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Manhattan Prosecutors Are Trying to Connect Lots of Sordid Dots
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Manhattan Prosecutors Are Trying to Connect Lots of Sordid Dots

Plus: What’s behind Judge Aileen Cannon’s delays in Donald Trump’s classified documents case?

Welcome back to The Collision, where we’re approaching the end of another eventful week. While one criminal trial for Donald Trump continues (the hush-money case in Manhattan), a couple more will get an indefinite delay (the classified documents case in Florida and the election-interference racketeering case in Atlanta). We’ll try to catch you up on what you really need to know about all the major developments.

The Docket

  • The week kicked off for Donald Trump with an additional $1,000 fine from Judge Juan Merchan, who ruled that the former president had committed one more violation of the extensive gag order placed on him. After last week’s ruling from Merchan, that brings the total fines for Trump to $10,000. But that’s not all! Merchan warned Trump that further violations could result in incarceration, though the judge did say, “The last thing I want to do is put you in jail.”
  • Here’s a story that was zipping around MAGA circles this week. Fox News reports that Matthew Colangelo, one of the lead prosecutors in the hush-money case, was paid $12,000 in 2018 by the Democratic National Committee for “political consulting.” Colangelo is both a career attorney and a loyal Democrat, having served in both the Obama and Biden administrations as well as in the New York state attorney general’s office before joining the Manhattan district attorney’s office in December 2022. 
  • House Oversight Committee Chairman Jim Jordan, a Republican, has had Colangelo in his investigatory sights for a while, and last week sent a letter to Attorney General Merrick Garland requesting documents for an investigation into supposed “coordination” and “politicization” of the Manhattan case by way of the Justice Department. And in one of Trump’s morning statements this week outside the Manhattan courthouse this week, the former president claimed the prosecution “all comes out of the White House” and that it’s “all Biden.”
  • On Wednesday, the Georgia Court of Appeals granted Trump’s application for interlocutory appeal of the March decision by Fulton County Superior Court Judge Scott McAfee not to disqualify the prosecutor of the case against him. After it was revealed earlier this year that Fulton County District Attorney Fani Willis had a romantic relationship with a special prosecutor she had hired to work on the case, Trump and some of his co-defendants had sought to dismiss the case or to at least remove her from the case. McAfee’s ruling did neither, but he was pretty harsh in his assessment of Willis’ judgment. Furthermore, the judge required either Willis or the special prosecutor, Nathan Wade, to step down—which Wade did. Trump’s team now has 10 days to file its appeal—and what it really means is that the Fulton County trial will be delayed even further.
  • Speaking of Fulton County, Willis’ former paramour Wade spoke to ABC News this week in an interview that might be summed up in the phrase “no regrets.” Wade argued there was nothing improper in the relationship he had with Willis nor with the circumstances of his hiring. He did acknowledge, however, that the timing of their relationship “could have been better.” He also voiced confidence in the case against Trump and his dozen-plus codefendants: “I believe that, you know, there’s going to be that day of reckoning where a Fulton County jury there in Fulton County, Georgia, would have to make that decision.”

The Sordid Tale Manhattan Prosecutors Are Trying to Tell

Manhattan District Attorney Alvin Bragg speaks during a press conference on March 21, 2024, in New York City.  (Photo by Michael M. Santiago/Getty Images)
Manhattan District Attorney Alvin Bragg speaks during a press conference on March 21, 2024, in New York City. (Photo by Michael M. Santiago/Getty Images)

Stormy Daniels, the pornographic actress whose receipt of $130,000 from Donald Trump via Michael Cohen forms the central issue of the case in Manhattan, testified this week. We’ll spare you the details of her salacious, explicit testimony about her sexual encounter with Trump back in 2006. You can read about it and Trump’s angry reactions here.

This week, we’d prefer to dive into the less sexy but more relevant substance of the prosecution’s case as it’s been building over the last week. It’s impossible to know whether the jury will accept the arguments that Trump falsified business records with the intent to commit a felony—a tall order, to be sure. And it’s hard to see how any Americans still undecided about the upcoming presidential election will be swayed by either a conviction or an acquittal.

Yet for all the public seems to know about the former president’s warts, flaws, and personal peccadilloes, the prosecution’s witnesses have continued to detail parts of a story that has yet to be fully told, at least in the context of a court of law: As Trump was on the brink of being elected to the White House, behind the scenes he and his team were operating in a most unusual and disreputable way. Revealing this story was the promise the prosecution made in its opening statement, but we now have some of the details.

A quick primer on what’s been alleged: In the final days of the 2016 presidential campaign, a company associated with Cohen, Trump’s lawyer and “fixer,” reached an agreement with Daniels to purchase the rights to her story about a sexual encounter with Trump from 10 years earlier. This came about because of an agreement made in 2015, shortly after Trump became a presidential candidate, with the publisher of the National Enquirer, David Pecker. Trump’s team would tip off Pecker’s publication on negative stories about his GOP rivals, and Pecker would alert Cohen if anyone with a negative story about Trump was shopping it around to publications like the Enquirer. Cohen could then, as he did with Daniels, pay enough money to secure a subject’s silence.

