The views expressed in this publication are entirely those of the author and do not 

necessarily reflect the views, policy or position of the United States Government, 

Department of Defense, United States Special Operations Command, or the Joint 

Special Operations University.

Authors are granted academic freedom provided their work does not disclose 

classified information, jeopardize operations security, or misrepresent official U.S. 

policy. Such academic freedom empowers authors to offer new and sometimes 

controversial perspectives in the interest of furthering debate on key issues.

JSOU Press Publications are available for download at:

http://jsou.libguides.com/jsoupublications
Richard Rubright, Ph.D.

Senior Faculty, JSOU College of Special Operations

As Senior Faculty at the Joint Special Operations University, United States Special Operations 

Command (USSOCOM), Dr. Richard Rubright teaches in the fields of special operations, 

strategy, and counterinsurgency. When not teaching U.S. and foreign special operations 

communities through USSOCOM, he conducts research on topics of strategy and policy. He also 

serves as an adjunct professor at the National Intelligence University where he teaches strategy 

to intelligence professionals. He completed his Ph.D. in Strategic Studies at the University of 

Reading, United Kingdom. His prior education was conducted at the University of Utah, where 

he studied history and political science, as well as the University of Glasgow, United Kingdom,

where he completed a Master’s in International Politics. Dr. Richard Rubright also has

experience in the U.S. Army Special Forces. His research and study of strategy and military 

topics spans 20 years and includes research in Yemen and Iraq while observing combat patrols.

During this time he has worked on Defense Department-funded projects on terrorism and 

deterrence, force protection measures through technical means, as well as conducted data 

collection overseas.
On the cover

Left: statue of Chinese military strategist and philosopher Sun Tzu located 

in Yurihama, Japan. Public domain photo. 

Right: Statue of Italian philosopher and writer Niccolo Machiavelli located 

in Florence, Italy. Public domain photo.
1

or the past four years the United States has struggled to come to grips with the increasingly 

complex conflict in Syria. Much of this malaise is a result of strategic deficiency at the 

executive level. However, the problem goes far deeper than a transient administration. The real 

issue lies within our strategic culture and our inability to break from the standard Western 

Liberal Democratic naiveté when operating at the political level in the international arena. In

essence, we are our own worst enemy when it comes to strategic proficiency. We have the talent, 

and we have the guidance of past masters, but we lack the understanding and willingness to 

follow the wisdom of the past to inform our actions in the present.

What follows reflects the musing of the author alone; a deeper scholarly effort may come 

later and offer more depth and clarity to the issue. For now the purpose of this short work is to 

contextualize the ongoing conflict in Syria through the combined lens of Sun Tzu and 

Machiavelli, juxtaposed to the normative trend the West has followed ever so ineffectually since 

the conflict began in Syria. Let me be clear upfront; this is not a call to action, nor is it realistic to 

expect a contextualization so far from the paradigmatically preferred or politically stated norm as 

to effect change in policy. Rather, the work is an alternative view of the conflict that should be 

read as a cautionary tale concerning our lack of proficiency in strategy.

This work is broken down into three distinct parts, the first being the contextualization of 

the conflict and the actors involved, to include the proxies. The author hopes to do this justice in 

such a brief format as the situation is incredibly complex with many unknown variables and 

intentions of the actors involved. The second part lays out the strategic principles of Sun Tzu as 

pertaining to the conflict to provide a strategic framework with which the reader may make sense 

of the conflict’s complex nature. The challenge of Syria is arguably the single best contemporary 

example of Sun Tzu’s potential for contribution to strategic understanding and principles to 

which, ironically, the Western world seems oblivious. The third and final part is concerned with 

U.S. action keeping in mind Machiavelli within the Syrian conflict as informed by Sun Tzu’s 

strategic principles. This section acts as the “so what” portion of the work to make it at least 

tangentially relevant even if what is later postulated is normatively unrealistic.

