Actually, yes. I don’t think I’d consider him a friend, per se, but we’ve spoken on a number of occasions. He was a student of mine in the MI pre-command course when he was a promotable LTC and we spoke a few times when he was Director of DIA.
Definitely not a “get-along-to-go-along”, political general so typical of today’s Army. He has his own opinions and isn’t afraid to voice them - even when it pisses people off; which is why he’s no longer on active duty. Mike is a soldier and not a politician and, should Trump win and Mike be his VP, a LOT of flag officers would get very, very nervous.
If you’re interested in seeing how and what he thinks, check out this link: https://www.cnas.org/files/documents/publications/AfghanIntel_Flynn_Jan2010_code507_voices.pdf. This is but one of a number of things that Mike did that pissed off Army and joint leadership. He completely circumvented the normal DoD approval process to publish things that he thought needed to be said and I know a number of other GOs agree with him - at least privately.
(Wiki) "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, Joint Task Force 180 in Afghanistan until July 2002. He commanded the 111th Military Intelligence Brigade from June 2002 to June 2004. [5]Flynn was the director of intelligence for Joint Special Operations Command from July 2004 to June 2007, with service in Afghanistan (Operation Enduring Freedom) and Iraq (Operation Iraqi Freedom). He served as the director of intelligence, United States Central Command from June 2007 to July 2008, as the director of intelligence, Joint Staff from July 2008 to June 2009, then the director of intelligence, International Security Assistance Force in Afghanistan from June 2009 to October 2010. [5]
In September 2011, Flynn was promoted to Lieutenant General and assigned to the Office of the Director of National Intelligence. His duties included public, private, and international outreach and engagement. Flynn's primary influence within the U.S. intelligence community was with regard to operational units across all the services, especially in the intelligence, surveillance, and reconnaissance arenas, as well as information technology and organizational design.
His largest command ever was a brigade command, and it was a brigade of intel types. None of his bronze stars are said to have the "V" device, and he has no silver stars, only a legion of merit.
He is not a combat general, he has participated in wars that haven't gone that well, and he has been sufficiently acceptable to this administration to have a high position within it.
To his credit, he sounds like a bit of an old time democrat, he has stood up for the United States, he has resisted the capitulation to radical islam, and he has paid the price for honest outspokenness.
Just being honest, though, I really don't see him rising to the level of a Dwight Eisenhower or a US Grant, both victorious, combat victors in major wars.