Two RI Brothers: Two USA Generals

Wednesday, September 14, 2011


With two of her sons in the military, Helen Flynn has the right to worry on many days of the year, last Tuesday, however, was not one of them. On September 6th Helen Flynn felt nothing but pride as her son Charlie Flynn was promoted to the rank of Brigadier General, joining his brother, Michael Flynn, who is a Major General and special assistant to the deputy chief of staff G-2 of the Army—that’s a lot of stars for one Middletown family.

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Michael and Charles Flynn

It’s exceptionally rare for two brothers to attain the rank of General, let alone for one to preside over the other’s promotion ceremony—as Michael did when he pinned the star onto Charlie’s uniform last Tuesday.

“As you can imagine with a large family, we’ve had many, many enjoyable and heartfelt moments over the years,” said Clare Eckert, Charlie’s older sister, “but Charlie’s promotion tops the chart of special and proud memories.”

Eckert isn’t exaggerating about the size of the family either—Charlie is one of nine siblings, all of whom managed to be present for the promotion ceremony at Fort Leavenworth in Kansas. Family members came from as far away as Canada and California for the event, where Michael spoke eloquently about the humble heroism of his brother’s time in Iraq—which included protecting vital road access to the Green Zone.

Two Brothers - Global Impact

The two brothers have more in common than simply holding some of the highest offices in the US military, though. Both are graduates of the ROTC program at URI and both have served extensive tours in Afghanistan and Iraq. The two also worked very closely together on the staff of retired four-star general Stanley McChrystal—the previous commander of Coalition Forces in Afghanistan. Michael served as his Director of Intelligence, while Charlie—then a colonel—served as his Executive Officer.

Charlie calls McChrystal one of his most respected mentors, and attributes much of his career’s success to the guidance provided by the retired General. Charlie was put under commander McChrystal at a young age, a “sweet spot” as he calls it, “the time when you’re deciding whether or not you want to go for the career.”

In reference to McChrystal and Lt. General John Vines, Charlie states “I would not have enjoyed the successes had they not shaped and molded and influenced me to the degree that they did and still do.”

Charlie also credited his father for his achievements, especially for encouraging him to follow in Michael’s footsteps and enroll in the ROTC program at URI—a program which he has “nothing but good things to say about.” In fact, URI will be inducting Michael into their ROTC Hall of Fame later this month.

Not only did these various mentors guide Charlie in his early military career, they were also a large part of why he stayed for so long. “I enjoy working with young people,” says Charlie, who the opportunity to mentor young men is one of his favorite parts of the job. “I want to help them in the same way many of my former mentors helped guide me” he says.

Intensity, Humility, and Compassion Towards Others

Charlie’s sister Clare Eckert agrees, she sees both Mike and Charlie as being alike in their “intensity, humility, and compassion towards others.” According to Eckert, Michael is the louder one of the two, but neither are “big chest pounding men,” instead they are both incredibly humble, and she has always been impressed by their ability to empathize with others. “Turns out Charlie’s a great teacher,” remarks Clare.

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The Flynn brothers with their proud mother Helen

As much as he enjoys his job, Charlie also acknowledges the difficulties inherent in a military career. He hates being separated from his family for extended periods of time, and is pained every time he has to witness the tragedy of a family being ripped apart.

And even though both brothers were overseas at the same time, they rarely saw each other—not counting when they worked together on McChrystal’s staff. Their path’s crossed occasionally, often times as one was coming and the other going, but for the most part they were wrapped up in their individual duties.

These were serious duties too. Before his assignment to Fort Leavenworth, Charlie was the commander of various Airborne Divisions and Parachute Regiments, and earned multiple awards including the Legion of Merit and the Bronze Star Medal.

Michael’s long career stretches back to his role as a platoon leader in Operation Urgent Fury in Grenada under president Reagan. More recently, Michael gained recognition for his incisive and bold critique of the Army’s Intelligence practices in Afghanistan.

“When they hug, they hug hard,” says Eckert, who is still overwhelmed by the sense of pride and happiness she feels for her brothers. “It’s a tremendous honor for our family to have two brothers who are true gentlemen, great husbands and fathers, and such strong leaders of men and women for our country.”

At the end of the day, few could have put more succinctly the feelings of gratitude and respect felt towards these two generals than their own 87-year-old mother Helen, who, when asked her feelings, said simply “pity the enemy.” Amen to that.


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