. According to the rough transcript of that call, Trump told the new President, “I will have Mr. Giuliani give you a call” and that “Rudy very much knows what’s happening.”

It also conflicts with the testimony of Gordon Sondland, Trump’s ambassador to the European Union, who testified that Giuliani was essentially running point for Trump on Ukraine matters – trying to arrange a quid pro quo of a White House meeting for Ukraine’s new president in exchange for his help investigating interference in the 2016 elections, former Vice President Joe Biden, and his son Hunter Biden, who served on the board of a Ukrainian energy company known as Burisma. There is no evidence of wrongdoing by either Joe or Hunter Biden.

“Secretary Perry, Ambassador Volker and I worked with Mr. Rudy Giuliani on Ukraine matters at the express direction of the President of the United States,” Sondland testified. “We did not want to work with Mr. Giuliani. Simply put, we were playing the hand we were dealt. We all understood that if we refused to work with Mr. Giuliani, we would lose a very important opportunity to cement relations between the United States and Ukraine. So we followed the President’s orders.”

Another layer of messiness

The news that Giuliani was negotiating personal financial deals with the very same people he was seeking information from added another layer of messiness to the shadow diplomacy operation he was running.

The Post and The New York Times reported this week that Giuliani pursued hundreds of thousands of dollars in business from officials in Ukraine at the same time that he was using his connections there to unearth damaging information about the Bidens.

While the deals weren’t consummated, the revelations are important because, first, they undercut Giuliani’s repeated claim that he has no business in Ukraine, and second, they suggest Giuliani was preying on potential clients in Ukraine who were desperate for stronger ties to the United States and his main client, the President of the United States.

The New York Times review of documents showed that Giuliani entertained an engagement with the Ukrainian Ministry of Justice, which would have paid his firm $300,000 for his help in finding stolen money.

A draft proposal reviewed by the Times more directly spelled out that Giuliani would have represented Yuriy Lutsenko, Ukraine’s former top prosecutor. The New York Times said the unsigned draft proposal outlined an agreement where Lutsenko would have paid at least $200,000 to retain Giuliani’s firm and the husband-and-wife legal team of Joseph E. diGenova and Victoria Toensing, who are also tied to Trump. (The House impeachment inquiry has established that Giuliani worked closely with Lutsenko to try to advance an investigation into the Bidens as well as the 2016 election).

Giuliani has said that he doesn’t charge the President for his legal services. And the former New York Mayor defended himself on Twitter Wednesday evening calling The New York Times “#FAKENEWS.”

“I did NOT pursue a business opportunity in Ukraine, as they misrepresented. I could have helped them recover $7B in stolen money, but I didn’t. Was paid Zero,” Giuliani tweeted.

An hour later, he tweeted: “NYT and WAPO trying to destroy my credibility because I know their lies to cover up Biden.”

Trump is famously transactional, casually casting off even lifelong friends in his employ such as Cohen, who went from being a “fine person with a wonderful family” in Trump’s estimation to a liar and “a rat.”

Giuliani played a key role in Trump’s takedown of Cohen, appearing on multiple networks to portray Cohen, who he’d once praised, as “an incredible liar” and a “scumbag.”

As his legal troubles mount, Giuliani has insisted that he still has the confidence of the President even though the two appear to be talking past one another through media interviews.

During an appearance on Fox this past week, Giuliani rejected the notion that the President would throw him under the bus: “I have insurance,” he said mysteriously.

Giuliani later claimed he was joking, but it seemed like a warning to the President that he is skilled in Trump’s form of Twitter jiu-jitsu, and he won’t go down like Cohen without a fight.