Silvio Berlusconi, former prime minister of Italy and a billionaire media tycoon, died of leukemia on Monday at age 86.

During his time in the public eye, Berlusconi, nicknamed Il Cavaliere (the knight), became well known for a string of scandals, distasteful comments, and controversial friendships.

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Here are some of Berlusconi’s biggest controversies as the world remembers the late politician.

Supported Putin

While Russia was in the midst of attacking Ukraine last year, Berlusconi reminded the international public he was good friends with Russian President Vladimir Putin and defended his ally’s decision to invade Ukraine.

Berlusconi said in October 2022 he remained in cordial correspondence with Putin, admitting that Putin sent him “20 bottles of vodka and a very sweet letter” for his birthday. “I replied with bottles of Lambrusco and an equally sweet letter,” he added.

In February, the Italian billionaire even blamed Ukrainian President Volodymyr Zelensky for the war, according to Politico.

Praised Mussolini

In a 2003 interview with the Spectator, Berlusconi defended Benito Mussolini, the Italian fascist dictator, and went so far as to claim that “Mussolini never killed anyone.”

“Mussolini sent people on holiday to confine them,” he said, adding that the dictator was a “benign” leader.

Made insensitive comments after a natural disaster

Just after an earthquake devastated the central Abruzzo region of Italy in 2009, Berlusconi visited the survivors who were living in emergency tents and said they should view the aftermath as an extended “weekend of camping.”

The earthquake took over 300 lives, leaving tens of thousands of others homeless.

Accused of sexual relations with a minor

In 2010, Berlusconi became embroiled in a sex scandal that involved his interactions with Karima El Mahroug, a 17-year-old who became better known as Ruby The Heart Stealer. Critics called for his resignation, to which he replied, “It’s better to like beautiful girls than to be gay.”

Mahroug lifted the lid on Berlusconi's notorious "bunga bunga" parties held at his villa in Milan, leading to months of salacious stories in the press.

Berlusconi was initially found guilty of paying Mahroug for sexual services while she was under the age of 18, but this was subsequently overturned on appeal. It was only in February of this year that he was eventually cleared of bribing witnesses to lie about the events connected to Mahroug, but his reputation never recovered.

Despite the accusations he faced, Berlusconi never apologized for his interest in younger women and denied doing anything inappropriate with the girl.

“As always, I work without interruption and if occasionally I happen to look a beautiful girl in the face, it’s better to like beautiful girls than to be gay," he said.

Compared himself to a religious figure

While attending a dinner with his supporters in 2006, the Italian politician said, “I am the Jesus Christ of politics.”

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The statement prompted backlash from Berlusconi's enemies and even caused his supporters to question him.

“I am a patient victim, I put up with everyone, I sacrifice myself for everyone,” he said.

'Tanned' Barack Obama

In 2008, Berlusconi offered curious praise for then-president-elect Barack Obama, describing him as “young, handsome, and tanned.”

He subsequently claimed he was joking.

"If some people don't have a sense of humor, then it's their problem," he said.