Robert Hoffman had a risky perspective on life- “I plan to have fun with this until someone does kill me or I have enough money to disappear.” Hoffman wrote in his diary. Robert Hoffman: The spy who struck out – Robert Patrick Hoffman II was still half-asleep when he heard the knock. He opened the door of his Virginia Beach home to find a beautiful woman with “Subtle, Eastern European features.” She said her name was Olga. She was wearing a low-cut turquoise blouse, black skirt and 3-inch heels. And her jewelry? Well, that was all a blur. “Was too focused on her face,” Hoffman would later write of the woman who invited him to become a Russian spy. “Then the package, then her cleavage, then her face again.” Meet the latest American to be convicted of attempted espionage: a retired sailor so enamored with a woman’s breasts that he wrote about them in his diary. Hoffman is scheduled to be sentenced on Monday to at least 15 years in federal prison, but he is not your classic spy. The 40-year-old divorced father of three is more like Mr. Bean than James Bond. He walked into the FBI’s Norfolk field office in 2012 to speak with an agent while under surveillance by the same agency. That didn’t keep the unemployed former submariner from turning over top-secret information to FBI agents posing as Russian spies. Despite his sometimes goofy demeanor, federal prosecutors said, Hoffman put his country at risk. Hoffman grew up in Buffalo, N.Y., the youngest of five children. His father was killed when Hoffman was 2, leaving his mother to raise him and his four sisters. He graduated from high school in 1991 and joined the Navy. He served honorably for two decades while stationed in Florida, Pearl Harbor and eventually Hampton Roads, earning more than a dozen achievement and commendation medals along the way. He worked as a cryptologic technician, a job that required him to gather and analyze electronic intelligence. Hoffman was never able to make the rank of chief petty officer, though. He was repeatedly passed over for promotion and retired in late 2011 as a petty officer first class. It wasn’t Hoffman’s service record that drew the FBI’s attention. His defense attorneys say it was his love of women. While deployed about three years ago in Bahrain, the bald, powerfully built sailor befriended a group of young women from Belarus. The women worked at a club that marketed itself toward young servicemen and expatriates. Hoffman would buy the women overpriced drinks, and they would sit and talk with him. The FBI opened its investigation into Hoffman in spring 2012 after learning of his trip and subsequent retirement from the Navy. They started by having a female agent respond to a personal advertisement that Hoffman posted on Craigslist. The undercover operative was a 22-year veteran who used the pseudonym “Tracey Tea” on dates. She and Hoffman exchanged dozens of emails during a five-month courtship and even went out a couple of times at Virginia Beach’s Town Center. Hoffman spoke openly with the agent about his career with the Navy, his work aboard submarines and his top-secret security clearance, according to court testimony. The FBI took its investigation to the next level on Sept. 21, 2012, when they sent Olga – another undercover agent – to his door with a Soviet medal and a letter from a “friend” in Moscow. A few hours later, Hoffman emailed a man he thought was a Russian spy and volunteered his services. “I look forward to renewing our friendship,” he wrote. Robert Patrick Hoffman Hoffman traded several emails over the next two months with his “Russian” handler, whom he knew only as “Vladimir.” He also made three trips to First Landing State Park in Virginia Beach to drop off information that the FBI later recovered. During his last visit, he left his handler an encrypted flash drive that would have helped the Russians track American submarines and avoid detection by U.S. warships, according to court testimony. Hoffman declined an interview request through jail officials, but he documented most of his dealings with the supposedly Russian agents in a so-called “Operations Log.” The eight-page diary, which he eventually turned over to the FBI, offered insight into his thoughts. Prosecutors described the diary during Hoffman’s August jury trial as “self-serving.” Defense attorneys countered that Hoffman included several unflattering details about himself. Among other things, Hoffman wrote about Olga’s beauty, his money problems, his desire to help the United States as well as the Russians and his willingness to die. “While I do understand that these games have dire consequences, I’m at such a point in my life that even if I get killed, I don’t really care,” he wrote after expressing his wish to contact the FBI about the Russians. “I plan to have fun with this until someone does kill me or I have enough money to disappear.” Hoffman, who by then was studying computer and network security at ECPI University, also said he didn’t trust his handler. “My thought that Vladimir is an idiot, or new at this espionage thing, is growing well on the mound of evidence he provides me,” Hoffman wrote in an entry dated Oct. 2, 2012. “Or this whole thing could be a setup against me and they suck at it.” Hoffman – who asked the Russians to call him “Sasha Andrews” – was never paid for the information he provided his handler. In his messages to Vladimir, however, he asked for help finding a job that paid at least $45,000 a year. If they wanted him to travel, he wanted a per diem equal to that paid by the U.S. General Services Administration. In addition, “tasks that involve taking a life… require significant compensation, either monetary or via favors.” The FBI’s investigation took an unexpected turn on Oct. 31, 2012, when Hoffman drove to the agency’s Norfolk field office and asked to speak with an agent. He confessed to communicating with a Russian spy and asked for help catching him. The FBI did not let on that the Russians were fake. Special Agent James Dougherty allowed Hoffman to go home but told him to stop communicating with Vladimir. Eight days later, Hoffman sent a coded message to his handler. The subject line read, “The power is out,” a phrase he was told to use if something was wrong. It took a federal jury about 90 minutes to convict Hoffman of one count of attempted espionage. The charge could carry a death sentence, but prosecutors on Monday will ask for 30 years. Defense attorneys James Broccoletti and Keith Kimball plan to argue for no more than 15 years. Consider that such a person could be one of your employees or co-workers, or former employees, looking to take a walk on the wild side and becoming a threat to your business. Be sure you have business espionage countermeasures part of your security program. [Read more at the Virginian-Pilot] [Update from the Virginian-Pilot: Hoffman got 30 years.] …Defense attorneys argued at trial that Hoffman engaged the Russians because he wanted to help the United States catch them. They noted that he approached the FBI after the third drop and provided agents with copies of all of his correspondence with Vladimir as well as a piece of tape and a trash bag his handler had touched. Hoffman described himself in court as a U.S. “spy and a spy hunter.” 
“It was a kindness of mine to offer to help the FBI,” he said.
Story of a modern spy, who didn’t make it.
[He] also said he didn’t trust his handler. “My thought that Vladimir is an idiot, or new at this espionage thing, is growing well on the mound of evidence he provides me. Or this whole thing could be a setup against me and they suck at it.” It was a set up, by the FBI, and he was caught.