Small Wars Journal

Malcolm Gladwell, Insurgent Strategy, and the Primacy of Strategic Flexibility

Thu, 06/19/2014 - 7:09am

Malcolm Gladwell, Insurgent Strategy, and the Primacy of Strategic Flexibility

Samuel R. Greene


Malcolm Gladwell uses high pressure defense as a metaphor for insurgency in his newest book, David and Goliath. The lesson he draws is that the weaker party should always choose asymmetric strategies. Just as a full-court press can help a weaker basketball team defeat a stronger opponent, insurgency should be the strategy of choice for a weaker side in a conflict. This thesis is representative of many arguments that a monolithic approach to insurgency or counterinsurgency can be successfully applied across many different conflicts. This paper argues instead that the decision to wage an insurgency as opposed to conventional war, as well as a government’s response to an insurgency, should be dependent on the context of a given conflict. Through an analysis of pressure defense in basketball and soccer as well as brief case studies of successful and unsuccessful insurgencies, this paper demonstrates that the desirability of a strategy of insurgency varies from case to case.


Malcolm Gladwell links a strategy of insurgency to the strategy of high pressure defense used in basketball and soccer in his newest work on underdogs. In David and Goliath, Gladwell weaves together the academic research of Ivan Arreguín Toft and the unlikely success of an inexperienced middle school girls’ basketball team with his customary clarity and humor.[i] But his use of high-pressure defense as a metaphor for insurgency leads him to treat asymmetric warfare as a monolithic strategy that invariably offers the weak the best chance of success, and indeed an advantage over conventional “Goliaths.”

Unfortunately, Gladwell has repeated an all too commonly held fallacy that suggests, with apologies to Tolstoy, that successful insurgencies and counterinsurgencies are all successful in the same way.[ii]  In both sports and insurgency, nothing can be further from the truth. Just as the success of high-pressure defending in sports varies depending on a wide range of factors, so the likelihood of success in insurgency varies case by case. Arguing, as Gladwell does, that “David can beat Goliath by substituting effort for ability—and substituting effort for ability turns out to be a winning formula for underdogs in all walks of life, including little blond-haired girls on the basketball court” turns a strategy that is useful in certain contexts into a mantra that has little basis in reality.[iii] Instead, good strategic decision-making comes from an accurate understanding of the specifics of a particular reality, including the strengths and weaknesses of the home team and away team as well as the external environment.

High Pressure Defense and Insurgency

High pressure defending in soccer and basketball is a strategy that is useful in certain conditions. It involves applying defensive pressure close to the opponents’ goal or basket, disrupting their ability to establish an offence and rewarding the team applying pressure with easy scoring opportunities. Gladwell uses the success of a successful girls’ basketball team that employed full court pressure as a substitute for traditional basketball skill as an analogy for the advantages of asymmetric strategies of warfare.

Teams that are good at pressing tend to have certain advantages. Pressure requires high levels of fitness, which can be trained, but also high levels of athleticism and speed, which are part of team selection—coaches who employ high pressure tend to prize athleticism, sometimes at the expense of other qualities.[iv]

Similarly, teams that are defeated by pressure often have technical deficiencies. In soccer, high pressure takes advantage of the likelihood of defenders to have limited technical skills. In basketball, pressuring the inbounds takes advantage of space and time constraints to punish weak ball handling. However, teams with excellent technical proficiency and good preparation (or a speedy point guard like NBA Hall of Famer Garry Payton) can have great success against pressure.[v] In fact, many leagues limit pressure in basketball in youth development leagues because young players have not yet developed the necessary technical skill to combat such strategies. Further, in soccer, the terrain and conditions are variable—high pressure may work better on a midwinter game in hailstorm on a frozen field than on a pristine field in 80 degree weather. Strategies in sports cannot be applied uniformly.

