The cash, delivered in a suitcase to a Berlin hotel room in September, was intended as the first installment of a $1 million payout, according to American officials, the Russian and communications reviewed by The New York Times. The theft of the secret hacking tools had been devastating to the N.S.A., and the agency was struggling to get a full inventory of what was missing.
Several American intelligence officials said they made clear that they did not want the Trump material from the Russian — who was suspected of having murky ties to Russian intelligence and to Eastern European cybercriminals. He claimed the information would link the president and his associates to Russia. But instead of providing the hacking tools, the Russian produced unverified and possibly fabricated information involving Mr. Trump and others, including bank records, emails and purported Russian intelligence data.
The United States intelligence officials said they cut off the deal because they were wary of being entangled in a Russian operation to create discord inside the American government. They were also fearful of political fallout in Washington if they were seen to be buying scurrilous information on the president.
The Central Intelligence Agency declined to comment on the negotiations with the Russian seller. The N.S.A., which produced the bulk of the hacking tools that the Americans sought to recover, said only that “all N.S.A. employees have a lifetime obligation to protect classified information.”
The negotiations in Europe last year were described by American and European intelligence officials, who spoke on the condition of anonymity to discuss a clandestine operation, and the Russian. The United States officials worked through an intermediary — an American businessman based in Germany — to preserve deniability. There were meetings in provincial German towns where John le Carré set his early spy novels, and data handoffs in five-star Berlin hotels. American intelligence agencies spent months tracking the Russian’s flights to Berlin, his rendezvous with a mistress in Vienna and his trips home to St. Petersburg, the officials said.
The N.S.A. even used its official Twitter account nearly a dozen times to send coded messages to the Russian.
The episode ended earlier this year with American spies chasing the Russian out of Western Europe, warning him not to return if he valued his freedom, the American businessman said. The alleged Trump material was left with the American, who has secured it in Europe.
The Russian claimed to have access to a staggering collection of secrets that included everything from the computer code for the cyberweapons stolen from the N.S.A. and C.I.A. to what he said was a video of Mr. Trump consorting with prostitutes in a Moscow hotel room in 2013, according to American and European officials and the Russian, who agreed to be interviewed in Germany on the condition of anonymity. There remains no evidence that such a video exists.
The Russian was known to American and European officials for his ties to Russian intelligence and cyber criminals — two groups suspected in the theft of the N.S.A. and C.I.A. hacking tools.
But his apparent eagerness to sell the Trump “kompromat” — a Russian term for information used to gain leverage over someone — to American spies raised suspicions among officials that he was part of an operation to feed the information into United States intelligence agencies and pit them against Mr. Trump. Early in the negotiations, for instance, he dropped his asking price from about $10 million to just over $1 million. Then, a few months later, he showed the American businessman a 15-second clip of a video showing a man in a room talking to two women.
No audio could be heard on the video, and there was no way to verify if the man was Mr. Trump, as the Russian claimed. But the choice of venue for showing the clip heightened American suspicions of a Russian operation: The viewing took place at the Russian embassy in Berlin, the businessman said.
At the same time, there were questions about the Russian’s reliability. He had a history of money laundering and a laughably thin legitimate cover business — a nearly bankrupt company that sold portable grills for streetside sausage salesmen, according to British incorporation papers.
“The distinction between an organized criminal and a Russian intelligence officer and a Russian who knows some Russian intel guys — it all blurs together,” said Steven L. Hall, the former chief of Russia operations at the C.I.A. “This is the difficulty of trying to understand how Russia and Russians operate from the Western viewpoint.”
American intelligence officials were also wary of the purported kompromat the Russian wanted to sell. They saw the information, especially the video, as the stuff of tabloid gossip pages, not intelligence collection, American officials said.
But the Americans desperately wanted the hacking tools. The cyberweapons had been built to break into computer networks of Russia, China and other rival powers. Instead, they ended up in the hands of a mysterious group calling itself the Shadow Brokers, which has since provided hackers with tools that infected millions of computers around the world, crippling hospitals, factories and businesses.
No officials wanted to pass on information they thought might help determine what had happened.
“That’s one of the bedeviling things about counterintelligence and the wilderness that it is — nobody wants to be caught in a position of saying we wrote that off and then five years later saying, ‘Holy cow, it was actually a real guy,’” Mr. Hall said.
American intelligence agencies believe that Russia’s spy services see the deep political divisions in the United States as a fresh opportunity to inflame partisan tensions. Russian hackers are probing American voting databases ahead of the midterm election this year, they said, and using bot armies to promote partisan causes on social media. The Russians are also particularly eager to cast doubt on the federal and congressional investigations into the Russian meddling, American intelligence officials said.
