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Covert Action in Irregular Wars: Unraveling the Case of Timber Sycamore in Syria (2012-2017)

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03.04.2025 at 06:00am
Covert Action in Irregular Wars: Unraveling the Case of Timber Sycamore in Syria (2012-2017) Image

Abstract

The Central Intelligence Agency ran a covert operation in Syria from 2012 to 2017 called Timber Sycamore. This qualitative case study employs content analysis and descriptive inference to analyze declassified documents, government records, and other primary sources surrounding this shadowy case. This study finds that the operation suffered from numerous challenges stemming from oversight shortfalls, limited vetting, and accountability problems. Some weapons disbursed under the program were diverted to groups like the Islamic State, while certain groups trained in the program subscribed to the very Salafi-jihadist ideologies that U.S. forces were deployed to the Middle East to counter. This case offers lessons on complications that Title 50 and Title 10 programs pose while training, equipping, and controlling irregular forces beyond the contours of ordinary security cooperation programs.

 

Introduction

Rumors swirled in 2019 that the United States had trained and equipped elements of the Islamic State (ISIS) in Syria. This Iranian government disinformation stream added to reports surfacing since 2013 about a secret Central Intelligence Agency (CIA) operation arming Syrian rebels. The U.S. government did little to counter the narrative surrounding this covert action known as Timber Sycamore. President Trump finally ended the program in June 2017 after some alarming updates in the President’s Daily Brief. But what was really going on in Syria during those five years?

A thread of truth wove through some of those reports. Missiles and small arms did indeed fall into the hands of ISIS. A group from Jordan’s General Intelligence Directorate in fact made millions diverting weapons into the black market. Worse, some of the partner forces subscribed to the very Salafi-jihadist ideologies that other U.S. forces were there to eliminate. As such, Timber Sycamore is an instructive case study on the complications of CIA and Special Operations Command (SOCOM) programs running in parallel under different authorities. Although the goal of regime change in Syria materialized years later, significant challenges beset the operation—including oversight shortfalls, limited vetting, and lack of accountability.

Old Habits, New Problems

The CIA has long worked alongside the military in general and Special Operations Forces (SOF) in particular. Relationships built in World War II matured in the Vietnam War, where the CIA and SOF established the Civilian Irregular Defense Groups to counter the Viet Cong. The Phoenix Program was another close collaboration in which Vietnamese government agents worked with SOF assistance as the CIA coordinated overall. In practice, this meant a CIA officer and a SOF member shared responsibility at each echelon. The military member fell under different authorities depending on whether they were in charge or second in command to the CIA officer. The conflict expanded unofficially into Laos, and SOF again had to innovate to fund their irregular partners. This method of integrating SOF elements into unique command relationships with the CIA was later known as “sheep dipping.”

Sheep dipping emerged from the CIA’s need to employ SOF in certain Title 50 activities while avoiding restrictions and complying with the 1954 Geneva Accords. Title 50’s legal basis for sheep dipping subjects non-CIA executive branch entities to the CIA’s rules in each covert operation, including contractors and SOF, while simultaneously remaining beholden to the sending organization’s own rules.

The 2011 Bin Laden raid was a dramatic demonstration of sheep dipping. There, Joint Special Operations Command (JSOC) operators worked under the overall leadership of the CIA director while the JSOC commander held a secondary role. But nowhere was sheep dipping more apparent in recent history than at the CIA’s operations centers in Jordan and Turkey. Starting soon after the Arab Spring reached Syria, SOF and American contractors worked alongside the CIA under Timber Sycamore, covertly training and equipping the opposition.

The Arab Spring of Our Discontent

The U.S. government began seriously contemplating a covert action in Syria in 2012 amid the unfolding Arab Spring. Domestic realpolitik drove President Obama to ultimately approve Timber Sycamore in a presidential finding he was long reluctant to support. Meanwhile in Syria, President al-Assad made the rational choice to strengthen relations with Russia and Iran while choosing not to focus on defeating ISIS, all to prolong his survival at the Syrian people’s expense. The CIA’s goal for the covert action was to overthrow President Bashar al-Assad’s regime. An overt military operation targeting ISIS ran simultaneously, but the focus of Timber Sycamore was Bashar al-Assad’s government, not ISIS.

