Why the Mightiest Superpower on Earth Hasn’t Won a War in Decades

Originally published in the September, 2015 issue of Playboy

More than 200,000 American soldiers are deployed in 150 countries around the world. A single aircraft carrier can deploy more fighter jets than most countries can. The U.S. economy and culture dominate even in the most hostile corners of the globe. So why can’t America win its wars?

That may seem an odd question, yet it is difficult to look at the record and come to any other conclusion: For decades, the U.S. has not won the wars it has fought, at least not in any traditional sense. From Somalia in 1993 to Kosovo in 1999 to the roiling carnage of Iraq and Afghanistan, the Victorian idea of “victory” through defeat of an enemy has simply not made sense in the context of the people and groups who fight. But because the U.S. foreign policy community remains tied to such ancient and outdated ideas, the wars America fights will continue to end in a muddle.

Over time, the U.S. has become less and less capable of defining victory in its wars. In the first Gulf war, victory was straightforward: the military defeat of Saddam Hussein’s army and the liberation of Kuwait from its brutal occupation. But the next conflict in which the U.S. fought, in Somalia, did not have a concrete goal. There are a lot of reasons for that, but they begin with the nature of the conflict itself. Somalia was not a conventional conflict, with two sides squared off against each other and the U.S. military on one of those sides. Somalia was something else—essentially a war against chaos, fought in the hope that U.S. troops, with UN backing, could bring the many warring factions to heel and impose a new government on the country. It failed.

While the wars in the Balkans involved more traditional forces, they resulted in a difficult and tenuous peace despite more than a decade of occupation by European forces. NATO was able to defeat Serbian forces on the battlefield, but the peace remains fragile: Ethnic violence is still a difficult problem in Sarajevo, and Kosovo is still occupied by thousands of NATO troops enforcing calm. It might be peace of a sort, but it is certainly not victory.

Looking at the 21st century, defining an enemy and then determining how to achieve victory against it is more difficult than ever before. The ongoing wars in Afghanistan and Pakistan, the Islamic State in Iraq and Syria, Al Qaeda as well as Iran-backed militants in Yemen, Al Qaeda and Islamic State fighters in Libya and Al Qaeda groups in Mali and Somalia make it difficult to see how the application of military force could ever be expected to address the reasons those wars began in the first place. America’s military is incredibly powerful, but it is not the right tool for the job of winning.


So why can’t America do better?

It would be easy to say the United States hasn’t learned a thing, but the messy reality is that we have perhaps learned too much from our first 14 years of the war on terror. Government officials know they left two jobs undone, but they’re also aware of how unsupportive the American public is of eternal, expensive warfare.

U.S. officials are also unwilling to admit they messed up. “Mistakes were made,” as the saying goes, but those mistakes don’t happen in a vacuum. The Iraq war was, from conception to withdrawal, a complete disaster, and its execution stands against everything senior military officers learn in war college about strategic planning. The official line that good things happened in Afghanistan—look at all the children in school!—ignores the fact that the country remains completely ungovernable and the Taliban controls more territory every week.

Yet American leaders have split into two camps (like everything else in America, there are two and only two sides of the issue): One sees a failure to kill enough and wants to go all-in with troops and a massive air campaign in half a dozen countries, while the other wants to pull back and remain uninvolved. So far President Obama has generally done the latter while trying to do just enough to appease the interventionists. This split also represents a fatal breakage of America’s war politics.

The difficulty in every single war zone under discussion here is that the U.S. has a poor record of playing a constructive role, but that doesn’t automatically mean American absence is the best policy. The militants planting bombs are not some distant, foreign problem. Every single conflict we talk about has the potential to cause state collapse and with it the collapse of regional trade and security. That’s a big deal, but it goes further: Groups like the Islamic State are actively recruiting people to their cause. (ISIS alone has signed up more than 20,000 people from outside Iraq and Syria to fight on its behalf.) Every single head of state in the West is worried that their citizens who join the fight will eventually return home, radicalized and wired for violence. Already European officials regularly raid houses believed to host ISIS-radicalized terrorists. And as U.S. policy makers look at the churn these groups produce, they are left with two contradictory impulses: the public demand that they “do something” about this rise of militancy and the public revulsion at the idea of spending money or deploying troops to do it.

