Jun 7, 2018 10:18 AM

Some might say Jon Kenneth Dollard’s flying career started before he could walk.

The East Hampton Airlines pilot grew up watching his father, Kenneth Dollard, now 80, pour his heart and soul into his job as an air traffic controller for the Federal Aviation Administration, where he worked for 38 years.

Flying was in his blood.

“He was born with it,” Kenneth Dollard said of his 47-year-old son, adding that his youngest son, Christopher Dollard, 43, also is a pilot, first for the U.S. Navy and now for Southwest Airlines.

A Hampton Bays resident, Jon Kenneth Dollard, an instrument-rated commercial pilot with ratings for single- and multi-engine aircrafts, was well versed in flying his employer’s Piper Navajo PA 31.

On Saturday, at approximately 3 p.m., the private four-seat plane in which Mr. Dollard was flying his employers, Ben and Bonnie Krupinski, who own East Hampton Airlines, and their grandson, William Maerov, crashed into the water roughly two miles off Indian Wells Beach in Amagansett. As of Wednesday, two bodies have been recovered, though they have not been identified, and the search for possible survivors has ended.

On Monday, Mr. Dollard took comfort in the fact that his son died while he was doing what he loved.

He recalled how thrilled his son was when he was offered the job working for the Industrial Road charter flight service approximately nine years ago. “He would always say how lucky he was,” he said. “He loved the company.”

More importantly, he loved the people.

Kate Gilroy of Sag Harbor, a longtime friend of Mr. Dollard’s, said on Monday that the Krupinskis were much more than employers to Mr. Dollard: “They were like family,” she said.

She recalled meeting up with Mr. Dollard when she moved to Sag Harbor four years ago, and going for dinner with the three of them via private aircraft.

“That day, he had said, ‘I know you’re new to the area,’ and we went out to dinner with Ben and Bonnie,” Ms. Gilroy said. “He was a ‘no man left behind’ type of guy.”

Mr. Dollard and Ms. Gilroy’s older brother, John Gilroy, 46, had been best friends since 1980, when they were third-graders at Briarcliff Elementary School in Shoreham. Mr. Gilroy couldn’t be reached for comment.

“We’ve been privileged with knowing one of the most considerate, compassionate, interested, engaging, chivalrous, intelligent, and quirky-silly-clever-funny spirits that many of us will ever meet in this lifetime,” Ms. Gilroy wrote in a Facebook tribute to Mr. Dollard. “For 38 years, Jon has been the Second-Older-Brother-I-Never-Asked-For and for the past 24 hours, the source of my Heart. Breaking. Over. And. Over. And. Over. Again—in a sick and surging ebb [and] rushing flow—made ever the more painful knowing there are those who feel his loss greater than I do.”

Mr. Dollard is survived by his wife, Ana Dollard; his mother, Jean Dollard, 71; his father, Kenneth Dollard; and his three brothers, Todd, Jason and Christopher.

Ms. Dollard could not be reached for comment.

Scott Santangelo of Hampton Bays said that Mr. Dollard would always rave about his wife’s cooking. “My wife is the best cook in the world,” he would always say. “She made the best turkey stuffing.”

On Monday, Kenneth Dollard described his son as a “very personable and friendly guy,” recalling the days he worked at World Pie and Bobby Van’s in Bridgehampton, and Oakland’s Restaurant in Hampton Bays, to help pay his way through college.

Vanessa Parsons of Living Art Aquariums in East Quogue recalled the late nights she would work side by side with Mr. Dollard at Oakland’s on Dune Road.

“Jon was the kind of guy you felt lucky to know,” Ms. Parsons said. “If you’ve ever worked in the restaurant business, you know how quickly your fellow servers can become like family.”

However, the two shared much more than a few fond memories waiting tables. Ms. Parsons and Mr. Dollard shared a love of the sea, and surfing, as well as a love of music. “He was just great to be around,” she said.

Christopher OKunewicz of Southampton recalled the frequent conversations he would have with Mr. Dollard, who would often be seen pouring drinks behind the bar at World Pie on the weekends. “He had such a warmth to him,” he said on Monday. “His character and his personality, he was such a really nice guy.”

Tom Logan of Shoreham was another close friend of Mr. Dollard’s, calling him an “extraordinary person.”

“To put Jon into words is almost impossible,” Mr. Logan said. “He was a free spirit who loved his brothers, loved his parents, loved his friends, and most of all loved meeting new people.”

He added that Mr. Dollard would make friends with anyone regardless of their “cliques” in school.

“He saw no boundaries growing up,” said Mr. Logan, who grew up with Mr. Dollard from elementary school through high school. “He would go to the city with the skaters to ride his skateboard one night, and be with the wrestling team the next night. The following weekend, he would be off with his theater friends. That’s what I loved about him—he didn’t care what people thought about him. He just cared about people.”

In 1990, Mr. Dollard graduated from Shoreham Wading River High School, leaving behind the old memories to make new ones.

He earned his bachelor’s degree in political science from Salisbury University in Maryland, where he roomed with Chris Rathmann of Catonsville, Maryland, for two years. “You are one in a million,” Mr. Rathmann said of Mr. Dollard on Facebook. “You made me laugh everyday.”

In 2009, Mr. Dollard moved to Florida and enrolled in the Delta Connection Academy, which was then headquartered at the Orlando-Sanford International Airport before merging with Aerosim Technologies in 2010, and earned his pilot’s license roughly a year later.

“He got hooked,” Mr. OKunewicz said. “I think there are certain people out there who get the bug, and once you get that bug, that’s really it.”

Mr. Dollard’s passion for flying showed when he got his first job right out of school at Brookhaven Airport, where he worked as a flight instructor for a year before being hired by East Hampton Airlines.

In recent months, he could be seen flying over Montauk with Ms. Gilroy, in the same Piper Navajo, helping her capture “amazing” coastline aerials for a climate change documentary focused around the U.S. Army Corps of Engineers sandbag seawall project, recently built on the beach in Montauk.

“He was a larger-than-life guy,” Ms. Gilroy said. “If he knew that you were in need of something, he would help you make that happen. The world was made just a little bit better by having Jon Dollard in it. “

A memorial service honoring Mr. Dollard’s life will be held in the coming weeks, according to Ms. Gilroy’s Facebook page, though details are not yet finalized.