Timber Sycamore included training, equipping, supplying, and sustaining Syrian irregulars, while Congress also set funds aside for construction and paying fighter stipends. Throughout the program’s life, Congressional committees tried numerous times to stanch funding and change vetting requirements, all to no avail. Over the years, the U.S. government began redirecting assets assigned to Timber Sycamore to the broader effort to defeat ISIS. Operation Inherent Resolve increasingly consumed resources, drawing attention from regime change. These shifts were apparent in the fluctuations in SOF on the ground in Syria, as troop levels floated between 300 to 900 SOF at any given time. These variations reflected the shift away from regime change and toward countering ISIS in the evolving U.S. policy in Syria. The appeal of covert action faded while the threat of ISIS grew, but not before the U.S. government exhausted the regime change option.

Covert Options: Rumblings of Regime Change

The implications of Syria’s civil war grew dire in 2012 as the Arab Spring awakened the long-simmering opposition to President al-Assad. Salafi-jihadist groups joined in, while Russia and Iran looked on. Syria was fast becoming a theater of great power competition. The U.S. government’s decision to embark on a program to oust al-Assad inadvertently aligned with the interests of erstwhile foes like al-Qaeda, ISIS, and local affiliates. The sensitive nature of American support to irregular forces in this context allowed one viable option: covert action.

But covert action is more likely to fail as a foreign policy tool than other means of diplomacy, military action, and economic activity. The 64 covert actions conducted from 1947 to 1989 achieved under a 40 percent success rate in reaching even their basic short-term objectives. Despite this, some favor covert action as a risk mitigation tool regardless of their propensity to promote risk escalation and unforeseen negative outcomes. A major appeal of these inherently risky, often destructive operations is their deniability.

Covert action conceals sponsorship while sometimes allowing the activity to be observed. In contrast, clandestine operations conceal the activity conducted without necessarily concealing government affiliation. Narratives can veer in undesirable directions because of this concealment. Special activities have long served as foreign policy tools, and covert action in Syria is not new.

Indeed, an operation against the pro-Soviet government in Syria in 1957 was an early case of covert action. The CIA learned that the Soviet Union was seriously considering military intervention in Syria and that the Syrian government accepted an unconditional loan from the Soviets. The CIA continued describing Syria as “a center of instability” a decade later. Nor was regime change a novel concept. The CIA thoroughly analyzed regime change outcomes for Bashar’s father in 1986, drawing on a 1978 analysis from a relatively tamer report entitled “Syria Without Assad: Succession Politics.”

Following from those Cold War-era approaches, the U.S. government would wield Timber Sycamore to achieve policy outcomes rather than to secure domestic Syrian interests or spread democracy. Events before the operation shaped how parallel operations between the CIA and SOF were aligned in execution. Operational challenges eventually forced a reversion to covert action exclusively, but the downfall of Timber Sycamore was already in motion by then.

Nadir of Diplomacy, Dawn of Covert Action

The Arab Spring was in full swing when a CIA-led Syria task force briefed Congressional intelligence committees in early 2012 about plans to help Syrian rebels overthrow President al-Assad. Around the same time, Ambassador Robert Ford shuttered the U.S. Embassy in Damascus. The mission went into exile at U.S. Embassies in Amman and Ankara. ISIS was expanding in the vacuum of Syria’s civil war, and the United States had been tracking iterations of this group for years after it emerged from Abu Musab al-Zarqawi’s al-Qaeda in Iraq. The intelligence community watched as ISIS seized territory in eastern Syria and the Syria-Iraq border. But ISIS’s growth was initially a distraction from the more pressing issue of regime change.

The National Security Council debated the wisdom of a presidential finding to take advantage of the weakened Syrian regime throughout 2012. The U.S. government ignored President al-Assad’s offer to abdicate via a Russia-brokered agreement in February that year, believing that he was already on the brink of overthrow. But a quick U.S. military intervention to achieve this was an unpopular option, partly because a lengthy rebellion was considered more likely to seal al-Assad’s ouster. Secretary of State Hillary Clinton and CIA director David Petraeus advocated for a presidential finding to invigorate that rebellion in discussions with President Obama. As the debate continued, the CIA was already covertly providing weapons and support to Syrian rebels, concealing U.S. sponsorship via Saudi Arabia, Turkey, and Qatar.

