How the Trumps turned an election victory into a cash bonanza

A lot was at stake for Melania, too: She was looking for a buyer for a documentary about her transition back to first lady. Her agent had pitched the film, which she would executive produce, to a number of studios, including the one owned by Amazon.

As the meeting approached, Melania consulted with director Brett Ratner on how to sell her idea to the world’s third-richest man. Melania regaled Bezos and his fiancée, Lauren Sánchez, with the project’s details at dinner.

Just over two weeks later, Amazon, a company that prides itself on frugality and sharp negotiating, licenses his name to companies selling, for example, a $100,000 18-carat-gold tourbillon watch. There are no requirements that those businesses disclose who is making purchases.

In another departure from his first term, companies and individuals can now buy shares in Trump Media & Technology, the publicly traded holding company that includes the president’s social media business. Trump transferred his shares in the company to a trust run by his oldest son, Donald Trump Jr.

The Trump Organization, meanwhile, has been in talks to reclaim its hotel in D.C., the lease for which the Trumps sold in 2022 for $375 million. The price of a membership initiation fee at Trump’s Florida resort hit $1 million in the months before the election—up from $200,000 in 2017. Days before taking office, the president and his family began selling $TRUMP and $MELANIA crypto tokens. The market cap of $TRUMP quickly climbed to nearly $15 billion, though it has since fallen off significantly.

Don Jr. joined a series of corporate boards, which sent those companies’ stocks soaring. Even Trump’s youngest son, Barron, has shown interest in following in his father’s dealmaking footsteps. The 18-year-old and two others registered an entity in Wyoming last year called Trump, Fulcher & Roxburgh, which one of the partners described as a high-end real-estate development company. The entity was dissolved in November after much press attention.

About half of the postelection windfall has come from leaning on old adversaries in Silicon Valley and the press to settle censorship and defamation lawsuits Trump had previously filed against them. Most of the cases had been languishing.

The election changed things.

The president feels he now has considerable leverage over former adversaries, according to people familiar with his thinking. “When we won the election, it was time to go," said John Coale, one of Trump’s outside lawyers who brought the suits against the social-media companies with another lawyer, John Q. Kelly.

Coale strategized with the president-elect about bringing up their lawsuit against Meta ahead of a visit Mark Zuckerberg made to Mar-a-Lago in November, according to a person familiar with the conversation. The suit, filed more than three years earlier, had accused Meta of violating Trump’s right to free speech when it suspended his Facebook account after the 2021 riot at the U.S. Capitol.

Over dinner, Trump made it clear that the lawsuit needed to be resolved if the Meta founder wanted everything to be “kumbaya going forward," the person familiar with the conversation said.

Settlement talks began soon after. champion of the anti-woke, he has pursued a series of business ventures that are looking to capitalize on the conservative cultural shift driven by his father’s administration. “While establishment investors shut out companies that refuse to go woke, I want to lift these companies up," he posted on X last month.

Days after his father won, he announced he would become a partner at 1789 Capital, a venture-capital firm that invests in conservative companies. Its investments include Tucker Carlson’s media company, Last Country. A spokesman for 1789 declined to comment.

He also took on roles at several companies that could stand to gain from federal policies, ranging from Pentagon spending to regulations for online-betting marketplaces to tariffs on China.

In the past month, he has joined the board of the prescription access platform BlinkRx and become a strategic adviser to Kalshi, a prediction-market startup. “As a longstanding advocate for media accountability, Donald Trump Jr. was a natural fit," Kalshi said. BlinkRx declined to comment.

A spokesman for Don Jr. said he isn’t involved in government lobbying or influence-peddling and that he typically works with companies that reflect his conservative worldview.

Announcements of Don Jr.’s involvement have sent some companies’ stock soaring—along with his potential earnings.

After drone manufacturer Unusual Machines named him an adviser on Nov. 27, the firm’s shares skyrocketed 249% over the next two days. His 331,000 shares in the company as of Dec. 5 were worth roughly $1.6 million more than they were the day before his advisory role was announced.

