Small Wars Journal

Winning Insurgent War and Pragmatic Libertarianism

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Last Spring, about 4,500 copies of the book Winning Insurgent War: Back to Basics were distributed to various schools within the US military education system.  A ‘Second, Slightly Improved Edition,’ has come back from the printers and will be delivered soon, hopefully before this Christmas, 2011.  Lost copies and knock-off printings of the first edition can be bought on-line.  As its cover insists, it is not a military manual, and its contents are tolerated rather than endorsed by the US Army hierarchy.  Its publication owes to the existence of a peculiar unit at Ft. Leavenworth to which, for more than a quarter century, the US Army has given unique leeway to choose and develop subjects for research and writing.[i]  The book, in other words, is not doctrine.  It launches its discussion from observations about impunity and anonymity, then to many related topics in 144 sections.  It also invites those interested in influencing the outcome of ‘internal’ armed conflicts to weave together ideology, politics, methodology, intelligence practices, operations, and strategy as seamlessly as possible.

Whether or not the book achieves that synthesis, the author felt that the attempt itself required a more-or-less visible and fixed ideological azimuth.  This feeling came partly on the heels of an observation that the general run of literature on COIN (counterinsurgency) proceeded from wobbly, if un-admitted, political philosophy.[ii]  This in turn seemed to have a channeling effect on the development of the suite of available ideas about plans and projects, with predictably unpredictable consequences in practice.  For instance, a hidden statism might induce acceptance of the term ‘failed state’ as describing an elemental societal defect.  Just that one little philosophical predisposition could lead to programs intended to strengthen a central government, with results that might not be applicable to a local culture or in line with American principles.  The political philosophy of Winning Insurgent War is at least supposed to be visible, if not entirely consistent or explainable.

Basics.  The subtitle of the book is “Back to Basics,” which begs the obvious question: “So… what basics? The classic principles of military strategy?” Yes, but Winning Insurgent War also argues for moving the balance of intellectual attention back toward a more traditional empiricism, toward what some Marxists and Maoists might call the “objective” conditions, and away from too much love of the magical, spun or solipsistic reality.  ‘Back to basics’ reminds to not be so overwhelmed by technological changes that we suppose them to override the historical lessons of warfare.  Technology is important, and the winners will often be those who wield it best, but while new gizmos change the speed of things, they cannot be said to change principles.  Consider a couple of passages from the prologue to Saul Alinsky’s Rules for Radicals:

What is the alternative to working inside the system?…Spouting quotes from Mao, Castro, and Che Guevara, which are as germane to our highly technological, computerized, cybernetic, nuclear-powered, mass media society as a stagecoach on a jet runway at Kennedy airport?[iii]

Remember, we are talking about revolution, not revelation.  You can shoot too high as well as too low.  First, there are no rules for revolution any more than there are rules for love or rules for happiness, but there are rules for radicals who want to change the world; there are certain central concepts of action in human politics that operate regardless of the scene or the time. To know these is basic to a pragmatic attack on the system.[iv]

Alinsky asserts that the shibboleths of revolutionary icons are remote to the environment of new technologies.  He simultaneously offers that there are some principles the revolutionary can still follow.  Winning Insurgent War spouts a lot of quotes, including from military commanders like Grant and Napoleon.  At one level they may seem hardly germane in a war of remotely controlled aerial vehicles.  Still, those quotes illustrate timeless lessons that the warrior can gainfully apply to a wide plane of situations.[v]

Not left, right, or middle.  For lack of a better term, Libertarian Pragmatism, or perhaps Pragmatic Libertarianism, seems to work as a label for the political-philosophical drift of the book.  It is just too much work to explain exactly what that hybrid is or does.  What it tries not to do, however, is fit along some spectrum of left-to-right, conservative-to-liberal, or Republican-to-Democrat.  When Jay, Madison, Hamilton and their collaborators discussed their revolutionary enterprise, they did so without reference to some imaginary left-right ideological spectrum, that paradigm being instigated in the context of the follow-on French Revolution.  The Americans had not set their identity as the simple polar opposite to kings and bishops; they aimed to create an enlightened social contract in which individual liberty could flourish, men might self-govern and the geography of collective control would be as local as practicable.  Earlier, the actions that would place American theory in time and space were announced to the world in a document, the Declaration of Independence, which was less about social contract, and more about defiance and the legitimacy of violence.  So Winning Insurgent War tries to find inspiration in both the classic liberalism of the founders as well as the existentialism of the founding.