The CIA learned that although Qatar and Saudi Arabia were helping funnel U.S.-provided weapons to Syria, Gulf countries were independently funding and equipping an array of Salafi-jihadist rebels that were not among the U.S.-backed groups. A presidential finding could corral Gulf Arab support and regain control over the situation in Syria. In December 2012, the State Department issued a public statement that “Transition is coming one way or the other [in Syria]” and “the only way forward is for Assad to step aside.” Clearly, corners of the U.S. government were already moving toward regime change even before President Obama signed off.

Talks hastened after Syria’s regime attacked civilians with chemical weapons in Eastern Ghouta on 21 August 2013, killing around 1,400 civilians. President Obama finally relented. Timber Sycamore went operational: the Free Syrian Army and others now had the CIA and SOCOM support and the U.S. gained control over much of the foreign support to Syria’s rebels. The presidential finding authorized the first train and equip operation for 50 Syrian opposition fighters that summer. Small arms, ammunition, and anti-tank (TOW) missiles followed. Agents purchased weapons in Eastern Europe and the Balkans, shipping them through Saudi Arabia and onward to Syria via Jordan and Turkey. However, competing Gulf Arab objectives and Turkey’s border policies at times contravened U.S. interests. Internal frictions between CIA and SOCOM equities also negatively affected the operation from the beginning.

Parallel Universes: Intelligence, Special Operations, and Security Assistance

Three U.S. programs ran in parallel to one another in Syria. The CIA and SOCOM worked together. Meanwhile, the State Department ran a non-lethal assistance program for Syrian opposition leaders in Turkey through the Bureau of Conflict and Stabilization Operations (CSO). The CIA largely remained aloof from the State Department’s Title 22 security assistance programs and some Title 10 security cooperation activities despite the different aid sources sometimes going to the same or related groups of Syrians and regional partners.

In 2012 alone, the State Department’s CSO spent $24 million assisting just 500 Syrians with setting up media services and building governing capacity. A new program began after CSO’s operation ended in 2017. Like CSO’s program, the Syria Armed Moderate Opposition Support program provided only non-lethal assistance to Syrian opposition groups in contrast to Timber Sycamore and the Syria Train and Equip Program (STEP). The department later allocated $177 million to security assistance programs for Syria in 2016. By 2018, this had increased to $191 million annually, all separate from Timber Sycamore.

The CIA owned two operations centers for Timber Sycamore on bases in Turkey and Jordan. Officials from Saudi Arabia, Qatar, France, and Britain also shared spaces at these centers. Bases, camps, and support systems dotted Syria and Gulf Arab states. Rebels assigned to Turkey’s Joint Operations Center belonged to the “northern front,” training at bases in Gaziantep and Antakya. Rebels in Jordan organized under the Military Operations Center and comprised the “southern front.” In Syria, the northern front centered around Idlib and northwest Syria. The southern front centered around places like Al Tanf, Dara’a, Al Suwayda, and the approaches to Damascus. In Jordan alone, 600 men trained monthly in 2014. Syrian opposition leaders at the CIA-run operations centers told their handlers what equipment and training they wanted, and the CIA then communicated the requests to the broader U.S. government and partners. Saudi and Emirati officials delivered funding and more weapons.

Saudi Arabia and the United States purchased weapons inside the European Union while Jordan and Turkey facilitated their transfer into Syria. The United States represented on end-user certificates that the weapons were solely for end use by the U.S. Department of the Army, thereby concealing the true recipients from European weapons suppliers while ignoring non-retransfer clauses in those certificates. Weapons arrived by air in Saudi Arabia, and the CIA received them at the operations centers in Turkey and Jordan.

The Syria Engagement Team trained their Syrian partners on the basics at the two operations centers. The Syria Engagement Team consisted of CIA Ground Branch, government contractors, and 5th Special Forces Group operators. Required subjects for the irregulars included small unit tactics, combat casualty care, and physical fitness. Cycles lasted two to three weeks. Afterward, the trainers gave each man about $200 plus the weapons with which they trained. Select graduates took media classes focusing on content creation to help promote their achievements on social media. Others took train-the-trainer classes.

Several thousand fighters trained in all locations under Timber Sycamore between 2014 and 2016. The U.S. provided at least 10,000 rebels with weapons. Over 60,000 rebels in at least 42 groups worked under Timber Sycamore both in and outside Syria during the program. In the northern front, somewhere between 30,000 to 35,000 CIA-backed rebels fought under various banners in Idlib alone in May 2017. At least 30,000 Syrians fought in the southern front, with half this number in the Salafi-jihadist militia called Jaysh al-Islam. However, some groups were relatively less extreme and were therefore eligible for advanced weapons like TOW missiles.

