Long before he set foot in the White House, Donald Trump had his sights set on expanding his real estate empire into Ukraine. The billionaire-turned-president dreamed of building a Trump International Hotel in Kyiv, a venture that could have reshaped his global brand. But despite ambitious plans and high-level discussions, the deal never materialized. So what went wrong?
The Billionaire’s Bold Plan
In a 2007 sworn deposition, Trump revealed that he had considered expanding his business into Ukraine as part of a larger international strategy that included Moscow, Warsaw, and Istanbul. He confirmed that his company had pursued the idea of a Trump-branded hotel in Kyiv before March 2005. His children, including Donald Trump Jr., Ivanka, and possibly Eric, even visited Ukraine to explore potential opportunities.
A Troubled Partnership
Trump’s real estate ventures in Ukraine weren’t solo endeavors. His company worked with Bayrock Group, a development firm linked to convicted felon Felix Sater. The Trump Organization also explored partnerships with other Ukrainian investors. However, those deals fell apart when investors began questioning Trump’s financial stability. Reports suggest that backers wanted him to contribute more capital or remove his name from the project altogether—terms Trump was unwilling to accept.
The Lawsuit That Changed Everything
The full extent of Trump’s Ukraine ambitions surfaced during a legal battle with journalist Timothy O’Brien, author of TrumpNation: The Art of Being the Donald. The book alleged that Trump’s net worth was far lower than he claimed—estimates ranged from $150 million to $250 million, significantly less than the billions he often touted. Trump sued for $5 billion, arguing that the book’s claims scared off potential investors, including those in Ukraine. However, the case was dismissed in 2009, and an appellate court upheld the ruling in 2011.
The Truth Behind the Collapse
By the time Trump testified in 2007, he still believed a Ukraine deal could happen. But ultimately, none of his projects in the country came to life. With investors hesitant and financial scrutiny mounting, Trump’s Ukrainian ambitions faded into history.
A Pattern of Failed Foreign Ventures
Ukraine isn’t the only country where Trump’s business dreams ran into trouble. His hotels in Toronto and Vancouver were later rebranded, and his Panama hotel had his name removed in 2018. Interestingly, he also once floated the idea of annexing Canada and taking back the Panama Canal—suggesting his business interests and foreign policy views were sometimes closely intertwined.
Where Trump Stands on Ukraine Today
Since leaving office, Trump has distanced himself from pro-Ukraine rhetoric. Unlike most U.S. allies and members of Congress, he has suggested Ukraine should negotiate with Russia and even temporarily halted military aid. His stance has raised questions about how his past business aspirations might still shape his political views.
Trump’s lost Ukrainian empire is a fascinating what-if—one that could have dramatically altered his business legacy and global influence. But in the end, the deal that never was remains just another chapter in the long and complicated story of Trump’s international ambitions.
