• Trump took over the family real estate business in 1971 and used it to build his business brand.
• As the family's businesses expanded, they faced lawsuits and financial volatility.
• Here's everything to know about the Trump businesses and increasingly complicated ethical questions.

When President-elect Donald Trump was growing up, he worked in the offices and on the construction sites of his father's real estate business, Elizabeth Trump & Son. By 1973, he had taken over the company and given it a now well-known name: The Trump Organization.

In the decades since, Trump has pursued global real estate development, reality television shows, a media conglomerate, cryptocurrency, and branded products like Bibles. His signature company has faced financial and legal turmoil throughout the years, but has become synonymous with his trademark brand of business success.

When Trump took office in 2017, he handed formal control of the Trump Organization to his two elder sons, Donald Trump Jr. and Eric Trump. Some questioned whether conflicts of interest persisted for the then-president, who had simultaneous political and professional power. Now that Trump has won a second term in the White House, the Trump Organization will again have to navigate a murky business landscape.

Here's everything to know about the Trump Organization and the family's business ventures, including financial volatility, lawsuits, and an increasingly complicated web of ethical questions.

Company history

Fred Trump was born in New York City in 1905. He started building and selling homes in Queens when he was 19, eventually developing properties in Brooklyn and Staten Island as well.

The president-elect was involved with the business since childhood and began officially working for his father shortly after graduating college. He took over the company in 1971 and renamed it in 1973.

Key business areas

Real estate

After taking over, Trump helped expand the business, buying properties in Manhattan and outside of New York. He developed the Grand Hyatt Hotel in 1976, despite not having enough money to buy the property (this is among the early plot points in 'The Apprentice,' a 2024 movie about Trump's business rise).

By the 1980s, Trump had established himself as a real estate mogul, boasting properties like Trump Tower and beginning to pursue casinos in Atlantic City, New Jersey. The Trump Organization faced financial challenges in these years, with multiple Trump-owned properties filing for bankruptcy in the early 1990s. The president-elect used bankruptcy protections to restructure the company's debts and maintained his image as a successful businessman.

Today, the Trump Organization's website lists eight hotels, five of which are in the U.S. It also lists residential properties across the country and globe, with a focus on New York. In addition to the real estate holdings, the organization lists 18 golf courses it owns or is developing.

Entertainment ventures

In 1996, Trump bought the Miss Universe Organization, which included Miss USA and Miss Teen USA. He sold the company in 2015, after NBC dropped the show due to remarks he made about Mexican immigrants during his 2016 presidential campaign. The beauty pageant has been awash in controversy in recent years, and some contestants have said that Trump would look at them as they changed backstage.

Trump starred as himself in a reality show, 'The Apprentice,' which he hosted from 2004 to 2015. Aspiring business leaders battled each other in challenges and Trump served as the judge, telling a contestant each week, "You're fired!" The show and its spinoff, 'The Celebrity Apprentice,' helped expand Trump's national reach. NBC cut Trump's ties with the program in 2015.

After leaving the White House in 2017, Trump formed Trump Media & Technology Group and its flagship product, Truth Social. He founded the company after being kicked off of many mainstream social media sites for his actions on January 6 and now owns a majority stake. Trump Media's financial health shifts with the president-elect's political prospects. Many consider it a "meme stock," since its share price doesn't correlate to its profitability.

Trump Media's stock soared after Trump won the 2024 election. The president-elect's stake in the company is his most valuable asset, valued at around $3.5 billion in December, 2024.

Trump-branded products

Since his earliest business days, Trump has profited from branded products, starting with his buildings themselves. During his reality television days, he attached his name to everything from board games to steaks.

Trump has continued to sell branded products as a political figure, and financial disclosures released in August reveal that he made more than $12 million off of NFTs and books alone. He also sells sneakers, cologne, and a Trump Bible.

Leadership and ownership

The Trump Organization is a collection of around 500 privately held companies. Trump ran the day-to-day operations of the company prior to becoming president, but handed control over to his two oldest sons, Donald Trump Jr. and Eric Trump, when he moved into the White House in 2017.

The company's leadership is composed largely of family loyalists. Eric and Donald Trump Jr. are currently the executive vice presidents.

Since the 1970s, most presidents have put their assets into blind trusts, a financial arrangement whereby an independent trustee controls the holdings. During the 2016 campaign, Trump put his assets into a trust controlled his older sons and Allen Weisselberg, the Trump Organization's chief financial officer at the time. The arrangement was not as extensive as a blind trust structure.

Trump resigned but didn't sell his stake in the company, which promised not to make any new foreign deals while Trump was president. The Trump Organization also hired an outside ethics advisor at the time and said it would donate any profits from foreign governments to the Treasury Department.

Various parties sued Trump over alleged violations of the Constitution's emoluments clause, which prevents presidents from receiving payments or gifts from foreign governments. International governments with interest in US policy decisions spent money at various Trump properties during his term. Three cases about the clause were dismissed without resolution after Trump left office.