So the question facing America is not whether to get involved. We’re already involved and facing the consequences of that involvement every day. The question is how America should be involved, and it is the question not being debated.

This is because the politics of America’s wars have failed. The military can do combat just fine, but the politics of war that give the military scope and direction have fundamentally broken down. The problems plaguing America’s modern wars, from Kosovo in 1999 to Yemen in 2015, stem from an inability to work at the political level both domestically and in the conflict zone. And as long as our politics remain broken, no one should hold out much hope for a satisfying response to the frenzied unraveling of country after country as Islamist militants reduce once-proud cultures to horrifying charnel houses.


No one person is responsible for the political failure of America’s wars. It’s too easy to point at the inane shenanigans of the George W. Bush administration and place the blame there. It does not make sense to point at the fevered dream of the first few years after the September 11 terror attacks, when people said everything had changed but it really hadn’t. The dysfunction goes deeper, to a fundamental disconnect within American politics that is reflected in disjointed and ineffective policy abroad. Bolstered by overheated happy talk to the press and entrenched in magical groupthink, there is no countervailing force at work in American politics.

If anything, the incentives in our political discourse go in the wrong direction. Advocating the use of force, no matter how ill-considered, is richly rewarded. (Think of the pundit William Kristol, who has faced no professional consequences for his relentless advocacy of war.) Conversely, opponents of war who criticize the use of force to achieve foreign policy goals are punished harshly: MSNBC foreign policy correspondent Ashleigh Banfield criticized the media fever promoting the 2003 run-up to the Iraq invasion; the network took her off the air. She now covers court cases on CNN.

At this basic level, the public discourse on war in America has simply stopped working. You could see this at play in the earliest stages of the war in Afghanistan, in 2001. The pundits, who faced intense pressure to support the war regardless of the facts, called it a masterpiece before the shooting had even stopped. Writing in Foreign Affairs just seven months after the conflict began, Michael O’Hanlon, a military expert at the Brookings Institution who still preaches the finesse of American military power, said the war “may wind up being more notable in the annals of American military history than anything since Douglas MacArthur’s invasion at Inchon in Korea half a century ago.” It had “deprived Al Qaeda of its sanctuary within Afghanistan and left its surviving leaders running for their lives”—Osama bin Laden, of course, would remain at large for nearly a decade.

O’Hanlon was expressing the zeitgeist inside the Beltway: Riding high on the NATO-led air war over Kosovo in 1999 and thoroughly impressed with the technological modernization of the U.S. military, foreign policy wonks believed the rapid collapse of the Taliban had little to do with the inherent weakness of the Taliban regime or the brittleness of Afghan society after two decades of horrifying, bloody conflict, but rather was due to American expertise and prowess.

The reality, however, is that during the early days of the war in Afghanistan the U.S. badly misunderstood the country’s politics. The special operators who deployed in October 2001 established a liaison with the very monsters who’d made the Taliban look like saviors when they emerged from the civil war in 1994. Afghans knew who these brutal men were even if the American officials in charge did not.

From the U.S. perspective, the Taliban were the real enemy: They had hosted Al Qaeda, declined to hand over Osama bin Laden after September 11 and had to be attacked in response. By failing to understand the political background of Afghanistan, the U.S. poisoned every diplomatic and military effort it made there. By playing to the Northern Alliance warlords so heavily, the U.S. guaranteed the Taliban would have a disenfranchised constituency to mobilize for their insurgency, which is still going on today.

That perspective never made it into mainstream American discourse about the war. Afghanistan experts abounded—many were left over from the previous American war there, during the Soviet invasion in the 1980s. Yet the voices of those who knew better, who understood Afghanistan, were swept aside, replaced by a panoply of “foreign policy experts” who were learning on the job while imposing a new government on the country.

