As a Manhattan grand jury nears a possible decision to indict Donald Trump over his hush money payment to a porn star with whom he had an affair, the former president is on a relentless and aggressive campaign to discredit Michael Cohen, his former “fixer” who did the dirty work.
That effort intensified (and got a bit weird) on Monday, when the grand jury heard from a MAGA-friendly lawyer who briefly advised Cohen years ago—only to turn on him now. Robert Costello called Cohen an unreliable liar, taking the remarkable step of betraying someone he deemed a former client.
Talking to reporters on a New York City street, Costello waved around papers saying that grand jurors deserved to see nearly 330 emails tracking his private interactions with Cohen to “see the full picture.”
The Daily Beast has reviewed those emails, which do indeed tell a more complete story—one in which the Trump White House tried and failed to keep Cohen in line, eventually positioning him to testify against his former boss.
The emails show an attempt to establish a backchannel running from Cohen—who was suddenly being investigated by the feds over the $130,000 payment to adult film star Stormy Daniels—all the way to then-President Trump. Costello had long been associated with Trump acolyte Rudy Giuliani, so an opportunity presented itself to establish a Cohen-Costello-Giuliani-Trump chain.
The New York Times previously obtained these emails, using them to document how Cohen turned on Trump. However, this account goes into further detail.
This story starts on April 9, 2018, when the FBI first raided Cohen’s temporary digs at the Loews Regency hotel, just a few blocks away from Trump Tower. Department of Justice Special Counsel Robert Mueller’s team probing Trump-Russia allegations left it up to New York federal prosecutors to begin looking into Cohen’s role in the hush payment for violating campaign finance laws.
Jeffrey Citron, a real estate lawyer who already knew Cohen, reached out to him a week later and offered “insight” from his well-connected law firm partner: Costello, an ex-deputy chief of the criminal division at the very same office doing the investigation. Cohen responded the next day, welcoming the help—and immediately met with them both at the hotel that afternoon. Costello mentioned his connection to Giuliani, who was at the time briefly serving as the president’s cybersecurity adviser.
Citron and Costello remembered telling Cohen he had a clear exit from his troubles: cooperate by giving up a bigger fish. According to internal firm notes recounting the meeting, the pair asked Cohen if he knew of any dodgy activity involving Trump—to which he mentioned nothing, save for a potential scandal about “a lot of money missing and unaccounted for” from Trump’s 2017 inaugural committee, which would later be mired in scandal. But they recalled that Cohen did admit to getting reimbursed for the Daniels payment by Trump—a point that would someday be revived by the Manhattan DA. Still, Citron and Costello left the hotel under the impression that Cohen had a clean past, with nothing to give up to the feds.
In later conversations with House Intelligence Committee investigators, Costello told them that Cohen swore he had no dirt on Trump himself that could serve as a get-out-of-jail card, according to internal firm notes, obtained exclusively by The Daily Beast.
“Hope we helped. Bob and I would love the opportunity to be part of and work with your team as we believe we can help you on many levels. Hang tough and think straight,” Citron wrote to Cohen right after the April 17 meeting.
Costello kicked right into action, devising a plan to keep Cohen safe—one that relied on a presidential pardon from Trump, internal emails at the firm show. And Costello seemed eager to share that with him after the New York Daily News quoted a longtime Trump legal adviser warning that Cohen could be pressured to flip on his boss.
“More reason to contact Michael and show him the escape hatch,” Costello wrote to his law partner.
That option seemed all the more promising on April 19, when Giuliani announced he was joining Trump’s legal team to try to shut down the special counsel probe that led prosecutors to Cohen. It was a position of direct influence with the president himself.
“I am sure you saw the news that Rudy is joining the Trump legal team. I told you my relationship with Rudy which [sic] could be very useful for you,” Costello wrote to Cohen that evening.
“Great news for Rudy,” Cohen replied.
The next day, Costello told his New York firm partners that “we are officially part of Cohen’s team. Have been authorized to reach out to various players!”
“Are we retained with actual money?” one partner replied. The question would prove foreboding.
Over the next few months, Cohen essentially ghosted Costello, getting dozens of emails with commentary and advice but barely ever responding. The shift followed a suggestive email by Costello that seemed to say too much.
“I spoke with Rudy. Very Very Positive. You are ‘loved.’ If you want to call me I will give you the details. I told him everything you asked me to and he said they knew that. There was never a doubt and they are in our corner. Rudy said this communication channel must be maintained. He called it crucial and noted how reassured they were that they had someone like me whom Rudy has known for so many years in this role. Sleep well tonight, you have friends in high places,” Costello wrote to Cohen from his iPad on April 21.
“P.S. Some very positive comments about you from the White House,” he added.
But when Costello shared that with his law firm partner, he reeled.
“Thought no more emails,” Citron said.
“The emails are safe and privileged. He specified he wanted me to email him after I spoke with Rudy,” Costello replied.
Costello kept up the pep talks over the following weeks, calling it a “win” when a respected federal judge was chosen to monitor the FBI’s handling of Cohen’s legal records and dismissing claims that feds tapped Cohen’s phones as “psychological warfare.” But Cohen didn’t respond to any of them.
By early May, Cohen came to regret ever toying with the idea of using the man who had the president’s ear. Giuliani appeared on Fox News on a Thursday night to discuss the Stormy Daniels payoff with host Sean Hannity—only to shock viewers by laying out the basic facts District Attorney Alvin Bragg Jr. is now using to indict Trump.
