In Shadow and Secret: Peering into the Soul of Obama’s Presidency

In this essay, I summarize and reflect upon Daniel Klaidman’s Kill or Capture: The War on Terror and the Soul of the Obama Presidency (2012). My review is broad, but is particularly attuned to the issues surrounding targeted killing.


Klaidman’s book animates a lot of the personal animosities, feuds, and tribal bickering that define the White House’s West Wing. Two figures in particular stand out as representing the conflicted ‘pragmatic’ and ‘principled’ sides of Obama’s own beliefs: Rahm Emmanuel, the President’s former Chief of Staff, and the Justice Department’s attorney general, Eric Holder. Emmanuel, now the Chicago mayor, refused to engage issues that would sap popular American will, and often marginalized Holder when he insisted on closing Guantanamo or trying Khalid Sheikh Mohammad in a Manhattan court. This clash between politics and principles would eventually be won by politics, as Obama consistently compromised on issues that were red lines in his campaign for election – such as military detentions, closing Guantanamo, the use of official secrets, and indefinite detention. And as the title of the book suggests, one of the many questions that would haunt Obama’s presidency was whether the U.S. could ‘kill’ or ‘capture’ an enemy anywhere in the world. The answer would be decidedly the former: as the raid in Abbottabad, Pakistan clearly demonstrated, this was an administration that would be characterized by its ‘kill first, ask questions later’ approach.

The book opens with Richard Clarke, a counterterrorism veteran that has worked for four Presidents stretching back to Ronald Reagan. The data is May 2007. Clarke meets with a younger Senator Obama to advise him on foreign policy and offers him a stark warning: “As President, you kill people” (p.15). Fast-forward to November 6, 2009, and Obama meets with a man who would become a crucial figure his counterterrorism strategy: John Brennan. At his transitional Chicago office, Brennan stated that America could not ‘win’ the war on terror without tackling ‘upstream factors’ that push young Muslims to violent radicalism. He also told the president-elect: “You need to target the metastasizing disease without destroying the tissue” (p.23). This ‘surgical’ approach was an early sign that drones and a lighter military ‘footprint’ would be favoured options for the President.

In mid-January, 2010, Obama wanted to a mark a clear breakaway with the Bush administration by closing Guantanamo. This was Obama’s first executive order. Greg Craig, a renowned lawyer and White House counsel, was tasked with overseeing the deconstruction of the worst excesses of Bush’s war on terror. Michael Hayden, director of the CIA, was not happy: he saw the program of ‘enhanced interrogation’ as an invaluable tool of human intelligence. Hayden would soon reassert his position. A day after the pomp and ceremony of the executive order, the CIA launched its very first drone strike under the Obama administration. The target was a social gathering in ‘Karez Kot’ in South Waziristan. And yet, instead of hitting suspected Taliban militant, the Hellfire missile killed a prominent tribal elder and members of a pro-government peace committee. Obama was deeply troubled, and summoned Hayden to the Situation Room asking for an explanation over vetting procedures for drone attacks. It was then Obama first learnt of ‘signature strikes’ (p. 41), and was not satisfied with the procedure. Hayden forcefully defended the signature approach, but Obama had a litany of questions (p. 42).

In the end, Obama left it for others in his staff to spar with the CIA – Tom Donilon, deputy national security adviser, told Hayden “We have to review how we do this stuff” (p. 42) and “I’m not sure I’m comfortable with how we’re doing it” (p.42).

Implicit was that the White House might want a bigger role in managing the strikes – for Obama, having a tight grip was a natural impulse, underscored by the botched strike from the previous day.  Hayden saw this as a red line; sure the president had issued the covert ‘finding’, but the director didn’t want to have to call the White House up every time a strike was requested. For the time being however, Obama relented on signature strikes and delegation authority. But he did tighten some procedure: The CIA director would no longer be allowed to have his deputy sign off on a strike as a proxy. Only the DCI would have sign-off authority. And the White House reserved the right to withdraw signature authority in the future, as it would do after an errant attack killed civilians, or to settle diplomatic relations with Pakistan. Obama was never comfortable with signature strikes. “He would squirm”; “He didn’t’ like the idea of kill ‘em and sort it out later’”. (p.43). Still, the President allowed the program to grow exponentially.

Photo: The principals sit in the Situation Room of the White House, overseeing ‘Operation Neptune’s Spear’, the raid that killed Osama bin Laden.

For a while the U.S. military had been ‘itching’ to take the fight to Somalia, something that seemed the opposite of Obama’s ‘winding down’ of the wars of 9/11.  Somalia, in March 2009, was already a ‘ticking time bomb’ when a chance arose to take out a member of al-Shabab, an offshoot of the Islamic Courts Union (which controlled Somalia until U.S.-backed Ethiopian forces invaded the country in 2006). Admiral Mike Mullen, then Chairman of the Joint Chiefs of Staff, wanted to carpet bomb the location where the suspected terrorist was located. Hoss Cartwright, the vice chairman, dissented; the Shabab strike was a no-go. But what emerged in early 2009 was a partnership that would endure in America’s shadow wars: Obama, Hoss Cartwright, and John Brennan. “The three forming a kind of holy trinity of targeted killings’ (p.51). Indeed, Cartwright and Brennan would consult Obama before every strike. 

