• The Star Staff

The Trump docket: A look at the fights fueling Trump’s big legal bills

By Eric Lipton

Long before he moved into the White House, Donald Trump had cemented his reputation as a lover of lawsuits, turning to federal and state courts for battles big and small. Trump once even boasted, “I like beating my enemies to the ground.”

Since becoming a public official, he has remained litigious. But he now has found a variety of new ways to fund his legal fights, often without having to personally cover the tab, by turning to money donated to his campaign committees.

Here are some of the highlights of what could be dubbed the Trump Docket, a dizzyingly diverse collection of lawsuits and other legal actions filed by Trump or against him since he began his bid for the president.

It helps explain why he and his political allies have spent nearly $60 million of donor money on legal and compliance bills since 2015, far more than any other president.


Trump has been particularly aggressive since he was elected in using the legal system to try to silence or challenge his critics — a tactic he also frequently turned to during his decades as a real estate executive. This has resulted in a series of claims against one-time campaign or White House aides, such as Jessica Denson, who worked as a phone bank supervisor and Hispanic outreach coordinator during the Trump campaign in 2016.

Denson alleged that she was the target of abusive treatment and sexual harassment by another campaign staff member. Trump then filed an arbitration claim asserting that Denson had violated a confidential agreement she had signed. A lawyer for Trump, Lawrence Rosen, pushed a federal court judge in New York on the matter.

Initially, the American Arbitration Association ruled against Denson and ordered her to pay almost $50,000 in attorneys’ fees and other costs. But the payment demand was overturned by a New York state court in February, and more recently, Denson — with the help of a high-profile legal team led by David Bowles, a prominent New York lawyer — has taken on Trump as part of a class-action lawsuit that she hopes will nullify many of the nondisclosure agreements that other campaign workers signed.

Bowles and others on Denson’s legal team argue that these nondisclosure agreements are illegal.

Trump has used campaign funds, or the assistance of his Justice Department, to target other former aides who have been critical of him, including Sam Nunberg, a former political adviser to Trump; Omarosa Manigault Newman, a one-time White House aide, and Cliff Sims, another former White House aide. Rosen’s firm, which works out of 40 Wall Street, an office building the Trump family owns, has handled several of these cases for the Trump campaign and has been paid $1.46 million in campaign funds, Federal Election Commission records show.


Trump’s legal team, using campaign funds, has initiated a series of lawsuits against news organizations. The suits challenge certain opinion articles, or in one case a television advertisement, that feature Trump, in litigation that First Amendment lawyers say is very unlikely to be successful, but which has brought Trump continued attention in his efforts to paint the news media as biased and inaccurate.

In one, the Trump campaign claimed that an article in The Washington Post — which is clearly marked as an opinion piece — was false and defamatory.

Other targeted news organizations are The New York Times and CNN. The Trump campaign has also sued an NBC affiliate in Wisconsin, accusing it of running an advertisement prepared by the liberal Priorities USA Action super PAC that made claims that Trump considered false about the administration’s efforts to respond to the coronavirus outbreak.


A long list of payments have been made to lawyers who represented aides to Trump who were called to testify during the investigation by the special counsel, Robert Mueller, into Russian interference in the 2016 election as well as the investigations last year by Congress of Trump’s freeze on military aid to Ukraine.

Campaign funds were also used to help pay for the legal team that defended Trump during the impeachment proceedings in the House and Senate. Legal fees associated with other investigations or lawsuits that targeted members of Trump’s staff or family also were covered, including those for Jared Kushner, Trump’s son-in-law and senior adviser, and Donald Trump Jr., campaign finance records show.

This includes $67,214 in payments through this year by the Donald J. Trump for President campaign to Robert Trout, a Washington lawyer who represented Hope Hicks, the White House aide to Trump.

A $196,439 payment in May from the Republican National Committee shows up for Alan Dershowitz, a lawyer who helped Trump during the Senate impeachment trial, even though he said he did not intend to accept any money. (Dershowitz said that the “fee was donated to charity.”) Payments from campaign accounts totaling $821,607 went to the law firm of Marc Kasowitz, $611,250 to a nonprofit group run by Jay Sekulow and $435,000 more to a law firm associated with Jane Raskin, all of whom played a role in representing Trump during the impeachment debate and other matters.

There is no record of any payment to Rudy Giuliani, a personal lawyer for Trump who has said he is offering his legal advice for free.


One other entity that has provided extensive legal services that benefited Trump personally has not submitted bills to his campaign: the Justice Department, which has played a key role in defending or arguing in favor of positions held by Trump in cases that related to his personal finances.

The Justice Department routinely represents any president in many matters related to official duties or issues with constitutional implications. But in Trump’s case, the department has weighed in on cases in which Trump has a personal interest. The names of at least 20 Justice Department lawyers appear on court filings related to the fight over Trump’s tax returns and claims that he is violating the U.S. Constitution by accepting payments from foreign governments.


Another big focus of campaign legal spending has been the growing list of lawsuits that Trump and his political allies are pursuing to limit mail-in voting, in states including Nevada, California and Pennsylvania.

Among the law firms working on this include a recently created group called Elections LLC, which corporate records show was set up by Stefan Passantino, a former White House ethics lawyer for Trump. Elections LLC has been paid $430,000 in campaign funds, while a second firm that Passantino works at, named Michael Best, has been paid $231,495 by the Republican National Committee, records show.

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