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Malcolm Gladwell, Upsets, and Red Teaming

In the May 11, 2009 issue of The New Yorker, Malcolm Gladwell penned a fascinating study of what happens when underdogs break the rules. The article has relevance to red teaming as Gladwell examines the studies of political scientist Ivan Arreguín-Toft:

David’s victory over Goliath, in the Biblical account, is held to be an anomaly. It was not. Davids win all the time … at every war fought in the past two hundred years between strong and weak combatants. The Goliaths, he found, won in 71.5 per cent of the cases…. Arreguín-Toft was analyzing conflicts in which one side was at least ten times as powerful—in terms of armed might and population—as its opponent, and even in those lopsided contests the underdog won almost a third of the time.

In the essay, Gladwell uses basketball and the full court press as an analogy for unorthodox means by which less talented but more motivated and harder working basketball teams can achieve parity against teams which are talent-rich.
      Gladwell then continues along this line of reasoning and describes Lawrence of Arabia’s surprising victory against the Turks in the Battle of Aqaba. Lawrence utilized a military tactic similar to the full court press, by substituting effort and daringness–crossing a vast stretch of desert–to compensate for the lack of weaponry and equipment. The Turks, believing they were safely ensconced, were completely routed by Lawrence’s Bedouin force.
      Gladwell’s main argument can be distilled into the following points:

  • Effort can trump ability.
  • The underdog has the best means to defeat a superior enemy only when it does not play by the rules of the game.
  • Surprise is essential, and creating havoc in an opponent’s decision making cycle often confuses the enemy, overloads their processing ability, and breaks down their ability to coherently respond to an unstable situation.

      Gladwell is a great writer and his insights into red teaming, general psychology, and “upsets” are worth reviewing. But ultimately none of the main points in the essay should surprise students of military history.
      A particularly misstated moment occurs when Gladwell writes that “Insurgents, though, operate in real time.” This seemingly innocent observation seems to preclude that counterinsurgents or Goliaths operate absent of real time. Time is literally no more suspended for the underdog than for the expectant victor. A better way to describe what Gladwell perhaps intended to convey is that “Successful insurgents or combatants who are underdogs achieve initiative and possibly victory through speed, effort, and surprise.” And while Gladwell uses the Lawrence of Arabia historical vignette, multiple historical vignettes have, in fact, illuminated these principles: Washington crossing the Delaware against the Hessians during the Battle of Princeton (surprise-effort), Mao’s Long March (effort) to avoid total destruction by Nationalist forces, and even Japan’s attack against Pearl Harbor (surprise-effort).
      But the three examples provided above and the Lawrence of Arabia analogy used by Gladwell only describe tactical success. Mao and Washington did not win their revolutionary wars because of one surprise victory but because they were successful for a prolonged period and in multiple areas (excellent leadership, disciplined force, and a general mastery of the principles of war). The Japanese, on the other hand, ultimately failed in their endeavor to tip the scales in the Pacific theater despite having achieved complete surprise at Pearl Harbor.
      Tactical surprises are commonplace, and underdogs seek to employ them at every opportunity. In a sustained campaign, however, events that were once deemed surprises can quickly become viewed as commonplace events (for example, the use of improvised explosive devices, or IEDs). Therefore, underdogs often need more than tactical surprise to achieve strategic victory. Even in the basketball game analogy, a full court press can possibly win a game, but to win the season requires more then just a team that employs a surprise tactic.
      The takeaway, then, is that red teaming analysts need to analyze both “normal” and surprising events. To use another sports analogy, boxers are felled both by the hard punches they absorb as well as the punches they fail to see coming. One lucky punch doesn’t always end the match. Likewise, organizations that are adaptable and have strong underlying basics should not feel threatened by the occurrence of “black swans.” Strong leaders and smart intelligence officers understand this concept, and hence planning for any campaign always combines consideration of not only the most likely course of action but also the most dangerous course of action (usually the shocking and surprising event).
      Another interesting counter to Gladwell’s main points can be found in a letter to The New Yorker by Ben Jacobson:

And there is some danger in adopting a philosophy of achieving short-term goals at the expense of the organization’s long-term health. Of course, guerrilla armies and startup companies have little to lose—they either win or die, so the lesson for them is clear. But should those lessons be applied to the rest of us? Real innovation lies not in David-like strategies but in recognizing the right contexts in which to use them.

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