The book was inspired almost as much by a rejection of ideas as by adoption or proposition.  Among those rejected: that, a. winning was somehow an unsophisticated or unreasonable goal, b. insurgent conflicts were necessarily slow processes, c. good guys were more often counterinsurgents than insurgents, and, d. the classic principles of military strategy did not apply.

This list of rejections is a strawman to be sure, since few practitioners or theorists actually assert those positions in their extreme form.  The suite of contentions presents a high bar of proof, too -- a bar artificially lowered by finessing a set of definitions regarding what it means to win, how much time a ‘short’ period contains, and how one determines goodness.  Tautological sins aside, the arguments are still clear enough.  Maybe just the simple consequences of the author’s attitude, they do not have to rise to the status of philosophy to still be useful.  Many of the flourishes placed at the end of the book’s sections are supposed to expose solidarity with both the attitude and the philosophy.  The libertarian part favors (in the context of a thoughtful social contract) weighting toward individuals and voluntary associations against concentrated power.  The pragmatic part recognizes moments for abandoning theory altogether and just going right to a punch in the face.

Oath. A secret army, midwife to the revolution, was mustered before the revolutionaries’ public declaration of purpose.  Once revealed and then victorious, that Army did not afterwards buttress a political party or a race of people, but rather an experimental and fragile social contract evidenced by a piece of written law.[vi]  There is no quick way to explain all the knots binding the various allusions in Winning Insurgent War, and some of the book’s flourishes are of admittedly little weight.  The book, nevertheless, is about something important.  It is about the purpose of the professional soldier, and especially the purpose of the professional American officer.

American soldiers take an oath to defend the Constitution of the United States of America against all enemies foreign and domestic.  Curiously, once given, the oath is followed by a career during which there is almost no guided discussion regarding what the Constitution says or means or how it came to be -- an irony supported almost by definition as an aspect of American military professionalism.  Such discussions might be overly political.  Indeed they could be nothing less, but now, living in a world in which the validity of the Constitution is itself being questioned and new wars are labeled as counterinsurgencies, one has to wonder what such an oath means.

Winning Insurgent War proposes indirectly that we actively weave ideology into our decisions; be ideological; allow ideology to define lesser words like ‘legitimacy,’ a quality of condition which professors and politicians decorously order American officers to achieve, to implement, to effect.  Tall orders to be sure.  They can be followed, however, perhaps best of all by Americans, because Americans are still equipped and moved by their ideological inheritance to perceive honor in these conflicts, and they remain willing to put their lives and souls at hazard.  Hopefully, the book is not just about winning, but about winning in light of an oath.

Pulp.  The book has a luxuriant cover featuring a beautiful woman in a verdant landscape.  The woman is both Miss Liberty and Miss Justice, abstractions to which we traditionally assign female images.  There is also an assortment of other characters, real and fanciful, the whole scene being contemplated in the foreground by a less attractive Sherlock Holmes.  On the interactive version of the cover, the visitor can find ‘Easter eggs’ that release a variety of members of the animal kingdom.[vii]  The cover gives the work a first impression intended as a retreat from the affected tonal weight of the general run of strategy books.  The whimsicality, on the cover as in the text, serves to lighten the existentialism drill.  There are things -- like filth, venality, desperation, rape, epiphany, atonement, dishonor, gore, nihilism -- not generally mentioned in manuals about where to place various pieces on the battlefield, but which cannot readily be separated from violent conflict as actually lived.  The movie Pulp Fiction goes right at those things, and yet remains whimsical if not comedic in doing so.[viii]  Winning Insurgent War is no way as entertaining as Pulp Fiction, but at least invites strategy planners to reconsider Tarantino-like postmodern impressions.