Controversies and legal challenges

The company's legal troubles predate Trump's time in the White House, stretching back to the era of Fred Trump's leadership.

In 1973, the Justice Department sued Fred and Donald Trump for alleged racial discrimination. The parties settled and the Trumps didn't admit any wrongdoing. The company's business practices continued to receive scrutiny throughout the rest of the 20th century, especially as it faced financial difficulties.

Trump borrowed money to fund new projects like hotels and casinos, and in 1990 his dad bought more than $3 million worth of casino chips to help a venue make an interest payment. Later, the state of New Jersey found that the transaction was an illegal loan and levied a fine of $65,000.

Over the past three decades, Trump and his companies have been engaged in many lawsuits, ranging from bankruptcy proceedings, to fights with gambling patrons, to personal defamation suits. Recently, the company has been entangled in both a civil and criminal fraud trial in New York.

In the civil case, the state's attorney general accused the Trump Organization of misleading banks and insurers about property values. A Manhattan judge found Trump guilty in February 2024 and ordered the company to pay almost $364 million before interest, with Trump personally responsible for nearly $355 million of the penalty. By March, judges had lowered Trump's bond to $175 and the president-elect has appealed the case. As part of this case, Weisselberg, the company's former CFO, was sentenced to jail time after admitting to perjury.

On the same day the AG first filed the civil fraud case, Trump formed "Trump Organization II" in an apparent attempt to protect his holdings. Anticipating that Trump might try to move his holdings to a company that isn't being sued, the judge made him tell a court-appointed monitor about "any corporate restructuring, disposition or dissipation of any significant assets."

New York's criminal suit against Trump ended in 34 convictions, making him the first former president convicted of a felony. A 12-person Manhattan jury found Trump guilty on 34 criminal counts of falsifying business records to hide a $130,000 hush-money payment to Stormy Daniels, an adult film star. The judge in the case has indefinitely postponed Trump's sentencing and the president-elect is now arguing that the case should be thrown out entirely because he has presidential immunity. In July, the Supreme Court ruled that presidents are broadly immune from prosecution, and Trump's legal team is arguing the same should be true for presidents-elect.

Next steps for the Trump Organization and other businesses

Now that Trump is headed back to the White House, the Trump Organization once again finds itself in a thicket of legal and ethical questions. The company may or may not reinstate its ban on foreign deals once Trump is sworn in for a second term and has business in countries central to America's foreign policy agenda, like Saudi Arabia.

In addition to the Trump Organization, Trump Media is another ethical gray area, as people with a vested interest in policy decisions could buy advertisements on Truth Social or shares of stock. Doing so would raise Trump's net worth, given that he owns a majority stake in the company.

In September, Trump announced a family crypto venture, World Liberty Financial. The platform is marketed as a way for traders to borrow and lend cryptocurrencies. Donald Trump Jr., Eric Trump, and Barron Trump are all involved in the venture. A document from the company lists all four of them as part of the team, but says no Trump family members are employees or officers. Ethics experts have said that World Liberty Financial could also pose conflicts of interest since Trump will oversee crypto regulations as president.

The Trump Organization, Trump Media, and World Liberty Financial did not respond to Business Insider's request for comment.

As Donald Trump returns to the White House promising to obliterate business as usual in Washington, the city's lobbyists are preparing for a seismic shift in how — and where — they do business.

"Florida is becoming the power nexus for the country," Bill Helmich, a lobbyist and close Trump ally, tells Business Insider. "It's where decisions will get made."

It's a sentiment echoed by Evan Power, a lobbyist who's serving as chair of the Florida GOP. "Florida is now the epicenter of Trumplandia," Power says.

A dozen leading lobbyists, some of whom spoke with BI on the condition of anonymity, say that having a significant presence in Florida is now an essential part of doing business in Washington. First and foremost, that means hiring lobbyists in the state to work the hallways and links at Mar-a-Lago, where Trump and his inner circle have been charting the transition and making Cabinet picks. A presence at the resort — along with the golf courses Trump owns in West Palm Beach, Doral, and Jupiter — is now seen as a major currency in the lobbying game.

Never before, lobbyists say, has the geographic center of power shifted so dramatically with the arrival of a new administration. In many respects, they say, Palm Beach is going to be the new K Street — the headquarters of the political-influence industry — particularly since Trump no longer owns a luxury hotel blocks from the White House.

What's more, the consensus among lobbyists is that anyone who hopes to influence Trump this time around will have to dispense with traditional lobbying conventions. "We can't do this the same old way," says one prominent lobbyist with ties to Trump. "Trump is such a wild card, and that gives him a lot of leverage. Cookie-cutter lobbying efforts probably won't work like they used to."

