Rosa Brooks, a law professor at Georgetown University, served as an Obama appointee at the Defense Department from 2009 to 2011.

After a spate of news stories this summer citing tensions between President Barack Obama and his top military commanders over the possibility of U.S. intervention in Syria, White House chief of staff Denis McDonough hastened to assure the Washington Post that everything was, in fact, copacetic: The president “appreciates” candid military advice “above all else,” McDonough insisted, and has “close, and in some instances warm, relationships with his military chiefs,” as the Post put it. During my own time at the Pentagon, where I worked as an Obama appointee from the spring of 2009 until mid-2011, few seemed to hold this view. I recall asking one general, recently back from Afghanistan, if he’d shared his experiences and insights with the president. Rolling his eyes, he told me grimly that the White House preferred the military to be seen but not heard.

Curious about whether things had changed since then, I asked a dozen serving and recently retired senior military officers with high-level White House access, many of whom were not comfortable speaking on the record, if they knew of any military leaders with whom the president had a close and warm personal relationship. In every case, the initial response was a long silence. “That’s a great question,” said one retired senior officer, after a lengthy pause. “Good question. I don’t know,” said a second. “I don’t think he’s close to anyone,” commented a third. He just doesn’t seem to have any interest in “getting to know” the military, a retired general concluded.


Of course, there’s no law that requires the president to invite his top generals for pajama parties or rounds of golf, and being “close” to military leaders is no guarantee of sound decision-making. But all of this raises an increasingly relevant question: How has the president—the man who promised to “ finish the job” in Afghanistan, close the door on the unpopular Iraq War and “ end the mind-set that got us into the war in the first place”—managed a military he often seems to regard with mistrust and unease?

***

“Americans are deeply ambivalent about war,” Obama told a National Defense University audience in May. He might have been speaking about himself. Despite his campaign promises, Obama has been embroiled in a series of military adventures, some of his own making. Although the last U.S. troops finally withdrew from Iraq in December 2011, there are today almost twice as many American troops in Afghanistan as when Obama was first elected. Obama also presided over a seven-month air campaign in Libya and has accelerated a covert drone war that has so far killed an estimated 4,000 people in Pakistan, Somalia and Yemen. Through all this, the president has continued to express his dismay over the nation’s militarized foreign policy: “We cannot use force everywhere,” he insisted in May. “Perpetual war … will prove self-defeating, and alter our country in troubling ways.”

After more than a decade of combat, many military leaders share Obama’s concern about the costs of perpetual war. But most of those interviewed for this article—an array of current and former Pentagon brass who have collectively had charge of many of the wars on Obama’s watch—also expressed the fear that the president’s ambivalence about military force has morphed into ambivalence about the military itself. The generals told me they believe this double ambivalence has contributed to a series of strategically incoherent White House decisions—and, despite McDonough’s reassurances, most of my sources said tensions between the White House and the military are running worryingly high.

The latest cause of heartburn inside the Pentagon is undoubtedly Syria. On Aug. 21, according to the United States and its allies, the forces of Syrian leader Bashar al-Assad launched a chemical attack on a rebel-held area, crossing the “ red line” Obama had drawn. Obama responded by declaring his intention to “send a message” to Assad via targeted military strikes.

No soldier in his right mind would guarantee ‘no boots on the ground,’” a retired senior commander told me. “You can never make such guarantees.”

The timing was awkward. Only days before the chemical weapons attack, Gen. Martin Dempsey, the chairman of the Joint Chiefs of Staff, had gone on record pooh-poohing the idea of U.S. military action in Syria, emphasizing the risk of escalation, the importance of being “realistic about the cost we incur in blood and treasure” and “the limits of military force.” Dempsey grew more circumspect in subsequent congressional testimony, but “his body language,” says retired Army Maj. Gen. Paul Eaton, Dempsey still suggested he was thinking, “I can’t believe how dumb this is.”

Former Defense Secretary Robert Gates was explicitly critical in a September speech: “I believe that to blow a bunch of stuff up over a couple days, to underscore or validate a point or a principle, is not a strategy.”

According to most of those I interviewed, Gates’s scathing words reflect an unhappiness with the commander in chief that is widely shared in the military. “The military does not take kindly to people asking them to do things without thinking them through,” Eaton observes. “Military guys get kind of bemused when civilians tell them it’s OK to blow people to smithereens using bombs, as long as you don’t kill them with chemical weapons.”

