Richard Daniel O’Leary was 5 years old or so when he first stood in awe of the ocean.
Born and raised in Auburn, he’d been around water, sure. He thought the local lakes and ponds were OK, and the Androscoggin River was pretty the days it rushed over the falls and didn’t flood. But Old Orchard Beach was love at first sight.
“That did it for me,” he said. “It was just a stunning event.”
Decades later O’Leary graduated from the Maine Maritime Academy and joined the Navy. He worked for the Merchant Marines and the U.S. Merchant Marine Academy in New York, and he helped manage the Norfolk Port and Industrial Authority in Virgina. He started his own cruise and cruise promotion business, a successful company that employed 2,500 people and allowed him to keep his life on the water.
Now 79, O’Leary is retired, the grandfather of 15 and a self-published author about his life in Maine and his time with the sea.
“It’s been quite an adventure starting in Auburn, Maine,” he said.
O’Leary was born in Auburn to an Irish immigrant father and a Maine mother. He was one of four children — the only boy — and although his father was a hard worker who cared more for his family than he did himself, jobs and money were scarce.
“I grew up in terrible places. We lived in all kinds of horrible rents all over town, and for a while I was kind of ashamed of that, ashamed of the whole thing. I sometimes used to go out the back door of one of the houses where we lived because I didn’t want people to know I lived there,” he said.
As a young boy O’Leary rarely thought about the water around him, except when the Androscoggin River overflowed its banks. Then one day his parents took him to the beach.
“I fell in love with the ocean,” he said. “I kind of made a vow as a little kid: that’s for me.”
As he grew, O’Leary worked hard in school and delivered the Lewiston Evening Journal to help bring in money for the family. He dreamed of returning to the ocean.
“I used to sneak over to the railroad station there in Auburn and look at the Flying Yankee train because it was going through to Old Orchard,” he said.
O’Leary graduated from Edward Little High School in 1950 and enrolled in the Maine Maritime Academy in Castine. With scholarships and assistance, the school would be free. And it would get him that much closer to the water.
But just before his senior year, O’Leary’s dream nearly fell apart when his school subsidies were drastically reduced. O’Leary left college. His plan: work for a year and save up enough to return.
“Everyone told me ‘You’ll never do it,'” he said. “But I did.”
O’Leary began working at a Lewiston bakery making doughnuts and sandwiches, selling coffee and driving a food truck down to the mills to sell food to the workers there. He started there earning 62 cents an hour, making him the bakery’s lowest paid employee. By the end of the year he was such a good worker that he earned $1.60 an hour, making him the highest paid.
He returned to the Maine Maritime Academy and finished his final year. Soon after, he joined the Navy, where he was assigned, to his surprise, to be ship’s navigator, a job that required him to gauge where the ship was and where it should be by looking at the stars and estimating the ship’s course and speed.
“The next day I’m knocking on the captain’s door, and I went in and said, ‘Look, I’m sorry, there’s been some mistake. I’ve studied some navigation, but I’m not qualified to navigate a big ship like this.’ And he said, ‘Ensign O’Leary, if the Bureau of Naval Personnel says you’re qualified, you’re qualified.’
“So, you know, there were some big adventures that followed. I wasn’t qualified,” he said. “I slowly got better and better until I was over in the Mediterranean and I was navigating not one ship but eight at the end, two-and-a-half years later.”
O’Leary’s work with the Navy made his father proud. During one of O’Leary’s visits home, his father asked him to put on the Navy uniform and come with him to a favorite downtown coffee shop.
“He says to the manager, ‘What do you think of my boy?'” O’Leary recalled.
But although his father was proud of him and the Navy got him a life on the water, O’Leary wanted to use his Maine Maritime degree. He left the navy and got a job with the Merchant Marines. Within a couple of years he was working on the SS United States, the biggest, fastest passenger liner in the world. He stayed for five years and crossed the ocean 250 times.
It was his childhood dream realized.
“It was incredible, big and fast and beautiful and glamorous. It was everything,” he said.
O’Leary would eventually give up life on the water to work first at the U.S. Merchant Marine Academy and then with the port authority in Norfolk, where he helped promote the port to cruise ships. The year he started, the Norfolk port got one cruise ship a year. By the time he left a decade later, it was getting 39. O’Leary left when the Norfolk port authority merged with others in the state. It was time, he decided, to work for himself.
“I had been successful in attracting the cruise ships and I love ships and cruising, so I started basically a cruise ship marketing company,” he said.
With the backing of investors, O’Leary started Cruise Ventures. In 1972 he was the only employee. Twenty years later he would have 2,500 people working for him and would own his own fleet of 600-passenger cruise ships. His tiny cruise ship marketing company turned into a giant marketing, promotion, travel and cruise business that gave passengers a weeklong cruise experience in a three-hour sail.
“Each ship had dining, drinks … and two live bands, and the waiters and waitresses did a Broadway review,” O’Leary said. “At the high point we were moving 17,000 people per day.”
In 1990 O’Leary sold the cruise ships to a French company. In 2005 he turned over the travel offices and marketing and promotion business to his employees.
He retired and, with his wife, split his time between Ogunquit and Naples, Fla. He spends many of his days on the beach, but for a couple of months he also spent a lot of time in front of a keyboard.
O’Leary has written and self-published “One with the Sea,” a 275-page memoir about going from poor boy to successful businessman.
“At the beginning I didn’t know whether I should be proud of it or not,” he said. “But people really like it.”
Now 79, O’Leary occasionally gets to visit his old hometown. He was last in Lewiston-Auburn a few weeks ago to see a high school friend.
But most of O’Leary’s life is on or near the ocean. He has a boat and he sails, just like he dreamed when he was a child.
“I’ve had a pretty lucky life,” he said.