Theirs was a relationship borne out of the murky world where Russia's state security services mingled with the criminal underworld.
While Yevgeny Prigozhin's Wagner military company grew into one of the most influential structures in Russia, Vladimir Putin became increasingly dependent on its battlefield successes in Ukraine.
But it was in the seedy scene of early 1990s St Petersburg that their paths first met, during the politically fraught years after the collapse of the Soviet Union.
Both men originate from Russia's second city and cultural capital.
Home to the Hermitage art museum and Imperial Winter Palace, it is also considered the crime capital of Russia and a base for powerful gangs.
The exact circumstances of their first encounter are unknown, but Prigozhin was fresh out of jail and Mr Putin had recently returned from a mission in East Germany as an officer with the Soviet security service, the KGB, and was looking for a way into politics.
Convicted for the first time at 17, Prigozhin was no stranger to crime. After a suspended sentence for theft in the late 1970s, he was given a lengthy jail term for robbery in 1981.
He and two others had grabbed a woman by the neck in the street and tried to strangle her, before running off with her winter boots and earrings.
When he left prison in 1990, Russia was a very different place. Instead of the old Soviet chief, Leonid Brezhnev, reformist leader Mikhail Gorbachev was in power, the Berlin Wall had fallen and perestroika (restructuring) was well under way. see more
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