“Scrappy” Says: The Military Needs Westporters. And Westporters Need The Military.

As graduation looms, Staples High School seniors have one foot in the only life they’ve ever known. The other edges tentatively into the unknown.

Most, however, head in the same direction: college. A few will take a gap year, or go to work. An even smaller number march toward a very un-Westport-like destination: the military.

One Staples grad wishes more would consider the armed forces.

“Scrappy” — his nickname, because he’s “a small dog who loves to fight” — graduated in 2004. He’s not using his real name, because of the sensitive nature of his work.

He thinks only 3 others from his class joined the military: one entered a military academy; one enlisted right after high school, another after college.

Scrappy took the path of “every Fairfield County kid”: he went to college, then worked at a hedge fund.

“It was the most miserable period of my life,” he says.

He searched for something more fulfilling. Air Force Special Operations fit the bill.

He trained for nearly 2 years. His first time back in Westport — after spending 10 months in 4 different states — he realized it was “different” than the rest of the country. His eyes had been open wide.

Yet Scrappy did not realize how different until another visit. He’d been in Libya — not far from Muammar Gaddafi when he was killed — and now sat at the Black Duck bar, with a friend.

They’d shaved their war beards. They looked not unlike the 2 guys sitting nearby, wearing polo shirts with the Bridgewater logo.

“They were talking about how hard their day was,” Scrappy says. “They’d had to endure 4 meetings!”

Years later, he still shakes his head at that image.

“They were able-bodied 25-year-olds. They could have done a lot more to save the world than short the price of copper.”

Scrappy feels he is doing his part. He’s been deployed 6 times — to Afghanistan, the Middle East, all over Africa. Much of his work has been in the intelligence community.

Everywhere, he meets someone from Fairfield County. They’re always surprised at which town he’s from. Very few Staples graduates do what he does.

Their unfamiliarity with the military shows when they ask things like, “Did you kill someone?” (“I’ve been trained to do heinous things,” he admits.)

Air Force Special Operations members serve in hot spots around the world.

They also assume he has PTSD. “That comes straight from the media,” Scrappy says. “But it’s like arguing with a 4-year-old. They can’t believe I’m fine.”

Westport’s disengagement from the military — and what the military does — hit Scrappy hard when he was with some old friends at a restaurant here. They had no idea our troops are still fighting — and dying — in Afghanistan.

“There’s no military base anywhere near here,” Scrappy notes. “Our taxes haven’t risen to fund war. Westport is a worldly town. But unless you know someone who serves, this is a part of American life that people here just don’t think about.”

Scrappy remembers that a previous Staples principal “hated” the military. She banned recruiters from campus, and discouraged students from applying to the service academies.

He believes the military needs members from this area. “Fifteen years from now, there won’t be enough people to fill our ranks. Between obesity, ADHD and drugs, there’s going to be a shortage of able bodies.”

Scrappy calls Fairfield County “a great breeding ground for the military. People here are healthy, intelligent and worldly.” Most members of Special Ops and the intelligence community have college degrees, he notes.

The intelligence community needs intelligent people.

His service has not been easy. Scrappy broke his back. He endured 13 surgeries. He’s deaf in one ear.

The last 10 years have been “the worst experience of my life — and the greatest.” He married a team member — a doctor he met on active duty in England. His combat search and rescue team saved over 120 lives. Their motto — “That Others May Live” — is ingrained in all that he does.

He’s helped rescue Americans — and Taliban and Al Qaeda members. “We try to kill them. But if they’re injured, we try to save them. We need to get intelligence from them too.”

Scrappy has traveled all over the world. He’s seen places few Americans ever go to. He has met “the coolest, greatest, most resilient” people in Somalia and Kenya. “Experiences like those change you dramatically.”

The military has taught him “stress inoculation.” He has learned how to keep his head in the most dangerous situations, engineer a solution, and push on.

“That’s the most valuable tool anyone can have,” Scrappy says. “It goes far beyond how to strip a weapon or jump out of a plane.”

Scrappy says that after being in a dozen firefights — and stabbed in close combat — he was scared only once.

It happened here. He went to Westport Pizzeria — and found it was gone.

Panicked, he called his mother. To his relief she told him it’s still here, around the corner on the Post Road.

19 responses to ““Scrappy” Says: The Military Needs Westporters. And Westporters Need The Military.

  1. Adam Vengrow

    Really great writeup Dan, would be great to connect with Scrappy. I love westport. It is an amazing town with many great people, in an awesome part of the world. Mostly thinking about my own kids and educating them about the real world, and history and future being created, i wanted them to understand the tole our military plays, while also knowing that thr military along with the police and fire and all first responders are our line of defense. I lost many friends in 9-11, and sadly as kids grow up and take subways in new york or engage any other major city, it is just not like westport. You cannot leave your door open and trus everyone like you feel like you can in Westport. For all that, we brought Catch A Lift Fund for post 9-11 combat wounded Veterans to Westport. We are going on 5 years. The flipside is we have shown men and women how great a society can be and our Vets have shown us and our kids what sacrifice for others and belief in a greater good looks like. Great art cle and thanks for sharing.

  2. To Scrappy – thank you for your very worthy, insightful thoughts and, more importantly, your service. It’s an honor to share our hometown with you.

