Yevgeny Prigozhin made his name as the profane and brutal mercenary boss who in June mounted an armed rebellion that was the most severe and shocking challenge to Russian President Vladimir Putin’s rule.

Prigozhin was aboard a plane that crashed north of Moscow on Wednesday, killing all 10 people on board, according to Russia’s civil aviation agency.

The 62-year-old’s extraordinary journey took him from prisoner and hot dog vendor to elegant St. Petersburg restaurateur, and then from propaganda wars to the grisly battlefields in Ukraine.

As an instrument to project Russian power globally, his soldiers-for-hire were deployed to Africa to provide security for warlords and fought in Syria to shore up the regime of President Bashar Assad.

In May, they seized the Ukrainian city of Bakhmut in a rare victory for Russia in the war, but Prigozhin complained bitterly about the Defense Ministry’s conduct of the fight, saying it had denied ammunition to his forces.

As the war slogged on, Prigozhin dropped his public reticence and began releasing social media videos in which he lauded his troops and increasingly denounced Russia’s defense establishment for alleged mismanagement of the war and denying weapons and ammunition to his forces.

He abruptly escalated his scathing criticism in June by calling for an armed uprising to oust Defense Minister Sergei Shoigu.

On June 23, his forces left Ukraine and seized the military headquarters in the southern Russian city of Rostov-on-Don. He ordered them to roll toward Moscow, saying it was “not a military coup, but a march of justice” to unseat Shoigu.

He called off the action less than 24 hours later in a deal struck by Belarus President Alexander Lukashenko.

In a televised address, Putin had vowed to punish those behind the armed uprising led by his onetime protege. He called the rebellion a “betrayal” and “treason.”

But under the deal allowing Prigozhin and his forces to go free, Kremlin spokesman Dmitry Peskov later said Putin’s “highest goal” in the deal with the Wagner chief was “to avoid bloodshed and internal confrontation with unpredictable results.”

Prigozhin lived most of his life in the shadows. The owner of a high-end restaurant, he won Kremlin catering ventures that earned him the nickname of “Putin’s chef,” but he was mostly known only in the rarefied circles of the elite.

As the head of the Internet Research Agency, a “troll farm” that focused on interfering in the 2016 U.S. presidential election, he was barely visible.

But he barged into world view when mercenaries from his Wagner Group entered the war in Ukraine in 2022, becoming infamous both for their bloodthirsty fighting and their miserable treatment as cannon fodder in the eastern city of Bakhmut.

As part of the deal to defuse the crisis, an investigation into his mutiny was dropped, and he agreed to move to Belarus. He later appeared in videos, saying his soldiers would be deployed to Africa.

A recruitment video released earlier this week showed him at an undisclosed desert site in military fatigues and holding an assault rifle as he said his company was seeking “real warriors” and “continuing to fulfill the tasks” it had promised to carry out.

Prigozhin and Putin had long ties. Both were born in Leningrad, now St. Petersburg.

During the final years of the Soviet Union, Prigozhin was in prison — a decade by his own admission — although he never said for what crimes.

Afterward, he owned a hot dog stand and then fancy restaurants that drew interest from Putin. In his first term, the Russian leader took then-French President Jacques Chirac to dine at one of them.

“Vladimir Putin saw how I built a business out of a kiosk. He saw that I don’t mind serving to the esteemed guests because they were my guests,” Prigozhin recalled in an interview published in 2011.

His catering businesses expanded significantly, and in 2010, Putin helped open Prigozhin’s factory, which was built on generous loans from a state bank. In Moscow alone, his company Concord won millions of dollars in contracts to provide meals to public schools.

He also organized catering for Kremlin events and provided meals and utility services to the Russian military.

In 2014, Prigozhin co-founded the Wagner Group, even though private military companies are technically illegal in Russia. It came to play a central role in Putin’s projection of Russian influence in global trouble spots, first in Africa and then in Syria.

Wagner fighters reportedly provided security for African leaders or warlords in exchange for lucrative payments, often including a share of gold mines or other natural resources. U.S. officials say Russia may have used Wagner’s work in Africa to support the war in Ukraine.

In 2017, opposition figure and corruption fighter Alexei Navalny accused Prigozhin’s companies of violating antitrust laws by bidding for $387 million in Defense Ministry contracts.

In December 2021, the European Union accused Wagner of “serious human rights abuses, including torture and extrajudicial, summary or arbitrary executions and killings,” and of carrying out “destabilizing activities” in the Central African Republic, Libya, Syria and Ukraine.

An online video surfaced in November 2022 that showed a former Wagner contractor, who allegedly had gone over to the Ukrainian side but was later recaptured by Russia, beaten to death with a sledgehammer. The Kremlin turned a blind eye to it, despite public outrage and demands for an investigation.

His troops captured Bakhmut in what was likely the bloodiest and longest battle of the war. Prigozhin has said that 20,000 of his men died there, about half of them inmates recruited from Russia’s prisons.

As his forces fought and died en masse in Ukraine, Prigozhin repeatedly raged against Russia’s military brass.

In a May 2023 video, Prigozhin stood next to rows of bodies that he said were those of Wagner fighters. He accused Shoigu, the defense minister, and the chief of the general staff, Gen. Valery Gerasimov, of incompetence and of starving his troops of the weapons and ammunition they needed.

“These are someone’s fathers and someone’s sons,” Prigozhin said. “The scum that doesn’t give us ammunition will eat their guts in hell.”

His remarks were unprecedented for Russia’s tightly controlled political system, in which only Putin could air such criticism.

Asked about a media comparison of him to Grigory Rasputin, a mystic who gained influence over Russia’s last czar by claiming to have the power to cure his son’s hemophilia, Prigozhin once snapped: “I don’t stop blood, but I spill blood of the enemies of our Motherland.”

After Prigozhin’s rebellion fizzled and he decamped to Belarus, Putin said the Kremlin “fully funds” Wagner. He added that authorities would investigate whether Prigozhin might have diverted any of the 80 billion rubles ($936 million) in state funds he allegedly received in 2023 for delivering food to the Russian army.

Prigozhin first gained attention in the U.S., when he and a dozen other Russian nationals and three Russian companies were charged with operating a covert social media campaign aimed at fomenting discord ahead of Donald Trump’s 2016 election victory.

They were indicted as part of special counsel Robert Mueller’s investigation into Russian election interference. The U.S. Treasury Department sanctioned Prigozhin and his associates repeatedly in connection with both his election interference and his leadership of the Wagner Group.

He responded to the 2018 indictment with sarcasm, which was typical for the outspoken mercenary leader.

“Americans are very impressionable people; they see what they want to see. I treat them with great respect. I’m not at all upset that I’m on this list,” the RIA Novosti news agency quoted him as saying. “If they want to see the devil, let them see him.”

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Associated Press writer Dasha Litvinova in Tallinn, Estonia, contributed to this report.