For this reason, particularly the highest levels, high pressure is usually one tool in a broad strategic toolbox. Coaches who only employ one strategic framework are an aberration; Jose Mourinho, one of the most successful managers in world soccer, argues that a successful manager has “…to be ready to change it [strategy] around…” depending the abilities of his players and other conditions.[vi] The strategy canon echoes these sentiments; long ago, Sun Tzu wrote that “just as water retains no constant shape, so in warfare there are no constant conditions. He who can modify his tactics in relation to his opponent and thereby succeed in winning, may be called a heaven-born captain.”[vii]

Yet Gladwell, drawing on the work of Ivan Arreguín Toft, uses an analogy from sports to argue for a universal advantage of insurgency for a weaker actor. In How the Weak Win Wars, Arreguín Toft suggests that a historical study of insurgencies shows that stronger powers nearly always defeat weaker forces when both sides use traditional tactics. However, he contends, on the basis of a data-set of conflicts between 1816 and 2003, that asymmetric tactics have a much better likelihood of success than symmetric conflict. Similarly, if conventional forces resort to what Arreguín Toft calls “barbarism” against asymmetric conflict, they have a much higher likelihood of success.[viii]

Gladwell uses this account to argue that non-conventional strategy is always the better choice for the weaker actor. The thrust of Gladwell’s interpretation of Toft suggests that high pressure or insurgency is ipso facto the ideal strategy for the weaker side; “Logically, every team that comes in as an underdog should play that way, shouldn’t they?” Insurgency will not always result in victory for the weak, but it will invariably give them the best chance of winning. George Washington’s attempt to develop a conventional army after early success with asymmetric strategies was by this reading profoundly misguided.[ix] However, Gladwell suggests that many weak powers are reluctant to adopt counterinsurgent methods because they are challenging and fail to fit with conventional practice; “It is easier to dress soldiers in bright uniforms and have them march to the sound of a fife-and-drum corps than it is to have them ride six hundred miles through snake-infested desert on the back of camels…Underdog strategies are hard.”[x] What sets apart successful underdogs is a can-do “attitude” and a willingness to disregard the established logic of creating a force equipped for traditional strategies in warfighting or sport.  High pressure defense or its military equivalent of asymmetric warfare is invariably the best strategy in the face of a numerically superior and better equipped “Goliath.”

The problem with this argument is that not all “Goliaths” are made equally. Stronger powers vary in both commitment and quality. Just as a good passing team can often defeat high pressure defending while a team with limitations in ball control might struggle, so too does the composition and expertise of a traditional power vary. Some Goliaths possess considerable manpower but limited quality in their military forces or commitment to the conflict among their soldiers and their populace. Others may possess forces well-disposed to waging counterinsurgency. “Davids” are also made differently. In some cases, the weak foe can build a conventional force that can defeat the traditional power, while in other cases limitations in the composition of forces, divided popular support, or unsuitable terrain make asymmetric warfare a poor choice.[xi] Brief studies of historical cases illustrate the importance of context.

The Importance of Context: Examples of Insurgency and Counterinsurgency

In considering cases of insurgency, I use cases that describe four different archetypes of potential conditions. Only in two of them is insurgency an ideal strategy. In some cases, conditions are not well suited to insurgency, such as in the United States at the time of the American Revolution or the Malaysian Emergency. Alternatively, conditions may be well suited to conventional strategies, such as in the first phase of the Salvadoran Civil War. In such circumstances, adopting a strategy of insurgency would not be optimal. In contrast, some cases are not well suited to conventional warfare, as occurred in the second phase of the Salvadoran conflict, or are particularly conducive to insurgency, such as the Arab revolt. In such circumstances, insurgency is likely the best approach.

