It’s been two weeks since Rudy Giuliani joined President Donald Trump’s legal team, and already he’s adopting his client’s habit for haphazardly tossing bombshells.

In an interview Wednesday night with Fox News’ Sean Hannity, the former New York City mayor let slip that Trump knew about the $130,000 in hush money that longtime personal lawyer Michael Cohen paid Stephanie Clifford, the porn actress known as Stormy Daniels who alleges she had affair with Trump. “They funneled [the money] through a law firm, and the president repaid it,” Giuliani said, by way of explaining that the payment “not campaign money” and was “perfectly legal.”

Giuliani was attempting to defuse a key legal question: whether Cohen broke campaign-finance laws in paying Clifford. If the money was connected to Trump’s ongoing presidential campaign, then it may count as an in-kind campaign contribution by Cohen—one that apparently went unreported to the Federal Election Commission and exceeded the legal limit for individual donations under federal law.

Cohen already faced an uphill battle in proving otherwise: He wired the money to Clifford on October 27, 2016, a full twelve days before the election, which strongly suggests a connection on its own. But then Giuliani, in a Thursday morning appearance on Fox and Friends, made things worse by admitting that Trump and his campaign benefited from Cohen’s payment. “Imagine if that came out on October 15, 2016, in the middle of the last debate with Hillary Clinton,” Giuliani told host Steve Doocy. “Cohen didn’t even ask. Cohen didn’t ask. Cohen made it go away. He did his job.”

Journalists and legal experts quickly realized the significance of all these admissions. Trump, who confirmed his role in the payments on Thursday, had previously claimed that he didn’t know where the $130,000 had come from, and Cohen had disavowed any presidential involvement. “Neither the Trump Organization nor the Trump campaign was a party to the transaction with Ms. Clifford, and neither reimbursed me for the payment, either directly or indirectly,” Cohen said in February. “The payment to Ms. Clifford was lawful, and was not a campaign contribution or a campaign expenditure by anyone.”

After the Hannity interview on Wednesday night, Giuliani told The Washington Post that the president was “very pleased” about it. He also told the paper that he had planned days earlier to reveal Trump’s role in the payment—and did so with Trump’s consent. “He was well aware that at some point when I saw the opportunity, I was going to get this over with,” Giuliani said.

Nonetheless, Giuliani’s candid remarks may end up causing more legal trouble for both Trump and Cohen in the long run. Rick Hasen, a UC Irvine law professor who specializes in election law, explained the potential damage:

If what Giuliani says is true, and if the payments were made to help the campaign and not (just) to help Trump personally, the campaign may be implicated in illegal activity. If Trump knew that Cohen was advancing him a $130,000 loan for campaign purposes, that would have to be reported by the campaign, as would the payments Giuliani said Trump made in installments to Cohen. These would be campaign expenditures that the committee has to keep track of.

Even those closer to Trump’s orbit saw danger. George Conway, the husband of White House adviser Kellyanne Conway who withdrew from consideration to lead the Justice Department’s Civil Division, tweeted without comment an excerpt from FEC regulations on Thursday morning. It states that loans or gifts to a candidate aren’t considered part of the candidate’s personal funds. The implication is that even under Giuliani’s description, Cohen may have still broken federal election laws.

<blockquote class="twitter-tweet" data-lang="en"><p lang="und" dir="ltr"><a href="https://t.co/bsZKAUJpu3">https://t.co/bsZKAUJpu3</a> <a href="https://t.co/xJgZXrvSuT">pic.twitter.com/xJgZXrvSuT</a></p>— George Conway (@gtconway3d) <a href="https://twitter.com/gtconway3d/status/992015378762096640?ref_src=twsrc%5Etfw">May 3, 2018</a></blockquote> <script async src="https://platform.twitter.com/widgets.js" charset="utf-8"></script>

Giuliani didn’t limit his damage to the Clifford story, either. He also linked the dismissal of former FBI Director James Comey to Comey’s refusal to publicly exonerate Trump of wrongdoing in the Russia investigation. “He fired Comey because Comey would not, among other things, say that he wasn’t a target of the investigation,” Giuliani told Hannity on Wednesday night. “He’s entitled to that. Hillary Clinton got that and he couldn’t get that. So he fired him, and he said, ‘I’m free of this guy.’”

Those remarks could end up bolstering an obstruction-of-justice case against the president. Trump already acknowledged to NBC’s Lester Holt that he had been thinking about “this Russia thing” when he decided to fire the FBI director. The president also told Russian officials in the Oval Office that removing Comey freed him from “great pressure.” Giuliani’s comments only support the interpretation that Trump removed Comey for his personal benefit in a criminal investigation.

That Giuliani so dramatically undermined his client on live television isn’t a surprise. He pulled off something similar in an entirely separate legal battle more than a year ago.

Last January, Giuliani appeared on Fox News the day after Trump issued the first version of his controversial travel ban against seven Muslim-majority countries. Giuliani was happy to discuss his own role in crafting the executive order, including the use of national-security claims to mask the ban’s true purpose. “How did the president decide the seven countries?” Fox News host Jeanine Pirro asked Giuliani. He replied, “I’ll tell you the whole history of it. So when [Trump] first announced it, he said, ‘Muslim ban.’ He called me up. He said, ‘Put a commission together. Show me the right way to do it legally.’”

Federal judges were also happy to use Giuliani’s admission in their rulings to block the ban’s implementation. “Nor is there anything ‘secret’ about the [president’s] motive specific to the issuance of the executive order: Rudolph Giuliani explained on television how the executive order came to be,” Judge Derrick Watson wrote last March, citing Giuliani’s remarks as evidence of the order’s anti-Muslim bias.

Trump’s reliance on Giuliani for legal advice reflects a deeper problem as the federal investigations surrounding him gather steam. His legal strategy so far appears to be predicated on punching back rather than crafting a sound defense, which helps explain why he’s had so much difficulty hiring and retaining lawyers. More conventional attorneys like John Dowd and Ty Cobb have recently left the team, leaving brawlers like Giuliani and Jay Sekulow, a frequent Fox News guest, to navigate the Russia investigation instead.

A notable exception to this trend would be Emmet Flood, a veteran Washington litigator who advised Bill Clinton during the 1998 impeachment saga. Trump hired Flood on Wednesday to bolster his defenses as he negotiates a perilous interview with special counsel Robert Mueller’s team. The move signaled a more aggressive approach to defending the president after months of cooperation. But Giuliani’s media tour only a few hours later underscores how little may actually change.

The article has been updated.

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