When a Los Angeles internet entrepreneur decided that his company should lend money to Alexander Smirnov, an Israeli-American businessman fluent in four languages, he did so in part because Smirnov boasted of a highly respectable background.

“He was representing himself as working for the FBI,” Dmitry Fomichev recalled in an interview about the 2012 loan, which Fomichev would later say in a lawsuit Smirnov never repaid. “He said, ‘I’m a very powerful guy.’”

Several years later, Smirnov again disclosed his work with law enforcement to investors who put up $100,000 in cash for a company he was touting called Grand Pacaraima Gold Corp., the investors later alleged in a suit of their own against Smirnov.

It was true: Smirnov was a source for the FBI. But as a confidential informant, he wasn’t supposed to be broadcasting his government work, and experts and former agents said his apparent decision to do so raises significant questions about his credibility.

Smirnov’s work with the FBI burst into public view last month when federal prosecutors accused him of lying to authorities about a multimillion-dollar bribery scheme involving President Biden and his family.

The 37-page indictment blew a hole in the Republican-led effort to impeach Biden, which drew on the bribery allegation. At the same time, the indictment raised puzzling questions: How did Smirnov go from a low-profile businessman and emigrant from Soviet Ukraine to an FBI informant? And how did he then go from a valued government asset for more than a decade to what prosecutors now describe as a liar and conduit for Russian disinformation?

While mostly based in California, Smirnov led a peripatetic life that, according to court documents, included frequent foreign travel to Ukraine, Israel and various European countries. He once listed his home address at a location that appeared actually to be a traffic median, records show. Multiple times, aggrieved business associates grew so suspicious of his activities that they hired private investigators to learn more about him, according to interviews and court filings.

A review of Smirnov’s business record, as well as years of legal disputes involving the 43-year-old, point to what former agents said were problems with his credibility that should have raised red flags for the government long before prosecutors charged him with lying. Especially glaring is the possibility that he was disclosing his government work, they said.

“That’s a cardinal sin,” said Robert Mazur, a former undercover agent who helped manage informants.

Smirnov’s revelations should have caused the FBI to drop him as a source or at least “read him the riot act” and become highly suspicious of him, said Jerry Hester, a former FBI agent who worked organized-crime cases involving informants.

Informants are key to the FBI’s work, and agents often rely on unsavory characters who gain the trust of suspected criminals to gather evidence of unlawful activity. Still, Hester said, informants are admonished that divulging their role jeopardizes sensitive government probes.

“If he did that, I would have immediately closed him for cause,” Hester said. “If you’re out telling people you’re working for the Bureau, you’re of no value to me.”

An FBI spokeswoman declined to comment.

Smirnov pleaded not guilty last month to making false statements to a federal agent and falsifying records. He has been jailed in Los Angeles pending his trial. His attorneys, David Z. Chesnoff and Richard A. Schonfeld, declined to answer questions about his past, saying, “inquiries into his prior business dealings only deflect from the important question of the accuracy of his prosecution.”

An immigrant and FBI informant

As an FBI source, Smirnov passed along information used in criminal investigations, according to prosecutors. His indictment states that Smirnov was sometimes authorized to break the law to help further investigations but that he was repeatedly instructed to tell the FBI the truth.

Instead, prosecutors allege, Smirnov presented information in 2020 that he knew to be false: He reported that Biden and his son Hunter each took $5 million to help the Ukrainian energy giant Burisma avoid prosecution in the former Soviet republic.

The indictment was brought in federal court in Los Angeles by special counsel David C. Weiss, who has also lodged tax and gun charges against the president’s son. In asking a federal judge to keep Smirnov behind bars until trial, prosecutors argued that the onetime informant claimed extensive foreign contacts, including to Russian intelligence agencies. They portrayed him as part of an ongoing foreign plot to interfere with U.S. democracy by spreading disinformation about the Bidens.

An attorney for Smirnov said in court last month that any sensitive connections he was cultivating overseas came “at the direction of the government.” Meanwhile, Smirnov’s record in the United States reveals little that would establish whether he actually had ties to foreign intelligence agencies. A spokesman for the special counsel declined to comment.

Smirnov grew up in Ukraine when it was still part of the Soviet Union and was raised speaking Russian, according to a declaration submitted to the court by his cousin, Linor Shefer, a real estate agent and reality TV star living in Florida. She declined to comment.

