Brett Ryan was weeks away from marrying the woman of his dreams. He had a waterfront condo, a good job and a bright future. Or so everyone thought. When his mother threatened to expose his lies, he decided she had to die

In 2007, when Brett Ryan was 26 years old, he found himself $60,000 in debt. He was living with his family in a large detached house on Conference Boulevard, not far from where the Rouge River separates Scarborough from Pickering. This was not the life he’d imagined for himself.

Brett was always smiling and polite. He volunteered at SickKids and refereed Little League games at the local community centre. He was good-looking and generous, and he made friends easily. After high school, he’d enrolled at U of T, but it was too much for him, and he dropped out. While his best friends built reputable careers in finance, health and education, Brett worked as a house painter, a summer job turned full-time gig. He went from job to job in an old Dodge Dakota with nothing but his worn ­paintbrush and his wide smile. But underneath that veneer, he was becoming desperate.

Rather than concede failure, he sought to patch over his problems with cash. On October 20, he robbed his first bank: the CIBC at 371 Old Kingston Road, just an eight-minute drive from home. He wrapped his face in hospital bandages, hung his left arm in a sling and shuffled into the branch holding a sheaf of papers. At the counter, he handed the teller a note indicating that he was carrying a gun under the sling and demanding $2,000 or more. The teller quickly complied. Brett received only $1,115, but he made off without getting caught. He was hooked. Over the next eight months, he robbed another 12 banks along the 401 and around his neighbourhood, including his home branch. He stole a total of $28,000.

Brett owed his success to the fact that he’d never been arrested before. The hold-up squad obtained fingerprints from the crime scenes, but no matches ever turned up in their system. At one point they had 25 officers sitting outside banks along the 401 for three weeks, hoping the culprit might turn up. Brett embraced the theatricality of his crimes. After hitting a second bank with the bandage disguise, he bought a high-quality glue-on beard at a costume supplier. The disguise earned him the nickname “the Bearded Bandit” in the media. He also donned a Gilligan hat, glasses, a plaid shirt and a dark jacket.

After one of Brett’s heists, police spotted his truck on an external camera and tracked him to his home. By the time he entered his last bank, the TD Canada Trust at 3115 Kingston Road, the police had been surveilling him for two weeks. He must have suspected something was up: he strode into the bank, then quickly turned around and walked out, where the police were waiting. He pleaded guilty, and spent the next seven months in custody, awaiting trial.

One day in January 2009, Brett sat in a small, windowless courtroom at the Ontario Court of Justice on Eglinton Avenue. Several of his close friends had written letters of support, detailing his generosity and volunteer work. Justice Paul Robertson cited Brett’s “stellar background” in his sentencing report. “[He is] a person who has integrity, who has given of himself to his community, who has given of himself to others, and who is truly a productive member of society,” Robertson said.

“You are not a youth, but you, in my view, are youthful,” ­Robertson told Brett. He did have a sweet face. His skin was creased from his big, goofy smile, with deep-set dimples that made his cheeks puff out when he mugged for the camera. His eyes were intelligent and warm. When he was younger, he kept a shaggy surfer’s mane, then switched to a spiky, gelled look. He was the kind of guy you’d expect to find buying Beaver Tails on the boardwalk, not robbing banks.

Robertson concluded that the crimes were “completely out of character.” He sentenced Brett to five years, but with time served and early parole, he was back home with his family in late 2010, ready to start fresh.

Outside prison walls, Brett found a harsher world than the one he’d known before. He could no longer avoid his debt and filed for bankruptcy. He couldn’t hide his past from prospective employers who googled him. He tried to resume his house-painting business, but most potential clients wouldn’t let him into their homes when they learned about his record. And who could blame them? As he approached his 30th birthday, he couldn’t escape the self-inflicted realities of his life: he was a bankrupt ex-con with a high school education and no prospects.