The Context

Syria is not a conflict in isolation, an irony every time we (the author included) refer to it as a 

conflict in Syria. The one constant in the entire conflict is that ISIS is considered the adversary, 

and everyone wants to eventually see them destroyed as a political entity if not as an ideology.1

However, the truth is not so simple. While ISIS may be universally reviled at the state level, and 

all state parties involved in the conflict may pay lip service to the goal of defeating ISIS as the 

 

1 Brian Whitaker, “Saudi Arabia is Right to be anxious over its ideological links with Isis,” The Guardian, 6 January 

2015, accessed 7 October 2015 at: http://www.theguardian.com/commentisfree/2015/jan/06/saudi-arabiaanxious-ideological-links-isis.

F
2

priority, the truth is that for most parties involved in the conflict swirling around ISIS, the group 

itself is of a secondary concern. Each actor and their chosen proxy actor(s), and even third party 

proxies all have political objectives and agendas that stretch far beyond the monolithic threat as 

Westerners often portray ISIS. It is politically expedient for states and their proxies to insist that 

the destruction of ISIS is the goal of their efforts; however, there are always other political 

considerations at play in the international realm, especially one as volatile as the Middle East. To 

be clear, this is not a conspiracy theory; no states involved (though some individuals within 

states) are in support of ISIS or want to see them expand and succeed in establishing a Caliphate 

with worldwide Muslim appeal. Rather, states are engaged in political maneuverings with 

ancillary benefits from the conflict as it evolves.

The conflict can be broken down into four main groups with ISIS and the popular support 

it draws from around the world constituting one of the four. Foremost, there is no state aligned 

with ISIS at the moment or for the foreseeable future. That leaves three other groupings as 

follows:

 The United States, The Kurds, Iraq, and proxy rebels the United States is trying to arm as 

a moderate alternative to the fundamentalist minded rebels.

 The Assad regime, Iran, Russia, Iraq, Hezbollah, and the Shi’a militias in Iraq.

 Turkey, Saudi Arabia, the Gulf States, Jordan, the Sunni fundamentalist rebels (possibly 

al-Qaeda affiliated), and the anti-ISIS Sunni Tribes in Iraq.

 ISIS (regional, cultural, and ideological appeal)

The listing above is for simplicity and by no means a comprehensive list of actors and 

characters involved in the conflict. The rebel groups and their affiliations are far too numerous 

to list in a comprehensive manner within the scope of this work. To make matters far more 

complicated, the listings above offer tolerably like-minded groupings which provide a somewhat 

more easily understood context as the relationships between the actors are looked at a bit more.

The reader should also note that the listings are not exclusionary. The United States and 

Turkey are in different groups even though they are cooperating to a certain degree, are NATO 

allies, and will have a continued working relationship, but there are groups diametrically 

opposed to one another. Take for example Saudi Arabia and Iran. Supposedly they are united in 

their efforts to defeat the threat of ISIS, but they are by no means allies and they certainly seek 

differing ends once (if) ISIS is defeated or destroyed. In the listings, Iraq and its tribes/militias 

figure prominently in all three groupings (and one could argue some Sunnis of Iraq are in direct 

support of ISIS). So while the listings are of some use, there is a cautionary point that they 

represent so many overlapping interests and animosities that they should only be used as a 

general frame of reference rather than a listing of separate entities with matching goals.

The listing also provides insight into the strategy of regional actors. Every state actor has 

a proxy involved in the conflict to some degree. Some proxies are well known, while others are 

more tacit in nature. One of the more interesting questions is whether or not ISIS is a proxy 

actor. Obviously, ISIS would not agree to such a status, but their acquiescence to any such 

designation may be completely immaterial. It could be argued that ISIS is, at least at the 
3

moment, a proxy actor of the Assad regime, Russia, and Turkey. The situations is dynamic and 

that flux will continue as will be described later, but for the moment, in Turkey’s case, ISIS is 

fighting their traditional irregular foe: the Kurdistan Workers’ Party (PKK). In fact, after a 

bombing in Turkey, the United States was given clearance to use Incirlik Air Base in Turkey to 

conduct missions against ISIS, and Turkey indicated it would participate in the fight against 

ISIS. Yet, Turkey has been more interested in targeted air strikes against the PKK than an effort 

to degrade ISIS.2 Likewise, as long as separate fundamentalist rebel groups are fighting each 

other (Al Nusra the al-Qaeda affiliate and ISIS) ISIS is a de facto proxy actor for the Assad 

regime, as it battles more secular threats. 

