Dennis Oland was raised in the same affluent milieu as his father, brewing scion Richard Oland.
The family has owned property in Rothesay, an upscale suburb north of Saint John, for decades. Dennis Oland, the elder Oland's only son, attended Rothesay Collegiate, the same private school as his father and several other family members.
He wrote about his fond childhood memories as a Royal Yacht Club "Club Rat," a junior sailor and "a great lover" of the family's boat, where he and his sisters would get some quality time with their dad.
Mr. Oland, born in 1968, graduated with a Bachelor of Arts from the University of New Brunswick in 1990 and worked in the investment industry in Toronto before moving back to Saint John. The New Brunswick Securities Commission lists him as an investment dealer with CIBC World Markets, Inc.
He headed the local YMCA and was elected chairman of the Maritimes branch of the Canadian Automobile Association.
He and his wife, Lisa, were active in the provincial Conservative Party. In an official gazette from April, 2004, he's listed as the official representative of the Saint John-Kings Progressive Conservative Party District Association, with the Gondola Point Road address as his home.
In an interview he gave to the Telegraph-Journal three years ago, Dennis Oland recalled that he didn't get to spend much time with his father growing up, except when it was to sail on the Aloma, the family boat.
"I didn't get to see him a lot and when we got on the boat that all changed," the younger Mr. Oland said in the interview, describing how "my father relaxed, a huge smile on his face" once he was aboard.
"My sisters and I grew up on this boat and with my father as the captain you could always count on a big adventure for every trip and he never let us down," Dennis Oland says in a history of the Aloma that he wrote for the Royal Kennebeccasis Yacht Club.
"If there was water we went there, and if there wasn't we sometimes tried anyway."
He recalled landing the boat on his own, on his first try – "the proudest 12-year-old in the world."
"Dammit," his grandmother said at the time, "you drive just like your father."