At the same time that Rudy Giuliani and his now-indicted pals were pushing for President Donald Trump to remove Amb. Marie Yovanovitch from her post in Ukraine, Trump administration officials were eyeing potential contenders to take over her job. One of the people in the mix, according to three sources familiar with the discussions, was Rep. Pete Sessions, a former Congressman who called for Yovanovitch’s firing. He is also a longtime ally of the former New York Mayor, and is believed to have taken millions of dollars from a PAC funded in part by Giuliani’s indicted cronies.

Yovanovitch is set to testify to the Congressional impeachment inquiry on Nov. 15. The circumstances of her removal from Kyiv are of keen interest to investigators, and she has said the whisper campaign against her left her blindsided. Witnesses in the inquiry have said they believed the people who successfully pushed for her ouster wanted to replace her with someone more pliable — and maybe even more friendly to their business interests. 

Conversations about Sessions—and another possible pick for the job, Raul Mas Canosa, a South Florida businessman with deep ties to the Cuban expat community—circulated inside and outside the administration from late 2018 through the early months of 2019, according to the sources. Lev Parnas, a Giuliani associate arrested last month for campaign finance violations, was part of discussions about Mas Canosa with associates in Kyiv, according to multiple people familiar with the conversations. One former State Department official said U.S. diplomats in Kyiv learned Mas Canosa was in contention after a rumor about him circulated in Ukrainian political circles.

A spokesperson for Sessions told The Daily Beast he was not offered the ambassadorship or vetted for it. Mas Canosa confirmed that he was approached about taking the position. 

Trump recalled Yovanovitch on April 29 after Giuliani and his allies launched a vociferous campaign against her. Yovanovitch has said she believed the people calling for her ouster wanted to replace her with a new ambassador who would help advance their business interests. Her recall generated rancor from Congressional Democrats, who suspected something strange was going on. But instead of replacing her with a political ally, the Trump administration dispatched veteran diplomat Bill Taylor to the embassy there as chargé d’affaires. 

Taylor told Congress he also sensed something was afoot, and came to believe the Trump administration was withholding military aid to pressure the country to investigate former Vice President Joe Biden’s son. Democrats are investigating the scheme as part of their impeachment inquiry into Trump. Taylor testified publicly before the inquiry on Nov. 13. Yovanovitch is scheduled to testify on Nov. 15. 

Sessions and Giuliani have been allies for more than 15 years, and Sessions has called the former New York mayor a friend. The New York mayor held a $1,000-per-person fundraiser for the Texas Republican in 2002, per New York magazine. And he cut a TV ad for Sessions in the final weeks of his hard-fought 2004 campaign. “When there's so much at stake for our country, we need people in Congress with the character to lead,” Giuliani said in the ad, according to a story from The Hill’s archives. Sessions, in turn, endorsed Giuliani’s unsuccessful 2008 Republican presidential bid, and urged social conservatives to back him despite his support of abortion rights. 

Ten years later, Sessions wrote a letter to Secretary of State Mike Pompeo in May of 2018 citing “concrete evidence from close companions” that Yovanovitch had “spoken privately and repeatedly about her disdain for the current Administration in a way that might call for the expulsion” of her from office.

In an October indictment, federal prosecutors charged Parnas and his business partner, Igor Fruman, with campaign finance violations. Prosecutors allege that the two men acted as straw donors for a foreign government official and gave money to a political action committee which has given up to $3 million to “Congressman-1,” widely reported to be Sessions. 

The indictment alleges that Parnas and Fruman “sought Congressman-1’s assistance in causing the US. Government to remove or recall the then-U.S. Ambassador to Ukraine.” The two allegedly sought Yovanovitch’s removal “at the request of one of more Ukrainian government officials.” 

Since-deleted Facebook posts show Sessions met with Parnas and Fruman on Capitol Hill on May 9, 2018. He sent the letter calling for the State Department to fire Yovanovitch on the same day. 

Since the Ukraine scandal broke, a federal grand jury in New York has subpoenaed Sessions for documents related to his interactions with Giuliani, Parnas, and Fruman, including the effort to have Yovanovitch recalled. 

Mas Canosa confirmed to The Daily Beast that he had been approached earlier this year to serve as ambassador Ukraine, but declined to say by whom. He said he has never met Giuliani, Parnas, or Fruman. 

“I really didn’t feel I was a good fit,” he said. “While I certainly was probably not a top choice, if I had been asked to serve I would have done so out of love of country, period, end of story.”

Mas Canosa indicated he had concerns about Yovanovitch. 

“She was not serving the president well, from what I was told,” he said of Yovanovitch.

Mas Canosa, a former Wall Street investment advisor who now runs a firm called Gladius Consulting, would have been an unorthodox pick to replace Yovanovitch. He’s never served as a diplomat, and most of his commentary has focused on Latin American and Cuban politics. His late brother, Jorge Mas Canosa, was a towering figure in Florida’s Cuban exile community and anti-Castro politics who founded the Cuban American National Foundation. There appears to be scant public evidence that Mas Canosa has any Ukraine connections. 

The campaign to install him didn’t get traction, according to one Trump administration official. “It was nixed early,” the official said. 

Despite that, conversations about Mas Canosa spread on Russian-language social media. On May 12, one obscure commentator who goes by the handle @prokhozhij on the Telegram messaging platform wrote that “The new US ambassador to Ukraine may be an American businessman of Cuban origin, Raul Mas Canosa.”

A little over a week later, the news had spread to more mainstream political commentators, including Taras Berezovets, a television host in Kyiv, Ukraine. On his Telegram channel, he posted that Mas Canosa, who “often appears as a commentator on Trump’s favorite Fox news channel,” was in line to be the next ambassador. 

Berezovets told The Daily Beast he “first learned about Raul Mas Canosa from my friends in Washington in May.”

Mas Canosa’s nephew, Jorge Mas Santos, contributed to Giuliani’s 2008 presidential campaign. And after Trump’s election, Mas Canosa told the Spanish-language publication Diario Las Americas that Giuliani deserved a spot in Trump’s cabinet. 

During her appearance before the House impeachment inquiry, the Trump National Security Council’s former top Russia staffer, Fiona Hill, testified that she was “told that these gentlemen, Mr. Parnas, Mr. Fruman, and Mr. [Harry] Sargeant had all been in business with Mr. Giuliani, and that the impression that a number of Ukrainian officials and others had had was that they were interested in seeking business deals in Ukraine.” Hill didn’t detail what those interests might be. But she said she believed that the reason Yovanovitch had been the target of smear campaign “seemed to be business dealings of individuals who wanted to improve their investment positions inside of Ukraine itself.” 

---with additional reporting by Anna Nemtsova