The CIA capitulated to delivering BGM-71E TOW missiles starting in 2014 after many requests from Syrian opposition leaders. The United States initially expressly withheld weapons that could be used for improvised air defense purposes. But the CIA judged that a rebel group called Harakat Hazzm was relatively moderate compared to some of the other groups, and so it was among the first to receive the missiles. TOW missile training took 35 days in Qatar and Saudi Arabia for cohorts of 100 trainees each. Cohorts received 10 TOW missiles from U.S. stocks, RPGs, ammunition, mortars, and three trucks modified for carrying the weapons after completing training. The CIA provided 10 additional TOW missiles if fighters recorded launches, retained spent components, and provided GPS coordinates for points of origin. In all, the CIA gifted TOW missiles to at least 14 rebel groups through Timber Sycamore.

Funding for Timber Sycamore could not be satisfied by CIA funding alone. Congress did give Timber Sycamore $1 billion annually, which was about seven percent of the CIA’s budget in both 2014 and 2015. This was one of the largest expenditures on a single covert action in CIA history. But Saudi Arabia also provided substantial financial support. And despite the CIA’s costs working out to about $100,000 per year per fighter, the SOCOM part of the operation, STEP, was significantly costlier in terms of dollars spent per trainee.

SOF teams began STEP in September 2014. The first 90 Syrians started their training on 7 May 2015. The program was expensive, with $500 million spent on 150 fighters just from September 2014 to October 2015. Congress obligated $346.8 million into another funding stream for weapons, ammunition, and supplies. This works out to about $10 million to train each person and $2.3 million per person for materiel. Major General Michael Nagata, then the commander of the Combined Joint Interagency Task Force-Syria, spoke in a December 2015 interview with the DoD inspector general, describing STEP as a “journey of experimentation,” likening it to starting a small business.

The billion-dollar experiment of STEP ended on 9 October 2015. By that point, the lead inspector general for Operation Inherent Resolve found that the DoD had not adequately satisfied oversight requirements set out by Congress. Fewer than five graduates from the planned 15,000 fighters were actively engaged in combat in Syria in late 2015. The DoD air-dropped a package of 50 tons of ammunition along with small arms on 10 October 2015, the day after STEP ended, in hopes of future reengagement with their Syrian partners.

SOF advisors again augmented the CIA months later to continue working with Syrian irregulars under Timber Sycamore, this time under new authorities. Separately, other SOF elements partnered with irregular forces from the Syrian Democratic Forces in 2016 under Operation Inherent Resolve in Northeast Syria to degrade and defeat ISIS. Ultimately, the waste from STEP forced a reversion to covert action only, but the embarrassing developments on the CIA side accelerated Timber Sycamore’s eventual downfall.

Best Laid Plans: The Downfall of Timber Sycamore

Timber Sycamore initially involved the two-pronged approach of the CIA and SOF advisors training and equipping Syrian rebels. However, the CIA rapidly lost control over weapons and trainees as ballooning costs soon forced policymakers to reevaluate the program. DoD costs were too high for too little gain and so the program reverted to only the CIA training and equipping. Meanwhile, the initial goal of removing President al-Assad remained out of reach.

A 2016 State Department dissent channel memo entitled “Syria Policy” called for expanding overt U.S. military operations in Syria. The same memo indirectly criticized Timber Sycamore, hinting at the operation’s inability to contain the conflict and influence al-Assad to abdicate. The administration had shifted its Syria policy in 2014 toward countering ISIS. The pivot toward prioritizing defeating ISIS over the overthrow of al-Assad undermined Timber Sycamore as Operation Inherent Resolve drew SOF advisors away.

Amid this internal reshuffling, Russia made its entree into Syria in 2015, throttling most U.S. activities there. The United States and Russia established a deconfliction cell in 2016 to reduce tensions between rebels in the Russian and U.S. sectors in Syria. But by then Timber Sycamore was in its twilight. Russian intervention aside, problems within the program ultimately generated enough bad publicity to devalue the deniability that a covert action could provide.

Negative press about Syrian trainees started surfacing. In one case, some of the Syrians trained under Timber Sycamore executed detainees. This triggered no reporting mechanisms because the program was exempt from human rights violation reporting requirements. But these executions still made headlines. Meanwhile, a Jordanian soldier shot and killed operators from 5th Special Forces Group as they trained their Syrian partners near Jordan’s King Faisal Air Base in November 2016. The previous November, the FBI discovered that the weapon a Jordanian used to kill two U.S. contractors and three Jordanians was from Timber Sycamore. Members of Jordan’s General Intelligence Directorate had sold it on the black market.

