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People pay tribute to Yevgeny Prigozhin at a makeshift memorial in Moscow, on Aug. 24.NATALIA KOLESNIKOVA/AFP/Getty Images

When Yevgeny Prigozhin’s private plane fell out of the sky shortly after taking off from Moscow on Wednesday, the biggest surprise was that Mr. Prigozhin had lived this long after humiliating Russian President Vladimir Putin.

Political rivals don’t live long and healthy lives in Mr. Putin’s Russia, as evidenced by the 2015 assassination of former deputy prime minister Boris Nemtsov outside the Kremlin walls. Opposition leader Alexey Navalny, who was seen as the biggest threat to Mr. Putin’s rule until Mr. Prigozhin and his Wagner mercenary group went rogue in June, survived a state-backed attempt on his life three years ago only to be sentenced to spend the next few decades in an isolation cell in a notorious prison outside Moscow.

Those perceived as traitors face similar fates.

Mr. Putin’s regime has never acknowledged any role in the 2006 assassination of former KGB agent Alexander Litvinenko, which was carried out using radioactive polonium, or the 2018 chemical attack on Sergei Skripal, another ex-KGB colleague of Mr. Putin’s who also sought a new life in the West. But there are no other credible suspects.

Mr. Prigozhin – as both a traitor and a threat to Mr. Putin’s power – was in a special category. The mere fact that he was still alive after leading the mutiny by his Wagner mercenaries, who left their positions in Ukraine and turned their guns toward Moscow before accepting a last-minute deal to abandon their rebellion, made the 70-year-old Mr. Putin look weak. That was something the Kremlin boss couldn’t tolerate for long.

With Wagner fighters at the outskirts of Moscow on June 23, Mr. Putin clearly felt he had no choice but to compromise. Mr. Prigozhin was allowed to go into exile in Belarus with his men. Gradually, he was lulled into believing that all was forgiven, to the extent that he apparently felt safe flying in his private jet in airspace controlled by Mr. Putin and his security services.

The explosion that knocked Mr. Prigozhin’s Embraer jet out of the air – killing all 10 passengers and crew on board – came exactly two months to the day he humbled the Russian President. With Mr. Prigozhin seemingly gone, so are the questions about what happens when you challenge Mr. Putin’s hold on power.

Mr. Prigozhin’s top lieutenant, Dmitry Utkin – whose call name “Wagner” gave the mercenary outfit its name – was also listed among those who died in Wednesday’s crash. The same day, General Sergei Surovikin, a former top commander in Ukraine who was seen as having sided with the mutineers, was dismissed from his post as the head of Russia’s aerospace forces.

While rumours will continue to swirl in Russia and beyond about whether Mr. Prigozhin was really on the Embraer – he released a video earlier this week suggesting that he was somewhere in Africa – Mr. Putin on Thursday expressed his condolences to Mr. Prigozhin’s family, and mourners began laying flowers outside the Wagner Group’s office in St. Petersburg. Mr. Putin said Mr. Prigozhin had returned from Africa “only yesterday” to meet with unnamed officials in Moscow.

Mr. Putin spoke of Mr. Prigozhin in the past tense. Both men hail from St. Petersburg, and until the mutiny, Mr. Prigozhin was seen as a close friend and ally who had earned the nickname “Putin’s chef” with his willingness to carry out whatever tasks the Kremlin asked of him.

“I knew Prigozhin for a very long time, since the early 1990s,” Mr. Putin said during a meeting on Thursday with Denis Pushilin, the Kremlin-appointed head of the occupied Donetsk region of Ukraine. Mr. Putin called the 62-year-old Mr. Prigozhin “a person with a complex fate and he made serious mistakes in his life,” while adding that he was “a talented person, a talented businessman.”

The New York Times reported Thursday that unnamed American and Western officials believed an explosion had caused the Embraer to crash. In a video posted to social media on Wednesday, a column of black smoke can be seen swirling above a small plane as it spins toward the ground in the Tver region, north of Moscow. A subsequent video showed the remnants of the plane ablaze, with several bodies visible amid the wreckage.

“Here is the subtle work of Putin’s killers. Shoot down/blow up a passenger plane over Russia,” Mr. Navalny wrote in a social-media post from prison. “A real terrorist attack, killing an absolutely uninvolved pilot, stewardess, etc.” Mr. Navalny’s messages are usually transmitted via meetings with his lawyers.

The apparent deaths of Mr. Prigozhin and Mr. Utkin, and the firing of Gen. Surovikin, are at once signals that Mr. Putin is still in charge as well as signs of his lingering weakness.

If the 18-month invasion of Ukraine had gone anywhere near according to plan, Gen. Surovikin would be strutting about Moscow, his chest adorned with medals celebrating his role in the capture of Kyiv. Mr. Prigozhin and his mercenaries would be back at work in Africa and the Middle East, trading military assistance for political and economic concessions.

Instead, one of Mr. Putin’s oldest allies – someone who served the Kremlin’s bidding until the full-scale invasion of Ukraine went awry – is dead.

Mr. Prigozhin wasn’t an opponent of Mr. Putin’s regime, he was a part of it. The caterer who had served meals to George W. Bush and Jacques Chirac early in Mr. Putin’s rule became so trusted that Mr. Prigozhin was given such sensitive tasks as leading the Kremlin’s efforts to tilt the 2016 U.S. election in Donald Trump’s favour.

Wagner’s thunder run toward Moscow, according to Mr. Prigozhin, wasn’t meant to threaten Mr. Putin’s hold on power, only to demonstrate how badly Defence Minister Sergei Shoigu and his top general Valery Gerasimov had mismanaged the war in Ukraine.

Instead, the brief mutiny appears to have reminded Mr. Putin that he can trust absolutely no one.

Other tyrants in history have found themselves in a similar position. And when violence and fear are the only tools a leader has left to protect their rule, they use them again and again.

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