In spite of the book having a subversive style intended to help contain human vicissitude, it also addresses a considerable number of simpler topics that go generally un-noted in the rest of mainstream strategy literature.  Section titles, for instance, include Poop, Heavy Machines, The Doomsday Book (about inventorying), School Lunches, Taxation and Debt, Anonymity, GIS, Roadblocks and Checkpoints, Dogs and Mules, Sex, and so on.

Beauty.  It is exactly the hostage condition of the beautiful woman on the cover that Sherlock is investigating.  Perhaps her name is Hedy Remedios Guzmán Lamarr.  Supposing most readers will know or be able to google who Hedy Lamarr was, the important features of her life that help weave together themes in Winning Insurgent War include that she: escaped both from an oppressive marriage and, having Jewish ancestry, from Nazi Germany; invented a frequency-skipping device which is to some degree technically and epistemologically the counterpart to the chaff invented by R. V. Jones to fool German radar; loved  life, but was expressly willing to kill; came to America; understood the real world of math and physics; but nevertheless was an actress.  Remedios is a character in Gabriel Garcia Marquez’ novel Cien Anos de Soledad.[ix]  With many of the same metaphorical qualities as Hedy Lamarr, Remedios had a purely incorporeal as well as physical nature, and usefully represents an element of Colombian self-concept.  Guzmán is also a Colombian reference, in this case to a gorgeous real-life model turned pet of a vicious drug lord.  Finally, she is emblematic of simple material desire.  In other words, the girl on the cover is what we fight for, and her abuse what we might fight against.  The socio-political condition allowing that abuse is summarized in the book as the granting of impunity.  Winning is thus defined as gaining or regaining the (hopefully but not necessarily virtuous) monopoly over the granting of impunity.

Zombies.  One might have figured Marxism-Leninism would shrivel up completely after the Soviet Union slipped quietly into the dustbin.  It did die, but its wretched shell staggers around trying to tear at what killed it.  Still here and still annoying, its corpse is called post-structuralism, a catch basin philosophical tendency that, when deconstructed, seems in most manifestations to be little more than anti-Americanism with some gory make-up.[x]

Impunity is the avoidance of punishment and as such the book’s premise about winning revolves around the capacity to punish or to deny that capacity.  Mens rea is the intellectual authorship of behavior a society deems illegal or immoral, and therefore subject to punishment.  Winning Insurgent War postulates mens rea as a singularly useful concept, given that the geography of mens rea often can be pinpointed and its influence neutralized.  Poststructuralists devalue the idea of punishment, and the related concept of mens rea, as being Western cultural system flaws.

Partly in light of that reasoning, the book posits poststructuralism as a philosophical delinquent.  Luckily, since poststructuralism has as yet no sophist card-carrying members who might claim personal insult, the author felt on safe ground bureaucratically to place a lot of anti-American ‘isms’ under the term’s ugly span.  On the other hand, “speaking truth” to power is supposed to be definitive poststructuralist action.  This fact “problematizes” (a favorite poststructuralist term) the anti-poststructuralist bile of Winning Insurgent War, because the poststructuralists are not all or always wrong.  The Constitutional framers were all about preventing the concentration of power, and were champions of citizen redress.  Saul Alinsky was, after all, an American product, too.  There is, however, no praise in Winning Insurgent War for the artificial or opportunistic creation of polarizing grievances, the destruction of wealth, or the violent reconcentrating of power in an intellectual or political vanguard.  Those exercises are for our Marxist-Leninist zombies.