The General Intelligence Directorate faced other scandals with the middlemen it employed. Middlemen like Tayser al-Sharif, known locally as Cheg Cheg, worked for Jordan’s General Intelligence Directorate to smuggle the weapons into Syria. Smugglers further on distributed the weapons to dozens of CIA-supported southern front rebel groups. Smugglers like Cheg Cheg charged fees of about $30,000 per truck to move weapons across Syria, and these smugglers moved thousands of truckloads. Smugglers used WhatsApp to arrange diversions to ISIS via Bedouin groups like “The Birds,” who operated in southern Syria’s Lajat lava fields.

Weapons diversions to U.S. adversaries struck the greatest blow to the program. In May 2015, a Bulgarian PG-7T rocket from Timber Sycamore turned up in an ISIS cache in Al Hasakah, Syria. In December 2016, a Syrian fighter in Jaysh al-Nasr used a Bulgarian-manufactured anti-tank guided missile system in Hama that the United States purchased for northern front rebels. Less than 60 days later, weapons from the same lot ended up in ISIS’s hands in Iraq.  Iraqi counterterrorism forces found still more in an ISIS cache in Ramadi in 2016. The rockets were exported from Bulgaria via Kiesler Police Supply to the U.S. Department of the Army on 23 June 2014. Iraqi forces recovered three more PG-7Ts from the same lot in ISIS caches in Baghdad in 2016. As time went on, still more weapons ended up with ISIS in part because accountability measures were insufficient.

Weapons transferred to Syrian opposition forces that ended up with ISIS also included small arms. Kurdish Peshmerga forces discovered Romanian Mitraliera medium machine guns in an ISIS cache that were part of a 250-weapon lot exported to the U.S. Department of the Army on 10 August 2012. By the end of the operation, many of the weapons delivered from Turkey, Saudi Arabia, and Qatar had ended up with ISIS, other Salafi-jihadist groups, and groups affiliated with the Muslim Brotherhood. The blurring lines of different authorities further complicated efforts to follow the rebels and track where the weapons went.

A Tale of Two Authorities: Title 50 and Title 10

The relationship between intelligence activities, special operations, and covert action is often misunderstood. In simple terms, intelligence activity reflects upon information already obtained so that estimates of future action can be made. In contrast, a goal of covert action is to cause an adversary to take certain future actions. Despite this simple distinction, the lines between Title 50 covert action authorities and Title 10 authorities peculiar to SOF can seem blurry. This is especially true of sheep dipping, but the haziness falls broadly.

The National Security Act of 1947 described how the CIA and National Security Council would interact. Traditional military activities were originally also written into Title 50, but Congress later separated these into Title 10. The legal basis for covert action stayed tucked away in a clause in Title 50. There, Congress mandated that the CIA was “to perform such other functions and duties related to intelligence affecting the national security as the National Security Council may from time to time direct.” The CIA and National Security Council interpreted these “other functions” to mean covert action.

Czechoslovakia faced a Communist overthrow the following year. The National Security Council stepped in with the first covert action under the new law. Their classified directive funded the CIA’s Office of Policy Coordination and outlined what the CIA should achieve in Czechoslovakia. Greece came next after the office merged with the Office of Special Operations in 1949. Dick Bissell, the first director of the merged offices, distinguished two types of operations. The first concerned intelligence gathering. The second type was influencing how other states behaved. Timber Sycamore resided in this latter category of covert action.

The CIA’s own account of covert actions up to 1973, known as the “Family Jewels Memo,” ranged from hiring the mafia to poison Fidel Castro to reading Russian mail in New York. At least one covert action was active per year from 1949 to 1974, including better-known operations in places like Iran and Guatemala plus Tibet, Italy, and others. More recently, President Obama authorized a covert action in 2011 to overthrow Moammar Gadhafi in Libya the same year JSOC raided Bin Laden’s compound in Pakistan, completing a covert action President Bush approved in a 2001 presidential finding.