  3. Tom Ziobro

    Thanks for posting “Scrappy”s” great message. Should be mandatory reading at Staples!

  4. Michael Calise

    A Great Message. A special feeling for all who are and have served!

  5. Mary Cookman Schmerker

    Great and important article. I wonder if Michael like I did began to think of our class mates who served in the Military. In our day every young man was required to enlist. Alan Doldge came to mind immediately and so did David Lawrence. I am fairly certain that Alan was a Navy Flyer and David Lawrence went to the Merchant Marine Academy. I am positive there were others. Thank you Scrappy for sharing your experience and for serving.

  6. Mary Cookman Schmerker

    P.S. I wish there was a edit feature! I am pretty sure that I remember that Michael Calise also served in the military. He is so modest that I don’t think he would brag…..

  7. Tom Duquette, SHS '75

    As a Westport kid who served for 31 years on active duty I have to agree with pretty much everything that “Scrappy” has to say. Certainly going into the service is not the conventional route have most Staples graduates pursue. Attending high school reunions most, if not all of my classmates are very surprised at my chosen career. Somebody has to do it and step up. The attitudes of civilians regarding military members is much as he has described, everybody has PTSD and is broken in some way they believe. Many do, but not all. I enjoyed my time in the military very much, and would not change a thing.

  8. Thanks for the post Dan, more importantly thank you for your sacrifices and service Scrappy. You bring honor to our town and our country.

  9. Jonathan Berg

    I was hoping someone else would do this but maybe not. Good for you for stepping up and serving and I’m glad you found your place in the world. But I have a big problem with several points here. Agree its absurd for civilians to assume everyone has it but the blanket dismissal of PTSD by implying something akin to “fake news” – its always easy to blame the media and anyway, it accidentally highlights the whole problem, that its taboo to admit the problem exists. The weird dig about ADHD, which I take great personal offense to. I can’t tell what he’s trying to imply here, whether that its fake or that people with ADHD can’t do anything or something else. But people with ADHD not only can serve but the military can actually be a great fit. Even, though less viscerally, the snide dig at people who have normal civilian jobs, participate in the capitalist economy, complain about meetings, and pay taxes. But of course I agree about Westport being regrettably distant from the military and about Westport Pizzeria being gone from Main Street.

    • Jonathan, I don’t think Scrappy meant anything pejorative about kids with ADHD. It’s that the medication they take disqualifies them from serving.

      • Jonathan Berg

        Ok, if that’s true then I appreciate the qualification. I’ll skip the questions it raises but its bizarre. I’d still have a beef with that policy but whatever, there are bigger issues in life.

  10. Roseann Spengler

    I would never ever want to see any of my grandchildren or anyone I care about to live that life. Why don’t we put energy into having a country based on making peace not war. Let’s give peace a real chance. Hopefully young people will find jobs that promote that world.

    Sent from my iPhone


  11. Eric William Buchroeder SHS ‘70

    I respect those who serve, but it was their decision. It was a sad and cynical day when Nixon ended the draft in ‘72. The pacifists cheered and didn’t care that it only prolonged the war. The military became a tool of the politicians rather than a protector of peace. It also became isolated from the citizenry at large. These wars have gone on for far too long.

  12. Jamie Walsh

    The old adage… “I would never do it again…but I would not have traded the experience for the World!” Comes to mind! Thank you Scrappy for your service and you are right…. more young adults, like yourself, from Westport could benefit from some level of service in any branch or reserve basis and develop a skill and at the same time contribute to serving our country and protect the Freedom of expression we so cherish.

  13. Kris Latchford

    Thank you for your service “Scrappy”!
    I also went the military route (Marine Corps) after Staples, and I found it to be the missing piece of my life puzzle. I was undisciplined, with out focus, and frustrated academically. The Corps gave me true focus, drive and ambition. I went to Texas A&M San Antonio after leaving the Marine Corps, and I excelled. The military is not for everyone, but for me I was right on time!
    I was and am grateful for the opportunity to serve this great nation!
    Kris Latchford

  14. Jeffrey Jones

    Thank you for your service to our country, Scrappy.
    And I believe you are right about Westport being a very strong reservoir of talent for numerous assignments of our armed forces. In fact, a friend of mine and I talked about that “fact” early in the Viet Nam war scenario.
    He enlisted in the Marines after after graduating from college. He served in ‘Nam, beginning as a lieutenant. Fortunately, he came home; so many didn’t. I was 1-Y, asthma deferred.
    Westport is blessed with proximity to the metro corridor of the East Coast, great schools and talented people that nurture young minds. What’s not to like for identifying and building a talented military [and intelligence]? The services have [occasionally earned] a bad rap. That’s fixable.
    Perhaps there will be more Westporters serving, building world peace in the nottoodistant….

  15. Phil Symonette

    Hi Scrappy,

    Thank you for the article and your service. My son has accepted a nomination to West Point for the class of 2023. He looks forward to serving his country proudly as you have.


  16. Liz Doyle Boyd

    Roseann, how selfish of you! My Dad was a war hero, and my son in law is in the Military. I am proud of people who serve, where would we be without them? I also have friends who lost a 23 yr old son in Afghanistan. Blessed be our Military, their families, and God Bless the USA