Cohen paid Daniels for the story out of his own pocket, then spent the next weeks and months trying to get reimbursed by Trump and the Trump organization. Despite the Wall Street Journal publishing—four days before the election—a story about his affair with former Playboy model Karen McDougal that included a mention of an alleged sexual encounter between Trump and Daniels, Trump went on to win the presidency. But from what we now know about that preelection period, it was clear Trump and his aides were desperate to keep Daniels quiet lest the one-two punch of her story and the recently released Access Hollywood tape spoil his electoral chances.

What we did not know until recent testimony was how exactly Team Trump was working to address a looming political crisis in this time of desperation. Take the testimony on May 2 from Keith Davidson, the attorney who negotiated with Cohen on behalf of Daniels back in 2016.

Davidson testified about the agreement he reached with Cohen, which included an exorbitant, seemingly unenforceable “liquidated damages provision”—what Daniels would owe if she breached the agreement. According to Davidson, Cohen requested the provision require Daniels to pay $1 million for every breach—nearly eight times the amount of her settlement payment.

“A Liquidated Damage Provision of $1 million, which was demanded by Michael Cohen, was so far in excess of the … settlement amount of the contract that it really served no purpose” Davidson said on the stand. Whether it was shoddy or greedy for Cohen to demand such a disproportionate damages provision, it’s certainly in line with how Trumpworld often ends up trying unsuccessfully to enforce restrictive non-disclosure agreements.

A little later in his testimony, Davidson told the story of a back-and-forth he had with Cohen as the Journal prepared to publish in January 2018 the full story about Trump’s affair with Daniels. At the behest of Cohen, Davidson said, he drafted a denial of the story for Daniels to provide the newspaper. A plain reading of this denial, which was read aloud in court, is that it’s false. The statement denies two important facts: that she had a “sexual and/or romantic affair” with Trump and that she received hush money from him. But Daniels would later testify this week that both of those facts were true. Davidson, however, said the statement “would technically be true with an extremely fine reading of it.” He went on to debate with the prosecution how inclusive the phrase “and/or” is and argued that Daniels was not paid hush money but a “consideration.”

The lawyerly parsing notwithstanding, the episode reflects the pressure Cohen was putting on Daniels and her attorney to stick to her denial well into Trump’s presidency. The Journal published the story without her participation, and within a few weeks Cohen publicly acknowledged the payoff, starting a chain reaction of events whereby Daniels also publicly acknowledged the affair and she and her flamboyant attorney Michael Avenatti became household names.

The testimony has been illuminating in other ways. On May 3, former Trump aide Hope Hicks took the stand to give an inside look of those final weeks of the 2016 election—from the release of the Access Hollywood tape to the publication of the story about Trump’s affair with McDougal. Among the interesting details was Hicks’ testimony that on the eve of the Journal’s November 4, 2016, publication of the McDougal story (which contained the first mention of a Daniels-Trump encounter), Hicks encouraged Trump’s son-in-law Jared Kushner to urge Journal owner Rupert Murdoch to hold off on publication to give the campaign some “extra time” to deal with the story. But Kushner was apparently no help.

“I think he said that he wasn’t going to be able to reach Rupert and that we should just work out responding and dealing with it,” Hicks said.

A former top Trump Organization accountant, Jeffrey McConney, testified on May 6 about the internal negotiations within the company about how to reimburse Cohen for his payment to Daniels. Eventually, McConney said, an agreement was reached that, starting in early 2017, Cohen would receive regular monthly payments—after the lawyer left the Trump Organization—in the form of checks from either a Trump-family controlled revocable trust or from Trump’s personal account. That meant a process of the Trump Organization sending checks down to the White House to have then-President Trump sign and return to New York so they could be disbursed to Cohen.

All of which is to say: This is not how most political figures operate. The preemptive agreement with the tabloid publisher, the massive payoff to the porn star through Trump’s “fixer,” the ongoing coordination with lawyers for that porn star to keep the story straight, the casual truth-stretching, the appeals to powerful friends in the media, the unusual bookkeeping—all of it has never been seen in the campaign and operation of a major presidential candidate. 

Which brings us back to Daniels’ graphic testimony this week about her unwanted one-night stand with the future president. It caps the entire sordid story of grubby dealings that, like the affair itself, Trump and his team do not want the public to know about.

In fact, during a break while Daniels was testifying Tuesday, the defense team requested Merchan declare a mistrial thanks to the witness’s “extraordinarily prejudicial” testimony. Merchan denied the request even as he admitted the prosecution went a little too far in what it elicited from Daniels—though he also wondered aloud why the defense had not objected more to her testimony.