For Washington lobbyists, that means changing the way they talk about the world to appeal to the hardcore MAGA loyalists who have succeeded at commanding Trump's attention and dominating his inner circle. "This is not Trump 2.0," says Justin Sayfie, a partner at Ballard Partners, a powerhouse lobbying firm with deep Florida roots and an office down the road from Mar-a-Lago. "It's more like Trump 5.0. This is the most anti-Washington president we've elected since maybe Andrew Jackson."

When it comes to lobbying, the big winner of Trump's first term was Ballard Partners. The firm's success offers some lessons for lobbying firms itching to capitalize on their ties to Trump and his inner circle and establish a beachhead in Florida.

Before Trump's unexpected victory in 2016, Ballard Partners had no presence in Washington to speak of. But its founder, Brian Ballard, had been part of Trump's inner sanctum — first as a top fundraiser in Florida, then as part of the president-elect's transition team. By leveraging his access to Trump, Ballard Partners was able to compete with the old white-shoe lobbying firms that have been the industry's dominant players for decades.

In 2017, the first year of Trump's term, Ballard added dozens of major clients, including Google, Amazon, Uber, American Airlines, Honda, the tobacco giant Reynolds American, the private-prison firm Geo Group, and the American Health Care Association. By 2020, Ballard ranked as the nation's seventh-largest federal lobbying firm in terms of income — an astounding feat for an office that was only 3 years old. Ballard's lobbying business in Florida, meanwhile, regularly ranks among the state's top-earning firms, making it ideally positioned to once again be the go-to lobbying shop for corporations and special interests eager to cozy up to Trump and his MAGA allies in Congress.

Corporate clients need lobbyists who appreciate that Trump is "disrupting the status quo in Washington," Sayfie, the Ballard lobbyist, says. "This creates a sense of both possibility — and great worry and anxiety to navigate."

Any presidential transition poses significant challenges for corporations. Business thrives on stability; it's hard to make plans in the middle of all the uncertainty that comes from shifting political philosophies, legislative goals, and regulatory ambitions. But lobbying insiders say Trump's presidential transition has brought a new level of unpredictability — one that also represents a golden opportunity, for those able to capitalize on it.

"Trump has a mandate from the American people and is using it," says B. Jeffrey Brooks, a partner at Adams and Reese, a law firm with more than 300 attorneys and lobbyists across the country. "It hasn't been this exciting on Capitol Hill since 1994, when Republicans had their Contract with America."

Through his appointments and his campaign promises, lobbyists say, Trump has clearly signaled his desire to remake Washington in Florida's regulation-slashing, "woke"-fighting image — and do so from the comforts of his "Winter White House," now a political redoubt for all seasons. Already, many of the top slots in Trump's administration are going to Floridians who have stuck by him through his many legal and political troubles. Among them are two former Ballard lobbyists: Susie Wiles, whom Trump has tapped to serve as his White House chief of staff, and Pam Bondi, his choice for attorney general.

"Trump's team has distinct, new views that are not old Washington," says Colin Roskey, a principal at the FHP Strategies lobbying firm who served as a deputy assistant secretary of health and human services during the first Trump administration.

Some major companies, lobbyists say, have been caught off guard by the rapid pace of Trump's transition moves. "They're freaking out a little bit," says Dave Wenhold, a partner at Miller/Wenhold Capitol Strategies, which provides clients with lobbying and strategic planning. "Things are going to be coming at them fast and furiously, more than before, and this is where the lobbying community can really show its value."

There's also a new way corporations can seek to influence Trump —without disclosing their influence. Unlike his predecessors, Trump is allowing donors — including foreign nationals — to finance his transition in secret, through unlimited private contributions. Those who bankroll his staff and travel before he takes office, lobbyists say, stand to build connections and curry favor with the once and future commander in chief. "People appreciate people who invested in them," says Power, the chair of the Florida GOP.

Taken together, Trump's singular take-no-prisoners style has lobbyists excited about the possibilities for influence. Scott Mason, a senior policy advisor at the lobbying firm of Holland & Knight who served as the director of congressional relations for Trump's presidential campaign and transition team in 2016, is blunt about the prospects of Trump 2.0: "It'll be a great year for the lobbying world," he says.

Having a good lobbyist, in fact, may be more important than ever. Whatever companies think of Trump and his policies, they now face the prospect of a president who speaks openly about pursuing retribution for what he perceives as slights. On the campaign trail, Trump threatened John Deere with tariffs, called for the prosecution of Google, and tanked Meta's stock price by denouncing Facebook as "an enemy of the people." In an environment of fear and uncertainty, lobbyists expect their business to boom — likely surpassing the record $4.2 billion clients spent last year on federal lobbying.

"You have to recognize how Washington affects your business," Mason says. "If you're not at the table, you're on the menu."

Dave Levinthal is an investigative journalist based in Washington D.C. He was a reporter and editor at Business Insider until 2022.