SOF elements sometimes overlap with CIA officers in time and space, especially in the context of unconventional warfare. This special operations core mission area involves enabling a resistance movement or insurgency to coerce, disrupt, or overthrow a government or occupying power. Although SOF elements carry out a variety of operations, actions, and activities, several Title 10 authorities tend to tread more closely to ongoing CIA operations than others. SOCOM has used iterations of what are now Sections 127e and 127d of Title 10 to support or run adjacent to Title 50 activities while other approaches, such as sheep dipping and preparation of the environment, take a different shape.

Prior to 2005, SOF sometimes relied on CIA money to fund unconventional warfare activities, such as Task Force Dagger. The temporary authorities in Section 1208 arose in 2005 and funded these activities through Title 10 instead of Title 50. Funding authorities were further restructured into an optimized solution to the thorny questions surrounding special operations that often ran adjacent to CIA operations.

Congress permanently enshrined this solution under Section 127e in 2017. This authorized $100 million annually for SOF to work with irregular partner forces toward counterterrorism objectives, usually supporting broader authorities like the Counterterrorism Execute Order (CT EXORD) or other regional and combatant command EXORDs. The DoD framed Section 127e as a way to reduce the special operations footprint in the Sahel-Maghreb and Horn of Africa. The authority indeed reduced the number of forces needed in those areas and redirected assets for strategic competition in Eastern Europe, Africa, and Asia. This redirection was enterprise-wide, with Joint Special Operations Command standing up the Counter-External Operations Task Force, or Ex-Ops, consolidating global counterterrorism operations at a single site in Jordan. SOF counterterrorism operations continued growing, reaching 78 countries by 2021. The changing funding landscape in which 127e lived was convenient for SOF teams deployed in Syria. They reoriented on counterterrorism activities after their support to Timber Sycamore wound down while their footprint remained. Related authorities like 127d helped enable SOF teams to keep training and equipping different partners in Syria.

Like 127e, Section 127d sprang from an older authority. Its predecessor, Section 1202, arose in 2017 and authorized SOCOM to purchase night vision devices, weapons, equipment, vehicles, and other supplies for irregulars and other partner forces. Funding for these irregulars parallels 127e programs, complementing training with equipment. Section 1202 became Section 127d in fiscal year 2024, while Congress increased annual funding from $15 million to $20 million. Other authorities complement these, such as Section 127f. That authority allows SOCOM $40 million annually for preparation of the environment and non-standard assisted recovery activities, key tasks required before executing certain special operations.

Oversight for these authorities is laxer compared to requirements for other Title 10 authorities like the major security cooperation programs found in Chapter 16. The programs are also difficult to track internally, as SOCOM’s own Major Force Program-11 (MFP-11) funding is “time consuming and difficult” to understand even for SOCOM’s own attorneys. MFP-11 is the vehicle for funds delivery under these programs. Oversight for 127d, 127e, and 127f includes operation summaries, descriptions of support, recipients details, funding obligations, operation timelines, and value assessments. But these authorities are exempt from human rights reporting laws that nearly all other partner-focused programs observe.

Oversight Challenges

Congressional oversight of covert actions has been a challenge since the National Security Act first set the legal basis for carrying them out in 1947. In 1973, Senator Stuart Symington made an observation about these oversight challenges that still affected later operations, noting that “This committee does not know of [CIA] activities in foreign countries with which we are not at war. It not only doesn’t make any sense, but it has resulted in heavy loss of both money and respect.” This loss of money and respect plagued covert actions in Vietnam in the 1960s, Afghanistan in the 1980s, and Syria in the 2010s.

Presidential authorization for covert action, known as a presidential finding, became a requirement in 1974 following numerous revelations about questionable CIA activities. Covert activity not already approved under an existing presidential finding now cannot receive Congressional funding. Congressional committees require numerous oversight products, ranging from notification timelines to substantive reports. Despite those requirements, covert operations continued leading to embarrassing and potentially destructive long-term outcomes. Examples include covert support to the Contra rebels in Nicaragua coinciding with the Iran-Contra Affair and the activity under Operation Cyclone in Afghanistan contributing to conditions for the Taliban seizing power in the 1990s and in 2021.

These outcomes are due in part to relatively weak enforcement of oversight requirements and lack of political will. The House of Representatives amended a rule demanding that the executive branch disclose every record associated with Timber Sycamore. The intelligence community released none. House Intelligence Committee members voted unanimously in November 2015 to cut funding to Timber Sycamore by $200 million, or about twenty percent. The legislation never made it for a full House vote. Likewise, Freedom of Information Act requests for Timber Sycamore started in 2019 but still nothing was released during the Syrian conflict.

