Flynn was commissioned in the U.S. Army as a second lieutenant in military intelligence in 1981.[7] His military assignments included multiple tours at Fort Bragg, North Carolina, with the 82nd Airborne Division, XVIII Airborne Corps, and Joint Special Operations Command, where he deployed for the invasion of Grenada and Operation Uphold Democracy in Haiti.[50][55] He also served with the 25th Infantry Division at Schofield Barracks, Hawaii, at the Joint Readiness Training Center at Fort Polk, Louisiana, and the Army Intelligence Center at Fort Huachuca, Arizona.[7]

Initially, Flynn was not going to be deployed to Grenada in 1983, but he was able to convince a superior officer to have him included. While serving there, Flynn took a 40-foot leap off a cliff to retrieve two soldiers stranded in the ocean and bring them back to shore to be airlifted. Though he was reprimanded for his unauthorized actions, Flynn garnered respect among his fellow soldiers for what he did.[52][56]

Flynn served as the assistant chief of staff, G2, XVIII Airborne Corps at Fort Bragg, North Carolina, from June 2001 and the director of intelligence at the Joint Task Force 180 in Afghanistan until July 2002. He commanded the 111th Military Intelligence Brigade from June 2002 to June 2004[7] and was the director of intelligence for Joint Special Operations Command from July 2004 to June 2007, with service in Afghanistan (Operation Enduring Freedom) and the Iraq War (Operation Iraqi Freedom). He and his superior, General McChrystal, streamlined all intelligence so as to increase the tempo of operations and degrade the networks of Al-Qaeda in Iraq.[57]: 24  He served as the director of intelligence of the United States Central Command from June 2007 to July 2008, as the director of intelligence of the Joint Staff from July 2008 to June 2009, then the director of intelligence of the International Security Assistance Force in Afghanistan from June 2009 to October 2010.[7][58] Flynn was reprimanded for sharing classified U.S. intelligence information on the Haqqani network to Pakistani officials in 2009 or 2010. The network, which had been accused of attacking American troops, was a proxy ally of Pakistan.[59]

On November 10, 2015, Flynn gave an interview to the Special Inspector General for Afghanistan Reconstruction (SIGAR) Lessons Learned project.[60] Washington Post published an audio recording of the interview and SIGAR's summary as part of the Afghanistan Pape.

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