“No soldier in his right mind would guarantee ‘no boots on the ground,’” another retired senior commander told me in frustration, after the president had promised just that. “You can never make such guarantees. And we need to be careful how we draw moral lines and distinctions in this terribly complicated civil war. In 12 years of war, the U.S. has won everything tactically and nothing strategically. Let’s not bomb somebody just to bomb somebody.”

The Syria episode reinforced the sense of a White House-Pentagon relationship in crisis, and media outlets eagerly stoked the controversy. “America’s Top Generals Are Mad as Hell, and They’re Not Taking It Anymore,” ran a headline in Foreign Policy. The Washington Post published a caustic op-ed by retired Army Maj. Gen. (and Fox News commentator) Robert Scales, who claimed that military personnel were “embarrassed to be associated with the amateurism of the Obama administration’s attempts to craft a plan that makes strategic sense.”

Elizabeth Sherwood-Randall, the White House coordinator for defense policy, assured me in an emailed statement that the president “relies heavily” on his senior military leaders to provide “candid, direct advice with respect to when and how military force can be used to achieve our national security objectives.” In my interviews, however, many senior military leaders complained of feeling baffled and shut out by a White House National Security Staff that, in their view, combines an insistence on micromanaging minor issues with a near-total inability to articulate coherent strategic goals. “The NSS wants to run the show, day to day and minute to minute,” laments a former military official, “so they have no time—they’re almost incapable of strategic thinking.”

Alluding to Carl von Clausewitz’s famous maxim, another recently retired senior general voiced similar frustration. “If war is ‘the continuation of policy,’ I’d like to know what that policy is—so I can avoid screwing it up, or wasting lives for no purpose.” But, he says, “I don’t understand the process by which the White House is making strategic or foreign-policy decisions. … There’s an appearance of consultation, but you know you won’t be listened to.”

Was there a single moment when Obama’s relationship with the military began to sour? Most observers point to the bruising 2009 debates about troop numbers in Afghanistan.

Immediately after his 2009 Inauguration, Obama set out to make good on his promise to “finish the job” in Afghanistan. He commissioned a sweeping review of U.S. policy and announced that he had authorized the interim deployment of an additional 17,000 U.S. troops in response to theater commander Gen. David McKiernan’s request.

By the end of February 2009, the president had adopted the new strategic objectives recommended by his interagency review team: From now on, the United States would emphasize the fight against al Qaeda—and build up the Afghan military’s security forces. But by mid-May, McKiernan, the first of several Afghanistan theater commanders under Obama to discover just how elusive “finishing the job” would be, had been fired. “War is a tough auditor,” retired Marine Corps Gen. James Mattis told me. Not every commander passes muster.

McKiernan was succeeded by Gen. Stanley McChrystal, who was in turn assigned to undertake his own 60-day assessment. But when word spread that McChrystal intended to propose a substantial new increase in forces, which Pentagon gossip initially put as high as 80,000 additional troops, waves of dismay spread through the White House. In late September 2009, a copy of McChrystal’s assessment was leaked to the Washington Post. Its bottom line was clear: If the United States did not pour significant additional resources into Afghanistan, and fast, the likely result would be “mission failure.”

I don’t think Obama really realized we were losing the war in Afghanistan until late in 2009,” a retired Army general with substantial Afghanistan experience told me. Furious at the leak—which they blamed on the Pentagon—and reluctant to accept McChrystal’s grim conclusions, senior White House aides engaged in strategic counter-leaks. In their version, McChrystal and the Pentagon were trying to box in the president by pushing to deploy tens of thousands more troops and refusing to consider other approaches.

After months of increasingly tense meetings, Obama came to a decision: Another 30,000 U.S. troops would be sent to Afghanistan, but after 18 months those troops would begin to withdraw. And the military wouldn’t be left to solve every problem on its own, the president promised; a “more effective civilian strategy” would promote improved Afghan governance and economic development. (The president’s “civilian surge” never truly materialized. In his book Little America: The War Within the War for Afghanistan, Rajiv Chandrasekaran quotes Brig. Gen. Kenneth Dahl’s sarcastic 2011 rejoinder to Karl Eikenberry, then the U.S. ambassador to Afghanistan, who said that the civilian surge had reached “the high-water mark.” “That’s great,” Dahl responded. “I can feel it lapping at my ankles.”)