The situation is even confusing when 

comparing state actors and categorizing them as 

proxies or not (states would obviously prefer the 

term ally). Are the Russians and their recent 

intervention in the conflict the proxy actor of the 

Assad regime, much the same way that Hezbollah 

is? Or is the Assad regime a proxy of the Russians 

and Iranians while Hezbollah is relegated to the role 

of a third party proxy? Such questions are relative to the perspective of the individual state and 

non-state actors involved and the specifics of their arrangements or agreements. Some of the 

actors are clearly proxies reliant upon the patronage of outside actors. Iraq, while sovereign in 

name, is certainly not the master of its own destiny in the Sunni areas of the country. The Shi’a 

militias in Iraq are likely directly under the proxy umbrella of Iran’s Quds Force.3 The Kurds in 

the North of Iraq and Syria have no illusions that U.S. support is important to their survival and 

have a reasonable expectation that the United States will continue to offer them support as long 

as the main stream Kurdish parties refrain from openly supporting the PKK and its ongoing 

conflict with Turkey. Finally, Iran finds itself in a very enviable position in the conflict as it is 

geographically separated from ISIS by the Kurdish and Shi’a areas of Iraq, yet also able to use 

both state and non-state actors as proxies to include Iraq, Shi’a militias, the Assad regime, and 

the quasi state actor Hezbollah.

With all of the convoluted factions, allies, proxies, and enemies united for a supposed 

common cause of destroying ISIS, the real question becomes, how has ISIS survived such an 

international onslaught of state and non-state actors all bent upon the organization’s destruction?

How could such a small group hold back so many enemies? Unfortunately, the fact that ISIS has 

not been destroyed is narrative boon for the organization and lends credence within their social 

and cultural milieu that their success and continued expansion is the result of Allah’s will (In 

Sh’a Allah). The reality, however, is that Iran, Russia, the United States, Turkey, and Saudi 

 

2 Pitor Zalewski, “Turkey Decides to Hit Kurdish Rebels Instead of ISIS,” Time, 14 October 2014, accessed 7 October 

2015 at: http://time.com/3507187/turkey-kurdish-rebels-pkk-isis-kobrani/.

3

Frederik Pleitgen, “We will destroy ISIS: Iranian militia vows to fight terror group,” CNN, 22 April 2015, accessed 7 

October 2015 at: http://www.cnn.com/2015/04/22/middleeast/iran-fighting-isis/.

... how has ISIS survived such 

an international onslaught of 

state and non-state actors all 

bent upon the organization’s 

destruction?
4

Arabia all have militaries capable of defeating ISIS forces and retaking the geographical area the 

organization has occupied, even if it cannot destroy the ideology that has obvious appeal to 

many. So the answer to the question of who is really fighting ISIS at the state level is no one.

But then again, why would anyone want to fight ISIS at the state level or expose themselves to 

the potential irregular conflict to follow? And most importantly, why fight a battle with your 

army when you can attack your opponents through a proxy, or better yet, not fight at all while 

others do it for you? Sun Tzu would be proud.

Sun Tzu and Syria

To quote Sun Tzu: “If he is internally harmonious, sow divisiveness in his ranks,”4and 

“Therefore, the best military policy is to attack strategies; the next to attack alliances; the next to 

attack soldiers; and the worst to assault walled cities.”5It would appear the United States has 

failed miserably at the first two options and has therefore defaulted to options three and four. It 

is undoubtedly difficult, one might even go so far as to say impossible, to attack another’s 

strategy, and much less alliances when we admittedly do not even have a comprehensive 

strategy ourselves. Yet the United States is flying sortie after sortie in support of ground troops 

that seem incapable of taking population centers in a population-centric conflict (Kobane and 

the determined Kurdish effort being the exception). Importantly, and alluded to in the beginning, 

attacking strategies and alliances would require strategic flexibility in both military application 

of force, but far more importantly, at the strategic and political level of thought.