Weak oversight problems were dramatically highlighted in 2018. That year, the president’s legal counsel issued a memorandum arguing he was permitted under Article II of the Constitution to conduct military operations in Syria without Congressional approval. Law professors at Harvard and the University of Chicago immediately opposed that opinion. Despite this, the president invoked the 2001 Authorization for Use of Military Force, designed for a different purpose, as the legal basis for striking Syrian military facilities in 2018 and assassinating an Iranian general flying out of Damascus in 2020. Arguments about how this strike may have violated laws and executive orders aside, the strike went off without any meaningful Congressional interference despite its flimsy legal basis. The dearth of mechanisms to vet partner forces further compound the problems this atmosphere of weak oversight invites.

Vetting Partner Forces

Vetting partners and maintaining accountability of equipment are usually a key component of a security cooperation with a foreign force. However, covert actions and 127e programs are not beholden to standards set for conventional security cooperation programs. Build partner capacity programs constitute a separate group of authorities under Section 333. These programs are subject to extensive oversight and are treated like light versions of foreign military sales cases. Those programs are rigorously assessed, monitored, and evaluated on par with other major security cooperation programs grouped under Chapter 16 in Title 10. In contrast, authorities like Section 127e are not subject to Leahy vetting and the equipment issued does not carry the same transfer, use, and protection requirements as Chapter 16 security cooperation programs.

Leahy vetting for human rights issues is a key component of evaluating partner forces, and its absence removes an essential ethical guardrail. In 2014, Congress expanded Leahy vetting to include assessments about equipping and supporting those forces. Despite this, Congress exempted Section 127e from human rights vetting and from statutory requirements to report sensitive military operations. Section 127e only requires a post facto description of whether partners under the program engaged in human rights violations, but it provides no guidance on what to do upon discovering such violations, unlike programs subject to the Leahy Amendment. These forces are also not run through the State Department’s international vetting and security tracking system for checking past human rights violations, while Chapter 16 security cooperation participants must. Additionally, rules required irregular forces under Section 127e to only undergo counterintelligence and force protection screening rather than the comprehensive screenings that partners under Chapter 16 security cooperation programs must. A bill introduced in 2022 in the House of Representatives attempted to require Section 127e programs to undergo human rights vetting, but the bill failed to gain support in the Senate.

Congress was not the only voice that went unheard. Trainers on the ground criticized the force protection screening, emphasizing its inadequacy. Yet scrutiny requirements remained unchanged. Vetting consisted of biometrics enrollment to verify that the Syrian fighters had not been detained or otherwise recorded in those databases. The 5th Special Forces Group and CIA Ground Branch trainers had long protested that this was also insufficient. Syrian fighters affiliated with Salafi-jihadist groups like Jabhat al-Nusra, ISIS, and Ahrar al-Sham were theoretically barred from training, but only if trainers learned of such connections from the trainees themselves.

Runaway Guns: Accountability over People and Equipment

Covert actions can lack rigorous quantitative and qualitative measures of performance and effectiveness, while biases can infiltrate assessments. The threshold for success can be as low as keeping sponsorship hidden rather meeting long-term mission objectives. In one telling example, the covert action leading to the creation of the Iraqi National Congress and the accompanying propaganda operation to overthrow Saddam Hussein in the 1990s placed an Iranian puppet in control of the transitional government. Congress has yet to meaningfully improve accountability mechanisms for covert actions and adjacent special operations.

Accountability was handicapped from the start. Timber Sycamore lacked mechanisms for tracking who was given which pieces of equipment and where that equipment ended up. In any case, U.S. export controls for weapons and equipment supplied to non-state forces are challenging to enforce because the U.S. cannot wield the same sanctions that normally influence state recipients to comply. Another problem was tracking which groups rebels eventually settled in after training. Some non-state partners are designated foreign terrorists or have been suspected of committing gross human rights violations. An exception to the rule prohibiting material support to these entities found in Title 18 allows U.S. officials to provide material support to foreign terrorist organizations like Jabhat al-Nusra’s successor Hayat Tahrir al-Sham. Granting these exceptions can have unforeseen consequences, as eventually happened in Syria.

Did Timber Sycamore Actually Fail?