Quips and Quotes.  Each of the 144 section titles is preceded by a lede notion.  Many of them are supposed to summarize a major point of the section, but the first, being the first words of the book’s text, are “He didn’t ask Al if he wanted fries with that.”  It references the most basic emotional underpinning of rebellion (disdain, contempt, scorn).  To better understand the concept’s energy, see the Urban Dictionary.[xi]  The last words of the book’s text (not including the Restatement or the Synthesis), are “License to Kill,” the title of the 2007 James Bond movie.  As we are aware, James was given a license to kill from none other than the archetypal sovereign of our age, Her Majesty, the Queen.  The movie quote is of uber-gangster Franz Sánchez warning 007: “Señor Bond, you got big cojones. You come here, to my place, without references, carrying a piece, throwing around a lot of money...but you should know something -- nobody saw you come in, so nobody has to see you go out.”  Bond, James Bond, is packing the empire’s antidote to defiant attitudes.  For the moment, however, James is in a bit of a bind.  The secrecy that gained him entrance into Sánchez’ lair also threatens Bond’s anonymous disappearance.  Alexander the Great, for his part, admired the captured pirate for his great boldness, but executed him anyway; Alexander was not going to put up with anyone else granting impunity in his great realm.

The quote used after the book’s Restatement is of another uber-gangster, Frank Costello, Jack Nicholson’s despicable character in the 2006 movie The Departed, saying, “I don’t want to be a product of my environment. I want my environment to be a product of me.”  Relevant here is not so much his amorality, but Costello’s attitude toward his surroundings.  There is another movie quote, from the book and movie No Country for Old Men that did not make it into Winning Insurgent War, but which should have.  It provides context.

“The crime you see now, it's hard to even take its measure.  It's not that I'm afraid of it.  I always knew you had to be willing to die to even do this job.  But, I don't want to push my chips forward and go out and meet something I don't understand.  A man would have to put his soul at hazard.  He'd have to say, "O.K., I'll be part of this world."[xii]

Sherriff Tom Bell had not been making his environment a product of him.  He had been responding, but duty came to mean confronting the evil world of the gangsters at the risk of his own soul.  Winning Insurgent War suggests that the new conflicts are a great moral hazard, and yet they can be won, in part, by adopting some of Frank Costello’s confidence that the environment can be shaped, not just met.

Section 7, Nonlinear Warfare, sports a Hemingway quote on the notion that the guerrilla’s first order of business is to stay alive, to “continue to exist” (clearly existential!).  A later Hemingway quote, after Section 143, serves to differentiate insurgency from mere organized criminality.  It contains the necessary ideological and emotional commitment and resolve.  "You learned the dry-mouthed, fear-purged purging ecstasy of battle and you fought that summer and that fall for all the poor in the world against all tyranny, for all the things you believed in and for the new world you had been educated into."[xiii]  Going back to criminality and to the other side of the government/anti-government ledger, the same section includes, immediately after the Hemingway quote, the following from True Grit:

Rooster:  I mean to kill you in one minute, Ned; or see you hanged in Fort Smith at Judge Parker's convenience.  Which will you have?

Ned:  I call that bold talk for a one-eyed fat man.

Rooster:  Fill your hand, you son-of-a-bitch.[xiv]


Hemingway’s is a paean to guerrilla legitimacy, while the writers of True Grit give us the rule of law in a nutshell.  Rooster Cogburn serves process, stating his intention to make an arrest, but if that is not to be, then a death warrant will suffice.  Ned’s response is simple insulting defiance.  So, in a section on the different definitions we tend to apply to organized armed groupings, these two quotes frame two general categories of a single defiance.

Heroes.  Oliver Wendell Holmes and Oliver Wendell Holmes Jr. contribute to the book’s attitude as a father-son pair of American lives.  Oliver senior was a doctor, inventor, and poet.  He was also a pacifist; a condition which guided him to be anti-abolitionist.  Oliver senior felt, correctly, that the zealous work of the abolitionists would lead the country into a deadly civil war.  Oliver junior, meanwhile, grew in his rebelliousness to identify with the movement and determined, in spite of his condition as scion of wealth, to fight.  His dedication to principle brought physical wounds, but also drew his father away from pacifism.  His father could not abide his own inaction in the face, not so much of injustice, but rather of his son’s willingness to confront that injustice, to kill to make better the Constitution’s promise.           Oliver Holmes Jr. today fills space in American military lore as much as anything because of his 1884 ‘Hearts Touched with Fire’ speech.[xv]  He was, moreover, a brilliant jurist who, sitting on the Supreme Court of the United States for three decades, may have influenced the course of American jurisprudence more than any other single man.  Justice Holmes, it can be said, was libertarian and pragmatic, and if Winning Insurgent War has a hero, it is Justice Holmes.  That hero is more likely a mash-up of him, his father, and Sherlock Holmes (Conan Doyle was among the Holmes’ friends, and legend has it that Doyle named his sleuth after one or both of the Olivers).