The policymakers of the United States have a serious deficiency in understanding that 

strategy is simply a bridge between military means and political ends. It is not a set-in-stone 

principle of Western Liberal Democracy, unalterable, inflexible, and ultimately only to be 

exercised in the most humane, transparent, and charitable way. Strategy is not for spreading 

democracy, bringing women’s rights to different cultures, or standing by inept and double 

dealing states out of some form of heroic self-sacrifice where right makes might in a world 

illuminated by our shining example. No. Strategy is the way in which one uses their means to 

achieve their ends. There is no moral component to it, and sometimes, there are conflicts with no 

absolute morally “right” side to them. The United States may choose only to engage the world 

from what it thinks is the moral high ground, fostering Western liberal democratic principles in 

an uncompromising fashion. This may be done to sell an effort publically on the home front, to 

congressional members whose party will take issue with any action while they are not in control 

of the executive branch, or it may be out of truly heartfelt obligation to always be a force for a 

better world. Yet, the world we live in, and especially the world of international intrigue and 

alliance, maneuvering of Syria today calls for an approach that Sun Tzu would recognize far 

better than our policymakers have over the last four years.

 

4 Caleb Carr, The Book of War: Sun Tzu the art of Warfare & Karl von Clausewitz On War (New York: The Modern 

Library 2000), 74.

5

Ibid., 79.
5

To contextualize Sun Tzu’s perspective in Syria requires a contextualization of the actors 

and their motivations. This is to say that each actor is operating under a certain theoretical basis 

that informs their political reality. A deep dive into each player and proxy would turn this work 

into a full-length book and as such is far beyond the scope of this work. But, we can take a few 

examples which highlight how 

Sun Tzu’s perspectives could be 

helpful. The United States sought 

to build a coalition of nations 

willing to confront and ultimately 

destroy ISIS. After constructing 

this coalition and making it clear 

the United States would not itself 

be sending in ground troops, in 

effect a facile strategy was born of 

coalition air strikes in support of 

inept Iraqi ground troops and the 

Free Syrian Army. Hope (never a 

good strategy) that the Free Syrian 

Army would grow and effectively 

remove Assad, combined with 

enthusiasm (also never a good 

strategy) that the Iraqi Army we 

spent billions on would turn back 

ISIS, resulted in paralysis. That 

paralysis exposed the weakness of 

our strategy (if you want to call it 

that). Iran recognized that weakness and moved to support Shi’a elements in Iraq, effectively 

attacking not only our strategy but our alliance with Iraq as well (Sun Tzu’s preferred method).

It quickly became clear that Shi’a elements were willing to fight for Shi’a areas, but with the fall 

of places like Mosul, Tikrit, and Ramadi it also became clear that the Iraqi Army was not willing 

to do so for Sunni areas. With a masterful move Iran undermined our strategy, alliance 

(coalition), and the ground forces we were counting on, really leaving the Free Syrian Army and 

the Kurds as our regional proxies.

Rather than an adjustment of our strategy, our paralysis continued at the theoretical and 

policy level. Yet we were standing firmly by our commitment that Assad must go and ISIS must 

be destroyed (never underestimate the inertia of bad U.S. policy decisions). And in truth, Assad 

was losing ground so we could hope (still not a good strategy) he would eventually be driven 

from Syria and a moderate future was still attainable. Yet, again the United States faced a 

setback as Russian forces moved in to bolster the Assad regime with modern military hardware 

and at least some troops on the ground. They did so with the announcement of their own 

Figure 1. Map of Syria from CIA World Factbook.
6

coalition to destroy ISIS (masterful! how could the United States argue with that goal?),6but 

their coalition included states unfriendly to the United States but not the Assad regime itself. In 

effect, Russia, much like Iran, attacked our strategy (the Free Syrian Army’s fight against 

Assad) to remove the Assad regime. Russia also attacked our alliances by including Iraq in its 

coalition against ISIS, further isolating our ability to affect the outcome of the conflict. Russian 

forces in Syria on the ground further attacked our alliance system as it makes the likelihood of 

Turkish intervention almost zero. While Turkey has stated that they too want Assad gone, they 

are not going to get into a direct ground war as a member of NATO with Russian (a nuclear 

armed country) ground forces. Again, much like the Iranians, the U.S. strategy and alliances had 

been attacked and to a tolerable degree neutralized, and the ground forces we hoped (continuing 

not to represent a strategy) would oust Assad were now well overmatched by the Russian’s 

technologic advantage.

