Russian President Vladimir Putin expressed his deep sorrow over the passing of former Italian Prime Minister Silvio Berlusconi, whom he considered a “dear friend.”

"For me, Silvio was a dear man and a true friend," Putin said in a message of condolence to Italian President Sergio Mattarella.

"I have always sincerely admired his wisdom and his ability to make balanced, far-sighted decisions even in the most difficult situations. During each of our meetings, I was literally charged with his incredible vitality, optimism and sense of humour," Putin shared his memories of Berlusconi. "His death is an irreparable loss and a great misfortune."

Putin and Berlusconi first met at the G8 summit in Genoa in 2001. They held dozens of one-on-one business meetings over the years in big politics and at various international forums in Russia and Italy and in many other countries.

Putin and Berlusconi not only worked together, but were on friendly terms for more than 20 years and occasionally holidayed together with their families.

They frequently met up, in both Russia and Italy, even after Berlusconi left office in 2011. Putin visited Berlusconi at his Rome mansion in 2013 in between official engagements, after the former Italian PM was expelled from Italy’s parliament due to a tax fraud conviction and couldn’t travel abroad.

Berlusconi has been one Putin’s strongest supporters in Europe and insensitive to Russia’s aggression in Ukraine. In 2015, the pair were lambasted by Ukrainian prosecutors after they opened a rare vintage, a 240-year-old bottle from Jerez de la Frontera. The Spanish wine, brought to Crimea during the reign of Catherine the Great by Count Mikhail Vorontsov, was thought to be worth more than €100,000.

Ukrainian prosecutors prepared charges against the winery’s director, for giving away Crimea’s national heritage. Berlusconi didn’t care.

“It was delicious,” the Italian billionaire-turned-politician said in an interview. “We visited this famous winery and they asked us to taste their wines. Then, unexpectedly they allowed us to taste this bottle of wine from the 18th century, of which they were very proud. It was fantastic.”

On another occasion in 2018 Berlusconi skipped his own party's annual conference and flew instead to Sochi to Russia to attend Vladimir Putin’s 66^th birthday celebrations. The year before he gave Putin a duvet cover with both their faces on it.

The nature of their close relationship has puzzled some analysts, who speculated there were murky businesses deals and wild “bunga bunga” sex parties lying behind the bonhomie.

Putin once described Berlusconi as “the last of the Mohicans” in Europe and a remarkable figure associated with the most important events in Italy's recent history. He highlighted Berlusconi's dedication to his country's interests and his significant contributions to its economic and social development, as well as its positioning in Europe and the global stage.

"A true patriot, Silvio Berlusconi has always put the interests of his country above everything else. Being at the helm of the Council of Ministers and holding other important governmental posts for many years, he did a great deal for the economic and social development of the country and for its firmer foothold in Europe and in the world arena," Putin said.

The Russian president also emphasised Berlusconi's invaluable personal contribution to strengthening Russian-Italian ties and his unwavering support for friendly relations between the two countries. Until the war in Ukraine, Italy along with France had been a major investor into the Russian economy, although both pale in comparison to the scale of German investment.

"In Russia, Silvio Berlusconi will be remembered as a consistent and high-principled supporter of strengthening friendly relations between our countries," Putin said.

Putin sought to use his close friendship with Berlusconi to further his agenda in Europe, in the same way that Putin leveraged close ties with German Chancellor Gerhard Schroeder to further ties with Germany to great effect.

In April 2002 halfway through his first term in office, Berlusconi was a guest at Putin’s dacha in Sochi, on the Black Sea. After drinking Russian tea before the television cameras, the two leaders retired to a small room on the second floor to discuss the big item of business: the creation of a new council to bring together Russia and the Nato alliance. At that time Putin had ambitions of moving closer to Europe and was even lobbying for Russia’s membership in the EU – a plan that was quickly shot down by Brussels. But Berlusconi was recruited as an ally by Putin to aid Russia’s closer integration into Europe.

After relations with Europe took a bath following the annexation of Crimea, Berlusconi sought to fashion a role for himself as an intermediary between Moscow and the West after Russia but as the former prime minister became more isolated in Italy, he became more willing than ever to defend Putin in public.

The wine-drinking break in Crimea came just as Putin was preparing to intervene militarily in Syria while re-engaging with world leaders at a UN General Assembly the same week where he faced overwhelming criticism for his military aggression in Ukraine.

In a telegram to President Mattarella, Putin extended his deepest condolences on the death of the outstanding Italian politician. He acknowledged Berlusconi's role as a true patriot who always prioritised the interests of his homeland. Putin regarded Berlusconi as the patriarch of Italian politics, highly respected both domestically and internationally.

"The most important events in the recent history of Italy are connected with the name of this remarkable man. A true patriot, Silvio Berlusconi always put the interests of his homeland above everything else," the Russian leader said.

Putin further characterised Berlusconi as an extraordinary politician known for his sincerity and openness. He highlighted Berlusconi's privilege of speaking his mind, a quality not often found in politicians of his stature.

"He was an unusual person for a politician because he was very sincere and open and had a privilege that politicians of this scale do not enjoy. That privilege of his was to speak his mind," Putin said on the Rossiya-24 television channel.

Berlusconi's death was reported by Corriere della Sera, marking the end of a long and influential career in Italian politics. The veteran leader, founder of the Forward, Italy! party, and three-time prime minister, died at the age of 86.