On July 7, 2011, Richard Oland, a 69-year-old Canadian businessman and former vice-president for Moosehead Brewery, was bludgeoned to death in his office on Canterbury Street in Saint John, New Brunswick. His son, Dennis Oland, came under suspicion for the killing and was charged with second-degree murder.

Dennis' first trial, the longest and most expensive trial in the history of Saint John, ended with his conviction on December 19, 2015. Throughout the high-profile court case, intimate details about the private lives of the entire Oland family were revealed.

Dennis was sentenced to life in prison, with a possibility of parole in ten years, as recommended by the jury. His lawyers immediately began the appeals process, seeking the appellate judges to either overturn the guilty verdict, order a new trial, or enter a full acquittal. The appeal was successful, and Dennis' conviction was overturned on October 24, 2016. On July 19, 2019, he was found not guilty on retrial.

Background Richard Henry "Dick" Oland (1941 – July 7, 2011) was the second-born son to Philip Oland, chairman and CEO of Moosehead Breweries, and Mary Oland. Richard and his older brother Derek were born and reared in Rothesay, New Brunswick, a suburb of Saint John. Several families living in Rothesay, such as the Olands, the Irvings, and the Crosbys are considered "old money", claiming some of Canada's highest incomes per capita.

Richard attended Rothesay Collegiate School, Regiopolis College, and the University of New Brunswick, obtaining a certificate of brewing technology. He wed Constance "Connie" Connell in 1965, and fathered three children: Elizabeth, Jacqueline, and Dennis. Richard was diagnosed with Asperger syndrome by one of his friends, a clinical psychologist.

By 1980, Richard, then a vice-president of Moosehead Breweries, vied with Derek for leadership of the company in a public and legal feud. Their father decided to select Derek to succeed him, resulting in Richard leaving the company in 1981. Starting from scratch, Richard found a niche in the Saint John business community with his development of three major enterprises: Kinghurst Estates Limited, Brookville Transport Limited, and the investment firm Far End Corporation. Richard became an accomplished businessman, amassing many awards and a fortune of nearly C$37 million. He was also in charge of organizing the 1985 Canada Summer Games, serving as the Saint John 1985 Canada Summer Games Society president.

Richard made Far End Corporation's premises his primary office space. Located at 52 Canterbury Street in the historic Uptown district of Saint John, the second-floor office space was rented from building owner John Ainsworth. Ainsworth operated his own business, Printing Plus, from the first floor of the building, and rented out the third floor to local bands to practice after office hours ended for the day.

Oland family relationship Richard was married to Constance "Connie" Oland for 46 years, though he also been in an eight-year relationship with his mistress, Diana Sedlacek. The Oland family has been characterized as having dysfunctional elements, with Constance telling authorities that Richard "did not get along with his brother, Derek Oland". Constance had also stated that Richard had "a very strong and controlling personality". An affidavit described that Richard "was not physically abusive but was emotionally and verbally abusive". Sedlacek told police that Richard did not have much respect for Dennis Oland, his only son, and "thought he was lazy". Constance similarly told investigators that Dennis frequently sought his father's respect, though "he had never been able to live up to his standards".

Murder Richard Oland was last seen alive in his office on July 6, 2011, where his son, Dennis, told police that he left at around 6:30 p.m. after around an hour of visiting the office. That same day, Oland was bludgeoned to death in his office. The last keystroke on his computer was recorded at 5:39 p.m., and Oland's iPhone, which had been the only object missing from the crime scene, last communicated at 6:44 p.m. through receiving a text message from Sedlacek.

Crime scene On the morning of July 7, 2011, Oland's body was discovered lying face down in a pool of blood in his office by his personal assistant, Maureen Adamson. Sgt. Mark Smith of the Saint John Police Force testified that the office was "one of the bloodiest crime scenes of his career, with the most blows to a victim." Forensic pathologist Dr. Ather Naseemuddin counted 45 wounds to Richard's hands, neck and head during autopsy. Six of these wounds were found on Richard's hands, likely due to Richard trying to protect himself from his attacker. These defensive wounds led to over thirty hair and fibre exhibits to be seized at autopsy for forensic examination, including three hairs found inside his hands and tissue samples from under his fingernails. The hairs could not be tested for DNA as they were lacking a root, and only Richard's DNA was found underneath his fingernails.R. v. Oland, NBJ 457 (NB CA).

The attack continued after Richard was defenseless on the floor. His skull had suffered catastrophic damage; the bones of his eyesockets were "like a cracked egg shell", possibly from him falling face-first into the floor, and a concave area spanning 10 cm in length, 7 cm across, and 2 cm deep was discovered at autopsy. Portions of brain matter were found on Richard's back.

