OSS: The Myth That Never Dies

It’s now apparent to anyone with open eyes that the Islamic State is on the march in Iraq and is not being halted by American actions. Obama’s ardor to defeat Da’ish can charitably be called diffident, so people are seeking answers for what’s gone so wrong here. To anyone versed in how the White House and the Pentagon get along, it’s evident that what experts term “the civil-military dialogue” over Da’ish is in a bad way.

Reports of American aircrews and special operators, who are the pointy end of our spear in Iraq, being upset by White House micromanaging the campaign against Da’ish, to the detriment of military effectiveness, cannot help but echo President Johnson’s failed efforts to bring Hanoi to the peace table in the mid-1960’s through airpower. Then there’s the issue of strategy which, to the extent it can be detected at all in our pseudo-war against Da’ish, is clearly lacking reassessment, since the enemy is winning despite our efforts.

Someone needs to be blamed, and as is so often the case inside the Beltway, the spooks offer a prime target. It’s always tempting to cite “intelligence failure,” since that’s shrouded in mystery and the Intelligence Community can’t always defend itself against such media accusations.

Along comes David Ignatius to explain that the root of our misguided war on Da’ish is an “intelligence deficit” — we simply don’t know enough about the enemy. It speaks volumes that the IC may not know enough about a country that we recently occupied for nearly a decade and have been at war with, or in, more or less nonstop since 1990. Ignatius cites General Martin Dempsey, the nation’s top military officer, explaining that the Pentagon was surprised by recent Da’ish successes. Blaming spooks, of course, is an easy thing to do when you have no clear strategy.

Yet there is ample evidence that our recent failures in Iraq stem not from a lack of intelligence, rather from top decision-makers, military and civilian, not knowing what to do about Da’ish. In particular, the Obama administration let Ramadi fall to the enemy, despite having “significant intelligence” about what was going to happen. This speaks to a failure of policy, not intelligence.

That said, Ignatius is a savvy journalist who has a close relationship with Langley, so when he says CIA isn’t doing a very good job in Iraq, that matters. Additionally, most of what he says about CIA shortcomings on the ground are accurate, particularly his charge that Agency personnel, confined “inside the wire” in places like Afghanistan and Iraq for their own safety, are missing out on important things.

This is undeniably true and it’s simply a fact that CIA’s operational model is better suited to a cold war than a hot one, particularly a conflict where the enemy would love to kidnap and torture CIA officers to death. That the Directorate of Operations, the Agency’s espionage arm, isn’t well suited to taking on hardcore mujahidin like Da’ish is both true and a truism. (For a primer on the DO and how CIA is organized and operates, see this.) Moreover, Ignatius explains:

For decades, the CIA and the military have tried to fix intelligence problems by relying on National Security Agency surveillance. But the jihadists have gone to school on the leaks about U.S. capabilities and learned to mask their operations.

That’s an oblique reference to the enormous damage caused by Edward Snowden’s massive theft of classified NSA materials, which has helped the terrorists in countless ways. So we need better human intelligence — but how to get it? That knotty problem Ignatius has a fix for:

Gathering intelligence against this 21st-century jihadist adversary, paradoxically, will require the kind of old-fashioned spying and resistance operations we associate with the CIA’s founding generation in the OSS.

As is inevitably the case whenever someone wants CIA or DoD to “get in the espionage fight” they cite the OSS. That’s the Office of Strategic Services, the CIA’s predecessor, established at the beginning of America’s entry in the Second World War. Few topics get American spy buffs more excited than mentioning the OSS, which won a reputation for swashbuckling derring-do, dropping agents behind enemy lines to stir up trouble. For anybody frustrated by the current Intelligence Community’s institutionalized risk-aversion and incomprehensible bureaucracy — and I’m among the first to decry these cancerous IC tendencies — the lean and mean OSS looks something like paradise.

In the first place, OSS was awash in smart young people, many of them Ivy Leaguers and social register types. Not for nothing did OSS detractors, who were numerous, deride the outfit as “Oh So Social.” Its boss, William “Wild Bill” Donovan was a connected New York lawyer and bona fide hero of the Great War, who had President Franklin D. Roosevelt’s ear. To say nothing of the excitement of jumping out of airplanes over occupied France to do secret spy stuff, which sounds more exciting and markedly less awful than, say, storming Omaha Beach.

The problem with getting weepy about the OSS is that it’s simply a myth. A myth that has generated countless books, mind you, but a myth all the same. In truth, the OSS did about as well as could be expected given that it was an instantly-created organization staffed and led by people without any experience in espionage. It was well intentioned but naive and unskilled and, while its bias for action was admirable (and something that today’s IC could use a healthy dose of), it often went badly wrong in the field.

