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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.
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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.
Prigozhin started out as a St Petersburg hot-dog salesman, but by the mid-1990s he had opened a restaurant. The Old Custom House is most likely the place the two men first met.
The menu of foie gras and oysters attracted local crime bosses as well as the city's powerful mayor, Anatoly Sobchak. Vladimir Putin, then aged 40, went there too as Sobchak's deputy.
Prigozhin's single restaurant became a chain and his clientele included politicians from far beyond St Petersburg.
By the turn of the century, when Mr Putin became president, the two men had become close associates and Prigozhin's nickname, Putin's chef, dates back to this time.
A photo shows Prigozhin serving dinner to him and President George W Bush.
For a man such as Russia's new leader, it was imperative to have a personal chef to ensure his food was safe to consume.
Ever the suspicious KGB mind, he had also served as the head of its successor, the FSB.
It was also convenient to have a man whose innermost secrets he would have known and whom he could influence.
With Vladimir Putin in the Kremlin, Russia's security services slowly began to take back control. Prigozhin took on a variety of Kremlin tasks, particularly those beyond the security services' reach.
Their association was now at arm's length, so the man in the Kremlin could plausibly deny involvement.
Prigozhin set up a media empire focused on spreading disinformation within Russia and abroad.
The stories it invented were often so fantastical that no state propaganda apparatus would dare to spread them.
As social media began to gain influence, he set up a "troll factory" whose main effect was to leave Russians with the feeling there was no such thing as truth and no point looking for it.
It took another decade before he admitted to being the brains behind the "Internet Research Agency".