The attack had left Richard's blood on every wall of his office. Blood spatter was seen on his desk, computer, chair, filing cabinets, and on an empty pizza box in the garbage can. Blood had also soaked through three layers of flooring, permeating the ceiling of the office below. Police analysts testified "the person who created these injuries would have significant bloodstains/spatter on their person and would be expected to transfer blood stains to the surfaces of other objects the person came in contact with."R. v. Oland, NBJ 312 (NB CA). Forensic analysts noted the blood pooling on the floor around Richard may not have occurred until after the attacker left the office, explaining why the scene contained few "transfer stains" and only one footprint, which was never connected to a suspect.

Dr. Matthew Bowes, the physician who reviewed Dr. Nasseemuddin's autopsy report, believed Richard was alive for the duration of the attack. Both Naseemuddin and Bowes believed he only survived the attack for five to ten minutes, but was alive for all of his injuries. Some injuries were believed to have been caused by a sharp edged weapon, while other injuries were caused by blunt force, indicating that either Richard was killed by a weapon with two different edges or two weapons were used. Bowes raised the possibility that a combat knife could have been a weapon. Sgt. Mike King testified that he suspected a roofer's hatchet to be a weapon. Cst. Stephen Davidson believed a weapon could have been a drywall hammer. No weapons were found at the crime scene, and no weapons were entered as evidence at trial.

The trial revealed that members of the Saint John Police Force had failed to protect the crime scene from contamination. Police used the office bathroom, where blood belonging to Galen McFadden (the son of Richard Oland's financial manager, Robert McFadden) was later discovered, for two days before the bathroom was tested for evidence. There was a backdoor near where Richard's body was found, leading to an alleyway that could have been an exit. Police went in and out the main door, without gloves, for nearly a week before anyone noticed they should have tested it for fingerprints. The footprint discovered by the forensics team had to be compared against police footwear, as several police officers, including Deputy Chief Glen McCloskey, walked through the crime scene unauthorized and without protective gear. McCloskey was later accused of suggesting that other officers lie under oath about his presence at the crime scene, and the Saint John Police Force was under investigation by the New Brunswick Police Commission for corruption and a potential cover-up.

Police interviews Shortly after being notified of Richard's death, members of the Oland family, including his wife Connie Oland, daughters Lisa Bustin and Jacqueline Walsh, and son Dennis Oland, arrived at the police station to give interviews and formal statements.

Connie reported that on July 6, 2011, she and Richard were both at home until Richard received a call from Maureen Adamson at 9:50 am, reminding him of an appointment in his office with two insurance brokers at 10:00 am. Richard then left home for the office, and that was the last time Connie spoke with him. Connie said it was not uncommon for Richard not to return to their residence at night. His daughter Lisa Bustin was interviewed alone. Bustin said that her father could have had anyone as an enemy, as he was "a hard-nosed businessman—pure business—and if you worked hard you would get his respect."

Dennis' interview lasted over five hours and was separate from those of other family members. Video footage showed Dennis providing Cst. Davidson with a written and verbal account of his activities for the day prior to Richard's death. Dennis believed that his father had high expectations of him, but that he was not meeting those expectations. Davidson told Dennis that cameras could verify whether or not he was telling the truth about his presence at his father's office, and asked Dennis what clothing he had worn the day before. Dennis said he was wearing "these pants, these shoes, a blue dress shirt, and a navy blazer."

At the half-way mark on the video footage, Davidson informed Dennis that he was the primary suspect in his father's murder. Davidson read Dennis his rights, and Dennis phoned attorney Bill Teed, who told him to stop talking to police. Davidson told Dennis that "there is absolutely no question in my mind that you did this, and I want to know why", and that his opportunity to speak with a lawyer was past. Dennis repeated that he did not murder his father. Police allowed Dennis to leave just after 11:00pm without making an effort to seize the clothes Dennis said he had worn the day before.

Robert McFadden, in his interview, conducted by Davidson, said he had left Richard's office at 5:30 pm with his son, Galen McFadden, as was usual. McFadden said his job was to manage Richard's finances, and that Richard had asked that a trust fund be set up for his heirs. McFadden said that upon Connie's death, the trust would be dissolved and the remaining assets would be distributed to Richard's three children. He said that after Connie's death, Dennis' portion of his inheritance would be reduced by $538,000, with $269,000 going to each of Dennis' sisters, covering the expenses of his divorce which had been paid for by Richard and allowing Dennis to retain the family home.

McFadden and Adamson testified that Richard did not leave the office between arriving in the morning and Maureen leaving at 5:45 PM, and that Richard was adamant that alcohol not be kept in the office. Toxicology reports from the medical examiner indicate that Richard had some alcohol in his blood.

Suspects