Timber Sycamore’s initial goal was regime change in Syria. The trajectory of the Syrian war changed dramatically with the flight of President al-Assad and his family to Russia in December 2024. The remnants of Timber Sycamore’s northern front, backed by Turkey, had finally taken Syria. But the Syrians who ousted al-Assad hailed from among the more extreme Salafi-jihadist factions to affiliate with Timber Sycamore. They had also joined with al-Qaeda and ISIS at different times. Now, in al-Assad’s place, the old al-Qaeda hand Ahmad al-Sharaa took over as the country’s interim leader.

Al-Sharaa was already a known quantity under his nom de guerre, Abu Mohammad al-Jolani. Indeed, his group had been one of the early benefactors of Timber Sycamore in the northern front. ISIS tasked al-Sharaa to create ISIS’s Syrian affiliate, Jabhat al-Nusra, upon his return from fighting under al-Qaeda against the U.S. invasion. Jabhat al-Nusra became the Syrian arm of ISIS until al-Sharaa decided to distance himself from the besieged caliphate in 2016. The group changed its name to Jabhat Fateh al-Sham and merged into what would become Hayat Tahrir al-Sham before taking control of the country in late 2024.

Al-Sharaa continued the Salafi-jihadist fight against al-Assad’s government during the intervening eight years between decoupling from ISIS and forcing al-Assad to flee. The rebranded Hayat Tahrir al-Sham remained a designated foreign terrorist organization but American delegations swiftly met al-Sharaa in Damascus in 2024. The $10 million bounty on his head, in place for seven years, vanished the next week. Echoes of Timber Sycamore were everywhere in this transformation, in both the rapid ascent of al-Sharaa and the apparent volte-face of U.S. policy toward a former al-Qaeda affiliate-cum-liberator inside a span of days. His ascent drew upon the decade-old northern front alliances made under Timber Sycamore, relationships incubated under Turkish supervision after the covert program ended. The CIA never had the opportunity to reach Timber Sycamore’s initial objectives. In an ironic twist, one of the program’s undesirables managed to see things through.

Conclusion

Syria today resembles an outcome dubbed the “Dark World Scenario” that the CIA described in a 2002 assessment of futures for the Middle East. The CIA believed this worst-case “bloodiest scenario” might follow a U.S.-led invasion of Iraq. The assessment warned that in the dark world scenario, “nationalist Islamist revolutions sweep away the old elites.” These CIA analysts were more prescient than they could have known. A Salafi-jihadist leader initially shunned from Timber Sycamore turned up a few years later in a lightning advance on Damascus and ousted the al-Assad family, achieving what the CIA had been contemplating since the 1970s.

Now, as the United States contemplates going after Mexican cartels in counterterrorism operations and overthrowing Iran’s regime, lessons learned from past failures become invaluable. But an internal review found that SOCOM inadequately shares lessons learned even within the organization. And the CIA as an institution continues struggling to salvage lessons out of past operations that can be applied to new problems. Esoteric policy debates continue about how covert actions should fit into U.S. national strategy while the chorus of simple missteps that brought down operations like Timber Sycamore and Operation Cyclone remain unresolved. The combination of poor oversight, insufficient vetting, and lack of accountability militated against Timber Sycamore’s success.

These problems remain. Exemptions from assessment, monitoring, and evaluation invite mistakes, runaway operations, and diverted resources. The expedited attention that dynamic conflicts require should not completely exempt covert action and SOF programs like Section 127e from active oversight, vetting, and accountability. The hard lessons of short-term gains bought at the expense of long-term failures continue to be instructive, from the Phoenix Program to Operation Cyclone, and now Timber Sycamore. Policymakers and practitioners must translate those lessons into action.

Note on Sources

This study analyzed declassified intelligence reports, official government records, pieces of legislation, Congressional testimonies, documents released via the Freedom of Information Act, and transcripts of interviews with those involved. Where applicable, news articles and other media were consulted to reduce discrepancies and verify claims made within the source material. The paucity of declassified documents, denials of Freedom of Information Act requests, and skewed accounts related to Timber Sycamore inhibit further exploration. Some program names and other identifying data were omitted.

About The Author

  • Before attending Yale Law School, Jonathan W. Hackett served 20 years as a U.S. Marine Corps interrogator and special operations capabilities specialist managing intelligence operations and special activities in dozens of countries across four continents. He is the author of Theory of Irregular War (McFarland 2023) and Iran's Shadow Weapons: Intelligence Operations, Covert Action, and Unconventional Warfare (McFarland 2025).

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