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Jailed Russian opposition figure and outspoken Kremlin critic Alexei Navalny died Friday in an Arctic Circle jail, the Russian prison service said. But his death is only the most recent of a long line of Vladimir Putin's critics who have been jailed, silenced or met brutal ends over the years. From plane crashes, accidental falls from windows to hangings, poisonings and health issues, many of the Russian President's critics appear to have been targeted in diverse ways. Many of the deaths are never solved and remain listed as accidental and suicides.
Here's a look at some of the high-profile deaths involving those who have criticised the Russian leader over the years -
Yevgeny Prigozhin
The former head of the Wagner paramilitary group was once one of the country's most powerful oligarchs and a member of Mr Putin's trusted inner circle. He died in 2023 at the age of 62 when the plane he was flying in exploded midair. Notably, the unexplained blast came two months after Mr Prigozhin led a failed mutiny against Russia's Ministry of Defence over a disagreement with the direction of Moscow's war in Ukraine.
He led a dramatic "march for justice" where armed men were seen heading towards the Russian capital in June 2023. As Mr Putin remained silent, the mutiny was suddenly aborted. Mr Prigozhin ordered his troops to lay down their arms, before they were relocated to Belarus under a deal brokered by that country's Russia-allied president, Alexander Lukashenko. But two months later, Mr Prigozhin plummeted from the sky when the jet he was flying on from Moscow to St Petersburg apparently exploded.
Kremlin critics and Western countries suggested foul play. However, the Kremlin denied any involvement in the downing of the aircraft.
Boris Nemtsov
Boris Nemtsov, a vocal Kremlin critic who was a deputy prime minister in the late 1990s under President Boris Yeltsin, was gunned down in February 2015 on a bridge close to the Kremlin in Moscow. According to the CNN, he had been arrested several times for speaking against Mr Putin's government. When he was killed, he was helping to set up a rally against the Russian military incursion in Ukraine, which began in 2014 with the annexation of Crimea and the support of supposed separatists in the Donbas in eastern Ukraine.
Boris Berezovsky
Boris Berezovsky was once a powerful Russian businessman who fell out with the Kremlin and fled to England. He had accumulated his wealth following the collapse of the Soviet Union. A large chunk of his fortune came from the sale of luxury cars. But his wealth and political influence skyrocketed when he bought into Russian media. He relocated to Britain after losing favour with Mr Putin's government.
In 2013, Mr Berezovsky was found dead on the bathroom floor of his UK home with a noose around his neck. British police said at the time that there were no signs of struggle and suggested that he had taken his own life.
Alexander Litvinenko
Mr Litvinenko was a former Russian spy turned Kremlin critic. A British inquiry determined Alexander Litvinenko had been poisoned at a London hotel bar in 2006 by two Russian agents who spiked his green tea with the highly radioactive polonium-210, CNN reported. Mr Litvinenko also always asserted that Mr Putin and the Kremlin were responsible for what had happened to him.
But the Kremlin has always denied the accusation and has refused to extradite the two agents accused of the poisoning to Britain.
Ravil Maganov
Ravil Maganov, the chairman of the board of Russia's second largest oil producer Lukoil, died six months after he openly criticised the war in Ukraine. He died after falling out of the window of a Moscow hospital. Russian state news agency Tass claimed his death was a suicide.
Anna Politkovskaya
Ms Politkovskaya was a vocal critic of Russia's war in Chechnya. She was gunned down in the entrance of her Moscow apartment in October 2006. Her death garnered international attention and it wasn't until June 2014 that five men were sentenced for the killing, but it remains unclear who ordered the murder.
But shortly after her death, Mr Putin denied any Kremlin involvement in her killing, saying that Ms Politkovskaya's "death in itself is more damaging to the current authorities both in Russia and the Chechen Republic ... than her activities".
Sergei Magnitsky
Sergei Magnitsky, a Russian tax adviser who exposed corruption, was detained without a trial and died in prison just seven days before he was set to be released. He was arrested in 2008 and died on 16 November 2009.
Alexander Perepilichnyy
Mr Perepilichnyy was a financier who became a whistleblower in 2010 when he handed over files to Swiss officials showing details of the $230 million theft of funds from the Russian treasury. He died during a jog close to London in 2012 after leaving Russia in 2009. While he was found to probably have died of natural causes, there are allegations that he was poisoned.
Notably, apart from the people mentioned above, at least 13 high-profile Russian businessmen have reportedly died by suicide or in mysterious circumstances over the past year, as per CNN.