Following the president’s decision, I saw both civilian and military officials work loyally to put the best possible face on a compromise that, in truth, left no one entirely happy. “The White House was convinced that the military had a vested interest in escalating the conflict,” says a former White House official. “They felt manipulated.” And less than a year later, McChrystal was forced to resign after a Rolling Stone profile quoted his top military aides mocking several senior civilian officials, including Eikenberry and Vice President Joe Biden.

The White House was convinced that the military had a vested interest in escalating the conflict,” says a former White House official. “They felt manipulated.”

For the White House, the lasting lesson was to take military advice with more than a few grains of salt. Former White House officials I spoke with generally agreed with the generals’ characterization of the concerns and mutual mistrust that marked the relationship. Obama “is now less deferential to the military,” adds a Senate staffer familiar with these debates. “There is some default mistrust.”

The Pentagon’s take on the Afghanistan debate was rather different.

“The [military’s] general stance is, ‘We can do this, but we want you to acknowledge the mess, cost and complexity,” says a former senior Pentagon official. To many in the military, McChrystal’s 2009 troop recommendations fell victim to a White House unwilling to acknowledge any of those things. “There’s a sense that the White House wants contradictory, impossible things … but won’t resource them,” a congressional staffer with previous military experience told me.

Indeed, most of the military leaders I interviewed said they believed that military recommendations often go unheeded by senior White House staff, who now assume that a risk-averse Pentagon exaggerates every difficulty and inflates every request for troops or money.

This assumption turns discussions into antagonistic negotiating sessions. As one retired general puts it, “If you said, ‘We need 40,000 troops,’ they’d immediately say, ‘20,000.’ Not because they thought that was the right number, but they just took it for granted that any number coming from the military was inflated.”

“Sometimes you want to tell them, ‘This isn’t a political bargaining process,’” another retired senior military official says ruefully. “Where the military comes in high, they counter low, and we settle on an option that splits the difference. Needless to say, the right answer is not always in the middle.”

A former White House official with Pentagon experience says White House staff often remain willfully uninformed about the logic behind military recommendations: They “don’t want to take the time to go through the slide deck or get the full briefing. Basically, they don’t want to know.”

Over time, of course, a White House tendency to split the difference is bound to create perverse incentives for military planners, making mutual mistrust self-reinforcing. “If you believe the mission truly requires 50,000 troops and $50 billion, but you know that the White House is going to automatically cut every number in half, you’ll come in asking for 100,000 troops and $100 billion,” says the aforementioned former White House official. “The military eventually starts playing the very game the White House has always suspected them of playing.”

The stakes are high, says former Deputy Undersecretary of Defense Kathleen Hicks. Whether the ostensible topic is Afghanistan or Syria, “the backdrop is really tensions over budgets and money. Senior military officials worry that they’re being asked to do all these [different] things, but who will fund it? Who’s looking out for the military’s institutional interests?” Meanwhile, she adds, “the White House suspects that the military is exaggerating the problems that will be caused by budget cuts, which just makes the military even more frustrated.”

Retired Army Lt. Gen. James Dubik, a veteran of Donald Rumsfeld’s rocky reign at the Defense Department, chalks up such misunderstandings to the cultural gap that often separates military and political leaders. There are several basic models of civil-military relations, he notes. The first is the traditional one of separate spheres of authority: “Civilians do policy; the military executes”—but still decides the means of execution.

In a second model, “Civilians are the principals, the military are specialized employees. The military can advise, but they must do what the boss says in the way the boss wants, no more and no less.” But, Dubik says, “most people in the military still favor the traditional separate-spheres model, while most people in the White House tend to think in terms of the employer-employee model. That’s a recipe for unhappiness.”

That culture gap between the Pentagon and the White House frequently feels unbridgeable. The military is hierarchical and structured; civilian organizations, even within the White House, are organized more loosely. To the military, “planning” is a meticulously defined process designed to develop implementable blueprints for action, down to the smallest logistical details; to civilians, planning often just means talking about what might happen in the future.

In my own brief time at the Pentagon, there were many moments when White House and military officials were so far apart that they might have been speaking different languages, forcing Defense Department civilians like me into the often awkward role of translators.

There was the White House staffer who called me up and asked me to have CENTCOM move a U.S. drone to Kyrgyzstan, for instance, in an effort to track an alarming outbreak of ethnic violence. When I told him why I couldn’t—the chain of command just doesn’t work that way, and in any case no formal planning or risk assessments had taken place—he quickly grew exasperated.

