Russian intelligence would have seen Paul Manafort as the perfect mark

For 30 years, my job as a CIA officer was to try to figure out how Russian operatives were trying to attack the United States. I oversaw intelligence operations in the former Soviet Union and the former Warsaw Pact and worked on counterintelligence and cybersecurity at CIA headquarters. So when I read the recent reports that President Donald Trump's former campaign manager, Paul Manafort, had offered to brief Russian oligarch Oleg Deripaska on the presidential election last year, I was alarmed.

Because to Russian intelligence in 2016, Manafort would have looked like the ideal spy. Someone like Deripaska is exactly how they would have gotten to him.

Deripaska, an aluminum magnate worth about $6.5 billion, is a member of Russian President Vladimir Putin's oligarchy. Putin demands fealty and pretty much whatever else he wants from people like Deripaska, who understand that if they don't live up to their end of the bargain, they could end up like another famous former oligarch, Mikhail Khodorkovsky, who displeased Putin and was sent to a tuberculosis-ridden prison for more than a dozen years.

Although Deripaska has repeatedly denied any connection to Russian intelligence, these oligarchs understand that in addition to making money for themselves and Putin, they occasionally will be asked to be the Kremlin's eyes and ears, and facilitators, if need be. Russia's security services work closely with them; unlike in Western democracies, there's no concept of a conflict of interest. Everyone has the same interests at heart: Putin's.

Manafort would have understood all of this clearly, of course. Before getting himself onto the Trump team, Manafort made a living as an influence broker, a sort of foreign lobbyist whose connections in Washington and elsewhere made him attractive to Deripaska and former Ukrainian president Viktor Yanukovych. If you choose to wade in that swamp, and you are trying to make money doing it, you cannot help becoming highly attuned to the power relationships in that part of the world.

From my experience with Russia, I believe it is highly likely that Ukraine's intelligence services would have at least run Manafort's name by their Russian counterparts, to ensure that an American working at the senior levels of the Ukrainian government was not also working for the CIA. Given Manafort's experience, I doubt this would have surprised or alarmed him. Deripaska's relationship with Putin was no secret when Manafort's firm began doing business with the billionaire in 2005. (Both sides say those business dealings concluded years ago.) Not long after that, WikiLeaks published a U.S. government description of Deripaska as "among the 2-3 oligarchs Putin turns to on a regular basis."

Manafort's representative says his offer to provide "a private briefing" on the campaign to Deripaska was part of an attempt to collect on debts. The meeting does not appear to have happened - Manafort spokesman Jason Maloni has denied it, and a spokeswoman for Deripaska has said The Washington Post's inquiries about whether Manafort briefed Deripaska "veer into manufactured questions so grossly false and insinuating that I am concerned even responding to these fake connotations provides them the patina of reality."

But Russian oligarchs, and their friends in the Russian government, keep track of who's who and what jobs they have or might end up with. The prospect of using Manafort's already existing - and already complicated - financial ties to one of Putin's closest allies would have been irresistible to Russian intelligence services.

In the world of Russian human intelligence collection, the ideal spy looks something like this: an individual with a significant financial vulnerability or motivation (such as debt or a threat of meaningful financial loss); someone with access to inside information of interest to the Russian government; a person who understands the need for discretion and, if necessary, secrecy. It is a plus to the Russian security services if the person in question also has ideological motivations (being pro-Russian, or at least not anti-Russia) and is already a known quantity.

Any Russian intelligence officer worth his salt would have identified Manafort - whom Deripaska had sued in 2014 in the Cayman Islands, alleging that he took almost $19 million without accounting for the money - as meeting all those qualifications. Russian intelligence would have been remiss had they not at least identified Manafort as an excellent target worth pursuit. If Manafort's willingness to brief Deripaska was actually passed along to the billionaire (the evidence is inconclusive), then half the work of the Russian services was already done: Someone who fits the profile of the ideal agent had signaled his eagerness to get back in touch with a close ally of Putin's.

From a counterintelligence perspective, a scenario where Manafort became a target of Russian operatives does not take a lot of imagination to come up with. It is an example of a Russian "seeding" operation, where the special services attempt to recruit an asset before that person ascends to a position of true power. This is one of the many ways Russian intelligence attempts to penetrate the senior-most levels of the U.S. government.

The fact that the briefing doesn't seem to have taken place doesn't necessarily mean that the Russians dropped the whole matter. The normal response from Russian intelligence in such circumstances would be to increase the level of discretion and secrecy for such a promising case. Ensuring any communication with Manafort would not eventually come to light would have been a priority. The Russians would have attempted to keep any additional contact with such a promising prospect out of the view of the public, out of unprotected email, off telephones and away from computers.

Without any doubt, the team of special counsel Robert S. Mueller III and the FBI are attempting to determine whether there were additional communications between the Russians and Manafort. Mueller's office raided Manafort's condo last month, and the New York Times has reported that prosecutors are threatening to indict him. As a former intelligence professional, I don't know whether Manafort broke any laws. That will be for his lawyers and the government's lawyers to argue over. But there's no question that he would have looked like a prime target to my former adversaries in Moscow.

Hall retired from the CIA in 2015 after 30 years of running and managing Russian operations.