Prosecutors say Smirnov lived in Israel between 1992 and 2006 and that his parents and sister still reside there. Between 2000 and 2006, he served as president of a “private mineral and logistic operation, with assets in Russia,” according to a filing with the Securities and Exchange Commission by a penny-stock company that sought to appoint him chairman of its board in 2011. The filing said Smirnov was fluent in Russian, English, Hebrew and Arabic.

By 2010, he was in the Milwaukee area, where he was going through a divorce, records show. Authorities have not said how he began working as an FBI source around the same time. But records show he soon headed west and lived in various parts of California with a woman, Diana Lavrenyuk, whom his attorneys have described in court documents as his “long term significant other.” Two years ago, prosecutors say, he relocated to Las Vegas.

Smirnov was living there, in a condo owned by Lavrenyuk, when he was arrested last month after disembarking from an international flight, according to prosecutors. Prosecutors portrayed Smirnov to the judge as a globe-trotting operator with no employment in Las Vegas but a range of murky business dealings.

Family members, by contrast, characterized him as a well-meaning immigrant enfeebled by an eye disease and firmly ensconced in the United States. “Alex has spent almost half his life here, more than he lived in any other country,” Shefer told the court, saying her cousin had “family, friends, and business partners in the United States that he would never jeopardize.”

Lavrenyuk’s adult son, a U.S. Marine Corps veteran and employee of the U.S. Labor Department, attested in a letter to the judge: “Alex always keeps his word. Family is everything for Alex, and he would not disappoint them by fleeing.” He didn’t respond to requests for comment.

Smirnov, for his part, said little when he appeared last month in court to plead not guilty and answer “yes” or “no” to routine questions from a federal judge. He was unshaven with trim dark hair and glasses.

Constant travels

Smirnov’s time in California appeared to carry with it warning signs about his reliability as an FBI source.

Not long after he arrived, American Express sued him in 2013 to recover more than $100,000 in unpaid charges, according to filings in California Superior Court.

His loan from Fomichev’s company, D&D Marketing, totaled $500,000 and was to be repaid within a year along with 5 percent interest, court records show. Fomichev, who was indicted in 2013 on tax and immigration charges and sentenced to three months of probation, said he received “not even one dollar back.”

In early 2015, D&D Marketing sued Smirnov for breach of contract and other allegations. The saga of the company’s months-long effort to figure out where Smirnov really lived, described in that lawsuit, sheds light on the informant’s mysterious lifestyle.

Smirnov was initially served a copy of the suit outside of a Los Angeles Rite Aid pharmacy, according to court papers. But when the plaintiffs sought to locate him again, he eluded their grasp, they explained in filings. One address Smirnov provided did not exist. Another was inside a gated community where the leasing office reported that Smirnov had moved out long ago.

In 2016, Smirnov found a Los Angeles lawyer and sought to fight a proposed default judgment of about $600,000, arguing in a filing that he had not been properly served.

“As part of my job I am constantly traveling,” he wrote.

Between March 2015 and April 2016, Smirnov wrote, he had been on at least six overseas trips, including to Israel and Ukraine; to Mexico; to Israel, Ukraine, Italy and Spain; again to Ukraine; again to Italy; and to Austria and the Czech Republic.

He told the court that he lived at an address in San Francisco. But Erin Brady, a lawyer for the company who later became a deputy attorney general with the California Department of Justice, quickly informed the court that the address corresponded not to a home but to a traffic median.

Neither Brady nor Smirnov’s attorney at the time responded to a request for comment.

In September 2016, the court finally rejected Smirnov’s bid to quash the judgment and ordered him to pay. The same year, Fomichev was sued by the Consumer Financial Protection Bureau for allegedly buying and selling fraudulent loan applications, but the case was dismissed in part because Fomichev had suffered a “psychotic break” and had been committed to a psychiatric hospital. Fomichev declined to comment on the episode.

By then, Smirnov was facing other accusations of breach of contract and fraud. In May 2016, two investors in Grand Pacaraima Gold Corporation sued him, alleging that he had pocketed their money and produced fake stock certificates. Smirnov, according to the complaint, “told Plaintiffs he was cooperating with authorities regarding fraud that did not involve Plaintiffs.”

The plaintiffs in the case had been indicted the year before in San Francisco as part of a wide-ranging racketeering and money laundering case.

