April 12, 2016 | Forbes

The Death Of Dewey Clarridge

In the summer of 1981, I was Special Advisor to Secretary of State Alexander Haig, and he asked me to try to find out what the CIA was up to in Salvador and Nicaragua.  “I’m afraid it’s one of those things that’s too big to hide but too small to succeed,” he said.

We were in the early days of the Contras, and it turned out that I knew the spook in charge:  Duane “Dewey” Clarridge, head of Latin American stuff at the Directorate of Operations.  A few years earlier I had gone to talk to Clarridge when he was station chief in Rome.  He’d been snooping around town asking questions about me and I didn’t like it.  So I called him and said “you got questions?  Here I am.”  He denied the whole thing, and I wrote him off as yet another CIA officer who had only a passing acquaintance with the truth.

Our relationship started off badly, let’s say.  Now I had to annoy him on behalf of the secretary of state, and things went better.  It was turnabout;  I was the snooper, openly so, and he was quite forthcoming. His big boss, Bill Casey, had previously put him in command of the new conter-terrorism center, and he instructed Dewey to harass the Nicaraguan Communist Sandinistas, who were smuggling guns and ammunition to their terrorist friends in El Salvador, with which we were allied.  His mission was duly reported to Congress, and Senate leaders—notably Ted Kennedy—approved it, provided it was sufficiently small.  They capped the operation at 800 men, which suited Dewey and Casey just fine.

But then something unexpected happened.  The next time Dewey went down south to talk to his 800, there were several thousand volunteers.  Once they saw the CIA working on their side, they assumed the United States would organize a mighty force to overthrow the Sandinista regime itself, and they wanted to be part of the presumed enterprise.

What was he supposed to do?  Kennedy et. al. would never believe that the anti-Sandinista Nicaraguans had just upped and multiplied, and Kennedy virtually accused Dewey of deceiving his committee.  He hadn’t, and over time the growth of the Sandinistas reached historic levels.  It ultimately became the largest secret operation in CIA’s history.  By 1983-85, the period in which Congress cut off funding, the Contra army was over twelve thousand.  It wasn’t all Dewey’s doing, but a lot of it was.  I once told him he had encountered the dialectic.  Having set out to create a small guerrilla force, he came to lead a genuine mass movement.

So Haig was right to be concerned.  It was too big to hide.  On the other hand it became big enough to succeed.

From then on, Dewey and I became buddies.  He’d spent most of his career in the Middle East, starting in Turkey.  Most of those guys went native, invariably siding with the Arabs on matters involving Israel, but Dewey was different.  He had lots of Arab friends, but he developed deep friendships with top Israeli spies as well, and in his last days, when I asked him if there were anyone he especially wanted me to call, he gave me an Israeli name.  Earlier he had put me in touch with some Turks.

In my book on Iran-Contra I described him this way:

He was an imaginative, aggressive officer, with the kind of flamboyant personal style that quickly endeared him to Bill Casey.  A smoker of fine cigars, an eccentric dresser who favored white suits, and a gourmet who resorted to a pasta diet when his appetite placed his wardrobe in jeopardy…

And so he was.  Oh, one other thing.  His home in Leesburg, Virginia,  was full of guns, from little pistols to a big brass canon in the middle of his living room, aimed out the big glass windows.  He was always ready.

Michael Ledeen is the Freedom Scholar at the Foundation for Defense of Democracies.