Before urging Ukraine to pursue investigations sought by President Trump, Giuliani raised the standing of a former client, Kyiv Mayor Vitali Klitschko, during a Madrid meeting last summer, according to people in attendance.

Rudy told him, Make sure Klitschko stays, Parnas, who participated in the meeting, told The Washington Post in an interview.
The following month, Giuliani took that same message to Twitter. Reducing the power of Mayor Klitschko of Kiev was a very bad sign, Giuliani wrote, implicitly chastising Zelensky, adding that the mayor, a former boxing champion, is very much admired and respected in the US.
Zelensky backed off the threat, and nearly six months later, Klitschko still remains in his post.
The Zelensky adviser in Madrid, Andriy Yermak, confirmed in a statement that he and Giuliani discussed Klitschko, but denied that Trumps personal attorney applied any pressure on Klitschkos behalf. Yermak said Giuliani told him he was not trying to influence him.
The previously unreported account of Giulianis discussions with the Ukrainian government about Klitschko provides another example of how the former New York mayor has used his perch as a close adviser to Trump to promote his personal interests.
In 2017, Giuliani sought to persuade Trump and other top administration officials to adopt positions advocated by Turkey, the same year he was working as a lawyer for a politically connected gold trader from that country facing criminal charges. In September, he urged Justice Department officials not to pursue a case against a wealthy Venezuelan energy executive who had hired him as a private attorney.
Giulianis activities have spurred deep unease among senior administration officials, who have said they are unclear when he is working on behalf of his private clients and when he is working in the interests of the president.
Attorney General William P. Barr counseled Trump in several conversations in the fall that Giuliani had become a liability, The Post previously reported.
Inside Giulianis dual roles: Power-broker-for-hire and shadow foreign policy adviser
And, in a draft manuscript of his upcoming book, former national security adviser John Bolton claims that Secretary of State Mike Pompeo feared Giuliani might be working on behalf of a client when he sought the removal of the U.S. ambassador to Ukraine, according to a person familiar with the project.
Giuliani told The Post that he has been careful to define his role as a private lawyer for Trump, not as a representative of the U.S. government, and chalked up scrutiny of his work to resentment.
People hate me for representing Trump, Giuliani wrote in a text message. The better you do the more bitter they become.
He noted that the president is not my only client or customer, adding, I still have opinions and work I need to do and its not expanded as a result of representing the President, it has of necessity declined so I can pay attention to my work for him.
What they are saying is true of any private lawyer for President, he wrote, adding: There is nothing to suggest that it has affected my work.
Asked about the Madrid meeting, Giuliani called Parnas, his former associate and client, a proven liar. Parnas, who is facing federal campaign finance charges, began speaking publicly about his role in the Ukraine pressure campaign in recent weeks drawing attacks from Trump allies, who say he seeking to reduce his criminal exposure.
Giuliani declined to say whether he sought to intervene on Klitschkos behalf, describing the boxer turned mayor as a good friend of mine over the years.
The balance of power at the Madrid meeting was decidedly in Giulianis favor. At the time, Zelenskys team was urgently seeking a White House meeting with Trump to send a critical signal to Russia, which has been fueling a proxy war in Ukraines east for more than five years. And days earlier, in a phone call with Zelensky, Trump had made it clear to the new Ukrainian president that he needed to deal with Giuliani to win White House support.
Zelensky has still not secured his White House meeting. I would be ready to go tomorrow, the Ukrainian leader said Friday during a joint appearance in Kyiv with Secretary of State Mike Pompeo.
Giuliani has had business ties in Ukraine for at least a decade, work that brought him into contact with prominent Ukrainian figures and politicians, including Klitschko.
A three-time world heavyweight champion known as Dr. Ironfist because of his doctorate in sports science, Klitschko is one of the most famous Ukrainian athletes. When he entered politics, the boxing legend said he wanted to bring the living standards he saw in the West to his native Ukraine.
In a previous interview with The Post, Giuliani said he was hired in 2008 as a political consultant to Klitschko, who at the time was making what would be an failed bid to become Kyivs mayor.
During a successful run for mayor in 2014, Klitschko hired Giulianis consulting firm to advise him on combating corruption and crime in Ukraines capital, Giuliani told The Post.
