In January 2009, the U.S. ambassador in Rome cabled Washington to raise an alarm. Russian President Vladimir Putin, the diplomat wrote, had cultivated a troubling relationship with the country’s Prime Minister, Silvio Berlusconi.

“Berlusconi admires Putin’s macho, decisive, and authoritarian governing style, which the Italian PM believes matches his own,” wrote the ambassador, Ronald P. Spogli. “From the Russian side, it appears that Putin has devoted much energy to developing Berlusconi’s trust.“

The ambassador noted with concern that the brash Italian billionaire, who was driven from office by scandal in 2011, was openly challenging U.S. policy toward Russia and echoing Putin’s views on issues from NATO expansion to Kosovo to missile defense.

And he shared reports from opposition party contacts of a more nefarious factor: talk that “Berlusconi and his cronies are profiting personally and handsomely” from business ties to Russia.

Seven years after that cable, disclosed by WikiLeaks, the Berlusconi-Putin bromance has acquired a new resonance, as foreign policy analysts and even some U.S. officials see unsettling echoes in the recent long-distance kinship between the Russian leader and Donald J. Trump.

It may even suggest that Putin is applying a specific method to the Republican nominee. In recent years Putin has befriended several major Western European politicians, including former leaders of France and Germany, who openly challenge U.S. and European policies toward Russia, including NATO’s buildup in Eastern Europe and economic sanctions punishing Putin’s annexation of Crimea from Ukraine.

Putin’s friendship with the Italian may simply demonstrate that the Russian leader has a natural chemistry with a rich, politically incorrect businessman.

But Trump is most frequently compared to the 79-year-old Berlusconi. Both men are wealthy populists known for their expensive tastes, outrageous rhetoric, relationships with women and all-around showmanship. Like Berlusconi, Trump has demonstrated an unusual affinity for Putin — along with notable dissent from confrontational U.S. and Western European policies toward Russia.

Putin’s friendship with the Italian may simply demonstrate that the Russian leader has a natural chemistry with a rich, politically incorrect businessman.

To some, however, it hints at something more.

“The parallels with Trump are a little too disturbing,” says a U.S. government analyst who closely tracked Russia’s relationship with Europe when Berlusconi was in office. “Putin is very strategic. He would focus on people’s vulnerabilities — whether their vanity or greed or financial needs.”

That view echoes the analysis of former deputy CIA director Michael Morell, who recently wrote in the New York Times that Putin, drawing from his background as an intelligence officer, had made a “calculated” overture to Trump early in the presidential campaign, “playing upon Mr. Trump’s vulnerabilities by complimenting him,” and turning Trump into an “unwitting agent” of Russia.

Asked about Trump in December, Putin described the New Yorker as “bright and talented,” words that clearly pleased Trump: “It is always a great honor to be so nicely complimented by a man so highly respected within his own country and beyond,” the mogul told reporters soon after. Since then, Trump has praised and defended Putin — including against the charge of having Russian journalists killed — and has pledged to establish better relations with Moscow.

Though Trump, in recent interviews, has downplayed his affinity for Putin, the Republican nominee has also taken several policy positions that echo the Kremlin line. He has questioned the relevance of the 67-year-old NATO alliance, called for U.S.-Russian cooperation against the Islamic State, and questioned U.S. and European sanctions imposed on Moscow after Putin’s forcible March 2014 annexation of Ukraine’s Crimean peninsula.

Prankster pals

Berlusconi, who remains close to the 63-year-old Putin, has offered similarly Putin-friendly views over the years. During a September visit to Crimea with Putin, Berlusconi called a 2014 referendum there in favor of Russia’s forcible annexation of the strategic peninsula “democratic” and “valid,” even though the U.S. and European Union have denounced the vote as invalid. Trump also recently cited the referendum as evidence that Russia’s claim on Crimea may be legitimate.

But Trump’s relationship with Putin — whom Trump says he’s never even met — remains embryonic compared to the extraordinary kinship between the Russian leader and his Italian chum.

Putin and Berlusconi bonded in the early 2000s, soon after each took office — Putin in 1999 and Berlusconi, who had already served one term as prime minister in the mid-90s, in 2001. Berlusconi holidayed at Putin’s dacha on the Black Sea, while the Russian stayed at the Italian leader’s villa in Sardinia. Even as Putin’s international reputation darkened, they hit the slopes in Sochi and dined in a tent on a wildlife reserve in giant fur hats.

They even became merry pranksters. During one Berlusconi visit to St. Petersburg, Putin jokingly startled his Italian pal: “Putin hid behind the pillar, and did ‘coo coo’ to me from behind!” he told the BBC in a 2014 interview.

U.S. officials suspected the friendship went beyond innocent antics. An October 2009 cable from the U.S. embassy fretted that Berlusconi had recently skipped a state visit by Jordan’s King Abdullah, claiming illness the day before a planned three-day visit with Putin. U.S. ambassador David Thorne wrote that Berlusconi had “left the impression that … he was husbanding his flagging energies for a blow-out party at Putin’s dacha.”