Joseph Benincasa, an attorney who represented the plaintiffs, said he didn’t think there was a connection between the two cases. But the fact that the people suing Smirnov were also government targets suggested to Hester, the former FBI agent, that Smirnov may have assisted the government in its case.

When informants are authorized to engage in what’s called “otherwise illegal activity” - conduct that would normally be criminal but is sanctioned to aid an investigation - they’re held to certain standards, Hester said. They’re expected to respond to legal complaints and not take money from the schemes, he said.

Once again, the plaintiffs reported difficulty locating Smirnov, court records show.

An investigator retained by the plaintiffs eventually spoke with Smirnov, who said he had returned to Wisconsin from California. According to email correspondence included in court filings, a manager at the apartment complex where Smirnov said he was living told the investigator that the unit’s tenant was actually a man named Boris Nayflish.

“His brother, Alexander Smirnov, stays with him,” the investigator wrote.

Crypto profits

Records show Nayflish is not Smirnov’s brother but was, in fact, formerly married to Smirnov’s current significant other.

The two men are bound together by business interests, documents show, including in companies that are now key to allegations from prosecutors that Smirnov has been dishonest with the government about his finances.

In Wisconsin, Nayflish is a prominent local advocate for Ukraine, helping to forge a sister-city relationship between Milwaukee and Irpin and speaking out against Russia’s 2022 offensive against its neighbor. In an interview with the Milwaukee Independent, he said he was born in Soviet Uzbekistan to Ukrainian parents and came to the United States in 1997, landing with his family at Chicago’s O’Hare International Airport with $800 in his pocket and making his way to Milwaukee.

On LinkedIn, Nayflish identifies himself as the director of global operations for Bitoftrade, a cryptocurrency trading platform. Smirnov has a significant stake in that company, according to an attorney for a Texas-based conglomerate, Economic Transformation Technologies Corporation, which recently bought out Smirnov’s stock in the crypto platform. The Texas-based conglomerate paid him $600,000 for the acquisition in 2020, according to the lawyer, James Daily.

Prosecutors cited the $600,000 transfer into a bank account they say is controlled by Smirnov and his significant other as evidence of the former informant’s murky business dealings. They said he had access to $6 million - acquired through “large wire transfers from what appear to be venture capital firms and individuals” - but failed to properly disclose his assets after his arrest.

Bitoftrade’s website advertises “advanced crypto trading features.” People who have been identified as Bitoftrade employees, either on its website or on LinkedIn, span the United States, Canada, Cyprus, Ukraine and Israel. Current and former employees either declined to comment or did not respond.

Credibility

Discussions about cryptocurrency enabled some of Smirnov’s early dealings with Burisma, the Ukrainian energy giant that in 2014 put Biden’s son Hunter on its board. In 2017, according to prosecutors, Smirnov presented Burisma as a potential partner for an unidentified American associate in the cryptocurrency business.

Smirnov was first introduced to Burisma leaders through Alexander Ostapenko, a Ukrainian government adviser and businessman who, as of 2020, worked for the CEO of a cryptocurrency business, according to an FBI document memorializing what prosecutors now say is Smirnov’s fabrication about the Bidens taking bribes from Burisma.

Neither Ostapenko nor the cryptocurrency CEO, Valery Vavilov, responded to requests for comment.

The FBI document was released by Sen. Chuck Grassley (R-Iowa) last summer as part of a Republican effort to press the FBI for details about the bribery allegations. In it, Smirnov’s name was redacted, and he was described only as a confidential human source. The unsubstantiated claims in the document soon became a foundation of the House GOP’s impeachment inquiry into Biden, and Smirnov’s identity was only revealed publicly by prosecutors when they indicted him last month.

In October 2023, several months after Grassley’s release, Scott Brady, the former U.S. attorney for the Western District of Pennsylvania, appeared before the GOP-controlled House Judiciary Committee to answer questions about the claims. Brady, who did not respond to a request for comment, had been tasked in 2020 by then-Attorney General William P. Barr to review information about Biden gathered in Ukraine by Trump attorney Rudy Giuliani.

Brady characterized the bribery claims as not thoroughly vetted as of 2020. At the same time, he told the committee that it was “correct” that the FBI considered that person credible at the time of the allegations.

Devlin Barrett, Dalton Bennett, Alice Crites, Chris Dehghanpoor, Razzan Nakhlawi and Aaron Schaffer contributed to this report.