My CIA Interview…

Once upon a time there was a clear-eyed, wet behind the ears, 24-year-old who believed national service was honorable. He was a liberal arts college graduate and Marine Corps fighter pilot about to finish his active duty obligation.

He never planned to make the military his career as much as he loved the flying, but he wasn’t sure what was next. Life was open ended. He thought about graduate school in English and a college teaching career. Tweed jackets with leather patches and all that. But that might be too tame. 

He was also thinking of adventure, and the Israel Air Force was at the top of its game. He wasn’t Jewish but that didn’t matter. It had the best trained military in the world and some of the newest and best fighter aircraft, so he wrote asking if they were looking for well-trained fighter pilots. He got no response. 

Then, there was law school. At the time, business school was considered second tier to law school for those without a clear career path. His father said, “You can always use a law degree.” It was the dictum and next step for the aimless college graduate.

But, there was also the Central Intelligence Agency, the CIA… America’s spy agency. If we’re talking adventure and intrigue in 1962, the CIA was the place to go. It was the height of the Cold War. Khrushchev was taunting America with his shoe banging at the UN. Allen Dulles had just retired as Director but Master Spy James Angleton was head of Counter-Intelligence. The Cuban Missile Crisis was just around the corner, so…

Not knowing what he was doing (or going to be doing) he impulsively sent a letter asking about employment. It was definitely, an after-thought, but it was all about covering bases.

I was that 24 year old and to my surprise, later that spring, I received an odd phone call. Without identifying himself, the mystery caller asked if I had requested an interview with a government agency? When I answered yes, I was told to be at the Ambassador Hotel in Los Angeles at a specific time and date later that month. On arrival I was to notify the front desk and ask for a “Mr. Winter,” whereupon I would be directed to “Mr. Winter’s room.

Looking back, it was laughable.

On the appointed day I showed up at the Ambassador and was directed to “Mr. Winter’s” room. I was met by a tall, Waspish patrician with a full head of salt and pepper hair, navy blue Brooks Brothers suit, white Oxford cloth button-down shirt, regimental striped tie and black wing tip shoes. His appearance screamed Yale and his manner confirmed it.

“Mr. Winter,” obviously his spy moniker, led me to a drawing room adjacent to the sleeping area where he asked what I knew about “The Company” and what was behind my interest in becoming one of its “officers.” I don’t remember what I told him, but I was pretty gung-ho at the time and probably said something about spending time overseas and looking for a job that was exciting and out of the ordinary.

I left the Ambassador and never heard another word from “The Company” or “Mr. Winter”. If offered the job I might have been flattered into it, but to the well schooled “Mr. Winter” I was obviously a terrible actor (liar) and would never have cut the mustard as a spy. There are those that are and those that aren’t. About 10 years ago I discovered that the wife of a good friend had been an undercover operative at the CIA for 30 years and all that time I thought she worked for the Department of Agriculture.

I’ve always been a big fan of spy literature – Len Deighton, John le Carre’, Alan Furst, and more recently David Ignatius – which probably explains my interest in the CIA back in the day. I love the twists and turns, but since Mike Pompeo’s tenure as Director the duplicity, suspicion, and untrustworthy characters have switched sides. Now it’s hard to tell the good guys from the bad. Real life intrigue has superseded the fictional kind for our attention. In the highly politicized Trump era I don’t trust anything, anyone, or any agency that’s touched the White House and that includes the CIA. I hope it’s an anomaly, but until the current cast of characters is dumped I’m putting my trust in fiction when it comes to spying.

Looking back at my job quest, I realize the decision was foregone. I rejected graduate school in English because I wasn’t interested in scholarship or teaching. I just liked books. And, the Israeli Air Force and CIA were not interested in me for undisclosed reasons.

“You can always use a law degree” was the obvious winner – sort of. My three years in Berkeley were three of the best years of my life, but my law career lasted less than a year. I was right when I told “Mr. Winter” that spending time overseas in an exciting out of the ordinary job was top of mind. 

After nine months at Loeb and Loeb in LA I quit. Next up was a pilot job at Pan Am including 10 years in Berlin. It was one of the best decisions of my life.