The Trump Docket: The Fights Fueling Trump’s Big Legal Bills

WASHINGTON — Long before he moved into the White House, Donald J. Trump had cemented his reputation as a lover of lawsuits, turning to federal and state courts for battles big and small. Mr. 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 Mr. 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.

Mr. 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.

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

Initially, the American Arbitration Association ruled against Ms. 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, Ms. Denson — with the help of a high-profile legal team led by David K. Bowles, a prominent New York lawyer — has taken on Mr. Trump as part of a class-action lawsuit that she hopes will nullify many of the nondisclosure agreements other campaign workers signed.

Here is a complaint where Mr. Bowles and others on Ms. Denson’s legal team argue that these nondisclosure agreements are illegal.

Mr. 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 Mr. Trump, Omarosa Manigault Newman, a one-time White House aide, and Cliff Sims, another former White House aide. Mr. Rosen’s firm, which happens to work 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.

Efrain Galicia is among the group of Mexican-Americans who demonstrated outside Trump Tower in New York when Mr. Trump was running for president. The protests featured signs with slogans like, “Trump: Make America Racist Again.” After Mr. Galicia claimed he was confronted by Keith Schiller, who was working as Mr. Trump’s bodyguard at the time, Mr. Galicia sued Mr. Trump in what has turned into a long-running court case. Here is an excerpt from Mr. Galicia’s affidavit, describing the incident.

Other lawsuits have been filed by demonstrators who claim they were beaten or pushed at Trump campaign rallies. Mr. Trump was represented in these cases by Jones Day, a prominent law firm that has received nearly $17 million in payments since Mr. Trump’s nomination in 2016 from the Trump campaign, the Republican National Committee and other joint fund-raising committees Mr. Trump helps run. Those payments have been both for legal work like this, and more traditional campaign-law compliance efforts.

Here the United States Court of Appeals for the Sixth Circuit rejects a claim filed by demonstrators at a 2016 rally in Kentucky, even though the court concedes Mr. Trump told his supporters to eject the demonstrators from the event.

Mr. 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 Mr. Trump, in litigation that First Amendment lawyers say is very unlikely to be successful, but which has brought Mr. Trump continued attention in his efforts to paint the news media as biased and inaccurate. Here the Trump campaign claims 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 Mr. Trump considered false about the administration’s efforts to respond to the coronavirus outbreak. Here is an excerpt from the complaint against the station, WJFW-NBC.

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

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

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

A $196,439 payment in May from the Republican National Committee shows up for Alan Dershowitz, a lawyer who helped Mr. Trump during the Senate impeachment trial, even though he said he did not intend to accept any money. (Mr. Dershowitz said that the “fee was donated to charity.”) Payments from campaign accounts totaling $821,607 went to the law firm of Marc E. 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 Mr. Trump during the impeachment debate and other matters. There is no record of any payment to Rudolph W. Giuliani, a personal lawyer for Mr. Trump who has said he is offering his legal advice for free.

One other entity that has provided extensive legal services that benefited Mr. 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 Mr. 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 Mr. Trump’s case, the department has weighed in on cases in which Mr. Trump has a personal interest. The names of at least 20 Justice Department lawyers appear on court filings related to the fight over Mr. Trump’s tax returns and claims that he is violating the U.S. Constitution by accepting payments from foreign governments.

Here the Justice Department comes to Mr. Trump’s defense after he sued to block the release of his tax returns.

Another big focus of campaign legal spending has been the growing list of lawsuits Mr. 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 Mr. Trump. Elections LLC has been paid $430,000 in campaign funds, while a second firm that Mr. Passantino works at, named Michael Best, has been paid $231,495 by the Republican National Committee, records show. Here is an excerpt from a lawsuit the Trump campaign filed in June in Pennsylvania.