Timber Sycamore was a classified operation run by the United States Central Intelligence Agency to supply and train the Free Syrian Army and moderate Islamist Syrian Opposition groups in their struggle against Bashar al-Assad's pro-Russia and pro-Iran Ba'athist regime during the Syrian Civil War. Starting in 2012, President Barack Obama had the CIA's Special Activities Division supply money, weaponry, and training to vetted "moderate" rebel groups with the help of Saudi Arabia, the United Kingdom, and regional Arab governments. The operation was run mostly from Syria's easterly neighbor, Jordan, a US ally; Saudi Arabia provided most of the money and weaponry to the Syrian Opposition, while the United States led the way in training the Syrian rebels from SAD-run training camps in Jordan. Saudi Arabia, Qatar, and Turkey shipped thousands of rifles, hundreds of machine-guns, and large amounts of ammunition to the Syrian rebels before "Timber Sycamore" launched in 2012, after which the CIA helped arrange arms purchases for the Saudis, including a large deal in Croatia in 2012.
The CIA ran the operation from Amman, from which they provided AK-47s, mortars, RPGs, BGM-71 TOW anti-tank guided missiles, night vision goggles, pickup trucks, and other weapons to Syrian rebel forces, with most of the weapons being purchased from the Balkans and Eastern Europe and shipped to the Middle East via Tasucu, Turkey and Aqaba, Jordan. By late 2012, The Daily Beast reported that 50 vetted Syrian rebel groups were receiving arms from the United States and its allies. From 2012 to 2017, the US-armed Syrian rebel groups killed or wounded 100,000 Syrian Arab Army soldiers and their allies, but the program began to lose its effectiveness after Russia intervened in the war on the side of the Syrian Arab Republic, launching airstrikes against the Syrian rebel groups and turning the tide of the war against them. At the same time, corrupt Jordanian intelligence officials stole several CIA-supplied weapons and sold them on the black market, and, while the intelligence officers were caught and fired after several months, their profits were not confiscated, and Timber Sycamore arms flooded Middle Eastern black markets with heavy weaponry. Bazaars at Ma'an in southern Jordan, Sahab in Amman, and the Jordan River valley became hubs of arms trafficking, and many Syrian rebel groups sold their US-supplied arms to Bedouin arms dealers in order to acquire cash to pay for more fighters. These Daraa-based Bedouin arms traffickers traded these weapons to ISIL via WhatsApp, and several moderate rebel groups joined forces with jihadist groups such as the al-Nusra Front and Ahrar ash-Sham in order to form stronger alliances against the Syrian government, leading to al-Qaeda-backed rebels also acquiring US weaponry. As a result, the program was phased out in July 2017 at the directive of President Donald Trump, who replaced it with the "Syrian Train and Equip Program" of 2014-2015; this similarly ended in disaster, as only 54 trained-and-equipped fighters were deployed to battle with Division 30, and they were quickly routed by al-Nusra in July 2015. Trump proceeded to abandon the United States' support for the declining "moderate" rebel groups and instead increased the United States' support for the Kurdish-led Syrian Democratic Forces; the moderate rebel groups would either be defeated or merged into larger jihadist groups such as Tahrir al-Sham and Ahrar ash-Sham or merged into the pro-Turkish Syrian National Army, which became a fierce opponent of the US-backed Kurds.