AFTER DRONES mysteriously attacked Moscow late last month—were they from Ukraine, or from pro-Ukraine guerilla units inside Russia? were they a Russian false flag operation?—the reaction from the Russian side that got the most attention was not Vladimir Putin’s nor that of any of his TV propagandists. Rather, it was the colorful, angry, obscenity-laced tirade from Wagner Private Military Company head Yevgeny Prigozhin. In an audio message posted to his Telegram channel, Prigozhin did not lash out at the Ukrainians but at the “stinking animals” from the ministry of defense: “Get your assholes out of the offices where they put you to defend this country! . . . Why the fuck are you letting these drones fly into Moscow?” In an anti-elite jab that has also become his trademark, Prigozhin added that he didn’t care if the mansions in the super-wealthy Rublyovka suburb targeted by the drones went up in flames. It’s hard to say how many Russians heard his rant—Prigozhin is now blacklisted from the state-run television channels where most people in Russia still get their news—but quite a few probably shared the sentiment.

This was just one episode in the extraordinary Prigozhin drama of the last few months, which has included the protracted and horrifyingly bloody battle for the mid-sized Ukrainian town of Bakhmut—a “meat grinder,” in Prigozhin’s own words—and increasingly public and bitter brawls with the defense ministry and the top military brass. In May, this conflict escalated into what many took to be a swipe at his patron Putin: a viral video clip in which Prigozhin slammed an unnamed “happy grandpa” who blissfully ignores war losses and who may be “a total asshole.” Then, after announcing his fighters’ victory in Bakhmut, he gave a shocking interview in which he not only blasted the military leadership for mismanaging the war but seemed to question the war itself and warned of impending disasters. Suddenly, the man once dubbed “Putin’s chef” or “Putin’s cook” for catering Kremlin banquets was being touted as a voice of the opposition—or even as Putin’s prospective rival.

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Make no mistake: Prigozhin is an odious figure. The Wagner group, which the United States and the European Union may soon designate as a terrorist group, is known for atrocities not only in Ukraine but in Africa and the Middle East—and not only toward enemy combatants but toward civilians, nosy journalists, and its own errant members. In a widely reported gruesome incident last November, an apparent snuff video showed the sledgehammer bludgeoning of an ex-Wagner fighter who had talked about switching sides while in Ukrainian captivity and had ended up back in Wagner hands; Prigozhin responded with trollish comments alternating between gloating and faux denial.

And speaking of trolling, there is also Prigozhin’s role as the founder of Russia’s infamous “troll factory” whose mission is pro-Kremlin information warfare—a role that got him and three of his companies indicted by a Washington, D.C. grand jury in 2018 as part of Robert Mueller’s special counsel investigation. The versatile “chef” is, as the Bellingcat investigative group put it in 2020, “the Renaissance man of deniable Russian black ops.”

And yet today, Prigozhin’s recent statements are being approvingly quoted by Russian dissidents and Ukrainian commentators alike—even if such near-plaudits are often accompanied by near-apologies and reminders that the man is a thug and a war criminal. It’s not unusual to hear the moniker “happy grandpa” from Putin critics. Ukrainian journalist Roman Tsymbalyuk’s YouTube commentary on the Moscow drone strikes discussed Prigozhin’s reaction with unabashed glee; his colleague Dmitry Gordon has even said that a President Prigozhin would be much better for Ukraine than Putin.

What’s behind the Kremlin crony’s self-reinvention as a quasi-dissident and a possible contender for Putin’s job? Here, opinions differ wildly. Some think that Prigozhin is a talented psychopath; others that he’s crazy like a fox. Some say he is nothing more than Putin’s loyal attack dog, a useful weapon for bullying the generals and defense officials and keeping them under control. Others believe the attack dog is off the leash and snapping at his former master—either because Prigozhin is in disfavor and fighting for his life, or because the growing instability in Russia is enabling him to claim power in his own right, or because he has powerful backers who are using him in a game of their own.

The story of Prigozhin’s rise as a prominent—and, it seems, increasingly independent—player in Russia’s war in Ukraine, and by extension in wartime domestic politics, is a fascinating one. But to understand it properly requires a look back at his extraordinary career long before 2022.

YEVGENY VIKTOROVICH PRIGOZHIN WAS BORN in 1961 in St. Petersburg, or as it was still called then, Leningrad. His mother was a doctor, his father—who died when he was 9—an engineer; in the Brezhnev-era USSR, this certainly wasn’t an affluent background by Western standards, but a relatively comfortable and respectable one. Even so, young Yevgeny, whose skiing-trainer stepfather tried to steer him toward professional sports, began his adult life as a criminal: a two-year suspended sentence for theft in 1979 was followed by another arrest, this time for a string of burglaries and muggings committed with a gang of mostly juvenile accomplices—including a particularly violent robbery in which Prigozhin choked the victim until she passed out. This time, the 19-year-old got twelve years in a penal colony, with extra time for enticing minors into crime. At least according to his own narrative, Prigozhin made an earnest effort to reform halfway through his sentence and spent a lot of time reading, working out, and learning woodwork. Released in 1990 with time off for good behavior, he studied briefly in a college of pharmacy but was more interested in business, a new career path in a new Russia.

