"I guess as I approach my fifty-ninth birthday on the 10th of March, and after having done quite a few other crazy things in my life," he wrote in an email to a friend, "I am questioning just why, at this point, with seven kids and a great wife, why would I put myself in such jeopardy."
He would like some assurance, he added, that "I'm not going to wind up someplace where I really don't want to be at this stage of my life."
Levinson gambled and traveled to an island off the Iranian coast to meet with a U.S. fugitive he hoped to turn into his informant. There, his worst fears were realized - he disappeared and has since been seen only as a prisoner in a video that emerged about three years ago and in photographs showing him dressed like a Guantanamo detainee, in orange garb.
Since his disappearance in March 2007, U.S. officials have publicly insisted that Levinson went to Iran as a private investigator working on a cigarette smuggling case. In fact, he was also a contractor for the Central Intelligence Agency. As the real purpose of his mission became known within the government, it led to a scandal within the CIA in which three agency officials lost their jobs, for, in effect, using Levinson as part of an unauthorized spying operation.
The New York Times has known about the former agent's CIA ties since late 2007, when a lawyer for the family gave a reporter access to Levinson's files and emails. The Times withheld that information to avoid jeopardizing his safety or the efforts to free him. On Thursday, The Associated Press disclosed Levinson's role with the intelligence agency. In a statement, the White House said it had urged the wire service not to publish its article "out of concern for Mr. Levinson's life." After Thursday's disclosure, the Levinson family said it had no objection to The Times' publishing this article.
The Iranian government has maintained that it knows nothing about Levinson's fate. High-ranking U.S. officials have long said privately that they believe the Iranians view him as a spy and that he was being held by a group tied to Iranian religious leaders, possibly the Revolutionary Guard.
In many ways, the story that emerges from Levinson's files and dozens of interviews is that of an unusual spy, an aging but still passionate investigator searching for a way to keep his hand in the game. It is also the story of officials in a relatively obscure CIA office looking to push the boundaries between the agency's analytical side and its covert operations. An agency inquiry concluded that those analysts had encouraged him to take risks and then misrepresented his activities after he went missing.
To his family and friends, the government Levinson served for decades abandoned him for a time, initially making little attempt to find him or acknowledging why he went to Iran.
They started their own search, and a cast of unlikely figures was drawn into the hunt, many seeing it as an opportunity to get something for themselves. They included one of Russia's most powerful businessmen, Oleg Deripaska.
In late 2010, when his family received the tape of Levinson, they saw a man they barely recognized. He was gaunt. His shirt was threadbare. He was seated in a makeshift prison cell.
A CAREER REVIVED BY 'TOOTS'
Bob Levinson might have stayed at the FBI for his entire career, but he retired in 1998 because he needed money. He and his wife, Christine, had seven children, and there were college bills to pay.
After retiring, Levinson worked for several large investigative firms and then ran his own business from his home in Coral Springs, Fla. But he badly wanted a way back into government, and a CIA analyst named Anne Jablonski helped him out.
The two shared a specialty in Russian organized crime and were close friends. In emails, he called her "Toots" and signed off as "Buck."
In 2006, Jablonski worked for a CIA unit called the Illicit Finance Group that produced reports on subjects like money-laundering and international corruption. In the years after the Sept. 11 attacks, the CIA expanded greatly, hiring hundreds of outside contractors.
Levinson was thrilled when Jablonski told him in mid-2006 that he had been approved for a consulting contract.
He was told the finance group was interested in information about several countries, particularly Iran and Venezuela. In the case of Iran, CIA analysts wanted to know how it might respond to trade sanctions and also wanted potentially embarrassing information about Iranian officials, the investigator's notes show.
In the nine months before his disappearance, Levinson unleashed a flood of more than 100 memos that together read like a disjointed catalog of chaos, crime and intrigue from countries throughout Central and South America and Eastern Europe - mostly countries he was visiting as a private investigator.
After Levinson disappeared, some CIA officials questioned the value of his reports. But in 2006, Jablonski and her colleagues believed he was scoring points for them in the competition between the two sides of the agency, the analytical and the clandestine branches. Only the clandestine branch is supposed to operate covertly, but since the CIA had not established rules after the Sept. 11 attacks governing the operation of contractors, Levinson had a freer rein.
Levinson knew his way around some parts of the world, but he knew nothing about the one country that his bosses at Langley were most interested in: Iran.
The path that took him there began with another friend, Ira Silverman, a retired NBC investigative producer.
Levinson had been one of the newsman's sources for law enforcement tips, but now Silverman had a tip for the investigator. He could connect him with someone who might prove to be a source in Iran, Dawud Salahuddin, an American who had fled there in 1980 after assassinating a former aide to the Shah of Iran in Bethesda, Md.
The fugitive viewed many Iranian officials as corrupt, and Silverman believed he might be willing to share information. He particularly disdained a former Iranian president, Ali Akbar Hashemi Rafsanjani, privately claiming he had stolen millions in oil revenues and secretly invested it in Canadian real estate and other assets. Silverman introduced the two men by phone.
Levinson wrote that said he was going to Dubai to work on several non-CIA cases, including one involving cigarette smuggling, and hoped to meet someone there "or on an island nearby" who claimed to know about money laundering by Iranian officials.
Meanwhile, Silverman was helping to arrange Levinson's meeting with Salahuddin at the Maryam Hotel on the island of Kish, a short flight from Dubai.
On March 8, 2007, the investigator packed a small bag with toiletries, a change of clothes and gifts he had purchased.
"Off today for that place - all is set - best wishes and thanks for all your help in getting this arranged," he wrote to Silverman.
But by the next day, Silverman had heard nothing more.
As Silverman frantically worked the phones over the next few days searching for his friend, he got several explanations from Salahuddin. The fugitive first told the former newsman that he had been taken away for questioning by the Iranian police, who had made a surprise visit to the Maryam Hotel. When he returned the next morning, he was told that Levinson had just departed for the airport, Salahuddin told Silverman.
A few days later, Salahuddin said the authorities had taken Levinson to Tehran for questioning.
AN UNUSUAL SEARCH PARTY
Whether Levinson is still alive is a mystery. But his family and friends, and eventually, the U.S. government, have spent years trying to find him.
By mid-2008, the FBI was fully engaged in the hunt. At that time, two FBI agents met at a Paris hotel with a powerful new player who became secretly involved in the effort: Oleg Deripaska, one of Russia's wealthiest businessmen.
FBI officials were so confident about the plan that they told Christine Levinson to stay by the phone for a call from her husband. It never came.
In November 2010, an email with the video of Levinson attached was sent to Silverman and others. It was followed a few months later by another email with the picture showing him dressed as a prisoner. Around the same time, top FBI officials met with their Iranian counterparts for secret talks about Levinson. But they quickly fizzled.
On Thursday afternoon, the family received an email from an Associated Press reporter telling them the news organization planned to release an article within a few hours that would disclose Levinson's ties to the CIA, a secret the family had held closely.
Later that day, the family issued a statement calling for the U.S. government to "take care of one of its own," saying that "after nearly seven years, our family should not be struggling to get through each day without this wonderful, caring man that we love so much."
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