There are certain images that come to Islander John Hess’s mind when he thinks of Sept. 11, 2001, the day 25 years ago when al-Qaeda hijackers flew two planes into the World Trade Center in New York City. He recalls city streets obscured by smoke, the view of burning wreckage from the Tappan Zee Bridge, and the unmistakable feeling that the world — and his life — had changed for good.
Mr. Hess, a year-round Vineyarder and the founder of Hess Construction and Renovation, was working in New York’s financial district on the day of the attack, two blocks away from Ground Zero. He reflected on the experience in a conversation with the Gazette this week.
Mr. Hess’s family started visiting the Vineyard in the late 1960s and purchased a home here soon after. In the summers, Mr. Hess worked as a carpenter.
“When I wasn’t in school, I was always out here, working in the trades,” he said.
Though building was his passion, he felt pressure after college to pursue a career using his economics degree. He worked in finance for a decade and got a job at Susquehanna, a trading firm with a Manhattan office close to the World Trade Center. There, he worked for the specialist division on the floor of the New York Stock Exchange.
Mr. Hess went to work as usual on Sept. 11. He was 35 at the time. He remembers his commute that day as typical, even idyllic.
“The day was picturesque, not a cloud in the sky,” he said.
The stillness was interrupted by what sounded to Mr. Hess like a loud clap of thunder. He paused but forged ahead to his building.
“About three minutes later, I get up to my office on the fourth floor and look out my window, and there’s paper flying everywhere,” he said.
Upon turning on the television, he and his colleagues learned what the rest of the world was learning: a plane crashed into the World Trade Center. Smoke started billowing from up the block as more employees poured in, asking what was going on. His brother Mark Hess, who runs Edgartown Golf Club, called him from the golf club to make sure he was okay.
It became clear that everyone needed to run as far and as fast as possible. Mr. Hess helped five colleagues get out of the building, which proved difficult, as smoke clouded all the exits.
“As we were going down the stairwell, we heard the first building come down,” he said.
Outside, visibility was so low that they needed to follow the curb to get to the East River. They removed their shirts and tied them around their faces so they could breathe. When the smoke dissipated, he saw thousands of other New Yorkers alongside him, running from the disaster zone.
“It was a mass exodus,” he said.
He managed to get on a boat to New Jersey with about 100 other people. The boat circled Manhattan’s lower tip as the second tower collapsed. He remembers watching with the other passengers, wordlessly.
“It was just like a movie,” he said. “You can’t even comprehend it.”
Caked in ash and dust, they arrived at a makeshift emergency shelter in New Jersey, where 500 cots were set up to accept the injured. But the cots sat empty. That was the moment when Mr. Hess realized that the injured were few and far between — without much exception, there were survivors and there were the deceased.
“People either made it or they didn’t make it,” he said.
A stranger gave Mr. Hess and his colleagues the keys to his pickup truck. They drove it roughly an hour and a half to Poughkeepsie, N.Y., where they found a place to hole up and turn on the TV. He got the truck back to its owner a week later.
“We were there [in Poughkeepsie] for probably three or four hours,” he said. “By that time, we started to process everything.”
Mr. Hess lost many good friends that day — buddies from prep school working at places like Cantor Fitzgerald, located on the North Tower’s 101st through 105th floors, right above where the first plane struck. No Cantor Fitzgerald employee who reported to work at the New York office that day survived.
On the Island, others have similar stories.
“There were some people that were really affected on the Vineyard,” Mr. Hess said. “I know people that were on phones with significant others and talking about the North Tower, and then the phone line went dead when the plane hit the second tower.”
The stock exchange reopened the following Monday, on Sept. 17. Mr. Hess went back to work, passing debris-packed alleyways, filled five or six stories high. The smell of smoke and burnt steel lingered. He was so struck by the wreckage that he filmed all of it.
When he returned home that night to his wife, then pregnant with their first child, he told her he wanted to leave financial services, and New York, behind.
“I was like, you know what? I’m done,” he said.
It was the construction skills he learned over many Vineyard summers that allowed him to transition away from Wall Street. The family moved to Connecticut, where Mr. Hess started the first iteration of his construction business. He eventually moved the business to the Vineyard, where he’s spent the past 10 years. On the Island, he’s on the board of Sail MV and sails for the Edgartown Yacht Club, with a team headed for nationals at the end of the month.
He’s conscious of the fact that things could have turned out differently.
“I probably wouldn’t be talking today if those towers had fallen sideways instead of imploding on themselves,” he said.
A lot is wrapped up in Sept. 11 for Mr. Hess. That day was the impetus for him to live the life he wanted. It was also the day he watched Americans become more fearful and less trusting — a combination, he said, that can turn quickly to hate.
In talking about it, he finds some freedom from it. A quarter-century later, he hopes others continue talking about it, too.
This article appears in September 11, 2026.