In the first place, OSS attitudes towards secrecy were laughable. Thanks to lax security policies, it was deeply penetrated by foreign intelligence agencies. We know of at least a dozen Soviet agents inside the OSS and, even though one of them was a genuine hero, it’s safe to say that Moscow was very well briefed on OSS activities. This didn’t seem to bother Wild Bill, and despite the fact that President Roosevelt liked Donovan, he was careful to keep really important secrets out of slippery OSS hands. In particular, Donovan’s outfit was kept in the dark about the ULTRA secret and related important SIGINT successes against the Axis by the Army and the Navy. Sadly, OSS-style lackadaisical attitudes toward counterintelligence plague American espionage still, with deadly consequences.

Donovan was better at bureaucratic fighting than spying, and he waged non-stop campaigns against his main rivals — the FBI at home and Army intelligence abroad — to get OSS “in the fight.” Donovan got on the bad side of both J. Edgar Hoover and General George Strong, the Army G-2, and Roosevelt had to adjudicate turf spats among his espionage bosses with depressing frequency. OSS also was incautious about its domestic operations, which was why President Harry Truman disbanded Donovan’s outfit immediately after the end of the war, noting that the country did not need an “American Gestapo.”

Some OSS missteps were comical, perhaps most infamously in 1943 when Donovan had to be waved off stealing a code machine from the Japanese embassy in Lisbon, an operation that had been painstakingly planned. Donovan was very excited about this “black bag” job, which offered a crack into Japanese codes. General Strong was furious and demanded that the OSS stand down, since Army intelligence, the future NSA, had been reading those secret messages for years and theft of cryptographic materials might push the Japanese to change their codes, which would be a big blow to the war effort. Of course Donovan and his crew, not being cleared for ULTRA, knew none of this. Strong and the Army got the OSS out of the code-stealing business for good after the near-debacle in Lisbon.

Well-intentioned but harebrained is a fitting moniker for a lot of OSS activities. Its paramilitary operations in Europe and Asia, while undeniably brave, were assessed as being of little value to the overall war effort by the Army and the Navy. This was good stuff for movie plots, not winning wars, in the opinion of most generals and admirals, who were unimpressed by much of the intelligence Donovan was getting.

OSS also birthed the first formal “intelligence analysis” shop, Research and Analysis, which was staffed by leading academics and scholars in myriad disciplines who were brought into the war effort. Many of R&A’s leading lights were Ivy League dons but their overall impact on the war effort was low since their assessments, with few exceptions, were limited to the SECRET level and, here again, their lack of access to ULTRA, the war’s genuine intelligence triumph, was crippling. While CIA analysts to this day look to R&A as a model of excellence, you will search in vain for many scholars of such wartime caliber at Langley now.

There was one part of the OSS that lived up to its reputation, yet it’s the element that almost nobody knows about. That was X-2, the counterespionage branch, which was small, select, very hush-hush, and closely mentored by the British. It was also the only OSS element cleared for ULTRA, which it used to good effect in rooting out Axis spies in many countries. However, X-2 was tarnished in the long run since it gave CIA James Angleton, the genius/flake who headed Agency counterintelligence from 1954 to 1974, until reverberations from the Watergate scandal caused his downfall. Angleton is a widely misunderstood character, yet it cannot be denied that his emergence from X-2, where he was a real star, have unfairly tarnished that fine little outfit’s historical reputation.

OSS didn’t really die, of course, its parts were divvied up between the military and the State Department, only to be reassembled in 1947 with the birth of CIA, which claims the legacy of Donovan’s organization (some of it is likewise claimed by the military’s special operations community). Unfortunately, many OSS bad habits continued too, particularly a slipshod attitude towards counterintelligence. Early Cold War adventures such as dropping agents and supplies to resistance movements in Soviet-occupied Eastern Europe, which continued well into the 1950’s, were across-the-board failures, since all these daring, well-intentioned CIA operations were thoroughly penetrated by Soviet spies. They were compromised before they ever took place.

There are aspects of the OSS legacy that all American intelligence officers today should be proud of. Its can-do attitude and its intrinsic bias for action are things that today’s risk-averse IC could use a strong dose of. But doing espionage the OSS way, shooting before aiming while not taking counterintelligence seriously, will lead to more problems than solutions. Moreover, militarizing CIA, which is proceeding rapidly, is certain to cause troubles in the long run. CIA and the Intelligence Community need to do better. Assessing the OSS legacy honestly would be a good start.