The adviser to Ben Carson on national security who blasted him in a New York Times article Tuesday has a curious, intrepid past of his own, including connections to a private spy ring and an indictment in the Iran-Contra affair.

Duane Clarridge deeply embarrassed the Carson campaign when he told the Times that Carson may not be absorbing “one iota of intelligent information about the Middle East.” In the era of highly-scripted politics and blind quotes, a campaign adviser’s public disparagement of his own candidate is damning enough. But in Clarridge, Carson has found an adviser whose dubious tales of derring-do over the past 40 years are legendary and sometimes hilarious.

Clarridge has shown a uncanny ability to insinuate himself into scandals, cloak-and-dagger escapades, and assorted murky schemes on the fuzzy line between the real world and the clandestine one. His mere presence as a counselor to Carson is more evidence that the foreign policy neophyte has surrounded himself with an off-beat cadre of advisers.

Clarridge, now 83, was hired by the CIA roughly six decades ago. During his tenure at the agency, he rose through the ranks and served in top posts in Istanbul and Rome. In 1981, he was promoted to run the Latin American division of the agency. It was there that he became immersed in the Reagan administration’s long-running involvement in Nicaragua that culminated with the Iran-contra scandal.

Clarridge’s commitment to U.S. intervention is well documented. It has led him to defend the CIA’s tactics in Chile in the 1970s and the mining of Nicaraguan harbors in the 1980s.

“We will intervene whenever we decide it is in our national security interest to intervene,” Clarridge told Australian-born journalist John Pilger in a 2008 interview. “And if you don’t like it, lump it. Get used to it world. We are not going to put up with nonsense.”

In an interview archived by George Washington University, Clarridge divulged how he finally came up with the idea to place mines in Nicaraguan harbors. He told the interviewer, he was getting a lot of frustration from Washington to do something but he recounted that he had limited resources.

“Guerilla warfare experts will tell ya don’t hit the economic targets you make enemies of the people you need. I don’t believe, that’s not true, it maybe true in certain circumstances, but it is not an all encompassing rule, and everything needs to be looked at,” he said. “I knew we had ’em, we’d made ’em outta sewer pipe and we had the good fusing system on them and we were ready. And you know they wouldn’t really hurt anybody because they just weren’t that big a mine, alright? Yeah, with luck, bad luck we might hurt somebody, but pretty hard you know?”

In 1991 he was indicted in the Iran-Contra scandal for lying to Congress. His trial was never completed. In 1992 he was pardoned before George H.W. Bush left office.

From a Cold War spy, Clarridge transitioned into self-made operative in the war on terror.

The New York TImes reported as recently as 2011, that Clarridge was conducting a Middle East private spy ring from his home in Southern California.

Back then, the New York Times characterized Clarridge’s tips from spies on the ground from Pakistan to Afghanistan as “an amalgam of fact, rumor, analysis and uncorroborated reports” that he pushed “to military officials who, until last spring at least, found some credible enough to be used in planning strikes against militants in Afghanistan.” Once funded by money from the military, Clarridge managed to keep his network afloat with private donations after officials lost interest. He used the money to try and investigate “Afghan president, Hamid Karzai, in hopes of collecting beard trimmings or other DNA samples that might prove Mr. Clarridge’s suspicions that the Afghan leader was a heroin addict,” The Times reported.

In 2004, the Los Angeles Times reported Clarridge was using his own money to look at Saddam Hussein’s money ties to countries like France and Russia.

“It will be a huge bombshell if we can pull it off,” Clarridge said at the time.

In national security circles, Clarridge is seen as an off-beat privateer who walks the tightrope between sanctioned spy and citizen security activist. Still, he has taken on some high-profile clients, including the New York Times, who hired the company he worked for – American International Security Corporation – to help find and free kidnapped reporter David Rohde in 2008. Rohde managed to eventually escape from Taliban captivity, but according to a report from Gawker, someone who worked with him said “Clarridge was inflating his role in facilitating Rohde’s escape in an effort to justify AISC’s enormous fees.”

Carson’s reliance on Clarridge as an adviser – no matter how limited – speaks to the former neurosurgeon’s newness to politics. While Clarridge confided in the Times that Carson “need[s] to have a conference call once a week” to “make him smart,” the Carson campaign immediately rushed to downplay Clarridge’s role in the campaign, going so far as to portray him as a old man who was being taken advantage of by the Times.

Armstrong Williams- a confident of Carson’s–told Business Insider that Clarridge is just one of many foreign policy advisers Carson relies on and that the two men have only sat down for briefings twice. Armstrong told the outlet that Carson and Clarridge have communicated via the phone four times.

“Clarridge’s input to Dr. Carson is appreciated but he is clearly not one of Dr. Carson’s top advisers,” the campaign said in a statement Tuesday. “For The New York Times to take advantage of an elderly gentleman and use him as their foil in this story is an affront to good journalistic practices.”

In a final twist, the New York Times reporter whose story of Clarridge blasting Carson put the old CIA hand back in the news told the Washington Post that he obtained Clarridge’s name from none other than Williams himself.