Table: Four Archetypes

Traditional “powers” are not always conventionally strong

The Salvadoran Civil War provides a useful example of weakness in the stronger power. The Salvadoran government was clearly the stronger party at the onset of the conflict in terms of numbers, but its army had considerable institutional weaknesses. In the first stage of the civil war, the Frente Farabundo Martí para la Liberación Nacional(FMLN) was able to wage a successful traditional campaign—while the rebels were not able to compete in terms of absolute numbers, they were able to compete in quality and raise a substantial number of forces that could go toe to toe with the Salvadoran Army. Indeed, the FMLN was on the brink of winning a conventional campaign in the early 1980s until the US provided a massive amount of military assistance to the Salvadoran armed forces beginning in 1983.[xii]

Six billion US dollars in assistance served to turn the government army into a true Goliath, leading the FMLN to change their strategy to waging an insurgency that would prevent the government from outright victory and force a negotiated settlement that would achieve many of the FMLN’s political goals.[xiii] The US government’s efforts at making the Salvadoran Army an effective COIN force largely failed; instead, the armed forces and paramilitary groups alienated much of the population through brutal violence against non-combatants that did little to defeat their opponents. At the same time, the FMLN successfully transitioned to a guerilla strategy, resisting the far greater conventional force of the Salvadoran Army with the support of much of the country’s rural population and using its mobility to conduct guerilla operations that prevented government victory.[xiv]

Adopting such a strategy in 1980 would have limited the group’s possibility of defeating the government outright. Failing to adapt to massive infusion of US aid would have likely led to the group’s demise. Instead, the FMLN demonstrated strategic flexibility in changing their strategy as conditions in their environment changed, and were rewarded by a peace settlement that addressed many of the FMLN’s goals and led to the group becoming one of two dominant political forces in El Salvador—in 2009 and 2014, the FMLN candidate won the presidency.[xv] The decision to adopt a strategy of insurgency came in response to environmental changes. Adopting an insurgent strategy earlier would have limited the FMLN’s ability to challenge the regime for control of the country.

Insurgents cannot always swim like the fish

Mao famously observed that the insurgent should be inextricably linked to the broader population; in “…the relationship that should exist between the people and the troops[,] the former may be likened to water and the latter to the fish who inhabit it.” For Mao only the “undisciplined” turn the people away from the insurgency and cause the guerilla to become “like the fish out of its native element.” [xvi]

Yet sometimes swimming in the population is a difficult undertaking. One important example is Malaysia, where the British successfully used ethnic differences to frame perceptions of the insurgent campaign as ethnically driven. By defining the anti-government campaign in ethnic terms, the British were able to mobilize the majority Malay population against what they perceived to be a minority Chinese insurgency, easing the task of separating the insurgents from popular supporters.[xvii]

Similarly, the scope of Loyalist support in much of the US (and the indifference of much of the population) calls Gladwell’s criticism of George Washington into question. Historian Robert Calhoon estimates that about 15-20% of the settler population actively supported the British, while a significant number remained neutral. He finds that the “patriots received active support from perhaps 40 to 45 percent of the white populace,” and many Native Americans and slaves actively supported the Loyalists, rendering a classic insurgency difficult.[xviii] In the context of relatively limited support, Washington’s decision to develop a conventional force is a more sensible strategy than Gladwell credits.

Some ‘weak’ forces are well prepared for insurgency while others are better suited to conventional war

T.E. Lawrence’s Bedu were uniquely prepared for the type of war fought—far from being only “untrained rabble” as Gladwell suggested in quoting a contemporary description of the Bedu, their lives made them ideally suited to insurgency and less suited to traditional combat.[xix] Consider Wilfred Thesiger’s description of the Bedu with whom he crossed the Empty Quarter; “Bedu notice everything and forget nothing… These tribesmen are accustomed since birth to the physical hardships of the desert, to drink the scanty, bitter water of the Sands, to eat gritty unleavened bread, to endure the maddening irritation of driven sand, intense cold, heat, and blinding glare in a land without shade or cloud.”[xx] Such troops are the stuff of a desert insurgent’s dreams.

