Business dealings, fraud, and bankruptcies
Trump imposed or threatened sweeping tariffs on imports from Canada, Mexico, and China, roiling global markets and sparking fears of a trade war, before pausing some tariffs after last-minute negotiations with neighboring countries.
A New York judge ruled that Donald Trump committed fraud for years by inflating the value of his real estate assets on financial statements, ordering the dissolution of some of his business entities and setting the stage for a trial on remaining claims.
Allen Weisselberg, the longtime CFO of the Trump Organization, was indicted along with the company itself on charges of running a 15-year tax fraud scheme involving unreported employee compensation.
The Manhattan District Attorney's office expanded its investigation of the Trump Organization into a full criminal probe, examining potential bank and insurance fraud, tax fraud, and falsification of business records.
Multiple fraud lawsuits against Trump University gained national attention during the Republican primary, with former students alleging they were deceived into paying up to $35,000 for worthless real estate courses at what turned out to be an unlicensed institution.
The Trump Organization continued pursuing a deal to build a Trump Tower in Moscow, engaging in negotiations with Russian developers that would extend secretly through the 2016 presidential campaign.
Donald Trump brought the Miss Universe pageant to Moscow in partnership with Russian oligarch Aras Agalarov, an event that deepened Trump's financial ties to Russia and later drew scrutiny from federal investigators.
Donald Trump launched Trump University, a for-profit real estate training program that would later face multiple fraud lawsuits and result in a $25 million settlement after thousands of students alleged they were deceived.
NBC debuted 'The Apprentice,' a reality television show starring Donald Trump, which drew over 20 million viewers and transformed Trump from a regional real estate figure into a national brand and household name.
Trump declared a $916 million loss on his 1995 income tax returns, a deduction so large it could have legally allowed him to avoid paying any federal income taxes for up to 18 years.
Trump's Taj Mahal casino filed for bankruptcy, the first of six Trump corporate bankruptcies that would cost investors billions while Trump himself emerged largely unscathed.
Trump's reckless borrowing spree of the late 1980s caught up with him as his personal debt reached an estimated $900 million, forcing him to cede control of key assets to creditors and survive only through bank-negotiated bailouts.
Trump purchased the iconic Plaza Hotel on the corner of Central Park South and Fifth Avenue for $407.5 million, calling it the 'Mona Lisa' of real estate, but the overleveraged acquisition would become a financial albatross within two years.
Trump purchased the New Jersey Generals of the United States Football League, then pushed the upstart league into a disastrous antitrust lawsuit against the NFL that contributed to the USFL's collapse.
Trump Tower, a 58-story mixed-use skyscraper on Fifth Avenue, opened to the public, becoming Donald Trump's signature property, personal residence, and the physical embodiment of his brand.
Construction of Trump Tower on Fifth Avenue relied on a crew of undocumented Polish immigrants who worked 12-hour shifts for sub-standard wages, demolishing the Bonwit Teller building to make way for Trump's signature skyscraper.
Trump secured his first major Manhattan real estate deal by purchasing the aging Commodore Hotel near Grand Central Terminal and converting it into the Grand Hyatt New York, leveraging an unprecedented 40-year tax abatement from the city.
The Department of Justice filed a civil rights suit against Trump, his father Fred, and their company for refusing to rent to Black tenants in 39 buildings across New York City.
Donald Trump assumed control of his father Fred Trump's real estate company, renaming it the Trump Organization and shifting its focus from outer-borough housing to Manhattan development.