Part of that effort, the officials said, appears to be trying to spread information that hews closely to unsubstantiated reports about Mr. Trump’s dealings in Russia, including the purported video, whose existence Mr. Trump has repeatedly dismissed.
Rumors that Russian intelligence possesses the video surfaced more than a year ago in an explosive and unverified dossier compiled by a former British spy, and paid for by Democrats. Since then, at least four Russians with espionage and underworld connections have appeared in Central and Eastern Europe, offering to sell kompromat that would corroborate the dossier to American political operatives, private investigators and spies, American and European intelligence officials said.
American officials suspect that at least some of the sellers are working for Russia’s spy services.
The Times obtained four of the documents that the Russian in Germany tried to pass to American intelligence (The Times did not pay for the material). All are purported to be Russian intelligence reports, and each focuses on associates of Mr. Trump. Carter Page, the former campaign adviser who has been the focus of F.B.I. investigators, features in one; Robert and Rebekah Mercer, the billionaire Republican donors, in another.
Yet all four appear to be drawn almost entirely from news reports, not secret intelligence. They all also contain stylistic and grammatical usages not typically seen in Russian intelligence reports, said Yuri Shvets, a former K.G.B. officer who spent years as a spy in Washington before defecting to the United States just before the end of the Cold War.
American spies are not the only ones who have dealt with Russians claiming to have secrets to sell. Cody Shearer, an American political operative with ties to the Democratic Party, has been crisscrossing Eastern Europe for more than six months to secure the purported kompromat from a different Russian, said people familiar with the efforts, speaking on the condition of anonymity to avoid damaging their relationship with him.
Reached by phone late last year, Mr. Shearer would say only that his work was “a big deal — you know what it is, and you shouldn’t be asking about it.” He then hung up.
Mr. Shearer’s efforts grew out of work he first began during the 2016 campaign, when he compiled a pair of reports that, like the dossier, also included talk of a video and Russian payoffs to Trump associates. It is not clear what, if anything, Mr. Shearer has been able to purchase.
Before the Americans were negotiating with the Russian, they were dealing with a hacker in Vienna known only to American intelligence officials as Carlo. In early 2017, he offered to provide them with a full set of hacking tools that were in the hands of the Shadow Brokers and the names of other people in his network, American officials said. All he wanted in exchange was immunity from prosecution in the United States.
But the immunity deal fell apart, so intelligence officials decided to do what spies do best: They offered to buy the data. That is when the Russian in Germany emerged, telling the Americans he would handle the sale.
Like Carlo, he had previously dealt with American intelligence operatives, American and European officials said. He served as a fixer, of sorts, brokering deals for Russia’s Federal Security Service, or F.S.B., which is the successor to the old Soviet K.G.B. American intelligence officials said that he had a direct link to Nikolai Patrushev, a former F.S.B. director, and that they knew of previous work he had done helping move illicit shipments of semiprecious metals for a Russian oligarch.
By last April it appeared that a deal was imminent. Several C.I.A. officers even traveled from the agency’s headquarters to help the agency’s Berlin station handle the operation.
At a small bar in the old heart of West Berlin, the Russian handed the American intermediary a thumb drive with a small cache of data that was intended to provide a sample of what was to come, American officials said.
Within days, though, the deal turned sour. American intelligence agencies determined that the data was genuinely from the Shadow Brokers, but was material the group had already made public. As a result, the C.I.A. said it would not pay for it, American officials said
The Russian was furious. But negotiations limped on until September, when the two sides agreed to try again.
Late that month, the American businessman delivered the $100,000 payment. Some officials said it was United States government money but routed through an indirect channel.
A few weeks later, the Russian began handing over data. But in multiple deliveries in October and December, almost all of what he delivered was related to 2016 election and alleged ties between Mr. Trump’s associates and Russia, not the N.S.A. or C.I.A. hacking tools.
In December, the Russian said he told the American intermediary that he was providing the Trump material and holding out on the hacking tools at the orders of senior Russian intelligence officials.
Early this year, the Americans gave him one last chance. The Russian once again showed up with nothing more than excuses.
So the Americans offered him a choice: Start working for them and provide the names of everyone in his network — or go back to Russia and do not return.
The Russian did not give it much thought. He took a sip of the cranberry juice he was nursing, picked up his bag and said, “Thank you.” Then he walked out the door.
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