Ironically even our ally Turkey has been able to harness the wisdom of Sun Tzu against 

the United States. Turkey continues to target the PKK and People’s Protection Units (YPG)

fighting against ISIS, attacking both our strategy and alliances (I use the term ally with regard to 

the PKK loosely as they were designated a terrorist organization and are quasi proxies at the 

moment). With the three above examples the United States has been outmaneuvered in a manner 

very much in keeping with the ancient wisdom of Sun Tzu. The U.S. Air Force remains a potent 

instrument, though ashamedly, one that has all but been turned into a proxy force for Iran much 

as the Iraqi Army has. If the past patterns of political and foreign policy rigidity and ineptitude 

continue, I would expect to see a strategic move by Iran, Turkey, and Russia to isolate the 

United States from the Kurdish areas of Northern Iraq. This may of course not happen as we 

have been strategically neutralized, and further diminishment may not be required, especially if 

we continue to be an Iranian proxy air component attacking ISIS while other regional players 

continue to maneuver for advantage. Sun Tzu would not be proud of our performance, but 

Machiavelli would probably be apoplectic.

Machiavelli and Syria

Machiavelli would likely find Syria today not far removed from the context of his own time. A 

period when the Italian city states squabbled amongst themselves, rival factions were gaining 

and losing ground, religion played a massive role in the conflicts, outside invaders such as 

Charles VII of France made incursions, and there was pretty much no end in sight. He too, much 

like many ISIS fighters, dreamed of a political state and time from the past which he aspired and 

worked for its former glory—Rome rather than the Caliphate. Machiavelli may have taken a 

look at Syria today and wondered what all the commotion was about? He may have even 

sympathized with ISIS, yet he would undoubtedly have been repelled by the Islamic context 

rather than a Christian one.

 

6 Michael Gordon, “Russia Surprises U.S. With Accord on Battling ISIS,” The New York Times, 27 September 2015,

accessed 7 October 2015 at: http://www.nytimes.com/2015/09/28/world/middleeast/iraq-agrees-to-shareintelligence-on-isis-with-russia-syria-and-iran.html?_r=0.
7

But this section is to address the “so 

what?” portion, not rehash the historical 

context of Machiavelli and Florence.

Foremost, Machiavelli was a realist, and in 

his own strange way an optimist. His relation 

to the current crisis would be one of practical suggestions based upon the principles found not 

only in his well-known book The Prince, but also his lesser read work The Art of War (not to be 

confused with Sun Tzu’s The Art of War). Machiavelli understood the intrinsic link between 

politics and military force. In fact, while Clausewitz was the first to most succinctly make the 

connection of war being politics by other means, he was by no means the first to recognize the 

connection.7 So while Machiavelli would likely examine Syria from a practical political 

perspective, he would not be averse to military force being used to obtain the political objectives 

and certainly would not fall into the normative moral trap in which the United States has found 

itself. 

Machiavelli is often misunderstood to have said that it is better to be feared than to be 

loved. While true if a ruler had to choose between being feared and loved it was best to be 

feared, the ideal of the prince (meaning politic leader in general) is to be both feared AND 

loved.8 The goal then is to combine the principle of Machiavelli with the understanding of war 

from Sun Tzu to find the practical strategic way forward: to attack the enemies’ strategy and 

alliances while instilling fear and, if done correctly, inspiring devotion (love) from those we 

choose to support. There is no end state where across the region everyone looks to the United 

States with awe and thankfulness. With that in mind, it is time to change the political paradigm 

under which we are operating.