“The three men were making life-and-death decisions, picking targets, rejecting or accepting names put forward by the military, feeling their way through a new kind of war – Obama’s war” (p.53).

Photo: Eric Holder, Attorney General

The Obama administration had been left with the ‘hardest’ of Guantanamo cases – many detainees had already been released under Bush. Eric Holder appointed Matthew Olsen, a Justice Department lawyer to run the Guantanamo review (Olsen is now Director of the National Counterterrorism Center). Obama struggled intensely with Guantanamo legislation and wanted a non-presidential justification for detaining individuals: “I don’t think it makes sense for me alone to decide, just because I’m the president, who should be detained”, “I’m not comfortable exerting that authority”. (59). On March 13, 2009, a foundational document was rolled out that used congressional authority (the 2001 AUMF) for detaining individuals and maintained the U.S. could pursue the enemy outside the traditional battlefield, although this was restricted to al-Qaeda and its affiliates. It was also around this time that momentum for an investigation into CIA abuse was faltering, much to the chagrin of Holder. The attorney general had found at least 10 instances when interrogators went beyond what had been sanctioned. But there wasn’t their political will for an investigation; nor was there political will for trying Guantanamo detainees in Article III, or civilian, courts.

There have been three internments in US history – the Palmer raids, the Japanese internments, and post 9-11 detentions. Obama worried about the precedent indefinite detention was setting and feared Bush’s legacy was rapidly becoming his own. Justice Jackson, a dissenter in the Supreme Court’s upholding of Japanese internment, wrote that precedent “lies around like a loaded weapon ready for the hands of any authority that can bring forward a plausible claim” (p.142). But drones, on the other hand… 

“We’re killing these sons of bitches faster than they can grow them” Head of the CIA’s Counterterrorist Center, p.118

President Barack Obama had displayed an early proclivity to operate under the radar. Back in 2007 he said “I will ensure that the military becomes more stealthy, agile, and lethal in its ability to capture or kill terrorists”. Klaidman paints a picture of this ‘Covert Commander-in-Chief’ as a man who was initially conflicted over civilian deaths in drone strikes, particularly signature strikes, but rapidly embraced the shadow war spearheaded by the CIA and the military’s JSOC. Obama would often consult Panetta about the details of particular strikes, and he even gave the CIA whatever it wanted. For example, in October 2009, Panetta brought a CIA ‘wish list’ of items hoping to get around half of what he asked for. He got it all. Obama said “The CIA gets what it wants” – including more Predator drones, authority to go after larger ‘target boxes’ in Pakistan. For the former head of the CIA, “We’re conducing the most aggressive operations in our history as an agency” and “That largely flows from this president and how he views the role of the CIA” (p. 121).

The drone policy was in part incentivized by the lack of a detention policy. Killing was less politically risky than capture. Tom Donilon, the deputy national security adviser who had taken on the unenviable assignment of trying to forge a detention policy, rued that “We can’t be left in a situation where the only option for someone who has valuable intelligence is to kill him” (p.127).

Photo: Tom Donilon, National Security Advisor

Harold Koh, the State Department’s top lawyer, was charged with ensuring that American foreign policy adhered to international law. Obama was also keen to enrol lawyers in counterterrorism and the kill chain. By 2010 there were more than 60 lawyers in the CIA, and more than 10 in the CTC alone (p.206)—far more than under the Bush administration. He himself was left-leaning, and questioned the geographic expanse of the 2001 AUMF and therefore who could be subject to disposition. Koh did however accept the basic legality of targeted killings. He thought they were ‘acts of war’ permitted under domestic law by the 2001 AUMF and not assassinations. And targeted killings also fell safely within the remit of ‘self-defense’ under international law to prevent immanent threats to the U.S. homeland. But in Somali and Yemen, the administration’s legal authorities were far flakier. 

Photo: Harold Koh, Legal Adviser of the Department of State

In December 2009 Koh was asked to consider the legality of a series of targeted killings by JSOC in Yemen. Koh was given a classified PowerPoint presentation detailing a plan to attack US embassy in Sana’a. After 9/11 JSOC operated under a series of executive orders executed under the Bush administration and revised and expanded by Obama after taking office Unlike the CIA, JSOC was not required to brief Congress on clandestine operations, so in effect, JSOC had become the president’s ‘secret army’. After receiving ‘baseball cards’ of suspected terrorists to study, Koh joined a secure video conference with some seventy-five officials from across the counterterrorism bureaucracy and the White House. It was “killing by committee” (p.200). Every ‘kill or capture’ operation in ‘denied areas’ goes through an elaborate interagency vetting before being signed off on by the President. As Klaidman reveals: “So intimate was Obama’s involvement with JSOC that he personally signed off on each kill or capture operation conducted in Yemen and Somalia” (p. 205). The president was drawn to JSOC for the same reason he was the CIA: it was off the radar. For Koh, the military’s euphemisms were cold: “I kept slipping back and forth between the view of the predator and the view of the prey” he later told a friend” (p.201).

