Donald Trump has pursued business deals in Russia since 1987, and has repeatedly traveled there to explore potential business opportunities. In 1996, Trump trademark applications were submitted for potential Russian real estate development deals. Trump, his children, and his partners have repeatedly visited Russia, connecting with real estate developers and Russian government officials to explore joint venture opportunities. Trump was never able to successfully conclude any real estate deals in Russia. However, individual Russians have invested heavily in Trump properties, and, following Trump's bankruptcies in the 1990s, he borrowed money from Russian sources. Both Donald Trump Jr. and Eric Trump have said that Russia was an important source of money for the Trump businesses.

Efforts to build a Trump building in Moscow continued into June 2016 while Trump was securing the Republican nomination for the presidential election.

In January 2017, BuzzFeed News reported the existence of the then-unverified Steele dossier (also called the Trump–Russia dossier), which alleges connections between Trump associates and Russia. Trump responded the next day, and again at a February news conference, that he has no financial connections to Russia. In response to ongoing questions, White House press secretary Sean Spicer reiterated in May that Trump has no business connections to Russia. Also in May, Trump's tax lawyers sent a letter to the Senate Judiciary Committee saying Trump had not received any income from Russian sources over the past 10 years "with a few exceptions".

Trump's pre-Presidential business dealings with Russia were scrutinized by the special counsel, Robert Mueller.

In 1987, Trump visited Russia to investigate developing a hotel, invited by Ambassador Yuri Dubinin whom he had met in New York the year before. British journalist Luke Harding alleged in 2017 that this trip likely began a long-term cultivation operation typical of the KGB's Political Intelligence Department, under written directives initiated by First Chief Directorate head Vladimir Kryuchkov, to recruit politically ambitious Westerners susceptible to flattery, egotism and greed.

In 1996, Trump partnered with Liggett-Ducat, a small company, and planned to build an upscale residential development on a Liggett-Ducat property in Moscow. Trump commissioned New York architect Ted Liebman, who did the sketches. Trump visited Moscow again with Howard Lorber to scout potential properties for "skyscrapers and hotels". During that trip, Trump promoted the proposal and acclaimed the Russian economic market. At a news conference reported by The Moscow Times, Trump said he hadn't been "as impressed with the potential of a city as I have been with Moscow" in contrast to other cities had visited "all over the world."

By this time, Trump had made known his desire to build in Moscow to government officials for almost ten years "ranging from the Soviet leader Mikhail S. Gorbachev (they first met in Washington in 1987) to the military figure Alexander Lebed." Moscow's mayor, Yuri M. Luzhkov, showed Trump plans for a very large shopping mall to be located underground in the vicinity of the Kremlin. The mayor complimented Trump's suggestion that this mall should have access to the Moscow Metro, and it was eventually connected to the Okhotny Ryad station. Although the 1996 residential development did not happen, Trump was by this time well known in Russia.

Trump's business strategy included Russia in ventures intended to internationally expand his brand. He transitioned in the mid-2000s from building and investing in real estate to simply licensing his name to hotels, condominiums, and commercial towers. Although a strategy of taking a percentage from the sales was successful in other countries, Trump's terms were not agreeable to Russians and conflicted with their way of doing business with American hotel chains.