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A Spy's Career Tied To History

This is one in a series of Spy's Guide book reviews. For more, see

A spy’s career is tied to history. From the 1970s through mid-1990s, Jack Devine worked in the trenches of major historical moments. He was a young case officer in Chile during the Pinochet coup. He touched on the Iran-Contra Affair. He worked to supply Charlie Wilson’s War in Afghanistan. He rose through the ranks and became Acting DDO, head of the Directorate of Operations.

Good Hunting is about those moments, their contexts, and the players in Devine’s career. Some of the book is about the strategy. Some is about the events beyond his control. But most of it is about relationships.

For spies, relationships are how things get done. A source gives you information because of a relationship. A covert action happens because of a relationship. What you get from a foreign intelligence service is good or bad because of a relationship. Sometimes, you get betrayed by relationships.

Devine had a relationship with traitor Aldrich Ames. Not a close relationship, but they were together as trainees in the early 1970s. They worked together again in the Latin America Division and later in Rome. Ames was caught just a few years before Devine retired. Ames was a mole for Russians, and no one knew.

Before Ames was arrested, counterintelligence officers asked Devine who he thought could be a mole for the Russians. He immediately said Ames. The counterintelligence officers had asked other senior CIA officers to make a list of people they thought could be a mole for the Russians. They each had Ames on their list.

The Ames case is one where the data was there. Even a lot of the analysis was there. But until the question was asked, no one put it together. Until the question was asked, no one decided Ames was a mole. Until the question was asked, no one took action against him.

In the scientific method, questions come from hypotheses. In the world of intelligence, questions come from looking ahead. From deciding what actions are possible. You gather data to answer those questions. You analyze the data so you can answer those questions. So you can make a decision. And take action.

It looks like this (graphic from A Spy’s Guide To Thinking):

Key to every spy history are the questions being asked.

In Devine’s career, the questions asked were about American power in Latin America. The questions asked were about how to fight the Soviet invasion of Afghanistan (answered by the Stinger missile system). The questions asked were about how to manage the breakup of the Soviet Union.

Spies answer those questions via relationships. Devine, by all accounts, was good at relationships. He was good at creating positive-sum games. Good at creating alliances.

So good, he was able to start his own private intelligence firm after he left the Agency. Devine spends forty pages talking about what he’s done and who he’s met in that world. Now, he answers questions for businesses and people operating in difficult environments.

But stepping out of the CIA meant stepping out of history. Devine didn’t want to. You can read the regret in the latter pages of Good Hunting.

Devine loved his time at the CIA. He loved the questions he answered. He loved the relationships he made to answer those questions. He loved having a career tied to history.


One of the questions Devine answers is how to do a proper covert action. He lists six things:

1. Identify a legitimate enemy 2. Determine on-the-ground conditions 3. Ensure adequate funding and staff 4. Find legitimate local partners 5. Determine proportionality 6. Acquire bipartisan political support

In fact, these six things are necessary for any Zero-Sum Game, whether a covert action or a war.

In any Zero-Sum Game, your enemy must be identified. You must understand what will happen on the ground when it starts. You must be well-supplied and have the right people. You must have good allies. You must not take it too far (proportionality), if you want to keep the Zero-Sum Game from threatening other games. And your internal alliance, especially among decision-makers, must be strong.

For more on how Zero-Sum Games are played, see A Spy’s Guide To Strategy.

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