“You guys”—the Pentagon—“are always stonewalling us on everything. I’m calling you from the White House. The president wants to prevent genocide in Kyrgyzstan. Whatever happened to civilian control of the military?”

“You,” I had to tell him, “are the wrong civilian.”

As if to emphasize the culture clash, after episodes like this one, the response from some of my Obama administration colleagues in the White House was bitter: Had I “gone over to the other side?” one asked.

***

The military and the White House are not supposed to be on different “sides,” but there’s a long history of mutual recriminations; it’s practically an American tradition. Recall President Harry Truman’s theatrical firing of Gen. Douglas MacArthur amid the dispute over whether to escalate the Korean War; Dwight Eisenhower’s condemnation of the “military-industrial complex,” John F. Kennedy’s struggles with military leaders during the Cuban Missile Crisis; and Bill Clinton’s failed effort to end the ban on gay people serving openly in the military. And that’s just in the post-World War II era.

Dubik argues that critics of Obama’s relationship with the military have short memories. “This administration seems more inclusive and willing to listen than the last few,” he says dryly. And, he adds, if anyone imagines that military leaders are more comfortable with Republican administrations, “that’s baloney.” Charles J. Dunlap, an Air Force major general who retired in 2010, agrees: “The longer you’re in the military, the more you realize that there’s not all that much difference between administrations.”

The only thing worse than an overtly dissenting military is a covertly dissenting military. “Beware the silence of the generals,” one quips.

Disputes between military leaders and the White House can be healthy for a democratic society. After all, senior commanders have a legal and ethical obligation to provide the president and Congress with honest military advice, and although Dempsey’s openly expressed concerns about Syria may not have sat well with White House officials, says retired Lt. Gen. David Barno, “the chairman does have to say, ‘Here are the risks in that course of action.’”

In any case, warns another retired general, the only thing worse than an overtly dissenting military is a covertly dissenting military. “Beware the silence of the generals,” he quips. “Public silence doesn’t mean private inaction.” It is far better, he argues, to have top brass be “out in the open and accountable for what they’re thinking” than for them to be “speaking through proxies and doing back-channel manipulations.”

Meanwhile, the president is “right to ask his generals tough questions,” says Dunlap. Every administration prefers to present a united front with the military, but, as another retired senior military leader told me, the president needs to be comfortable if that proves impossible: “There’s nothing wrong with the president saying, ‘The military wanted something, but as president, I decided different, and here’s why.’ The president shouldn’t be afraid of that.”

That’s easier said than done. For this White House, the military is the proverbial 800-pound gorilla—more so than ever. After the Sept. 11, attacks, resources and authorities flowed lavishly to the Pentagon, which saw its budget almost double in the following decade. President George W. Bush’s administration “always wanted military guys between themselves and whatever the problem was,” recalls a retired general who served in senior positions during that period. And Bush was more than willing to spend the money needed to make that happen.

Meanwhile, budgets for civilian agencies and programs remained largely stagnant. “Ten to 15 years ago, the military was much smaller and less holistic,” notes another retired officer. Today’s military is doing more with more: It sponsors radio and television shows in Afghanistan, operates health clinics in Africa, provides technical assistance to courts and parliaments, engages in cyberdefense, carries out drone strikes in far-flung places, and collects data from our telephone calls and emails.

“It’s just the easiest way out of any problem,” says Eaton. “Give money to the military and let them deal with it.”

The relentlessly expanding U.S. military, Barno says, is becoming “like a super-Walmart with everything under one roof.” Like Walmart, the military can marshal vast resources and exploit economies of scale in ways impossible for mom-and-pop operations. And like Walmart, the tempting one-stop-shopping convenience the military offers has a devastating effect on smaller, more traditional enterprises—in this case, the outnumbered diplomats of Foggy Bottom. Or the boutique national security shop at the White House, where power lives but resources don’t.

And yet no one—least of all Obama—seems to know how to cope with the military’s relentless Walmartization. However committed the president is, in theory, to rebalancing civilian and military roles, Obama has found himself repeatedly turning to the Pentagon in times of crisis, whether in Libya, Syria or Yemen.

That, in the end, may be the real story of Obama and his uneasy relationship with a military he came to office determined to rein in.

“When the shit hits the fan,” says a former White House official, he’s “racing for that super-Walmart every single bloody time.”

Rosa Brooks , a law professor at Georgetown University, served as an Obama appointee at the Defense Department from 2009 to 2011.