He dared to challenge the authority of Vladimir Putin. Two months later, he was dead.

Yevgeny Prigozhin, who Russian authorities said was killed in a plane crash north of Moscow, led his Wagner private army out of the shadows and on to the frontlines of Russia's war in Ukraine, before overplaying his hand in a risky power struggle with the military establishment.

His jowled face, shaven head and booming voice made him instantly recognizable in Russia and around the world as he hurled abuse at Defence Minister Sergei Shoigu and Chief of the General Staff Valery Gerasimov, accusing them of starving his fighters of the supplies they needed.

In one extraordinary video, he shouted and cursed at Shoigu and Gerasimov, demanding ammunition so his men could keep fighting.

For months, Prigozhin kept escalating his feud with the top brass, crossing a series of lines as many wondered, in Russia and outside the country, why Putin allowed him to rage unchecked.

Yevgeny Prigozhin, top, serves food to Russian Prime Minister Vladimir Putin at Prigozhin's restaurant outside Moscow in 2011. – AP

He accused the defence chiefs of treason. At one point he threatened to withdraw his men – their ranks bolstered by convicts he had personally recruited – from the Ukrainian city of Bakhmut where they had fought the longest and bloodiest battle of the war.

Prigozhin performed a U-turn and Wagner fought on, eventually capturing the city in late May. But a turning point came weeks later when he rejected an order for Wagner fighters to sign contracts placing them under the control of the defence ministry.

Armed revolt 

On June 23, he launched an outright mutiny, seizing control of the southern city of Rostov and then advancing toward Moscow.

"Those who destroyed our lads, who destroyed the lives of many tens of thousands of Russian soldiers, will be punished. I ask that no one offer resistance," he said in one of a series of frenzied audio messages.

"There are 25,000 of us and we are going to figure out why chaos is happening in the country," he said, promising to tackle any checkpoints or air forces that got in Wagner's way.

A fighter of the Wagner private mercenary group visits a makeshift memorial in St Petersburg. – Reuters

Putin went on television the next day to denounce the mutiny as a "stab in the back" and promised a harsh response. But within hours the revolt was defused with a deal: The Kremlin said that in order to avert bloodshed, Prigozhin and some of his fighters would leave for Belarus and a criminal case against him for armed mutiny would be dropped.

For weeks, confusion surrounded the implementation of the deal, the status of Prigozhin and his whereabouts. The Kremlin said he attended a meeting with Putin five days after the mutiny. On July 5, state TV said an investigation against him was still being pursued, and broadcast footage showed cash, passports, weapons and other items it said were seized in a raid on one of his properties.

Two weeks later, a video appeared to show Prigozhin welcoming his fighters to Belarus. At the end of the month, he was photographed in St Petersburg while a Russia-Africa summit was taking place in the city.

In this image taken from video, Prigozhin speaks to a camera at an unknown location believed to be in Africa. – AP

His ability to move in and out of Russia apparently with impunity raised new questions about why Putin continued to tolerate him.

"In six months, Prigozhin will either be dead or there will be a second coup. I’m agnostic between the two but I can’t see neither of these happening," Christo Grozev, an investigative journalist with Bellingcat, told the Financial Times earlier this month.

Putin on Thursday described Prigozhin as a man who had made serious mistakes in life but a talented person who had fought for the "common cause". He expressed his "sincere condolences" to those who died on the plane.

Business man and warload 

Prigozhin emerged from years of operating behind the scenes to become arguably the most visible player in Russia's war after Putin himself. This caught many by surprise and was widely seen as a sign that he harboured long-term political ambitions to cap his unlikely rise from hot-dog seller and small-time criminal.

Born in St Petersburg on June 1, 1961, he spent nine years in Soviet prisons for crimes including robbery and fraud. Released in 1990 amid the Soviet Union's death throes, he launched a career as a caterer and restaurateur in his hometown.

He is believed to have met Putin, then a top aide to St Petersburg's mayor, at this time.

Taking advantage of his political connections, Prigozhin was awarded major state contracts, becoming known as "Putin's chef" after catering for Kremlin events. More recently he joked that "Putin's butcher" would be more appropriate.

Yevgeny Prigozhin, left, shows Russian President Vladimir Putin around his factory which produces school meals near St Petersburg in 2010. – AP

He built up a huge portfolio of interests across many countries, including in real estate, media and minerals. The US accused his operations of manipulating voters in the 2016 presidential election – something Prigozhin himself last year admitted – in favour of Donald Trump.

And to the last, Prigozhin was intent on drumming up business.