According to jurist and biographer Richard Posner, Holmes junior was an atheist, but that is by no means certain, and it is not a possible ingredient of his philosophy as adopted for Winning Insurgent War.[xvi]  Holmes was clearly a pragmatist, however, being part of the small crew of thinkers, which included the James brothers, which apparently invented the term.[xvii]  Pragmatism does not have an enforced rubric, and does not, for the purposes of the book, mean situational morality, moral fluidity, or that ‘ends justify the means.’  It is rather a sense of moderation that knows the timing of exceptions.  Admiring Aristotle, Holmes wrote, “He has the ideals of altruism, and yet understands that life is painting a picture not doing a sum,…”[xviii]  Saul Alinsky, the community organizer, evoked pragmatism, but, although a reader can discern overlap of perspective between Rules for Radicals and Winning Insurgent War, the pragmatism of Winning Insurgent War is not that particular pragmatism.[xix]

Without buying too much into some Hegelian love of war as the crucible of character, it might be agreeable, in this season of ‘Occupy Wall Street’ and the comings home of American warriors from the other side of the world, to note another quotation from Oliver Wendell Holmes, Jr. – this one from a speech given to veterans in 1895:

War, when you are at it, is horrible and dull.  It is only when time has passed that you see that its message was divine.  I hope it may be long before we are called again to sit at that master’s feet.  But some teacher of the kind we all need.  In this snug, over-safe corner of the world we need it, that we may realize that our comfortable routine is no eternal necessity of things, but merely a little space of calm in the midst of the tempestuous untamed streaming of the world, and in order that we may be ready for danger.  We need it in this time of individualist negations, with its literature of French and American humor, revolting at discipline, loving flesh-pots, and denying that anything is worthy of reverence—in order that we may remember all that buffoons forget.[xx]

Good bye.  Holmes says, “…when a man disregards current conventions, he must wait for the future.”[xxi]  Hopefully not too long.  The second printing of Winning Insurgent War ends with, “In the immortal words of Jean-Paul Sartre, 'Au revoir, Gopher.'”  Why? Because 1. post-structuralist French philosophers (derided in Sections 99, 100 and elsewhere) uphold Sartre as a chief existentialist forefather; 2. poststructuralists are the zombies of Marxism-Leninism; 3. Bill Murray, playing Bill Murray, pretends to be a zombie in Zombieland in order to not get eaten by the real zombies; 4. Murray is alluding to his role as the counterinsurgent Carl Spackler in Caddyshack; 5. Spackler has a license to kill from the “government of the United Nations"; 6. Gopher is a “Varmint Cong” insurgent tearing up the golf course; and, of course, 7. it’s the end.[xxii]


[i] The Foreign Military Studies Office (FMSO)

[ii] Let’s call this philosophical anosognosia.  That is to say, many of today’s English language strategy authors seem unaware of a disability caused by failure to unfold their ideas behind a defensible philosophical structure.  Worse, perhaps, would be that the authors might, intimately aware of the political philosophy that impels their writing, try to finesse it past the readers.

[iii] Saul Alinsky. Rules for Radicals. New York: Random House, 1971, p. xxi.

[iv] Ibid., xvii.

[v] This relevant maxim from Frederick the Great: “But, I repeat, theoretical knowledge is of no use if it is not supplemented by positive practice.” in Jay Luvass, ed. and translator. Frederick the Great on the Art of War. New York: Da Capo, 1999, p. 290.

[vi] This sentence can certainly be contested by historical example, but the point has been contested in practice, over time, including violently; and that the words and theory of the Constitution have survived, with the practice slowly moving toward the theory.