Similarly, from the earliest days of the Iraq invasion there were signs that something had gone horribly wrong. The U.S. decided to disband the Iraqi National Army and cleanse the government of former Ba’athists (who had formed Saddam Hussein’s political support). These oppressive institutions had held Iraqi society together for decades, but U.S. planners never effectively replaced them—creating a power vacuum that left Iraqi society violently fragmented. As a 2012 Joint Staff study concluded, “The U.S. government moved to establish a new sovereign Iraqi government and focused on long-term, state-of-the-art national infrastructure while ignoring early signs of an insurgency.” The U.S. wanted to build roads and a parliament while insurgents were busy planting bombs. The insurgency quickly mutated into a sectarian war fueled by Al Qaeda that is also still going on today.

As former Washington Post Baghdad bureau chief Rajiv Chandrasekaran documents in his book Imperial Life in the Emerald City, the U.S. eschewed experts on Iraq when it staffed up its bureaucracy there; rather, it preferred to hire people with political connections, preferably to conservative Republicans, and assumed their lack of knowledge about Iraq could be filled in as needed.

The result was disaster. Yet as the situation in Iraq grew steadily worse, a new word began filtering through internal channels of military discourse: counterinsurgency, or COIN. Soon military thinkers, professors at war colleges and think tank pundits began to suggest that the only way to defeat the expanding resistance to the U.S. occupation of Iraq and Afghanistan was a broad counterinsurgency strategy whereby troops would “live among the people” and “win by out-governing the opposition.”

Again, this was not an idea that came from the people who knew these countries best. Looking back, the strongest and loudest criticism of counterinsurgency came from those who anticipated the heavy cost such a policy would impose on the people who lived there. But that was immaterial: America’s war politicians didn’t want to hear considered opinion about how to navigate local politics; they wanted support for winning the war.

The problem is COIN has a lot of nasty baggage. COIN was how France colonized Africa. It was how France and Britain committed massive atrocities in Algeria and Malaysia. As recently as the 1950s, hundreds of thousands of Algerians and Malaysians died at the hands of European colonialists who literally killed their way to ignoble withdrawal. America tried counterinsurgency in Vietnam. It didn’t work. By the time Europe’s empires had collapsed, leaving millions living in ruin, COIN was interesting only to historians, not to anyone thinking about wars in the 21st century.

So when military planners thought they needed COIN in Iraq and Afghanistan, they didn’t know how to sell it. The general most closely associated with COIN, David Petraeus, had written his Princeton dissertation on the concept, and he developed the Army’s new manual instructing soldiers how to do it.

Team Petraeus sold COIN through a childish lie. Counterinsurgency had been a brutal failure elsewhere, so they tried a new tack: rebrand the idea with modern anthropological theory and historical research and sell it as the “graduate school of warfare.” American COIN would kill the bad guys while protecting the good guys. It would destroy terrorist networks and build up legitimate governments. But most of all, money, not bullets, would win the peace. Soldiers received on-the-job training. In addition to killing bad guys, they settled tribal disputes, paved roads, invested in local businesses and advised crooked local politicians how to govern their own people, all while not speaking a word of Pashto, Arabic or Dari. What could possibly go wrong?

Promises aside, American COIN was just as brutal as European COIN. Since 2007, Baghdad has been ethnically cleansed of its Sunni citizens. Disenfranchised and angry at a sectarian government the U.S. supported for years with money and weapons handouts, those Sunnis now form the support base for the ISIS militants everyone is worried about. Success created its own failure.

Meanwhile, in Afghanistan the rate of bombings is so intense, a Taliban fighter dies every 48 hours planting a bomb. Hundreds of thousands of civilians have been killed thanks to America’s efforts.


The wars did not have to turn out this way. But bolstered by a cadre of yes-men, neither the military nor the White House felt any need to define victory in either war. Frederick Kagan, the pundit most associated with the “surge” policy that gave troops space to withdraw from Iraq publicly, said the policy was meant to give Iraq “the space for political progress.” In 2008, despite that political progress not happening, Kagan declared the policy a success in The New York Times and supported the troop withdrawal as part of a job well done.

