As Putin’s Partner, Prigozhin Was Always Willing to Do the Dirty Work

Yevgeny V. Prigozhin, the mercenary leader who led an armed rebellion in Russia on Saturday, was never afraid of a dirty task, many say.

Emerging from jail as the Soviet Union was collapsing, he began his post-criminal career selling hot dogs on street corners in St. Petersburg, Russia. There, he befriended Vladimir V. Putin, then a minor official in the city government, developed a catering business and earned billions on government contracts when his friend Vladimir became prime minister and then president of Russia.

Mr. Prigozhin quickly earned the trust of his benefactor, who assigned him a number of important tasks that were best handled at arm’s length from the government. The first and most notorious of those was overseeing the Internet Research Agency, a troll farm founded in 2013 to flood the United States and Europe with disinformation that discredited liberal elites and promoted hard-right ideologies.

From there, he raised mercenaries to fight in Syria and Libya, and, most fatefully, founded the private military group Wagner, which emerged during Russia’s annexation of Crimea in 2014. It quickly earned a reputation for ruthless violence in pursuit of lucrative diamond and gold concessions, while building political influence for the Kremlin in countries like the Central African Republic, Libya, Mali and Sudan.

Throughout those years, Mr. Prigozhin kept an extremely low profile, never even admitting to the existence of Wagner, let alone his having a role in it.

That began to change during the war in Ukraine, as the Russian military suffered setback after setback and Mr. Prigozhin became disgusted with the greed, corruption and ineptitude he claimed to see in the upper echelons of the military.

“These are Wagner guys who died today; the blood is still fresh,” Mr. Prigozhin said, addressing Russia’s defense minister, Sergei K. Shoigu, and the commander of the armed forces, Valery V. Gerasimov. “They came here as volunteers and they die so you can get fat in your mahogany offices.”

As his critiques of Russia’s top military leaders grew more frequent and intemperate, he began to emerge as a public figure, insisting that his forces could do the job far better than the Russian regulars.

He recruited thousands of convicts from Russian prisons and threw them into the bloody fight over the Ukrainian city of Bakhmut, often with the ruthlessness and indifference to human life that he attributed to Russian commanders. Along the way he feuded with General Shoigu and General Gerasimov, accusing them of depriving his forces of ammunition to try to destroy Wagner, an action he said “can be equated to treason.”

For Mr. Prigozhin, a breaking point was reached on Friday night, when, he says, Russian forces attacked his men as they slept in their camps (something that Russia denies and that has not been independently confirmed). On Saturday, he led a force he claimed to number 25,000 out of Ukraine and into Russia, where he seized the city of Rostov-on-Don, a military hub, with virtually no resistance.

Always a complex figure, he was prone to vituperative outbursts and threats that were quickly forgotten or contradicted, as happened on Saturday. After first claiming he would march his forces all the way to Moscow, he reversed course later in the day. He had agreed to a proposal by the Belarusian leader, Aleksandr G. Lukashenko, “to stop the movement of armed persons of the Wagner company” and move to Belarus. In return, the Russian government would drop the charges of treason against him and grant amnesty to his soldiers.

It remains unclear if he can return to Russia, but he has capitalized on his feud with the generals to fashion himself as a populist political figure, fighting for humble servicemen and others suffering at the hands of “unqualified scoundrels and intrigants.”

He has contrasted that with what he sees as the decadence of Russian elites and the injustice in society.

“The children of the elite smear themselves with creams, showing it on the internet; ordinary people’s children come in zinc, torn to pieces,” he said, referring to the coffins of dead soldiers, and adding that those killed in action had “tens of thousands” of relatives. “Society always demands justice,” he said, “and if there is no justice, then revolutionary sentiments arise.”

Where Mr. Prigozhin goes from here is hard to pin down, as is the fate of Wagner.

If he remains in control of the company, and that is by no means assured, he will still command considerable military assets, but they will be devalued if they cannot rely on the support of the Russian military.

Apart from his standing force, Mr. Prigozhin claimed this month that 32,000 former convicts who had served with Wagner in Ukraine had returned to their homes in Russia. Many of these veterans have expressed strong loyalty to Mr. Prigozhin and have considered returning to its ranks, according to interviews with survivors and their relatives, providing an additional pool of potential recruits to the rebel cause.

Yet most experts believe Wagner’s real strength is far below what Mr. Prigozhin claims, and that he is hoping more Russian soldiers and security agents disgusted by the corruption and mistreatment they see will respond to his populist critique of the leadership and join his ranks.

The U.S. government estimated in December that Wagner had 10,000 professional soldiers. That number most likely fell in recent months as Wagner was forced to throw its most experienced units into battle to finalize the capture of Bakhmut, according to Ukrainian and Western intelligence officials.

Mr. Prigozhin himself said this year that after the capture of Bakhmut, his force would “downsize” as it prepared for new missions.

Notably, Mr. Prigozhin had managed to run a force numbering tens of thousands of fighters largely on cash. Veterans and their relatives had received salaries, as well as death and injury compensations, through an elaborate network of nameless intermediaries spread across the nation.

The mutiny is likely to have erased that logistical support. And most experts believe that no personal wealth can maintain a large military force capable of challenging a regular army for long, especially without access to the state-controlled financial system.

Earlier on Saturday, videos circulating on social media showed purported Wagner convoys moving through Russia toward Moscow with mounted tanks, air defenses and self-propelled rocket launchers. Most of the rebels’ convoys, however, appeared to be made up of unprotected trucks carrying soldiers.

Mark Galeotti, a Russia military expert, said the limited amount of heavy weaponry would make it difficult for Wagner to operate independently of the Russian military.

“Without artillery you can’t really fight straight-up warfare,” he said.

Before the crisis on Saturday, many analysts had said that Mr. Prigozhin was looking to transition to the political sphere in Russia, though he had been careful not to pose any threat to Mr. Putin.

“He sees his future at risk, and he is scrambling to present a place for himself after Bakhmut within the larger war,” said Jack Margolin, a Washington-based expert on Russia’s private military companies.

Neil MacFarquhar contributed reporting.