President Donald Trump's recent decision to allow a Turkish invasion into Syria that threatens U.S. allies has put the president's relations with Turkish president Recep Tayyip Erdogan under fresh scrutiny—and a new report is likely to only add to the controversy. Bloomberg reported Wednesday on a conversation Trump had in the latter half of 2017 with then-Secretary of State Rex Tillerson, in which Trump reportedly asked Tillerson to help him persuade the Justice Department to drop its criminal case against Reza Zarrab, an Iranian-Turkish gold trader—and client of Rudy Giuliani. Tillerson refused the request and immediately recounted it outside to then-Chief of Staff John Kelly, “emphasizing that the request would be illegal.”

Giuliani was not the president's lawyer at the time, and Bloomberg notes that it's unclear whether Trump actually realized the request was as “improper” as it actually was. The president, after all, has displayed an eagerness as of late to publicly declare his desire to see foreign leaders investigate his political rivals, and while Tillerson did not respond to Bloomberg about the reported conversation, he's suggested in the past that the president's request was hardly an isolated incident. “So often, the president would say ‘Here’s what I want to do and here’s how I want to do it,’ and I would have to say to him, ‘Mr. President I understand what you want to do, but you can’t do it that way,”’ Tillerson said in an onstage interview in Texas last year. “It violates the law, it violates treaty you know and he just, he got really frustrated when we’d have those conversations.” The White House and Kelly declined to comment to Bloomberg about Trump's reported request, while Giuliani, when asked if he had talked to Trump about his client, told Bloomberg, “Suppose I did talk to Trump about it—so what? I was a private lawyer at the time. . . . Maybe at some point I dropped his name in a conversation.” (When asked if he had talked to Tillerson, Giuliani responded, “You have no right to know that.”)

But Trump's involvement with Zarrab's case specifically also raises new questions. Zarrab was arrested in 2016 on a family trip to Walt Disney World for evading U.S. sanctions against Iran, with former U.S. Attorney Preet Bharara writing that Zarrab had “facilitated millions of dollars-worth of transactions on behalf of Iran . . . through a global network of companies located in Turkey and the United Arab Emirates.” Beyond that, Zarrab also had ties to the Turkish government, and, Bharara noted, was “engaged in a massive bribery scheme . . . paying cabinet-level [Turkish] governmental officials and high-level bank officers tens of millions of Euro and U.S. dollars” to facilitate his transactions. Zarrab's case was a priority for Erdogan, who, while not directly implicated in the sanctions evasion, was tangentially linked to the corruption. The Turkish president lobbied Obama administration officials, including President Barack Obama and former Vice President Joe Biden, for the trader's release, and the New York Times noted in 2017 that his officials mounted a campaign casting the case as “a conspiracy against Turkey” when it eventually went to trial. While the efforts to secure Zarrab's release were ultimately unsuccessful, Zarrab ended up taking a plea deal in November 2017—and was speculated to be cooperating with Robert Mueller's team in their investigation of Michael Flynn and his relationship with Erdogan.

Given Erdogan's involvement, the revelation that Trump was personally pushing for Zarrab's case to be dropped is likely to fuel new concerns about Trump's reportedly “fawning” relationship with the authoritarian Turkish president, as Trump seemingly prioritizes Turkey over the views of his own party by withdrawing troops from Syria and leaving the American-allied Kurds at risk. (Trump's relationship with Erdogan has also been scrutinized given Trump's real estate business in Istanbul, and an NBC News analysis found that Turkish officials have made more visits to Trump properties than any other government.) The president defended his wildly unpopular military decision Wednesday in true Trumpian fashion, saying that the Kurdish troops “didn’t help us in the Second World War. They didn’t help us in Normandy.” (Trump also dismissed a question on ISIS escapees by saying “they are going to be escaping to Europe.”) Lawmakers, meanwhile, are escalating their rare bipartisan condemnation of Trump's decision, as Senators Lindsey Graham and Chris Van Hollen released a bill Wednesday that would issue sanctions against Turkey. “The Kurds have been a great partner . . . Turkey under Erdogan has not been. I’m concerned about what can happen next,” Republican Sen. Roy Blunt told Politico Wednesday. “I wish the president would reconsider.”