By 2010, however, Kagan had declared withdrawal a failure, reversing his belief that Iraq’s sovereignty and independence from American occupation were good things. Kagan was not reversing himself; rather, Iraq’s politics had collapsed and a massive rebellion in Sunni areas against the Shia government had sprung up. (This was before the Syrian civil war and the emergence of ISIS.) Kagan thought the withdrawal allowed Iraq’s politics to fall apart, not that Iraq’s politics were the problem to begin with. He never grappled with the internal pressures and fissures of Iraq’s political challenges; he simply assumed that military force would be enough and would allow the Iraqis to work it out on their own.

Kagan was hired to do the same thing in Afghanistan. But by 2010, the war there was in its twilight stage as well. The Obama White House, much as the Bush White House had done in Iraq, set frustratingly vague victory conditions coupled with an arbitrary withdrawal date: Afghanistan should suddenly have a functional government, which would then defeat the Taliban, but even if it didn’t, U.S. troops were leaving in 2014. Somehow COIN would be the way this happened.

It is no surprise the plan failed in Afghanistan the same way it has failed in Iraq. But this failure of imagination is not solely Kagan’s fault. He is just the most prominent person to have benefited from the toxic relationship that has grown between the pundit class and the military leadership. COIN did not come out of nowhere; the tactics, operations and strategy to fight insurgencies and rebellions have been the subject of eternal debate in the military for many years, since before the 9/11 attacks. Rather, because COIN was being sold so cleverly by a politically ascendant general—Petraeus was already the subject of numerous glowing media profiles in 2004—the Washington machinery of policy punditry mobilized to endorse what everyone thought was a winning strategy. It didn’t matter that the strategy was not, in fact, a winner. COIN was how the war would be won, regardless of the dishonesty required to sell it to the public. And just as Iraq skeptics were pushed out of the public eye, so too were COIN skeptics prevented from participating in the policy. Those lavishly subsidized Pentagon war zone tours were available only to COIN boosters. (My own military embed requests in Afghanistan were denied in 2011 after I’d publicly criticized the strategy.)

Even before the war in Iraq, the military had shown itself unable to adapt quickly and nimbly enough to properly address the complex, dirty, low-technology modern battlefield. The Millennium Challenge war game, held from late July to early August 2002, modeled a conventional assault on a Middle Eastern country. The commander of the enemy forces, Marine Corps Lieutenant General Paul Van Riper, knew the U.S. could dominate any radio signals or computer messages his forces would send. He also knew the U.S. had panoptic-like knowledge of every military asset he had to defend his beach. So he used minarets and motorcycles to relay instructions and civilian aircraft and dinghies to swarm the invading Navy, with a devastating surprise ending: In the simulation, he sank 16 U.S. Navy vessels, including an aircraft carrier.

The Pentagon did not want to grapple with such a weakness at the heart of its very expensive military force. The politics of the Pentagon demanded that it win, so it rebooted the war game and scripted Van Riper’s moves to guarantee a victory.

Why was the military so resistant to facing a nimble, unconventional enemy? It wasn’t for lack of thinking: In the mid-1990s, in response to the disastrous withdrawal from Somalia and frustrating, uncertain results in the Balkans, President Bill Clinton issued Presidential Decision Directive 56, which detailed “key elements” of how the government could manage what it called “complex contingency operations.” Two years later, Marine Corps General Charles Krulak coined the Three Block War concept, whereby soldiers would engage in high-tempo combat, carry out peacekeeping operations and provide humanitarian aid to locals within the space of three city blocks. Neither Krulak’s vision nor PDD 56 formed an effective framework for how the military could rapidly adapt to a nimble, mostly ad-hoc adversary. The Pentagon can defeat organized armies—it’s good at it, and sometimes it acts as though it misses the days when that was what it did. In modern warfare, though, civilian vehicles can be transformed into bombs, sometimes with civilians still inside them. Soldiers ranked as low as corporal can be forced to make decisions with the power to win or lose an entire war. Local politicians will lie serially to your face while selling your weapons and positions to your enemy. Collapsed civilizations will have to be rebuilt.

