A report from BuzzFeed paints a somewhat different picture, however. Reporters Daniel Wagner and Aram Roston said Trump spent years trying to develop a business relationship with the Libyan regime, requesting a face-to-face meeting with Gaddafi and even taking Libya's U.S. ambassador golfing.
Gaddafi, who died in 2011, controlled Libya for four decades, quashing all opposition with a fervent brutality. Buoyed by oil wealth, he had been a major backer of terrorism, including the 1988 bombing of Pan Am Flight 103, which killed 189 Americans. He had been a prototypically cruel and bizarre dictator before Libyans rose up against him in 2011, prompting a civil war that eventually led to his death.
Yet, as distasteful as the idea of a wealthy American businessman and future presidential hopeful desperately seeking a business relationship with Gaddafi is, it was not exactly unique at the time. Trump was just one of many Americans hoping to make money from Libya before the 2011 uprising.
And perhaps the most notable thing about Trump's attempts to do business with Libya wasn't that they were made. It's that they failed.
Gaddafi had been at odds with the West for decades, filling his speeches with anti-imperialist rhetoric and using his financial clout to harm Western interests. But by the late 1990s, the Libyan leader had begun to reverse his antagonistic political relationship with the United States and other Western countries. Sanctions had worn his country down, and Libya was isolated after the collapse of the Soviet Union and facing new threats from Islamist groups.
As part of this new warming tactic, Gaddafi renounced his support for terrorist groups and publicly gave up his quest for nuclear weapons. He hired Western public relations firms to publicize his good deeds and lobby for him in Washington, London and Brussels.
Meanwhile, he began to pursue a domestic policy of economic liberalization, moving away from nationalized industries and toward privatizations with international investment.
These moves began to placate his former foes. Sanctions against the country were gradually lifted. The United States removed Libya from a list of state sponsors of terrorism in 2006 and restored full diplomatic relations with the country. Even the coldness in personal ties seemed to shift. In 2008, President George W. Bush became the first U.S. president to directly speak to Gaddafi, and Secretary of State Condoleezza Rice visited Libya shortly afterward. When the Libyan leader came to New York City the following year to attend the U.N. General Assembly, he spoke fondly of America's new president, Barack Obama. "We are content and happy if Obama can stay forever as the president," Gaddafi said in a 95-minute speech that left many weary.
The message was clear: Libya was open for business. The Washington Post's Robert O'Harrow and James Grimaldi would later describe the situation as a "Libyan gold rush," with international firms rushing to take advantage of the country's vast oil wealth. They pointed to the work of hedge funds and investment firms within the country, as well as large banks such as HSBC and Goldman Sachs — the latter of which was afterward accused of advising Libya's sovereign wealth fund to invest $1 billion in ultimately worthless ventures, a charge it denies.
U.S. diplomatic cables leaked in 2011 even revealed that disgraced American financier Bernie Madoff had approached Libya, though his attempts were apparently rebuffed.
It wasn't only financial firms getting in on the act, either: The New York Times reported that at least a dozen U.S. companies were involved in Libya, including household names such as Boeing and Caterpillar. It was not an ideal investment environment, however. The country was still a kleptocracy, making business somewhat chaotic. Coca-Cola had to temporarily shut down a bottling plant in the country after a squabble led to an armed confrontation over the plant between at least two of Gaddafi's sons.
The U.S. public was still not so open to Gaddafi, either, as evidenced by the furor over his visit to New York in 2009.
But there was a political logic behind all this business activity in Libya. "Immediate access to the U.S. and Western investment upon the removal of sanctions is the ultimate carrot,” is how one senior U.S. official explained it to The Post in 2011. The timing was probably crucial: Gaddafi had once been a major problem for the West, but after the Sept. 11, 2001, attacks, he could be useful in the new global war on terror.
But as Gaddafi's brutality was exposed yet again by the 2011 conflict, these investments looked more and more regrettable. Reporters began to scrutinize the deals, revealing just how opportunistic many were. Perhaps the biggest scandal erupted not in the United States but in France, with President Nicolas Sarkozy accused of taking more than $50 million of Gaddafi's money for his 2007 election campaign.
Regardless whether the allegations were true, Sarkozy apparently had little concern about moving against Gaddafi when the 2011 revolt occurred, with France and Britain becoming the two biggest backers of the rebels facing off against the Libyan state. The United States also supported forces opposing Gaddafi in what would become the Libyan civil war, suggesting that the ties formed by the economic investment in the country were easy to break — for Western powers, at least.
Despite his hopes for an economic relationship with Libya, Trump apparently felt no qualms about a military strike on Gaddafi. In 2011, he was recorded saying that the West should "knock this guy out very quickly, very surgically, very effectively, and save the lives," though he has since contradicted himself further on the matter.
Trump has been an unorthodox political figure throughout his White House campaign, apparently willing to seek common ground with authoritarian leaders, including Russia's Vladimir Putin. But Trump's courting of Gaddafi wasn't unusual at the time — it was, in fact, very orthodox.
And in hindsight, perhaps that's what is most worrying.
More on WorldViews