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John Owen Brennan was the Director of the CIA, serving from March 2013 to January 2017. Initially working as a counter-terrorism adviser under Homeland Security, Brennan's gained a reputation for being a yes-man to his superiors and a bully to his subordinates. He will never say anything negative or question anyone above him, but he will bust your nuts if you are lower-ranked than he is and you happen to do something that potentially embarrasses him. In short, a model DCI.
He spent 25 years in the CIA, alternating between adviser and analyst. He was an intelligence briefer to Bill Clinton, the chief of staff to then-CIA Director George Tenet, and led the CIA station in Riyadh, Saudi Arabia when the Khobar Towers bombing killed 19 U.S. servicemen (no, we do not think he caused the bombing or knew of the bombing beforehand). He was the head of the Terrorist Threat Integration Center, which compiled and passed through George W. Bush's daily intelligence briefings, including the embarrassment known as the Orange Terror Alert (later discredited as a false alarm).
Here's where things get dicey. Brennan advised Barack Obama on foreign policy and intelligence issues during the 2008 presidential campaign and transition which could explain why Brennan was Obama's first choice for CIA Director in late 2008. One problem – Brennan supported the use of torture and transfer of terrorism suspects to countries where they might be tortured. The controversy was enough that Brennan withdrew his name from consideration for the CIA Director spot. Predictably, Brennan then disavowed the same form of torture he supported while working for Obama as chief counter-terrorism adviser, proving that evil bald men have no shame.
During the 2008 run-up to the elections, one of Brennan's employees breached the passport records of Barack Obama, John McCain, and Hillary Clinton. The employee who breached the accounts was never fired, and a key witness in the case was found murdered outside his church while the investigation was still ongoing. The witness, Lt. Quarles Harris Jr, was cooperating with federal authorities at the time of his death. The investigation died with him. Hmmm.... suspicious.
In an uncharacteristic moment of clarity and self-enlightenment, Brennan prefers the term "extremist" over "jihadist" when referring to Muslim fundamentalists. He claims that using "jihadist", which means one who is struggling for a holy goal, gives "these murderers the religious legitimacy they desperately seek", which suggests the US is at war with the religion of Islam and not with the terrorists. Granted, that last part is completely fucked when you read the next segment.
Counter terrorism adviser
He was the first official in the Obama administration to publicly acknowledge the drone strikes in Pakistan, Yemen, Somalia, Libya, and Afghanistan. He tried to argue, in no small words, that it was more effective and less dangerous than ground invasions. The ACLU disagreed. He then "backpedaled" by reorganizing the process under the aegis of the Disposition Matrix database (or the kill list), by which people outside of war zones were put on the list of drone targets. The Disposition Matrix, or the kill list, creates a blueprint for tracking, capturing, rendering, or killing suspected enemies of the US government while cataloguing the "suspects'" biographies, locations, associates, and affiliations. This is just as bad as it sounds.
Director of the CIA
Surprised that it took this long before we got here, huh? Well, he's now earned the distinction of being the first CIA Director to earn the most "no" votes since Robert Gates and George H.W. Bush before him. The vote was 63-34, with Bernie Sanders, Patrick Leahy, and Rand Paul among those who voted against his appointment to the position. Elizabeth Warren and Sherrod Brown were among those who voted in favor of his appointment. Reports indicate that, among other things, Brennan has been tasked with blocking journalists' attempts at investigating and reporting on various infringements on human rights and civil liberties done by the White House.
A conspiracy theory has emerged that Brennan may be a secret Muslim. Snopes was unable to disprove this but negative proof is notoriously difficult. Still, Snopes finds no reliable evidence whatsoever for the claim and thinks it unlikely everyone connected with intelligence would have overlooked it if it were true. Wingnut and pro-Trump conspiracy theorists such as Ben Garrison have also claimed that Brennan has supported the Communist Party in the past. This is, bizarrely, kinda true (at least, if one counts a protest vote made in his youth as "support").