A prominent Taliban leader, who helped orchestrate the terror group’s resurgence whilst in exile in Qatar, was released from Guantanamo Bay in 2014, on the orders of then-President Barack Obama.

Former President Obama oversaw a deeply controversial prisoner exchange with the Taliban back in 2014, in which the US traded five dangerous militants for one US soldier who had deserted his post in Afghanistan.

At the time, Obama reassured the public that the release of these prisoners would not create trouble for US allies in Afghanistan, and they would instead remain in Qatar in exile.


However, they were left to freely plot and rebuild the terrorist organisation, before eventually orchestrating the complete takeover of the country over the last two weeks.

The Taliban Five

One of the prisoners in question, who is believed to be a highly ranked Taliban commander, is Khairullah Khairkhwa, who was arrested and sent to Guantanamo Bay back in 2002, for allegedly holding close ties with al-Qaeda leader Osama bin Laden.

Fast forward nearly 20 years later, during negotiations with President Joe Biden’s envoy to Afghanistan Zalmay Khalilzad, Khairkhwa sat directly across the table during the talks that organized the United States’ withdrawal from the country.

During the talks, Khairkhwa, who attended as part of the official Taliban delegation, declared that he intends to help form an Islamic government in Afghanistan through “political agreement.”


However, that all went out of the window after the US withdrew, leaving the Taliban to recapture the country almost 20 years after the initial US-led invasion.

After capturing the capital city of Kabul and raiding the Presidential Palace, Taliban fighters told Al Jazeera that the terror group intends to safely bring over the rest of their exiled leadership from Qatar.

One of the fighters who made the comments allegedly claimed that he was one of the Taliban Five that was released from Guantanamo Bay back in 2014.

Critics believe that the easy capture of Kabul, and the involvement of former Guantanamo inmates, show that the Obama-era “catch and release” policies of convicted terrorists helped facilitate the Taliban’s recent victory in Afghanistan.


The Taliban Five were released from prison in 2014 in exchange for the Taliban releasing deserted US soldier Sgt. Robert Bergdahl, who was captured by the terror group after he left his post in Afghanistan.

Bergdahl, after been hailed by President Obama, was later served with a dishonorable discharge from the military.

Broken promises

Khairkhwa was one of the prominent masterminds behind the Taliban’s return to Afghanistan, leaving a string of broken promises in his path that President Biden easily fell for.

Earlier this year, Khairkhwa promised that the Taliban would not attack the Afghan government if Biden committed to removing all US assets from the country, a promise that we now know to be a lie.


He also promised, like many other prominent Taliban figures, that there will be no revenge taken out on Afghan citizens who aided the allied invasion back in 2001, or on those who cooperated with the US-backed Afghan government and military.

However, reports have since surfaced that claim Taliban fighters have been going door-to-door in major Afghan cities with a so-called “kill list,” dragging citizens out of the homes and executing them on the spot.

Even President Biden’s own special envoy to the nation convinced White House officials that Afghanistan would not fall if the US withdrew, despite repeated promises by Taliban figures to establish a “strict Islamic rule.”

Many now believe that if President Obama, and Vice-President Biden, had left the Taliban Five to rot in the cells of Guantanamo Bay, then the Taliban would never have regained power as easily as they did, however, now the world knows that the 2,400 US lives that were taken on Afghan soil were lost for nothing.