One day in April last year, as war raged around Tripoli, two Russian operatives set out from the Libyan capital to meet the man they hoped to install as leader.
Saif al-Islam Gadhafi, the son and heir apparent of deposed dictator Moammar Gadhafi, had been holed up in an area around the Zintan plateau ever since his father was killed in a 2011 rebellion. A fugitive from the International Criminal Court, he was planning to claim what he saw as his rightful place.
Along came Maxim Shugaley, a veteran St. Petersburg election consultant, and his translator and colleague, Samir Seifan, with an offer to help make that happen. Russian polling showed that after years of civil war, nostalgia for the old regime was strong and the younger Gadhafi was among Libya’s most popular politicians.
This account of their meetings is based on notes taken by the Russians and seen by Bloomberg News after they were arrested in Tripoli. Some records of Russian involvement in Libya were published by The Daily Beast in collaboration with the Dossier Center and the Russian news site Proekt. Those seen by Bloomberg contain information that has not previously been revealed about interactions with Gadhafi, now 47.
The documents shed light on Russia’s apparent efforts to build influence at a time of U.S. disengagement.
The April get-together was the Russians’ last of at least three meetings with Gadhafi that year, according to Libyan officials, and he was brimming with plans.
Gadhafi wanted them to pass a message to Moscow that he had compromising material on Western politicians showing they had received campaign contributions from his family. He proposed that together they “think about how this information could be used,” one of the Russians noted in a memo at the time.
But the consultants weren’t there to discuss kompromat — material about a person that can be used for blackmail, extortion or public embarrassment. They had bigger things in mind.
Libya, which has Africa’s largest oil reserves, has been all but ungovernable since a violent NATO-backed rebellion led to the killing of Moammar Gadhafi, who had ruled for more than 40 years, enjoying warm relations with Moscow even as the West wavered between engaging and isolating the erratic dictator.
Almost eight years on from his ouster, the Russian consultants had been dispatched to plan the return of the Gadhafi regime.
The Kremlin had long thought about how it could maneuver its way back into Libya. Moammar Gadhafi’s downfall sidelined Moscow, leaving Italy, France and regional powers seeking the spoils while Libyan factions fought one civil war after another.
Moscow’s official line is that it works with all parties in Libya. Initially, Russia’s government kept contacts with both sides of the civil war while promoting Gadhafi as a future president.
By last September, however, Russia had shifted to flat-out support for Khalifa Haftar, a rebel strongman who controls the east, despite misgivings about his past connections to the U.S. and legendary unpredictability.
Russia’s Defense Ministry had maintained connections with Haftar for years. But different actors close to power in Russia have their own ideas of whom to back and how to support them.
Yevgeny Prigozhin, an insider also known as “Putin’s chef,” reckoned Gadhafi could be a good bet, according to three people familiar with his thinking, despite war-crimes charges against Gadhafi and the fact that he was in hiding.
A former restaurateur who found favor with President Vladimir Putin, Prigozhin branched out from catering into the mercenary business; he is best known as boss of the Wagner private security company, which has sent fighters and political consultants to Ukraine, Syria and Libya, among other hot spots.
In 2018, he was indicted by a grand jury in the U.S. for his companies’ alleged role in trying to sway the 2016 presidential election. Prosecutors have now dropped the charges.
As Bloomberg reported last year, digital documents collected from Shugaley and Seifan after their arrest linked them to a so-called troll farm, or digital propaganda and disinformation company, connected to Prigozhin. They also showed the company had been in touch with Gadhafi.
“Saif al-Islam is Prigozhin’s project,” said Kirill Semenov, a Libya expert at the Kremlin-funded Russian International Affairs Council. But others in the Kremlin had doubts about him.
By the start of 2019, Libya had been divided between a United Nations-recognized but weak government led by Prime Minister Fayez al-Sarraj in the west, including Tripoli, while field marshal Haftar held sway in the east and south. In April, Haftar decided to seize the capital. Haftar’s offensive on Tripoli faltered despite backing from the UAE, dragging the warring sides into a stalemate in the city’s suburbs. Tripoli turned to Turkey for military help, altering the balance of power in the conflict.
Haftar has denied that Russian mercenaries are fighting alongside his forces. Putin has publicly distanced himself from the mercenaries.
Moscow’s strategy of betting on multiple horses in Libya has hit headwinds before. In late 2018, Russia facilitated a phone call between Haftar and Gadhafi to get them on the same page, according to three people. It didn’t go well.
In his meetings with the Russian consultants, Gadhafi made no secret of his contempt for Haftar.
“Eighty percent of those fighting on the side of Haftar are my people,” he told them, according to the Russians’ records of the meetings. “When he takes over Tripoli, the people he considers his own will change sides. I know he wants to kill me, but he won’t be able to make that happen.”
Gadhafi predicted that elections would eventually take place whether or not Haftar won the war—and that he would come out on top. But first, he also sought some Russian assistance.
At one meeting, they discussed training consultants in Tunisia and building up a group of “specialists” who would distribute messages over social media. “He’s very interested in counter-propaganda,” the Russians noted.
They presented him with a slide show titled “Saif Gadhafi. Revival of Libya. Strategy.” It laid out steps for him to either become a candidate or support a leader in exchange for a role in a new government.
At their final meeting in April, Gadhafi promised to provide a list of military commanders loyal to him and to make arrangements to receive personnel from what the Russians described in the memo as “our Sudanese company.”
Shugaley and Seifan headed back to their Tripoli apartment, and were arrested soon after. A third Russian, Alexander Prokofiev, attended one of the meetings with Gadhafi, according to the notes seized by prosecutors, but left the country before the others were arrested.
An aide to Gadhafi confirmed he had met with the Russian consultants. He wanted good relations with Western countries too, but the Russians offered their help first, the aide said.
The two Russians are being held in a prison at Tripoli’s Mitiga airport, which also houses former senior regime officials and Islamist militants. The duo are accused of espionage and seeking to interfere in future elections.
Russia has privately campaigned for their release.