Gladwell is right to praise Lawrence’s strategic ingenuity. But rather than learning that the weaker foe should necessarily adopt insurgency, Lawrence’s story is one of matching available resources with the strategic context of the operation. Given both the abilities of his forces and the uncompromising desert terrain that would make conventional combat difficult, as well as the fact that Lawrence’s opponents were particularly vulnerable to his attack, his selection of a strategy of insurgency was similar to a manager adapting a strategy to suit the strengths of his or her team and the weakness of opponents. T.E Lawrence’s approach would have been unsuccessful with lesser allies—many failed insurgencies suffered because they lacked the hardiness and familiarity with the terrain that the Bedu possessed. Similarly, it is difficult for a squad of mediocre athletes to successfully apply high pressure defense. 

Conclusion: Attitude vs. Strategic Flexibility

Perhaps most problematic about Gladwell’s lack of attention to context is the broad implications it has for strategy.  Gladwell suggests that success in sports and insurgency is largely based on a willingness to adopt a particular approach. Because he suggests that insurgency is a difficult and unpopular strategy, success is also linked to a proper attitude that rejects conventional wisdom and embraces challenge.

Absent is a discussion of matching strategy with existing resources and forces and linking it to a particular environment. This flaw is certainly not limited to Gladwell, though he has a wider reach than most writers on asymmetric conflict. But the gospel of counterinsurgency has frequently been preached with a similar tone by members of the policy community who hope a particular approach or strategic framework can be applied across a host of very different insurgencies.[xxi] From Vietnam to Afghanistan and Iraq, the search for the “right” leader with the proper attitude and convictions to apply the correct approach has frequently been held up as the key to victory.[xxii]

Many of the doyens of strategic decision-making suggest instead that understanding the strategic context of a conflict should shape a state or an insurgent’s actions. An accurate assessment of both the global and regional environment as well as of the specifics of a particular reality is crucial for the strategist to craft the optimal approach to a given situation.[xxiii]

Indeed, bad decisions and ensuing strategic failures often come from an inaccurate understanding of the context—flawed assumptions about such factors as the extent of popular support for an insurgency (Iraq) and the capability of U.S.-backed government forces to oppose an insurgency (Vietnam), for example, have certainly played a role in suboptimal U.S. policymaking.[xxiv] Both of these failures have something else in common with Gladwell’s discussion of insurgency—a commitment to a particular approach to solving a problem rather than strategic flexibility.

Gladwell’s account of insurgency is thus doubly flawed. It is neither an accurate accounting of pressure defense as a fundamentally successful strategy at high levels of sport nor does it accurately reflect how strategic decisions should be made. In conflict and sports, sound strategic assessment and the flexibility to craft an approach that best reflects a particular reality is the recipe for successful strategy, not a can-do attitude toward applying a strategic dogma.

End Notes

[i] Malcom Gladwell, David and Goliath (New York: Little, Brown, 2013). An earlier version of his argument was presented in “How David Beats Goliath” The New Yorker (May 11, 2009). All quotes refer to the 2013 book unless otherwise noted.

[ii] See for example the claim that “good COIN practices run in packs” in Christopher Paul, Colin Clarke, and Beth Grill, Victory Has a Thousand Fathers: Sources of Success in Counterinsurgency (Santa Monica: RAND, 2010), 83, 92-93.

[iii] “How David Beats Goliath.”

[iv] Anson Dorrance, who has won 22 national championships at the University of North Carolina, has been criticized for preferring athleticism and size to technical skill in the high pressure 3-4-3 that he employs.

[v] For an example of how a skilled team that is prepared to face pressure can pass out of the press, see Bob Hurley, “End-of-Game Press Break ‘Flood’” (

[vi] Quoted in Gianluca Vialli and Gabriele Marcotti, The Italian Job (London: Bantam, 2006), 175-176.

[vii] Sun Tzu, The Art of War 6:32-33

[viii] Ivan Arreguín Toft, How the Weak Win Wars (New York: Cambridge University Press, 2005). Arreguin Toft, however, notes that developed states are increasingly less willing to engage in barbarism due to its political costs.