Soon, Prigozhin was managing a chain of food stores and opening hot-dog stands. (His self-serving English-language résumé designed in an attempt to extricate himself from U.S. sanctions credits a 1993 trip to the United States as the inspiration for the hot-dog business, though some versions of his biography claim he launched it in 1990.) By mid-decade, when Prigozhin created a company called Concord Management & Consulting as an umbrella holding for his ventures, he owned some thirty restaurants, bars, and fast food outlets well as a frozen-food factory. According to the aforementioned résumé, the holding’s total monthly profits exceeded a million U.S. dollars, though it’s unclear whether the text confuses profits with revenues.

Given what a jungle Russian business was in the 1990s, one obvious question is whether—or perhaps, more accurately, to what extent—Prigozhin was connected to organized crime and/or corrupt government officials. There is no known evidence of the former, perhaps because digging into such matters can have undesirable effects on one’s life expectancy. As for the latter, some Russian investigative reporters believe that Prigozhin’s connection to Putin goes back not to Putin’s visits to Prigozhin’s elite restaurants in the early 2000s, as Prigozhin has claimed, but to an earlier and murkier episode. Among his other ventures, Prigozhin tried to get into the casino business in St. Petersburg in the mid-1990s, when Putin was the city’s deputy mayor—and chairman of the supervisory board for gambling.

Be that as it may, Putin’s ascent to the presidency turned out to be very good for Prigozhin’s business. A 2001 Putin dinner with then-French Prime Minister Jacques Chirac aboard Prigozhin’s floating restaurant New World on the Neva river, with the restaurateur waiting on the illustrious guests in person, was the start of his role as host to dozens of foreign dignitaries (among them George W. Bush in 2002 and 2006).

Prigozhin’s catering business also took charge of Kremlin banquets—and began to get lucrative contracts for school breakfasts and lunches. It continued to get those contracts, and expand to more cities, despite numerous complaints of contaminated or spoiled food and outbreaks of food poisoning. Novaya Gazeta, the now-exiled independent Russian newspaper, notes that its reporters discovered Prigozhin’s school-meal contracts “by tracking cases of poisoning and complaints about the food”—including some 1,000 lawsuits by 2019. Even so, the Putin pal also became the principal supplier of meals to the military. Go figure.

Besides cronyism, Prigozhin’s success in business was reportedly aided by dirty tricks straight out of Better Call Saul. A 2018 Novaya Gazeta investigation, based on a detailed account by former Prigozhin associate Andrei Mikhailov with corroborating evidence from other sources, uncovered episodes in which he hired people to create a cockroach infestation in a hospital that rejected a contract for his meals and to simulate food poisoning after a banquet catered by a rival company.

But in the 2010s, the canny tycoon also branched out into new and more sinister specialties—including information warfare and mercenary warfare.

IT’S HARD TO SAY EXACTLY WHEN “Putin’s chef” became Putin’s troll-in-chief. The founding of the Internet Research Agency (later simply Internet Research), the company behind his infamous “troll factory” in the St. Petersburg suburb of Olgino with affiliates in Moscow and other locations, is generally dated 2013. However, a 2018 report by Oxford University’s Computational Propaganda Project, which partly served as the basis for the Mueller indictment, asserts that Prigozhin’s trolls were already active on Twitter in 2009—but with a focus on Russian audiences and on attacking and discrediting the anti-Putin opposition. (Organized efforts to harass and silence Kremlin critics and destroy democratic discourse on the Russian internet go back much further, with the first report on these operations appearing in 2003; but no one knows when Prigozhin got involved.) Around 2013, the troll farm’s operations shifted to foreign targets, mainly the United States and in Ukraine.

Mikhailov has said that the troll factory was Prigozhin’s own idea, not a Kremlin project. However, there is no question that its operations closely mirrored Putin’s agenda or that Prigozhin eventually became the Kremlin’s point man for information wars.

The trolls farms were only part of Prigozhin’s media empire—or perhaps “disinformation empire” is a better term. (At one point, he tried to set up an outfit whose sole purpose was to discredit reputable publications by feeding them “fake news” and then debunking the stories; apparently, it didn’t work out.) This empire includes not only fake news generators but pro-Kremlin news sites which have the appearance of bona fide media outlets and employ professional journalists, but can be easily used for disinformation and smears. One such site, the “Federal News Agency” or FAN, was involved in a bizarre 2015 incident chronicled in the New York Times Magazine by Adrian Chen, who traveled to Moscow to report on the troll factory only to become its target. Chen was tricked into meeting with a notorious neo-Nazi thug when a female Internet Research staffer agreed to talk to him in a café if she could bring her “brother.” Then, FAN—whose editor-in-chief had also met with Chen and heatedly defended his site’s legitimacy as a news organization—ran a lurid story, accompanied by photos, about the American journalist trying to recruit neo-Nazis to foment trouble in Moscow.