Allan Evans, chief executive of Unusual Machines, said Don Jr. has lent the drone-parts maker valuable business acumen rather than political influence. “He’s got really good insights to different types of investors," said Evans, adding that he recently visited Mar-a-Lago to eat breakfast with Don. Jr. “He definitely understands this segment."

Shares in PublicSquare Holdings, which bills itself as a conservative Amazon, shot up 270% after Don Jr. joined its board last year. As part of a consulting deal signed in August, Don Jr. was awarded restricted shares that were worth around $386,000 as of Thursday, in addition to a $42,000 monthly advisory fee.

A representative for Don Jr. said he had invested in the company before the election and helped take it public in 2023.

The company’s chief executive praised him in a statement at the time he joined the board: “Don’s passion for creating a ‘cancel-proof’ economy, his years of strategic business experience, and his leadership within the shooting sports industry offer important expertise at the board level."

Some of President Trump’s most audacious moves have been in crypto, where he has invested heavily while at the same time boosting the larger industry. After once denouncing crypto as a “disaster waiting to happen," Trump shifted his views on the campaign trail last year, pronouncing himself the “crypto president" and talking of turning America into the “crypto capital."

Around the same time, Trump and his sons Eric and Don Jr. helped launch World Liberty Financial, a crypto firm that has raised more than $300 million selling its digital token, $WLFI.

The venture offers an avenue for foreign entities and those with business before the federal government to increase the Trump family’s wealth. People who purchase the tokens aren’t visible to the public unless they disclose it.

In the months after the election, Justin Sun, a Chinese-born crypto entrepreneur, disclosed on social media that he bought $75 million of the token. Sun, who is battling a lawsuit from the Securities and Exchange Commission over alleged market manipulation, is now an adviser to World Liberty Financial. He has called the SEC lawsuit meritless and sought to dismiss it.

“Justin’s stated investment decisions are not politically motivated. Assertions implying ulterior motives are unfounded and misrepresent his intentions," said a Sun spokesperson.

Just three days before his inauguration, Trump officially endorsed the launch of his own meme coin, a type of digital token that’s essentially just a collectible with no underlying value. Following wild price volatility, the total value of all $TRUMP coins in circulation is now $3.3 billion. A similar coin launched on Jan. 19 by Melania has a market cap of about $210 million.

On paper, the Trump coin launch appears to have been lucrative for the family, although the financial connections are opaque. CIC Digital, described on the Trump meme-coin website as an affiliate of the Trump Organization, and an LLC called Fight Fight Fight own 80% of the supply of $TRUMP, though they are subject to lockups preventing them from selling immediately, according to the coin’s official website. Fight Fight Fight was registered in Delaware by Bill Zanker, a longtime Trump ally who has previously worked with Trump to launch digital assets. Its ownership hasn’t been disclosed.

In one of his first moves as president, Trump signed an executive order boosting the cryptocurrency industry, including creating a group to evaluate the creation of a national “digital asset" stockpile—which many in the industry hope would amount to a government stamp of approval.

Melania has also ramped up her moneymaking efforts in recent years, charging six-figure fees for speaking engagements, including two speeches for the Log Cabin Republicans, a conservative group that promotes LGBTQ rights.

It is unusual for a presidential candidate’s spouse to be paid to speak at a fundraiser in an election year.

The month before the election, Melania published a memoir. When CNN requested an interview with her, her book publisher said it would cost $250,000, CNN reported. CNN didn’t pursue the interview further, and the publisher later said the request was the result of a miscommunication. She also sells signed versions of the book for $250 and “Vote Freedom" gold vermeil necklaces for $600.

The Amazon deal for the first lady’s documentary came as Bezos was ingratiating himself to Trump, who once treated him as an enemy.

Write to Rebecca Ballhaus at rebecca.ballhaus@wsj.com, Dana Mattioli at dana.mattioli@wsj.com and Annie Linskey at annie.linskey@wsj.com