Nevertheless, the trick the prosecution must pull is weaving all of this together, and not just into a story that makes anyone paying attention feel icky. Prosecutors must convince the jury this all adds up to activities Trump engaged in with the intent of covering up a felony—specifically, a conspiracy to defraud voters in the 2016 election. That still matters—whether or not voters themselves dismiss the whole trial as old news.

What’s Eating Aileen Cannon?

Supporters and protesters of former President Donald Trump stand outside the Alto Lee Adams Sr. Courthouse in Fort Pierce, Florida, on March 14, 2024. (Photo by Joe Raedle/Getty Images)
Supporters and protesters of former President Donald Trump stand outside the Alto Lee Adams Sr. Courthouse in Fort Pierce, Florida, on March 14, 2024. (Photo by Joe Raedle/Getty Images)

This week, Judge Aileen Cannon postponed the federal criminal trial against Donald Trump for his retention of classified documents and obstruction that was supposed to start May 20 in Florida. It is now set to begin … well, actually, there is no new start date. 

Partisans on the left have accused Cannon of being in the tank for Trump, helping him delay the start of his trial until after the election for political gain. They point to some of her more bizarre rulings in his favor, including one that was unanimously reversed by three judges—two Trump appointees and a Bush appointee. They also note that she seems to be dragging her feet on all the pending motions that need to be resolved before the trial can move forward. She’s a Trump appointee, and perhaps she thinks this is her opportunity to get a promotion, they suggest. 

Partisans on the right argue that the slowness was inevitable because special counsel Jack Smith chose to bring a case that would require the resolution of all sorts of technical issues under the Classified Information Procedures Act (CIPA). If he wanted to move quickly, he could have charged Trump with obstruction and the trial could have started nearly immediately. But once Smith brought in the “willful retention” charges, it was clear this was always going to take forever. The judge has eight motions that all have to get resolved before a trial can start and that takes time. For example, last month she asked both parties to prepare their suggestions for how to instruct the jury before it deliberates toward a verdict. But because she hadn’t ruled on exactly what law would apply, she asked them to prepare two instructions depending on how she ruled on another pending motion. Another argument is that Smith caused some of these problems because he’s admitted that prosecutors can’t guarantee the documents in the boxes are in the same order as when the FBI took possession of them. Now that’s a whole thing. 

Sarah’s View

So who’s at fault for the delays? Right now it’s hard to say. Trump apologists are certainly correct that this was always going to take a while because of CIPA—but we haven’t even begun to jump through the CIPA hoops! Smith partisans are correct that these delays play into Trump’s hands, but that doesn’t mean the delays are because they play into Trump’s hands. 

Here’s another potential explanation: Aileen Cannon is an inexperienced trial judge who is in over her head and paralyzed by a fear of making the wrong decision while under the biggest spotlight in the country. So she isn’t making any decisions. 

Before being elevated to the bench, Cannon was a federal prosecutor. But she didn’t do trials—she handled appeals. Appellate lawyers are eggheads. (I’m married to one so I’d like to clarify that mine is a handsome egghead, but an egghead all the same.) They can easily take a dumb argument and spin it into a federal case (pun intended). 

Cannon insisting on researching every strand of spaghetti the Trump team throws against the wall would explain the unreasonable delays. It would also explain Cannon’s earlier ruling that was unanimously reversed on appeal: Cannon thought whether a special master should have been appointed to review classified documents seized in the case was a fascinating question of federal jurisdiction when in fact it was a misguided attempt to thwart a federal prosecution. Overthinking things is what appellate lawyers get paid big bucks to do. But if you combine that instinct with an overly cautious personality and then throw her into the rough and tumble, fast moving world of trial courts … maybe you get Aileen Cannon.

Or to put it more simply, never ascribe to malice what is adequately explained by incompetence.


Trump attorney Susan Necheles: “Am I correct that you hate President Trump?”

Stormy Daniels: “Yes.”

Necheles: “You want him to go to jail?”

Daniels: “I want him to be held accountable.”

–from cross examination by the defense in Donald Trump’s Manhattan hush-money trial, May 7, 2024

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Michael Warren

Michael Warren is a senior editor at The Dispatch and is based in Washington, D.C. Prior to joining the company in 2023, he was an on-air reporter at CNN and a senior writer at the Weekly Standard. When Mike is not reporting, writing, editing, and podcasting, he is probably spending time with his wife and three sons.

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Sarah Isgur

Sarah Isgur is a senior editor at The Dispatch and is based in northern Virginia. Prior to joining the company in 2019, she had worked in every branch of the federal government and on three presidential campaigns. When Sarah is not hosting podcasts or writing newsletters, she’s probably sending uplifting stories about spiders to Jonah, who only pretends to love all animals.