An only child, Ruppert’s family had close ties to the military and federal government. His father was a US Air Force pilot during the Second World War and later worked for Martin Marietta — which became Lockheed-Martin — "as a liaison between the CIA, the US Air Force, and Martin for booster programs," Ruppert wrote in a 2010 online autobiography.
Ruppert interviewed to be a CIA operative during his senior year at UCLA in 1973, he wrote, but turned down the subsequent offer. He became a cop with the Los Angeles Police Department (LAPD) and handled narcotics cases in some of the city’s most dangerous neighborhoods. The hours were long, and the job eventually got to him. He would later write that his work with the LAPD saddled him with "combat fatigue."
It was during his tenure at the LAPD that Ruppert met a woman named Nordica Theodora "Teddy" D’Orsay. Ruppert later wrote that their 15-month relationship "determined the course of my life…."
Teddy wasn’t a cop, but she and Ruppert met at a Marina del Rey cop bar in 1975. The two became infatuated with one another, and quickly moved in together. Early in their relationship, however, Ruppert became suspicious of Teddy. For a civilian, she was, he thought, a little too knowledgeable about guns and stakeouts and the day-to-day work of officers on a beat. She dropped names of LAPD cops as well as crime bosses and undercover agents.
When Teddy started staying out several nights per week and taking trips to San Francisco and Hawaii, Ruppert’s suspicions mounted. He treated Teddy as though she were a suspect in a crime. He gathered intel. It’s unclear what evidence he compiled, but Ruppert concluded that Teddy had ties to a San Francisco mobster and the shah of Iran. She grew even more distant. Then, in early 1977, she walked out on him.
After she left, Ruppert said, he became the victim of harassment: phone calls with dead silence on the other end; apartment searches while he was out; cars tailing him. He began sleeping with a gun under his pillow.
He became the victim of harassment: phone calls with dead silence on the other end; apartment searches while he was out; cars tailing him. He began sleeping with a gun under his pillow
Ten weeks later, Teddy finally called Ruppert and said that she was in the New Orleans area. Ruppert drove to Louisiana and found her, he later wrote, "equipped with a scrambler phone and night-vision devices, and working from sealed communiqués delivered by Naval and Air Force personnel." He concluded that "she was involved in something truly ugly" — "arranging for large quantities of weapons to be loaded onto ships leaving for Iran." She was also working with "associates" of a New Orleans mafia boss bringing "large quantities of heroin into the city." Ruppert would later say that he and Teddy had even been shot at outside a New Orleans-area bar — retribution, he concluded, for discovering too much about Teddy’s covert actions. Ruppert broke off the relationship and returned home.
When he shared what he’d discovered with LAPD intelligence officers, they "promptly told me that I was crazy," he wrote. Overwhelmed, he checked himself into a psychiatric hospital for a "much-needed" monthlong rest. Though he was eventually reinstated as an officer, both his reputation and interest in the job vanished. In November 1978, he resigned. In time, Ruppert came to believe that the LAPD was part of a larger narco-trafficking network.
Through the press, Ruppert tried to expose what he’d discovered. In 1981, he made persistent calls to a Los Angeles Herald-Examiner columnist in an effort to expose Teddy’s trafficking network. The columnist ultimately published a TWO-PART SERIES, "The Spy Who Loved Me." But the series’ findings were, at best, inconclusive. It cited "a retired LAPD intelligence officer, another FBI agent, and [a psychiatrist]" who agreed that Ruppert’s story may have been "what he believes to be the truth," but that there was scant evidence to prove it. "Each of these three professionals professed both a measure of admiration and a measure of fear of Ruppert," the series read.