He hailed a coup in Niger last month as a blow against "colonizers" and offered his fighters' services to bring order. As recently as Tuesday, he posted a video which he suggested was shot in Africa.

"The temperature is +50 – everything as we like," Prigozhin said, standing in a desert area with a rifle in his hands. The clip was accompanied by a phone number for people wishing to sign up.

Prigozhin's death raised a host of questions, not least surrounding the future of his business empire and the fallout for Putin and the war in Ukraine.

"The mutiny of EV Prigozhin is over. And everything is just beginning," political analyst Stanislav Belkovsky said.

Putin foes who have suffered mysterious fates

Russian mercenary chief Yevgeny Prigozhin is dead after a private jet on which he was listed as a passenger crashed north of Moscow with no survivors.

Prigozhin, 62, spearheaded a mutiny against Russia's top army brass on June 23-24, which President Vladimir Putin said could have tipped Russia into civil war.

Others who have opposed Putin or his interests have also died under unclear circumstances or come close to death.

Here are some details about these mysterious incidents:

Alexei Navalny

Russia's most prominent opposition leader, Alexei Navalny, was flown to Germany in August 2020 for medical treatment after being poisoned in Siberia with what Western experts concluded was the military nerve agent Novichok. Russia has denied any involvement.

Navalny earned admiration around the world for voluntarily returning to Russia in 2021. He was immediately arrested on arrival. He is now serving sentences totalling 11.5 years on fraud and other charges that he says are bogus. His political movement has been outlawed and declared "extremist". Navalny had an extra 19 years in a maximum security penal colony added to his jail term recently.

Sergei Skripal 

A former Russian double agent who passed secrets to British intelligence, Sergei Skripal and his daughter Yulia were found unconscious on a bench outside a shopping centre in the English cathedral city of Salisbury in March 2018.

They were taken to hospital in critical condition, and British officials said they had been poisoned with Novichok, a group of nerve agents developed by the Soviet military in the 1970s and 1980s. Both survived.

Russia has denied any role in the poisoning and said Britain was whipping up anti-Russian hysteria.

Vladimir Kara-Murza

A Russian opposition activist, Vladimir Kara-Murza said he believes attempts were made to poison him in 2015 and 2017. A German laboratory later found elevated levels of mercury, copper, manganese and zinc in him, according to medical reports seen by Reuters. Moscow denied involvement.

Alexander Litvinenko

Alexander Litvinenko, an ex-KGB agent and outspoken critic of Putin, died in 2006 aged 43 after drinking green tea laced with polonium-210, a rare and potent radioactive isotope, at London's Millennium Hotel, British officials have said.

Putin probably approved the killing, a British inquiry concluded in 2016. The Kremlin has denied involvement.

An inquiry led by a senior British judge found that former KGB bodyguard Andrei Lugovoy and another Russian, Dmitry Kovtun, carried out the killing as part of an operation that he said was probably directed by Russia's Federal Security Service (FSB), the main heir to the Soviet-era KGB.

Litvinenko fled Russia for Britain six years to the day before he was poisoned.

Alexander Perepilichny 

The 44-year-old Russian was found dead near his luxury home on an exclusive gated estate outside London after he had been out jogging in November 2012.

Alexander Perepilichny sought refuge in Britain in 2009 after helping a Swiss investigation into a Russian money-laundering scheme. His sudden death raised suggestions he might have been killed.

British police ruled out foul play despite suspicions he might have been killed with a rare poison. A pre-inquest hearing heard that traces of a rare and deadly poison from the gelsemium plant was found in his stomach.

Perepilichny had enjoyed a large bowl of soup containing sorrel, a popular Russian dish. Russia denied involvement.

Viktor Yushchenko 

Viktor Yushchenko, then a Ukrainian opposition leader, was poisoned during the campaign for the 2004 presidential election in which he ran on a pro-Western ticket against the pro-Moscow Prime Minister Viktor Yanukovich.

He said he was poisoned while having dinner outside Kyiv with officials from the Ukrainian security services. Russia denied any involvement.

His body was found to contain 1000 times more dioxin than is normally present. His face and body were disfigured by the poisoning, and he had dozens of operations in the aftermath.

He won the presidency in a re-run poll after Ukraine's Supreme Court struck down results declaring Yanukovich the winner amid street protests dubbed the "Orange Revolution".

Anna Politkovskaya 

Anna Politkovskaya, a journalist who reported on human rights abuses, was shot dead outside her flat in Moscow on Oct. 7, 2006, after returning home from the supermarket. The death of Politkovskaya, a 48-year-old mother of two, provoked an outcry in the West and underlined concerns about the dangers to reporters working in Russia.