“That money was not campaign money. Sorry, I’m giving you a fact now that you don’t know. It’s not campaign money. No campaign finance violation,” Giuliani started.
“They funneled it through a law firm,” Hannity clarified.
“Funneled through a law firm, and the president repaid it,” Giuliani revealed.
“Oh,” Hannity replied, stumbling. “I didn’t know that he did.”
“Yeah,” Giuliani asserted.
Two days later, Costello noted how Cohen began expressing reservations.
“On Saturday, Michael was claiming that he… was convinced that Rudy is screwing things up… I asked him if he would be coming to our office this week and he said definitely, but I do not know if I believe him. I am beginning to wonder if he really has the money to pay us,” Costello wrote to his law partner.
As the days went by, the frustration increased. Cohen wouldn’t sign the “retainer” agreeing to pay Costello for legal work. He stuck instead with a well-heeled Washington lawyer, Stephen M. Ryan, who was being paid for by Trump, emails show.
“Our issue is to get Cohen on the right page without giving him the appearance that we are following instructions from Giuliani or the President,” Costello told his law partner.
At one point, Costello expressed a worry that they were being “slow played.” Still, he continued to guide Cohen, defining legal terms that came up as part of the criminal investigation.
By the end of May, the backchannel plan seemed to be falling apart.
“Cohen again brought up the idea of a meeting with Giuliani and I said I could do that but only after we were officially retained,” Costello told his law partner, noting how Cohen had said “you are on the team but to make an announcement now would generate a media storm.”
When journalists began speculating whether Trump’s one-time fixer was about to be arrested, the Cohen-Costello-Giuiani-Trump rope started to fray.
On the morning of June 14, Costello texted Giuliani a warning: “He is very agitated and lashing out. Basically he needs a little loving and respect booster. He is not thinking clearly because he feels abandoned. I am very uncertain about our relationship with him.”
An hour later, Cohen fired off an email to Costello that seemed like a warning shot: a link to a Washington Post article documenting how the Trump campaign was actually discrediting him. The president’s one-time consigliere was getting dragged through the mud.
“They are again on a bad path,” Cohen cautioned.
Suspicions were raised when Cohen hired a new lawyer, Guy Petrillo, who had ping ponged between private practice and the Southern District of New York—the same DOJ office investigating Cohen. And, much to Costello’s horror, this guy had prosecuted cases in the 1980s alongside James Comey, whose eventual ascent to FBI director and subsequent firing by Trump gave the MAGA world the Trump-Russia special counsel headache in the first place.
“Does Cohen really want a friend of Comey as his lawyer?” Costello asked Giuliani in a text message thread that noted several other connections. “If you are looking for an anti-Trump gang of lawyers this is it. It would be a monumentally bad choice for Cohen and your team.”
Those worries were made reality when CNN reported that Cohen was now “willing to give information” about Trump, prompting Costello to write another note.
“He asked me to communicate with Rudy and have him tell the President that all of these stories about cooperating are bullshit,” Costello wrote on June 19. “I believe the real issue for Cohen is money. Who is going to pay for these lawyers.”
The last tug on the Cohen-Costello-Giuliani-Trump chain happened that week, when the comedian Tom Arnold claimed that he’d teamed up with Cohen to take down Trump—which apparently made the president himself squirrelly.
“The President has seen this and asked Rudy to reach out to me to reach out to Michael to find out what the truth is,” Costello wrote to his firm partner on June 22. “Rudy asked me to find out if Michael is asking for legal fees to be paid because as he said, ‘as far as I know we (trump) have paid all of his legal fees.’”
Citron responded by asking Costello to remind Cohen that “we have credibility with trump and that can only help him, plus fees Will be handled.”
When Cohen hired Lanny Davis—a Democratic operative who also served as Bill Clinton’s lawyer—it became clear to everyone involved in this backchannel ploy that the party was over. Costello texted Giuliani the news, expressing with certainty that Cohen couldn’t possibly afford such a high powered lawyer on his own. In a move that seemed like lobbing a grenade, Costello’s firm sent Cohen a legal bill for $43,857.85, according to a source.
The reaction was swift and severe.
“Jeff and Bob, at no time were you retained and any actions taken by Bob were all pursuant to calls he made me. There will be no payment to your firm,” Cohen wrote to them in mid-July, making clear in follow-up emails that he had never formally agreed to hire them.
When Costello detailed his version of their private talks—recounting how Cohen allegedly felt suicidal when they first met—Cohen rejected the notion of ever wanting to tap a secret line to the White House.
“Your recollection is extremely inaccurate and self serving. I will not waste either of our time refuting what you already know is disingenuous; specifically your peddling of your relationship with Rudy as a ‘back door’ channel to the WH… something I told you I did not want or need,” Cohen shot back.
When federal prosecutors finally unveiled the criminal charges against Trump’s fixer and nudged him to sign a plea agreement, the New York lawyers who once schemed to keep Cohen in the Trump fold were laughing.
“This is priceless,” Costello joked, linking to Cohen’s legal defense GoFundMe.
“You should follow this fool as he commits Hari Kari,” he later added, referring to the Japanese suicide ritual.
Cohen ended up serving more than a year in a federal prison, and these lawyers never sued him for unpaid fees. Asked about Costello this week, Cohen was brutal.
“Costello is a despicable person who, like so many lawyers carrying Trump’s water, will find himself with legal troubles of his own,” he told The Daily Beast.