In early 2019, Cohen sued the Trump Organization for allegedly failing to reimburse his legal fees; in July 2023, the parties reached a settlement ahead of a planned trial.

[25] In 2008, Cohen was named chief operating officer of mixed martial arts promotion company Affliction Entertainment, in which Trump held a significant financial stake.

"[27] In 2013, Cohen sent an email to the satirical news website The Onion, demanding that an article it had published mocking Trump ("When You're Feeling Low, Just Remember I'll Be Dead In About 15 or 20 Years")[28] be removed with an apology, claiming it was defamatory.

[30][31] Peter J. Gleason, a lawyer who filed for protection of documents pertaining to two women with sexual-abuse allegations against Eric T. Schneiderman, stated—without offering details or corroborating evidence—that Cohen told him that if Trump had been elected governor of New York in 2013, the latter would have helped bring the accusations to public attention.

[37] In January 2016, according to The Washington Post, Cohen sent an email to Russian politician Dmitry Peskov which was the "most direct outreach documented by a top Trump aide to a similarly senior member of Putin's government".

[46][47] On April 13, 2018, McClatchy Newspapers's Washington, D.C., bureau reported that Special Counsel Robert Mueller had evidence (including two sources) that Cohen travelled to Prague from Germany in mid-to-late 2016, which itself would not have required a passport stamp.

[51] In late January 2017, Cohen met with Ukrainian opposition politician Andrey Artemenko and Felix Sater at the Loews Regency in Manhattan to discuss a plan to lift sanctions against Russia.

"[90] Altogether the prosecutors have been given more than one hundred audio recordings from the material seized from Cohen in the April 2018 raid; reportedly only one of them featured a substantive conversation with Trump.

The recording had been classified as a privileged attorney–client communication by the Special Master reviewing the Cohen material, but Trump's attorneys waived that claim,[85] meaning that prosecutors can have it and use it.

Giuliani also noted that no payment was ultimately made, and asserted that Trump's team waived privilege and allowed the recording to be revealed because it shows no violation of law.

[93] On July 25, Cohen's attorney Lanny Davis released the actual recording to CNN, which played it on the air on the Cuomo Prime Time program.

[91] According to Aaron Blake at The Washington Post, "the tape provides the first evidence that Trump spoke with Cohen about purchasing the rights to women's stories—apparently to silence them—before the 2016 election.

[97] On May 14, 2024, Cohen testified that McDougal's hush money was undertaken "in order to ensure that the possibility of Mr. Trump succeeding in the election — that this would not be a hindrance" and that he did not alter the recording of the conversation.

In August, 2020 Cohen told CNN that there was no link between the favor and the endorsement saying “There is absolutely no connection between the photos and my personal request to the Falwells to assist the Trump campaign".

On July 6, 2018, Bechard filed a lawsuit against Broidy, Davidson, and Daniels' attorney Michael Avenatti, claiming the three had breached the agreement in relation to the cessation of the settlement payments.

[131] In May 2018, Daniels' lawyer Michael Avenatti posted a seven-page report to Twitter detailing what he said were financial transactions involving Essential Consultants and Cohen.

[140] Novartis released a statement May 9, 2018, that it hired the LLC to help the company understand the "health care policy" of the new administration, but it actually did not receive benefit for its investment.

The statement continued that Novartis made a decision to not engage Essential Consultants further, but it could not terminate the contract for "cause", raising concerns on why the company did not pursue reimbursement.

[141] Franklin L. Haney agreed to pay Cohen $10 million if he successfully lobbied for the United States Department of Energy to finance the Bellefonte Nuclear Generating Station, or a reduced fee if the funding targets were only partially met.

[149] The FBI obtained the warrant after a referral from Robert Mueller's Special Counsel investigation into Russian interference in the 2016 U.S. elections, although underlying reasons for the raid were not revealed.

[166][167] The Wall Street Journal reported on July 26, 2018, that longtime Trump Organization CFO Allen Weisselberg had been subpoenaed to testify before a federal grand jury regarding the Cohen investigation.

[196] Immediately following his release, Cohen said he would continue to "provide information testimony documents and my full cooperation on all ongoing investigations to ensure that others are held responsible for their dirty deeds and that no one is ever believed to be above the law".

The filing also stated Cohen "remained in close and regular contact with White House-based staff and legal counsel" as he prepared to provide false testimony to Congress.

[190][214][192] On July 2, 2020, Cohen was photographed dining at a Manhattan restaurant, which according to his lawyer Lanny Davis was not a violation of his prison furlough since he had not yet transitioned to house arrest.

A week later, he was taken back into custody after federal officials asserted he had refused to sign an agreement stipulating that he would have no engagement of any kind with the media—including publishing his "tell-all" book—for the remainder of his sentence, which encompassed the November 2020 elections.

He also tweeted on June 26 that a recent New York Times article entitled "Inside Barr's Effort to Undermine Prosecutors in N.Y." had revealed "only a part of the full story," using the hashtag #WillSpeakSoon.

[215][216] After being sent to the Metropolitan Detention Center in Brooklyn, he was returned to FCI Otisville and held in solitary confinement 23 hours each day, which prevented him from working on his manuscript on prison library computers.

Cohen denied he refused to sign the agreement, asserting his attorney had simply asked questions about it, at which point US marshals escorted him back to prison.

[230] On January 12, Fox News contributor and legal analyst Jeanine Pirro took a 20-minute, on-air phone call from Trump in which he claimed Cohen had fabricated stories to reduce the length of his expected sentence.

He said the president had reimbursed him for illegal hush money payments, suggested that he should lie to Congress and the public about the Trump Tower Moscow negotiations, and filed false financial statements with banks and insurance companies.