As the January 2009 cable noted, the officials also suspected that illicit money might be fueling the friendship. One October 2008 U.S. cable from Rome noted that “many (including his own party officials) suspect [Berlusconi] has a personally and financially enriching relationship” with Putin’s oligarch allies.

In recent weeks, allies of Hillary Clinton have fanned rumors and speculative press reports suggesting that Russian investments in Trump business ventures have influenced his views. Trump and his son Donald Jr. have made numerous trips to Russia exploring business deals there, and in 2008 Donald Jr. told an audience that Russian money makes up a “disproportionate share” of the family company’s assets. Trump has denied having financial ties to Russia, though his refusal to release his tax returns makes that impossible to verify.

The U.S. official said that, like Trump, Berlusconi — who left office in 2011 under a cloud of legal charges, including tax fraud and sex with a 17-year-old prostitute (for which he was cleared) — often took a friendly line toward Russia under the guise of his nation’s self-interest. “He seemed to be providing a very rational approach to Russia, but it was always on Russia’s terms,” the official said.

At various times Berlusconi defended Putin’s military incursion into the republic of Georgia, which the U.S. and much of Europe strongly denounced. He praised Putin’s leadership style. And after a fall 2008 meeting with Putin, Berlusconi echoed the Kremlin line that the U.S. had “provoked” Russia by backing independence for Kosovo, moving forward with missile defense systems in Eastern Europe and wooing Ukraine and Georgia closer to NATO. In a cable at the time, a senior U.S. diplomat in Rome wrote that the Italian leader wanted to “lobby the incoming U.S. President to take a softer line on Russia.”

"Berlusconi faces trial for bedding women," Putin said in September 2013. "If he was gay, no one would ever lay a finger on him."

“In reality, what he was doing was pushing Putin’s agenda with no real guarantee that Putin would ever compromise on our agenda,” says the U.S. official, who spoke to POLITICO. “I see a similar trend with Trump."

Other members of Berlusconi’s government often expressed surprise at the prime minister’s views, the official said — a view backed up by a diplomatic cable reporting that an unnamed Italian Ministry of Foreign Affairs official told U.S. diplomats in Rome that “she had no insight whatsoever as to what had animated” Berlusconi’s remarks on Kosovo and missile defense.

Putin, for his part, returned his friend's praise — and even defended Berlusconi from the charge he'd had sex with underage girls at his notorious "bunga bunga" parties.

"Berlusconi faces trial for bedding women," Putin said in September 2013. "If he was gay, no one would ever lay a finger on him."

Vintage Vladimir

Measuring the precise effect Berlusconi's views had on U.S. or European policy toward Russia is difficult. Samuel Charap, a former State Department official now with the International Institute for Strategic Studies, noted that "Italy, generally speaking, is one of the more Russia-friendly countries in Europe."

But Putin has also courted other prominent European leaders of his generation. After leaving office, the former German chancellor Gerhard Schroeder joined the board of the Russian energy giant Gazprom, and in 2014 he attended a lavish 70th birthday party thrown for him by a Gazprom subsidiary in St. Petersburg at which Putin was in attendance. Schroeder has reportedly infuriated his successor, Angela Merkel, with his comments downplaying the severity of Putin's incursions into Ukraine.

A recent visit to Moscow by former French President Nicolas Sarkozy, meanwhile, raised eyebrows in Paris and Washington, after Sarkozy — who may run for president again next year — warned against a new Cold War and spoke in favor of lifting sanctions on Russia.

U.S. officials bridle at the way such talk muddles their carefully orchestrated message of U.S.-Europe unity against Putin's aggression. And they say Berlusconi, who remains close to Putin, still does his share of the troublemaking.

During an October 2014 international summit in Milan, the Russian dropped in on Berlusconi's villa for a nightcap at 1:30 a.m. that reportedly lasted beyond 3 a.m. On a trip to Rome the next year, Putin again dropped in on his Italian friend, who pledged to use his enduring political influence to push for an end to European sanctions against Russia — and later publicly pledged to help “convince our American friends that the return to the atmosphere of the Cold War is inadmissible.”

Most memorably, perhaps, the two men paid a joint visit in September to Crimea — itself a political statement, given the landmass' disputed status. While touring a winery, the two men were shown several bottles of a dust-covered 1775 vintage wine imported during the reign of Catherine the Great.

Berlusconi asked whether it was possible to drink the wine; it was. Though it's unclear whether the men had more than "a taste," as the Italian later put it, some reports had them polishing off an entire bottle, priced at more than $100,000. Crimea's top prosecutor threatened criminal charges over what he called the violation of "the heritage of all Ukrainian people."

Berlusconi, for his part, was unfazed by both the political and oenophilic controversies.

"You should see the love, the gratitude and the friendliness that welcomed Putin" in Crimea, he told reporters, calling Putin the world's "No. 1" political leader. "Women threw themselves into his arms saying, 'Thank you, Vladimir. Thank you, Vladimir,'" he added.

As for the wine, Berlusconi pronounced it "delicious."