Former Wagner mercenary boss Yevgeny Prigozhin is believed dead after the plane he was listed as a passenger on crashed just north of Moscow, barely two months after he launched – and then aborted – a mutiny that Vladimir Putin labelled traitorous.
The Kremlin says accusations that Putin was behind Prigozhin's death are "a complete lie" but he's far from the only critic or adversary of the Russian president who died in sudden or mysterious circumstances – or in some cases obvious assassinations.
Here are seven others.
Russian journalist Anna Politkovskaya authored the book Putin's Russia, which accused the Kremlin of turning the country into a police state. She reported extensively on human rights abuses, particularly in Chechnya.
In 2006, she was shot dead at point-blank range in her apartment building.
Five men were found guilty of her murder, but the judge was unable to determine who paid the $US150,000 contract to have her killed.
Putin denied the Kremlin was involved.
Former Russian spy Alexander Litvinenko was in no doubt about who ordered Politkovskaya's murder – he accused Putin of being behind the killing.
Just two weeks after making the accusation, Litvinenko died in London in 2006 of radiation poisoning after drinking a cup of tea laced with polonium-210.
He had also claimed Putin, while running the Russian Federal Security Service (or FSB), was behind a series of deadly apartment explosions in 1999.
The European Court of Human Rights found Russia was behind his murder, ruling that Andrey Lugovoy and Dmitry Kovtun killed Litvinenko.
A UK inquiry found that the killing had probably been signed off by two men: then-FSB head Nikolai Patrushev and Vladimir Putin.
The day after Litvinenko died, Putin gave a blunt reaction.
"Mr Litvinenko is, unfortunately, not Lazarus," he said.
Lawyer Sergei Magnitsky was tightly aligned with one of Putin's most outspoken critics: American-British businessman Bill Browder.
Magnistsky was investigating a tax fraud scheme in Russia on behalf of Browder.
He was killed shortly after he testified to officials about the ploy.
"Five weeks after Sergei testified, the same officials whom he testified against arrested him, put him in pre-trial detention in Russia, where he was then tortured to get him to withdraw his testimony," Browder (pictured) told CBS in 2022.
Magnitsky died in a Russian jail in 2009, allegedly after being beaten and denied medical care.
His name currently adorns the Magnitsky Act, the law that allows the US government to sanction foreign officials who are human rights offenders.
Putin has consistently said Magnitsky died of a heart attack.
A one-time deputy prime minister under Boris Yeltsin, Boris Nemtsov was once considered a potential Russian president – only for Putin to end up succeeding Yeltsin.
Nemtsov went on to become one of Putin's most vocal critics, and continually denounced Russia's illegal annexation of Crimea in 2014.
In a February 2015 interview, Nemtsov said he was worried Putin would kill him for that criticism.
Two weeks later, he was shot four times in the back when he walking back from a Moscow restaurant.
Putin condemned the murder and took "personal control" of the investigation into it.
More than eight years later, no one has been held accountable for it.
Like Nemtsov, MP Denis Voronenkov was once part of the Russian government.
But he fled to Ukraine in 2016, going on to compare Putin's rule to Nazi Germany and labelling the annexation of Crimea illegal.
Also like Nemtsov, Voronenkov was aware he could be an assassination target, telling a fellow former MP who had fled Russia that he had been threatened by the FSB.
In March 2017, he was shot at least three times in the head and neck in broad daylight after leaving a hotel in Kyiv.
Ukraine's president at the time, Petro Poroshenko, called the killing an "act of state terrorism by Russia" – an accusation Kremlin spokesperson Dmitry Peskov called "absurd".
When the annexation of Crimea morphed into Putin's full-scale invasion in 2022, few Russian businessmen criticised the president.
One of them, though, was Ravil Maganov, the chairman of energy giant Lukoil. The company called for a ceasefire in March 2022, just weeks after the invasion began.
Six months later, Magannov was dead, with state media reporting he fell out a window – although Lukoil said his passing was the result of illness.
Only a few months later, Russian sausage magnate-turned-lawmaker Pavel Antov also fell out a window.
Antov had also criticised Putin's invasion in a hastily deleted Whatsapp message, which he blamed on an "unfortunate misunderstanding and a technical error".