The workings of Prigozhin’s troll farms, which exploited and fanned divisions in Western societies and (to quote Steve Bannon) “flooded the zone with shit,” have been extensively documented in legal proceedings, research papers, and media reports. But one remarkable, little-known recent incident in 2021 is worth mentioning. Prigozhin, whose media network includes a movie studio that makes occasional feature films advancing Russian propaganda narratives, trolled the Americans with a movie that literally turned his election interference into a fictionalized slapstick comedy. The movie, The 16th, reinvents the Internet Research Agency as a merry band of kid computer wizеs who set up a troll nest in an abandoned kindergarten in Olgino. All the kids want is to play on the Internet and experiment with manipulating public opinion for fun; but cloddish U.S. intelligence agents mistake them for Russian operatives and decide to hunt them down. The enterprising youngsters, one of whom is just six years old, then decide that the only way to save themselves is to “blow up the American Internet” and elect Donald Trump.

Then, in a very meta twist, Prigozhin’s Twitter trolls planted an entirely fake story about the nonexistent New York premiere of The 16th being raided and disrupted by the New York Police Department. His media conglomerate also commissioned promotional cameos for The 16th from Donald Trump Jr. and Rudy Giuliani—though it’s fair to say that neither had any idea what the cameos were for.

EVEN ASIDE FROM his mercenary army, Prigozhin’s “black ops” included not only online trolling but real-life harassment and violence. The Novaya Gazeta investigation links him to several attacks on dissident Russian journalists and bloggers, from beatings to at least one murder; Bellingcat has documented his goons’ surveillance and intimidation of journalists. But the Wagner Group traffics in violence on an entirely different level.

Like the troll farm, the private military company may have been Prigozhin’s own idea—though there is no doubt that it was created in close coordination with the Russian military, military intelligence, and top-level Putin staffers. A former high-ranking official in the defense ministry recently told the Guardian that Prigozhin presented the project to the ministry as an order from “Papa,” i.e. Putin; but the official was also convinced that it was Prigozhin himself who pitched the idea to Putin. The name “Wagner” came from the call sign of the group’s cofounder and Prigozhin’s business partner, Dmitry Utkin, a retired military intelligence officer said to have an obsessive interest in all things Third Reich.

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In 2022, when Prigozhin “came out” as Wagner’s chief after years of denials and even libel suits, he claimed that he founded the company in righteous outrage at the persecution of Russians in the Donbas. Wagner did, in fact, have a role in Russia’s illicit war in Eastern Ukraine—disguised as aid to a separatist insurgency—starting in 2014. But the mercenary group’s operations soon expanded to the Middle East—especially Syria, where Wagner fighters helped prop up the regime of Kremlin ally Bashar al-Assad—and to at least six African countries.

While Prigozhin likes to brag that the Wagner Group is currently the world’s best fighting force, its history suggests otherwise. In February 2018, anywhere from dozens to over a hundred “Wagnerites” were wiped out in Syria when they clashed with U.S. troops—which made the Russian leadership so nervous that they reportedly considered shutting down the group. (Prigozhin had to give assurances that no such unauthorized engagements would happen again.) The following year, Wagner forces hired to put down an Islamist insurgency in Mozambique withdrew after suffering heavy casualties; the militants were eventually defeated by regular troops brought in from Rwanda.

What’s not in dispute is Wagner’s linkage to war crimes and atrocities, including massacres of civilians, torture and rape. Many reports cannot be definitively verified due to the inherent difficulty of collecting evidence in war zones or under Wagner-friendly regimes. (Besides, investigating Wagner operations is a hazardous job: In 2018, three Russian journalists working on such an investigation were murdered in the Central African Republic. The unsolved killings were officially blamed on a robbery, even though the reporters’ equipment was not touched.) But the verified cases are bad enough. A United Nations report released last month confirms that over a four-day period in March 2022 in Mali, Wagner contractors were involved—in concert with the Malian Armed Forces—in the massacre of as many as 500 people, nearly all civilians, in the village of Moura. And then there’s the grisly, ISIS-like 2017 video in which several Wagner fighters in Syria are seen torturing and mutilating a prisoner before beheading him and burning his body.

In his recent explosive interview, Prigozhin asserted that the purpose of his work in Africa was to convince the world of Russia’s might and long reach—and, in one of his now-typical swipes at the regular Russian armed forces, added that it was a deliberate deception: “I was hoaxing them, blowing smoke in these foreigners’ eyes, making them believe that the Russian army was just as good. . . . Who knew we were gonna shit ourselves so close to home?”

But whether or not a patriotic con job was really one of Prigozhin’s motives, Wagner operations in the Middle East and Africa have a much more pecuniary side: Wagner’s contracts with local governments typically involve permits for extracting and developing oil, gold, diamonds, and other natural resources. The Financial Times reports that just from 2018 to 2022, Prigozhin’s take from those permits totaled $250 million.

PRIGOZHIN’S NEW CAREER as a Kremlin-sponsored warlord began in Ukraine; even before the start of Putin’s covert war in the Donbas in the spring of 2014, Prigozhin’s hirelings reportedly helped incite the pro-Russia unrest in the region that provided an excuse for that war. Now, the full-scale Russian war in Ukraine has become the stage for the latest and most bizarre chapter in Prigozhin’s career—a chapter that may be the last, or may be the start of an even more surreal career as a politician.