Klitschko has offered contradictory accounts of their arrangement, saying in a statement this week that he never had a business relationship with Giuliani. The Kyiv mayor also described Giuliani as a great friend of Ukraine and one of the most successful mayors in the world.
Klitschko said that he first encountered Giuliani in 2006 during a visit the former New York mayor made to Ukraine. Since then, they have met many times in New York and Kyiv, Klitschko said.
Considering our good personal relationship, sometimes I ask for his advice on municipal issues, he said.
Klitschko, a leader of Ukraines pro-Western revolution, won reelection as Kyivs mayor in 2015 with more than 65 percent of the vote. Like his political ally, former president Petro Poroshenko, he entered office amid high expectations that he would crack down on the corruption and cronyism that have characterized Ukrainian politics.
While Kyiv has largely prospered, and many regard Klitschko as an improvement over his predecessors, his detractors say that a number of the problems that have plagued the capital persist: poor delivery of services, substandard infrastructure and questionable construction projects.
They also accuse him of relying on high-profile projects like a $10 million glass-and-concrete bridge in the citys center instead of focusing on substantive reforms.
Klitschkos political future was thrown into doubt in April when Zelensky a comedian and political neophyte fresh off playing the president in a Veep-style Ukrainian television series trounced Poroshenko in Ukraines elections.
In addition to functioning as Kyivs elected mayor, Klitschko simultaneously has been serving as head of the Kyiv City State Administration under a deal he brokered with Poroshenko. That influential position, akin to the city manager, is appointed by Ukraines president.
Ousting Klitschko from the post would help Zelenskys team consolidate control over the Ukrainian capital, by far the countrys most important power center.
Zelensky informed Klitschko during a meeting in early July last year that he wanted to once again separate the positions and install his own appointee as head of the Kyiv administration, according to a video address Klitschko posted on Facebook after the meeting.
Klitschko would still retain the elected position of mayor, though his power would be greatly reduced.
In the Facebook post, Klitschko criticized the proposal as a rollback of Kyivs rightful power of self-government.
Leading the charge for Klitschkos firing was Andriy Bohdan, the former lawyer for Ukrainian tycoon Ihor Kolomoisky, whom Zelensky appointed as his equivalent to chief of staff.
On July 30, Bohdan stepped up the political broadside against the Kyiv mayor, telling Ukrainian news outlets in a briefing that Klitschko had lost control of the situation in the city over the past five years and was beholden to wealthy figures controlling the city council.
Klitschko said the comments made Bohdan look strange and incompetent.
Bohdan did not respond to requests for comment.
Last summer, amid speculation about whether he would be fired, Klitschko flew to the United States.
On July 31, the day after Bohdans comments, Klitschko met with Giuliani in New York, posting a photo on Facebook of himself and the former New York mayor seated in Giulianis office.
The meeting came just a week after Trump exhorted Zelensky in a July 25 phone call to coordinate with Giuliani on an investigation into former vice president Joe Biden and his son, who served on the board of the Ukrainian gas company Burisma while his father was in office.
In an interview, Parnas said he did not attend Giulianis meeting with Klitschko in New York, but was briefed on it afterward by both Giuliani and a lawyer for Klitschko.
Parnas said he was told by both men that, during the meeting, Klitschko complained to Giuliani that the Zelensky administration was trying to oust him and appealed for help.
He basically cried to Rudy, saying they were going after him unfairly, Parnas said.
Klitschko blamed Bohdan for his predicament, Parnas said, fueling Giulianis anger at Zelenskys chief of staff and, by extension, at the Ukrainian president, who had not publicly committed to investigations that would benefit Trump.
In written comments to The Post, Klitschko denied requesting Giulianis help.
I did not ask anyone for assistance. And our photo is a photo of a meeting of two public figures, Klitschko said. He said they discussed how Ukraine needs further support from our Western partners and friends after the shift in power, support for local government and its development.
Days later, Giuliani was due to hold a face-to-face meeting with Yermak, a top aide to Zelensky.
Giulianis primary goal for the Madrid summit was to press Yermak to get Zelensky to announce the investigations he sought on Trumps behalf, he previously told The Post.
