Vladimir Putin with Jose Maria Aznar, then Spain's prime minister, at Moncloa Palace on June 13, 2000. Reuters One of Russia's largest organized-crime syndicates allegedly operated out of Spain for more than a decade with the help of close allies of President Vladimir Putin, then the deputy mayor of St. Petersburg, Bloomberg reports.

Prosecutors in Madrid have filed a 488-page petition to charge 27 people with money laundering and fraud in connection to the St. Petersburg-based Tambov crime syndicate's setting up shop in Spain in 1996.

Vladislav Reznik, now the deputy head of the finance committee in Russia's lower house of parliament and a member of the Putin-aligned United Russia Party, faces charges accusing him of giving allies of the criminal organization's alleged leader, Gennady Petrov, positions in the Russian government in exchange for a share of the organization's assets.

"The criminal organization headed by Petrov managed to achieve a clear penetration of the state structures in [Russia], not only with the lawmaker Reznik but with several ministers," the Spanish prosecutors said.

Reznik denies the accusations, insisting his relationship with Petrov is "purely social."

Petrov is unlikely to face a trial — he fled to Russia when his villa on the Spanish island of Majorca was raided by the police in 2008, and Russia does not extradite its citizens.

Gennady Petrov with police officers during an operation against the Russian mafia on the Spanish island of Majorca in 2008. REUTERS/Dani Cardona (SPAIN) US officials briefed by Spanish prosecutor Jose Grinda in 2010 concluded that Putin ran a "virtual mafia" state that extended to Spain, where criminal networks have been established to do things the Kremlin cannot.

The Russian president's connection to Spain dates back to the 1990s, when he allegedly took no fewer than 37 secret boat rides to meet with several well-known Russian mafia leaders living in southern Spain — all while he was the head of the FSB (the successor to the KGB).

Putin reportedly entered Spain illegally, bypassing Spanish passport control by entering through Gibraltar, according to the book "Putin's Kleptocracy" by Karen Dawisha.

"This Petrov probe could change the narrative of Putin in the West — from being a Stalinist tyrant defending the interests of his country to being a product of gangster Petersburg who united authorities with organized crime," Stanislav Belkovsky, a Kremlin adviser during Putin's first term who consults at Moscow's Institute for National Strategy, told Bloomberg.

Putin during a session of the St. Petersburg International Economic Forum 2015 in St. Petersburg, Russia, on June 19. REUTERS/Grigory Dukor The network of Russian authorities with alleged ties to Petrov is vast: from former prime minister and current chairman of Gazprom Viktor Zubkov and former Defense Minister Anatoly Serdyukov, his son-in-law, to Deputy Prime Minister Dmitry Kozak and longtime communications minister/Kremlin adviser Leonid Reiman.

Russian law-enforcement official Nikolai Aulov — deputy to Viktor Ivanov, who runs the Federal Narcotics Service — was also one of Petrov's "most important" contacts in Moscow, according to the criminal complaint.