Westport’s 3-Star General Retires

Westport in the 1970s and ’80s was an “enchanted bubble,” Chris Weggeman says. “It was a privileged place to grow up.”

He played soccer and football, skied and was an Aspetuck Country Club diver. He had a tight circle of friends, and — working as a dishwasher at Mario’s, a landscaper and a gas station attendant — developed a strong work ethic.

But Westport was not a military town. Besides the Minute Man monument and VFW, Weggeman says, there was no sense of heritage about the men and women who served their country.

Westport still is not a military town. But it has produced at least one military leader of note.

Lt. Gen. Christopher Weggeman

Lt. Gen. Christopher Weggeman retired last month, after a stellar 34-year Air Force career. A 3-star general, his service included flying F-16s during Desert Storm and Desert Shield, base commander in Germany, and cyberspace operations.

He was posted all over the world. He led a life unlike nearly all his friends and relatives. He and his wife have settled — finally — in Tennessee.

But at Weggeman’s retirement ceremony in Virginia, he gave a special shout-out to the Westporters he grew up with. They joined some of the Pentagon’s top brass, in a rousing sendoff.

Weggeman credits Staples with honing his competitive spirit, academically and athletically. Thanks to an interest sparked in high school, h entered Purdue University as a neurobiology and human physiology major. Yet he heeded a call to serve, and joined the Air Force Reserve Officers’ Training Corps (ROTC) as a sophomore.

He planned to become a flight surgeon. But a colonel who had been a fighter pilot in Viet Nam inspired him to consider flying planes, rather than treating pilots.

While his parents were supportive, his father wanted to make sure Weggeman had a Plan B. “There are multiple points to wash out during training,” Weggeman notes.

That’s not Chris Weggeman at the controls. But it could be.

Friends had a media-focused view of the military. “They saw ‘Full Metal Jacket’ and thought I was at Marine Corps basic training,” Weggeman recalls. “They didn’t know the difference between commissioned and non-commissioned officers. They had no experience with the military. But I got support and love from all of them.”

The saying “timing is everything” is especially true in the armed forces. As a 25-year-old 1st lieutenant, he was thrust into the Gulf War. “It’s good to get combat experience — as long as you come back safely,” he says.

The Air Force has its own version of the Navy weapons school immortalized in “Top Gun.” (“The Air Force doesn’t make good movies,” Weggeman says.) He became a student while a captain — then returned as an instructor. To be able to train the next generation of fighter pilots was “nirvana.”

Christopher Weggeman, at flight school.

From 2010 to 2012, Weggeman led a wing command team in Germany. Including families, he was in charge of 16,000 people. “It was like being mayor of a town,” he says.

Then — after 25 years with fighter pilot experience, and over 2,800 flight hours — he pivoted to commanding cyberspace operations. For the last 9 year, that’s been his focus, at bases in Maryland, Texas and Virginia.

It was quite a change. But, Weggeman says, “You don’t fly much as a general anyway.”

Despite all he’s seen and done, the biggest challenge of his long career came on the home front.

“I was the one who took the oath to defend the Constitution,” he says. “My wife, son and daughter didn’t.” But they accompanied him. His wife Ann moved 21 times in 34 years. His son attended 3 different high schools.

Weggeman told his children about his youth in Westport. They did not have their own hometowns. And now that he and Ann have bought a place in Hendersonville, near Nashville, 25-year-old Sam and 22-year-old Olivia are off on their own.

Christopher Weggeman with his wife Ann, son Sam and daughter Olivia. This was the back page of the program for his retirement ceremony.

“I tell airmen: marry a teacher or nurse, because their careers are fungible,” Weggeman says, in praise of his wife. “Military people place limitations on their spouses’ careers. They have to tell employers they’ll only be there for 18 or 24 months.”

Ann is an outstanding emergency room nurse, he says with pride. “She crushed it everywhere she worked.”

“Timing is everything” applies to retirement too. There is a very limited path to become a 4-star general. Waiting another 3 years was less appealing than taking advantage of all he’d learned — particularly about cyberspace — and applying it to a new career in the private sector. He’s moving into a senior executive role, with Deloitte.

Without moving all the time.

“I have nothing but smiles. I’m grateful for all 34 years,” Weggeman says. “Now I’m ready to play the back 9.”

Chris and Ann could have moved anywhere. In addition to Olivia getting a master’s in biochemistry at the University of Tennessee, Ann having high school friends in the state, and the reasonable cost of living, the absence of a state tax — or a tax on military pensions — helped the couple’s decision to settle in the Volunteer State.

This photo of Christopher Weggeman and his daughter — taken when he returend home from his first Iraqi Freedom combat tour — now hangs in the Pentagon.

Speaking of volunteering: When Weggeman’s 34 years of serving his country were up, he paid tribute to the town where it all began.

“You all are so very important to me, to who I am today,” he said last month.
You shaped my formative years as we pushed the life-experience envelope, blazing in after-burner, or at least smoking tires in Dodge Challengers, Camaros, Malibus and GTOs.

“We roamed our little enchanted bubble town like we owned it. Who would have thought that this short, skinny, wise-ass Weggeman kid would have grown up to play Air Force. You were my trials, my teachers, my crucible and my forge.

“Steel sharpens steel. So thank you, 06880!”

For young people growing up now in Westport, Weggeman has a message: “In a town with such wealth and opportunities to do so many things, consider military service. No matter the length or what you do, you’ll get a chance to become a powerful leader.

“You will learn the value of a team. And you will become a better, more capable human being.”

Lt. Gen. Christopher Weggeman has made Westport proud. But he’s never been invited back for a Memorial Day celebration.

Perhaps he can deliver his important message — in full, 3-star general uniform — right here, next May. (Hat tip: Chris Tait)

5 responses to “Westport’s 3-Star General Retires

  1. Bill Webster

    Thank God for people like Christopher Weggeman. A true hero in anyone’s eyes. Thanks for your service!

  2. Chris, first of all, congrats on the success you had in the military and wishing you all the best in retirement.

    If you should see this, I am curious: I fully understand the various reasons why someone moving on up in his or her military career would be required to move multiple times early in that career. But once you reach a certain point, isn’t there a way the military could structure the system so that officers could have more stability in terms of where they live/work? Thanks.

  3. Justin Polayes

    Congratulation on retirement!

  4. Tom Duquette, SHS '75

    Congrat’s to a fellow Westporter who chose a military career too. LtGen Weggeman has achieved amazing success; being selected for flag rank is a rare honor and to make it to 3-stars even rarer.

    I would also echo his encouragement for Westport kids to consider taking ‘gap year(s)’ in the military; you don’t have to stay forever and it’s a great way to serve your country and get exposed to life outside of Fairfield County.

    Regarding Fred Cantor’s question about the assignment system; it’s always about the needs of the Air Force and the higher rank you attain the less say you have on future postings. Movement equals opportunity and gives the service the means to assess an officer’s leadership potential to move up to the next level. Also the constant changeover prevents leaders from becoming stagnant and organizations complacent. Enlisted members usually move far less than officer’s. Moving every 2-3 years is the one thing I disliked about my 31 years in the Army and Air Force

  5. Elizabeth Wakefield

    And he’s also on the 2021 Federal 100 – A list of 100 women and men who personify what’s possible in federal IT. Nice work Lt. Gen. Christopher Weggeman!