How Trump and Giuliani pressured Ukraine to investigate the presidents rivals
Kurt Volker, then serving as a special envoy to Ukraine, testified in the House impeachment inquiry that he had connected Yermak and Giuliani. Volker said he hoped the Zelensky aide could convince Giuliani that the new Ukrainian president was an anti-corruption reformer and break a logjam that appeared to be preventing Trump from granting the new leader a White House visit.
The Ukrainians hoped that by satisfying Giuliani, they could finally develop close relations with the Trump administration, text messages released by House impeachment investigators show.
Giuliani was pleased with the selection of Yermak, a former entertainment attorney, as Zelenskys representative for the meeting in Madrid, Parnas said, because he perceived Yermak as an equal, someone who played the same role for the Ukrainian president as he did for Trump: a lawyer and confidant.
Text messages show that Parnas updated Giuliani on Klitschkos situation the day before the Madrid meeting with Yermak. Parnas told The Post he knew Giuliani wanted to be prepared to discuss his onetime client in Spain.
Giuliani wrote in a text back to Parnas before the trip, I dont want us in their politics.
But Parnas said that when Giuliani met with Yermak, he was all about internal Ukrainian politics, defending Klitschko.
The meeting was held at a luxury hotel. Parnas said that he and Giuliani arrived first and secured a table in the impressive lobby. His business partner, Igor Fruman, had planned to join but skipped the meeting to assist a traveling companion of Giulianis whose luggage had been lost in transit to Spain, according to Parnas.
An attorney for Fruman declined to comment.
When Yermak arrived, the group exchanged pleasantries. Each one was like, Its so nice to finally meet you, Parnas recalled. They discussed how pleased they were that their respective presidents had finally spoken the previous week, he said.
After that, Parnas said, Giuliani got down to business.
Giuliani started going on about Klitschko and Bohdan, he said. Giuliani told the Zelensky aide that Klitschko was a great guy for Ukraine.
He said, He can bring more interest to Ukraine, more business. Hes a boxer. Americans love boxers, Parnas recalled. He said, Trump loves him. I think Trump knows him hes fought at some of his places.
Klitschko told a Ukrainian news outlet in 2017 that when he and his brother Wladimir fought at the Trump Taj Mahal in Atlantic City, they socialized with Trump.
Parnas told The Post he did not know whether Giuliani had ever discussed Klitschkos predicament in Kyiv with Trump.
In Madrid, Giuliani told the aide to Zelensky that he should make sure Klitschko remained in his powerful job, according to Parnas.
Parnas said that Yermak appeared open to Giulianis request.
Yermak basically said that he would do everything in his power, that he would personally meet with Klitschko and he would try to work it out, Parnas said. He promised Rudy.
In a statement, Yermak said he knew going into the meeting that Giuliani and the Kyiv mayor were well acquainted and confirmed that Klitschko came up during the conversation.
Giuliani inquired about my opinion of Vitali Klitschko as mayor, Yermak said. At the same time, he immediately made a disclaimer, so that I would not perceive this issue as an attempt to influence me.
Yermak said he told Giuliani he had known Klitschko for years, and that the boxer was elected and supported by the people of Kyiv.
On this, our conversation on the topic of Klitschko was over, Yermak said. Therefore, any allegation that at the meeting Mr. Giuliani tried to impose some kind of narrative on me or that some kind of agreement was reached … is not true.
The Post reported this week that Yermak has been urging the Ukrainian president to take a pro-Trump line to bolster his standing with the United States, according to diplomats familiar with the discussions.
Pompeo visits Zelensky in Kyiv, vows U.S. support for Ukraine will not waver
Parnas said that after discussing Klitschko, Giuliani then turned to the central issue that had brought them together: a proposed statement by the Ukrainians regarding investigations helpful to Trump.
They had to include a statement about Burisma and Biden, Parnas said Giuliani explained.
In early September, Zelenskys cabinet passed a resolution to remove Klitschko from his administrative post. Zelensky has not signed the document, leaving Klitschko in place.
In his statement to The Post, Klitschko said he said he did not know why Zelensky backed off his threat to remove him.
I cannot be responsible for the president, he said.
Stern reported from Kyiv. Natalie Gryvnyak in Kyiv contributed to this report.