Sure the destruction of ISIS would be nice, but that is not our problem. That is the 

problem of the people that have to live next door: Jordan, Iraq, Turkey, Lebanon, Israel, and 

Saudi Arabia. Together they have the means to deal with the problem, and it should be clear that 

they will have to deal with the problem because the United States will not, nor intends to solve 

this problem for them. It is the Middle East, and the future of the Middle East is going to be 

decided by the people that live in the Middle East. If they choose to march headlong into the 7th

century without collectively standing up, fighting, and potentially giving their lives for their 

societies, then so be it; the world will buy oil, be it from Islamic fundamentalists or others.

The problem, as pointed out in the section on Sun Tzu, is not ISIS; it is the series of 

alliances that are all waiting for someone else to deal with ISIS while they seek advantage. The 

United States should play to the same Machiavellian end as the rest of the crowd. The United 

States should make it clear it is offering no support for anyone in the region except for our 

Turkish NATO “ally” and the Kurds of Northern Iraq. This essentially removes the United 

States from the role as a primary actor and forces others to move toward their goals. In essence, 

 

7 Neal Wood Introduction to Niccolo Machiavelli, The Art of War (Cambridge: DeCapo Press translation 1965 

original publication 1521), xxvi.

8 Niccolo Machiavelli, The Prince (New Haven: Yale University Press 1997), 68, 72.

One thing is abundantly clear; there 

is simply no way to make everyone 

happy within the context of Syria.
8

the United States gets to choose when and where to play the spoiler rather than being taken 

advantage of as a proxy air force. No one in the region will attack Turkey, not only because of 

the size and ability of its military but every state actor knows that such action on any significant 

scale triggers a full NATO response. U.S. protection of the Kurds offers a connected sustainable 

base in Iraq, allows the Kurds to devolve from Iraq, yet retain a capable indigenous fighting 

force the United States can work with effectively. ISIS and the posturing become the problems 

of other countries.

As Russia effectively attacked our strategy and alliance to the Free Syrian Army, 

turnaround is fair play. Machiavelli stressed the need for an actor to use fear to be taken 

seriously. And in the international arena he could not be more correct, especially in the 

contextual combination of Russia’s behaviors in Ukraine and Syria. The United States knows 

exactly how to make Russia’s life miserable in a conflict, just ask Soviet veterans of their 

service in Afghanistan in the 1980’s. With a recruiting pool of hundreds of thousands of Syrian 

men and women of fighting age looking for a home in Europe, the building of Free Syrian Army 

training centers in southern Turkey, Northern Iraq, or elsewhere, backed by an unfettered 

unconventional warfare campaign and modern U.S weapon systems, the Russian enthusiasm for 

propping up the Assad regime could become very short lived. In fact, if a sanctuary for families 

deal was set up on condition of an individual’s participation in our proxy force, we may find a 

very fertile recruitment tool. Undoubtedly the Russians see this possibility coming and would 

want to limit air support to any Western-backed unconventional warfare proxy force, after all 

their air defense systems in Syria are certainly not for the ISIS Air Force. Still, methodically, 

with modern man-portable air-defense systems (MANPADS) controlled solely by U.S. special 

operations troops working in conjunction with an unconventional proxy force, the Russian effort 

would eventually reach a culminating strategic point and cause withdrawal. Assad’s days would 

be numbered, the Russian strategy and alliance would be attacked, and Russia may just once 

again fear American resolve.

The ISIS fight will continue for a long time to come if it does not disintegrate from 

within (a real possibility with time). The Sunni/Shi’a divide has become too far to bridge by the 

United States, and no amount of platitudes, righteously delivered speeches of tolerance, or UN 

resolutions are going to solve the problem at this point. If we can shift our policies to make the 

Russians pay, prevail in the west of Syria, and stand by the Kurds in a defensive role, then time 

will offer the United States an opportunity of some kind. Machiavelli would argue for patience; 

let the offending parties grind themselves down, and then in the end, do what is best for the 

United States. Just make sure that all parties see our ability to adjust, wisely and ruthlessly 

destroy an opponent when required, be loved by the Kurds, with a small dose of fear for the rest, 

and in the end adjust our strategy accordingly.

Joint Special Operations University

Center for Special Operations Studies and Research

7701 Tampa Point Blvd.

MacDill AFB, FL 33621