With the death of Italy’s Silvio Berlusconi on Monday, Russian President Vladimir Putin has lost one of his few remaining friends in Europe.

Putin’s long-standing friendship with the former Italian prime minister was as controversial as it was crucial to cementing ties between the two countries, which often made Rome one of Moscow’s strongest allies in the European Union.

Their glitzy, often strange bromance — in which Berlusconi once presented Putin with gift bedsheets emblazoned with an image of the two men shaking hands — frequently raised eyebrows in diplomat circles.

The bedsheets were apparently Berlusconi’s tongue-in-cheek response to revelations that Putin had once given Berlusconi an ornate double-bed, which was described in one of Berlusconi’s many tanged legal proceedings.

According to evidence, an escort who was paid to participate in Berlusconi’s recorded a conversation in which Berlusconi told an escort to wait for him in a bed, which the woman then described as “Putin’s.”

Some have speculated that Berlusconi, a billionaire, and Putin, a reputed billionaire, engaged in covert business deals. Others pointed to the expanding Russian-Italian trade relationship, particularly in energy,

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Linked by a shared boorish machismo, the two leaders were seen frequently together: at extreme fighting competitions in Russia, laughing at international news conferences, and in full gear for skiing trips alongside Putin’s sidekick, former Russian Prime Minister Dmitry Medvedev.

The two were also photographed drinking at one of Putin’s residences in large fur hats, and vacationing together in Sardinia. “Putin has never asked me for a single favor, and I have never asked a favor of him,” Berlusconi once said.

The friendship, which seemed to be based on a mutual self-interest as well as genuine affection, frequently courted scandal.

After Berlusconi resigned from office in 2011 amid multiple scandals, including allegations that he paid for sex with an underage sex worker (a charge for which he was later acquitted), Putin rallied behind him claiming that his Italian buddy would not have faced trial if he were gay.

“Berlusconi is being tried because he lives with women,” Putin told an audience at his annual Valdai conference with Russian and international foreign policy experts in 2013. “If he were homosexual, no one would lift a finger against him.”

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In 2015, Ukraine banned Berlusconi from the country for three years after he went with Putin to visit Crimea, which Russia invaded and illegally annexed the year before.

And last fall — months after Russia’s invasion of Ukraine, which turned Putin into a pariah on the international stage — a recording was leaked to the Italian media on which Berlusconi boasted that he had rekindled ties with Putin.

Berlusconi said Putin had sent him 20 bottles of vodka for his birthday and a “very lovely letter,” in which he claimed Putin had called him “number one among his five best friends.”

The incident reportedly caused friction with Italian Prime Minister Giorgia Meloni who has advocated sending weapons to Kyiv and described Russia’s invasion as an “unacceptable large-scale act of war by Putin’s Russia.”

In a tribute on Monday, Putin called Berlusconi a dear friend and an outstanding politician.

“For me, Silvio was a dear person, a true friend,” Putin said in a statement. “I have always sincerely admired his wisdom, his ability to make balanced, far-sighted decisions even in the most difficult situation.”

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