[ix] Gladwell, 30-32.

[x] Gladwell, 32.

[xi] See David Kilcullen, The Accidental Guerilla (New York: Oxford, 2009); Bard O'Neill, Insurgency and Terrorism (Herndon: Brasseys, 1990).

[xii] William Stanly, Protection Racket State (Philadelphia: Temple University Press, 1996), 226-228.

[xiii] John Booth, Christine Wade, and Thomas Walker, Understanding Central America (Boulder: Westview, 2006), 200-201; William Robinson, Transnational Conflicts: Central America, Social Change, and Globalization (New York: Verso, 2003), 89-90.

[xiv] See Tommie Sue Montgomery, Revolution in El Salvador 2nd edition (Boulder: Westview, 1995); Mark Peceny and William Stanley, “Counterinsurgency in El Salvador” Politics & Society 38 (March 2010): 67-94.

[xv] Samuel Greene and Stacy Keogh, “The parliamentary and presidential elections in El Salvador, March 2009” Electoral Studies 28 (2009): 666-669.

[xvi] Mao Zedong, On Guerilla Warfare trans. Samuel B. Griffith (Newport: Naval War College, 1950), 92-93.

[xvii] See Gian Gentile, Wrong Turn (New York: New Press, 2013), 35-58.

[xviii] Robert M. Calhoon, “Loyalism and Neutrality” in A Companion to the American Revolution Jack Greene and J.R. Pole eds. (New York: Wiley, 2000), 235. Italics mine.

[xix] Gladwell, 24.

[xx] Wilfred Thesiger, Arabian Sands (New York: Penguin, 1991), 52.

[xxi] See Paul, Clarke, and Grill, Victory has a Thousand Fathers.

[xxii] On the similar logic was present in many discussions of the merits of applying the strategy of the surge in Iraq to Afghanistan see for example Rick "Ozzie" Nelson, Nathan Freier, and Maren Leed, “Iraq versus Afghanistan: A Surge Is Not a Surge Is Not a Surge” (

[xxiii] See Terry Deibel, Foreign Affairs Strategy (New York: Cambridge University Press, 2007); 35-76.

[xxiv] On this point, see Richard Neustadt and Ernest May, Thinking in Time (New York: Free Press, 1986), 134-156.


About the Author(s)

Samuel R. Greene is an Assistant Professor of Strategy and Strategic Studies, National Defense College, Abu Dhabi, UAE and Near East South Asia Center for Strategic Studies, Washington, DC. The views expressed by the author are his own and do not reflect those of the National Defense College, the NESA Center, or any other entity.



Thu, 07/10/2014 - 3:00pm

The table for the four archetypes have two of the same headings ("Conditions well suited to insurgency") Is this correct, or should there be a "conditions not well suited to insurgency" heading??

Ned McDonnell III

Tue, 06/24/2014 - 8:01am

In reply to by Ilsa van den Broeck

Ever since I gave up half way through his first book, 'Tipping Point', I have found Malcolm Gladwell to be annoying through an unswerving instinct for the profoundly superficial. It seems to me that successful insurgencies have to mature into traditional fighting forces eventually to hold territory, particularly cities. The countryside can choke the cities off but the rising force must win legitimacy as the (near) monopolist of violence in its own right.

Ilsa van den Broeck

Mon, 06/23/2014 - 5:04am

I read this article with interest, as I have not read "David and Goliath" yet.
Considering General Sir Reginald Wingate's lifetime of experience in North Africa and the Middle East, I am not sure dismissing him as a "contemporary description" makes a lot of sense.
Secondly, although I tend to agree that insurgency is not always the best answer for a smaller group against a larger group, it is the way to bet. In addition, "insurgency" and "asymmetric warfare" are not are not always the same thing, which your article seems to lean in the direction of them always being the same.
Thanks, and I am sorry if I come across as harsh.