Category Archives: People

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.