Killer Koh’ as his liberal detractors would label him, decided to front Obama administration’s legal justification for targeted killing. On March 25, 2010, Koh gave a technical defense of targeted killings. He established his elaborate four-part test for striking people outside of regular battlefields:

1. The prospective target would have to be clearly part of AQ

2. He would have to be a senior member of the organization (uniqueness versus fungibility)

3. The target would have to be ‘externally focused’

4. There had to be evidence the target was plotting to strike (to comply with self defense rules. Koh developed a theory of ‘elongated imminence’, which he likened to a ‘battered spouse syndrome’

Bin Laden and Awlaki

In August 2010, Panetta had informed the White House on a lead for the hunt on Osama bin Laden. They had found his most trusted courier, Abu Ahmed al-Kuwaiti in the town of Abbottabad. There were two reactions in the White House: bomb or raid? Obama said the mission would be a ‘Title 50 operation’ conducted under the auspices of the CIA. A legal finding had already been prepared so that Justice Department approval was not necessary. On April 19, 2011, Obama was briefed again: Admiral McRaven presented the president with a detailed helicopter-assault plan with a team drawn from Red Squadron of SEAL Team Six. Obama was anxious at first, echoing anxieties of Defense Secretary Robert Gates—what if it went wrong? Gates had been a young CIA officer in the Situation Room the day of the disastrous Iran hostage-rescue mission in 1980. And yet, capturing bin Laden was never really an option (p. 245). The plan was in place: 79 SEALs would attack the Abbottabad compound. They would succeed in killing the unarmed al-Qa’ida leader.

At the same time in the spring of 2011, JSOC began advocating for a more aggressive ‘campaign’ in Yemen, and the CIA began pushing to expand its signature strikes beyond Pakistan to Yemen and Somalia (p. 252). But there was fierce debate in the administration: were AQAP and Shabab regional threats or ‘future Afghanistans’ that harbored internationally-focused terrorists? After the military proposed killing 11 AQAP operatives at once in May of 2011, an irritated Brennan cautions Obama, and neither wants to get sucked into Yemen’s civil war: so the initial list of 11 was reduced to 4 by Obama. But there was one Yemen case that Obama was fixated on: Anwar al-Awlaki, the al-Qaeda cleric. The Commander-in-Chief wanted updates at every Terror Tuesday meeting (p.261). Most lethal operations in Yemen had been conducted by the military, but in the summer of 2011, the Awlaki job fell to the CIA because “the United States had built a new drone base in a strategically located Persian Gulf country” (p.261). The CIA had better ties there than the military.

“What was striking was that JSOC accepted the CIA’s primary role in the hunt for Awlaki without complaint. Like the bin Laden mission, it was an example of the near-seamless integration of counterterrorism operations between the military and the CIA, a hallmark of Obama’s war” (p. 262).

The Justice Department had issued a yet-unseen memo in June 2010 detailing the legality of targeting an American citizen for death. They concluded it was lawful if capture was not feasible.

Closing Thoughts

And so, to conclude, what are we to make of Obama’s first administration? He definitely inherited a series of complicated legal and moral dilemmas from Bush’s war on terror—baggage that nobody wanted on their own turf. And Obama’s hands were certainly tied by Republican and Democratic hawks that prevented a range of possible solutions to Guantanamo detainees, especially the Article III trials that were so passionately defended by Eric Holder. But this picture of a President boxed into a corner is also misleading. In the shadows, Obama’s administration was certainly not ‘Bush-lite’. The program of targeted killings he inherited was expanded exponentially and to deadly effect. This certainly was not a pragmatic ‘middle way’; it was as much an ideological faith in the supremacy of the CIA and JSOC to deliver military solutions to problems Obama once saw as tactical rather than strategic, and in blatant disregard of the ‘upstream factors’ he had discussed with Brennan in the infancy of his election.

This was a White House that would centralize power in the hands of one man: Barack Hussein Obama, setting in motion a powerful precedent that will have unimaginable consequences. On the watch of a constitutional lawyer, the U.S. way of war has redefined itself, moving into the shadows; where the fog of war, law, life, and death is strangling.

Daniel Klaidman. 2012. Kill or Capture: The War on Terror and the Soul of the Obama Presidency. New York: Houghton Mifflin Harcourt Publishing Company.

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