[vii] <>

[viii] Quentin Tarantino’s film, Pulp Fiction, is not cited anywhere in the book.  Maybe it should be, but the film is too much better. Jules: “See, now I'm thinking: maybe it means you're the evil man.  And I'm the righteous man.  And Mr. 9mm here... he's the shepherd protecting my righteous [self] in the valley of darkness.  Or it could mean you're the righteous man and I'm the shepherd and it's the world that's evil and selfish.  And I'd like that.  But that…ain't the truth.  The truth is you're the weak.  And I'm the tyranny of evil men.  But I'm tryin', Ringo.  I'm tryin' real hard to be the shepherd.” Pulp Fiction (1994) was directed by Quentin Tarantino and written by Quentin Tarantino, Roger Avary.  Jules was played by Samuel L. Jackson.

[ix] Gabriel Garcia Márquez. Cien Años de Soledad, edición conmemorativa.  Buenos Aires, et al: Sudamericana, et al., 1976.  “Este libro se acabó de imprimir el 6 de marzo de 2007, día en que Gabriel Garcia Márquez cumple ochenta años y CXL aniversario de la ascención de Remedios, La Bella, al cielo.” (This book ceased printing on March 6, 2007, the day Garcia Gabriel Márquez’ eightieth birthday and the CXL anniversary of the ascension of Remedios, the Beauty, to heaven.), Ibid., post-index commemorative.

[x] Tag-along radical anarchists have to be included in here somewhere.  We could say they like to put on the same outfits and follow the same scripts, and so can fit, uneasy, under the post-structural umbrella -- at least until some neo-Bolshevik tries to lead them.

[xi] <>  Look for answers to the question, Why?

[xii] From the movie No Country for Old Men. No Country for Old Men (2007) was directed, and screenplay written, by Ethan Coen and Joel Coen, from the book written by Cormac McCarthy.  Ed Tom Bell was played by Tommy Lee Jones.

[xiii] Ernest Hemingway. For Whom The Bell Tolls. New York: Charles Scribner & Sons, 1940, p. 236.

[xiv] From the movie True Grit. 2010 Screenplay by Joel and Ethan Coen based on the novel by Charles Portis.

[xv] “Through our great good fortune, in our youth our hearts were touched with fire. It was given to us to learn at the outset that life is a profound and passionate thing.  While we are permitted to scorn nothing but indifference, and do not pretend to undervalue the worldly rewards of ambition, we have seen with our own eyes, beyond and above the gold fields, the snowy heights of honor, and it is for us to bear the report to those who come after us.  But, above all, we have learned that whether a man accepts from Fortune her spade, and will look downward and dig, or from Aspiration her axe and cord, and will scale the ice, the one and only success which it is his to command is to bring to his work a mighty heart.”  Richard A. Posner, ed. The Essential Holmes. Chicago: University of Chicago Press, 1996, p.86.

[xvi] Alluding to William James’ religious bent, Holmes wrote, “…I think as little of his philosophy as I do much of his psychology.” Ibid. p. 57.

[xvii] Henry and James, not Jesse and Frank.

[xviii] Posner, ibid., p. 58.

[xix] “…we are talking about revolution, not revelation.  You can shoot too high as well as too low.  First, there are no rules for revolution any more than there are rules for love or rules for happiness, but there are rules for radicals who want to change the world; there are certain central concepts of action in human politics that operate regardless of the scene or the time. To know these is basic to a pragmatic attack on the system.”  Alinsky, Rules for Radicals ibid., p. xvii.

[xx] Posner, Ibid. p. 91.

[xxi] Posner Ibid, p. 57.

[xxii] Zombieland (2009) was directed by Ruben Fleischer, and written by Rhett Reese and Paul Wernick; Caddyshack (1980) directed by Harold Ramis and written by Brian Doyle-Murray, Harold Ramis, and Douglas Kenney.


About the Author(s)

Geoffrey Demarest is a researcher in the US Army's Foreign Military Studies Office at Ft. Leavenworth, Kansas. He holds a JD and a PhD in International Studies from the University of Denver, and a PhD in Geography from the University of Kansas.  He is a graduate of the US Army War College at Carlisle Barracks, Pennsylvania, and of the School of the Americas at Ft. Benning, Georgia. Demarest's latest book is titled Winning Irregular War.