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For example, the ring’s presumed spymaster, Christopher R. Metsos, escaped arrest in the U.S. either because he was overseas or was tipped off to the others’ imminent arrests. Had Mr. Metsos been caught, the administration would have had more leverage on the Russians for a deal and might have obtained additional details on Russian intelligence networks, according to specialists.

“We have to do a damage assessment, and when you do a damage assessment, you want to have access to the individuals involved for an extended period of time so you can get new leads and ask questions,” said Michelle Van Cleave, former national counterintelligence executive, a senior counterspy policymaking post.

“We lost all that. We lost a clear window into Russian espionage, and my question is: What was the rush?”

One of the figures to emerge from the case is Alan Patricof, director of the venture capital firm Graycroft LLC and a donor to Democratic candidates, including Mrs. Clinton when she was a senator from New York.

Mr. Patricof acknowledged in a statement that he was the person outlined in the FBI criminal complaint who met several times with one of the Russian spies and who was targeted by the SVR in their efforts to skew U.S. policies in favor of Moscow.

The Russians spies, according to the FBI complaint, were tasked with developing sources in government, the business community and academia who could provide secrets and other information useful to Moscow.

The criminal complaint stated that in February 2009 a New Jersey-based Russian, who posed as Cynthia Murphy and was later identified as SVR officer Lydia Guryev, met several times with a “prominent New York-based financier” who was active in politics and a “active fundraiser” for a “major political party, name omitted.” He also was described as a “personal friend of [a current Cabinet official, name omitted].”

In response, the SVR wrote back to Guryev in a message intercepted by the FBI that the financier was checked in the Russian intelligence database and found to be “clean,” or free from intelligence connections.

“Of course he is very interesting ‘target,’” the SVR said. “Try to build up little by little relations with him moving beyond just [work] framework,” the intercepted SVR message said. “Maybe he can provide [Murphy] with remarks re: US foreign policy ‘rumors’ [sic] about White House internal ‘kitchen’, invite her to venues (to major political party HQ in NYC, for instance). … In short, consider carefully all options in regard to [financier].”

In a statement issued June 30, Mr. Patricof said he met Guryev, whom he knew as “Cindy Murphy,” after retaining a financial service to handle his personal bookkeeping, bill paying, accounting and tax services.

“During the course of that time, I met with her a limited number of times and spoke with her frequently on the phone on matters relating to my personal finances,” Mr. Patricof said. “We never — not once — discussed any matter other than my finances and certainly she never inquired about, nor did we ever discuss, any matters relating to politics, the government, or world affairs.”

Mr. Patricof said she had been employed by the company some 10 years before he became a client. “I highly doubt that I could have been an intended target by her.”

Mr. Patricof, through a spokeswoman, declined to answer questions about whether the FBI investigated the intelligence targeting or whether other Russians or their agents may have been involved in seeking information from him.

State Department spokesman P.J. Crowley, asked whether Mrs. Clinton was the Cabinet official mentioned in the complaint, said in an e-mail that “there is no reason to believe that the Secretary of State was a special target of this spy ring.”

Ms. Van Cleave and other former counterintelligence and intelligence officials questioned whether the quick spy exchange hampered efforts to fully unravel Russian espionage and influence efforts in the United States, information that is needed for a damage assessment and other information needed for stopping other, unidentified spies.

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