DONALD Trump is known for being spotted with high profile businessmen and celebrities, including former Miss Universe Olivia Culpo.

While some of these photographed relationships are one-off or rare encounters, the former president’s connection to the model and ex-beauty queen has a peculiar history, that also involves Russia.

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Former President Donald Trump and Olivia Culpo have ties going back more than 10 yearsCredit: Getty Images – Getty

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The two were first spotted together at a runway show in New York City in 2012Credit: Splash

The duo was seen chatting throughout the showCredit: Splash
Culpo, 32, was first spotted with the businessman-turned-president in 2012 at a runway show in New York City.

The show took place on September 7, 2012, at Trump Tower Grand Corridor, just months after Culpo – then 20 – had been crowned Miss USA.

Photos have resurfaced of the two sitting front row at the show, as then-teenager Kendall Jenner walked the runway.

Culpo was seen sitting with her ankles crossed and body angled towards Trump.

In one image, Trump leaned in to tell the pageant queen something closer to her ear.

Culpo appeared all smiles as she spoke to Trump, who would run for president just four years later.

Culpo was later crowned Miss Universe that December.

At the time, Trump owned the contest, having purchased it in 1996.

The duo was later connected a second time in a book published in 2018 titled, Russian Roulette: The Inside Story of Putin’s War on America and the Election of Donald Trump.

Written by journalists Michael Isikoff and David Corn, the book claimed Culpo was spotted at a raunchy nightclub in Las Vegas alongside Trump and the son of a Russian billionaire and popstar, Emin Agalarov.

The night out reportedly came after Trump had dinner with the popstar, who was looking for “an attractive woman for a music video,” according to an excerpt of the book, obtained by The Providence Journal.

“It seemed obvious to them that they should reach out to Miss Universe,” the book continues.

Trump and Culpo were allegedly photographed in the lobby of the nightclub, called The Act, which had been known for “lewd” and “offensive” “performance,” according to the book.

That same year, Culpo appeared in the Russian’s music video, according to Politico.

The night out with the Russian mogul came just months before Trump successfully brought the Miss Universe pageant to Moscow.

The 2013 Miss Universe contest was held in the Russian capital that November.

At the time, the New York businessman was also reportedly seeking to build a Trump Tower in the city.

Trump and Culpo were spotted together a third time at the Moscow pageant, posing for photos on the red carpet.

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In 2012, Culpo was crowned as Miss UniverseCredit: Getty

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Trump and Culpo were spotted together several times over the next year, including at a Las Vegas night club and in Moscow, RussiaCredit: Getty

The 2013 Miss Universe contest was held in RussiaCredit: Getty – Contributor
The two were photographed making Trump’s iconic handgun pose at the camera.

Several years later, Culpo appeared to distance herself from Trump who launched his presidential campaign and shockingly claimed that Mexico was sending “rapists and criminals” to the US.

At the time, Culpo had been set to appear as a judge in the 2015 Miss USA pageant.

However, she removed herself from the position after Trump’s comments went viral.

“When I heard Mr. Trump’s initial comments, my immediate gut reaction was to withdraw my involvement in the pageant, but I felt such a sense of obligation to the employees at the Miss Universe organization and the 51 women who had, like me, anxiously awaited the opportunity to compete for the title of Miss USA,” she said in a statement obtained by Cosmopolitan.

“I do not believe that Mr. Trump’s comments are a true reflection of the values of this organization at all. The employees who work 24/7 to give people the opportunity to grow as I did and contribute to countless charities are the real heart and soul of Miss USA and Miss Universe.”

Just months later in September, Trump sold his shares of Miss Universe.