By the time of the 9/11 attacks, the Department of Defense didn’t want to think about future Somalias. It wanted a big enemy and became obsessed with China. Fighting China was so sexy few ever thought to plan a response to the growing sophistication of Al Qaeda attacks on U.S. outposts. Bombings, from the Khobar Towers in 1996 to U.S. embassies in Tanzania and Kenya in 1998 to the USS Cole in 2000, suggested the most immediate threat to the U.S. wasn’t China but Islamist militants. With no strategic thinking about how to counter them, the U.S. instead relied on lobbing a bunch of cruise missiles into Afghanistan and Sudan in response. (There was never a formal U.S. response to the Cole bombing.)

Despite the past decade of war, the Pentagon still struggles to adjust to the reality of asymmetric warfare. It was IEDs, not Chinese stealth jets or Russian state hackers, that created multibillion-dollar agencies that spend billions of dollars on armored trucks and explosives detectors. Technologically unsophisticated insurgents who built $100 bombs killed thousands of troops and pushed the U.S. into an arms race it could never win. The Pentagon never addressed the reason bombs had become so effective against its troops; it just wanted to build a better truck.


The U.S. still hasn’t figured out how to win its many unconventional conflicts. And it is that uncertainty that causes so much heartburn in Washington. There is no immediately clear course of action when an offshoot of Al Qaeda forces the overnight collapse of a military you’ve spent $25 billion creating. There is no guidebook for how to respond when that same group floods YouTube and Twitter with ghastly snuff videos, cackling as they behead living prisoners and fill mass graves. Yet that is what happened last summer in northern Iraq.

It seems to be happening elsewhere as well: Groups pledging allegiance to ISIS in Libya have not only seized major cities and decapitated dozens of people, they have been spotted by satellite trying to prepare MiG-25 fighter jets for combat.

Last September the White House called Yemen its model for how to go after the Islamic State in Iraq. Almost as if in response to President Obama’s endorsement, Yemen immediately fell in a coup d’état staged by a Shia minority that has now allied itself with Iran. Saudi Arabia, which has supported radical Islamist groups in Syria, spent the first half of 2015 bombing Yemen to try to dislodge the Shia forces. Few policy makers like to talk about the “model” of Yemen anymore.

But what of other shadow wars? Pakistan has literally blown up in America’s face. The U.S. badly misjudged how Pakistan society and elites would react to a years-long campaign of covert drone strikes in their country. In Libya, the U.S. tried to implement regime change with no follow-up, no occupation troops and little reconstruction aid. It has been an abysmal failure. Beyond the embassy attacks in Benghazi, Islamist militants who pledge their loyalty to Al Qaeda control swaths of the country. A hands-off approach in Syria has not helped either: The country is a nightmare of chaotic violence. Despite some U.S. air strikes in Iraq, the untouched areas of the Islamic State in Syria mean the group is not likely to be defeated anytime soon.

The U.S. has had more luck in fighting its war on terror in Southeast Asia. Both the Philippines and Indonesia have shown that the U.S. can play a positive role with an effective government that takes an active part in its own counterterrorism campaigns. But most countries are not Indonesia or the Philippines. They are more like Somalia, with a mostly dysfunctional government, underdeveloped institutions, meddling neighbors and a lot of places the U.S. can’t reach very easily. Or they’re like Mali, where a French-led, American-supported campaign kept the southern half of the country free of militants but where the northern reaches are lost to Islamists.

These are the places that will stymie any future policy for countering terror. It seems America can’t really win, at least not the way we normally think of winning: Being balls deep as we are in Iraq doesn’t do it, but being hands-off as we are in Libya doesn’t either. The old model of assuming clear victory comes after battle simply doesn’t apply to the world anymore, and it should have no place in our discourse about war.

Maybe we need a new way of thinking about security challenges, one that isn’t tied to Victorian ideas of defeating an enemy on the battlefield. Maybe achieving victory looks like something else, such as shifting the danger from an acute to a minor threat. Maybe management is a better way of addressing challenges: A country might be a mess, but at least its militants aren’t attacking the homeland. Or maybe ignoring the situation entirely is the way to go.

If the past 14 years of warfare have taught the U.S. anything, it is that we have to pick our battles carefully. We cannot and should not be cavalier about the promises we make, the sacrifices we ask our soldiers to make or the outcomes we expect to happen. And we have to be honest about the threats that confront us and especially about our own capacity to address them.