His family had been shocked and mortified by Brett’s actions. His father, Bill, worked as a budget manager at the Toronto Star. Bill was quiet and health-conscious, teaching fitness classes at the local community centre but otherwise keeping to himself. Brett’s mother, Sue, was bubbly yet firm, a tough homemaker and lifelong gardener. She was also a diehard baseball fan: when her beloved Toronto Blue Jays won the World Series in 1993, she marched up and down the street banging pots and pans.

Brett was the third of four brothers. The eldest, Chris, worked as a TTC fare collector; he was shy in public but showed his goofy side to those who knew him well. Then came ­Leighland, the artistic one, who was two and a half years older than Brett. He played guitar and drums, studied photography at Ryerson, and restored vintage cabinets. The youngest, A. J., was six years Brett’s junior. He stood out for his intellect—he excelled so highly academically that his parents sent him to a school for gifted students. Brett declined to be interviewed for this story, but friends and neighbours remember him as the out­going jock of the bunch: an extrovert in a family of introverts. He suffered periodic bouts of depression, though he preferred to keep his problems to himself. He wanted to project an image of strength and positivity. He wanted to be admired, not pitied.

Sue Ryan was bothered by the fact that their neighbours gossiped about her family. “This neighbourhood is bad luck,” she told a friend. She and Bill sold their large home and bought a small postwar bungalow on Lawndale Road in Scarborough. The Ryans made the most of their new home. Sue set about transforming the front yard into an elaborate display garden, with flowering perennials, small shrubs and a statue of a cat. The project took her six years to complete, and despite her arthritis, she was out working almost every warm day. The whole time, she kept Brett’s history a secret from their neighbours.

Lawndale was a quiet street, and a familiar calm settled over the Ryans’ lives. Brett knuckled down and started taking the steps that, in time, could help him achieve the success he envisioned for himself. He worked low-paying retail jobs and, with some financial help from his parents, re-enrolled at the University of Toronto to pursue a degree in biophysics. He also made a concerted effort to be more open with his family. He visited a psychologist, who told him the chief lesson from his robberies was that if he wanted to avoid further trouble, he needed to be honest with those closest to him.

In September 2011, a friend set Brett up on a blind date with Kristen Baxter, an athletic blond physiotherapist. They met for the first time at the corner of York and Queens Quay, not far from her waterfront condo. Kristen lived the kind of ­blissfully normal life Brett wanted for himself. She had a good job and a nice home. She liked hiking and travelling and walking her fluffy wheaten terrier–poodle mix around Harbourfront. Her demure smile perfectly matched his delirious grin. They looked like the couple that comes with the picture frame.

Kristen knew about Brett’s criminal past, but his history didn’t stop her from falling in love with him. In January 2013, he moved into her condo building across from the Power Plant gallery. The glassy downtown tower was a dramatic change from his family’s suburban bungalow. ­Kristen’s condo was small, only 549 square feet, but it offered a gorgeous view of the lake beyond the Toronto Islands. Brett could barbecue on the roof, watch the planes land at Billy Bishop Airport and swim in the indoor-outdoor pool on the second floor. They travelled frequently, visiting tropical locations.

Roughly a year after Brett moved in with Kristen, his father died. Brett took care of his mom, helping her with some of the administrative tasks that Bill had once handled, and also performing odd jobs around the house for extra cash. He needed the money. He’d recently proposed to ­Kristen with a princess-cut diamond surrounded by a halo of smaller diamonds. Once again, his finances were unravelling, and as his bank account foundered, he began to build a web of lies. In 2015, he dropped out of school again. But he didn’t tell his fiancée. ­Kristen and his family believed that he was still pursuing his studies.

In the spring of 2016, Brett caught a lucky break and got a job with a Toronto tech firm. At last, it looked like he would finally escape low-wage work and start earning a real income. He celebrated his victory with Kristen and his family. But within days of hiring him, his new employer discovered his previous life as the Bearded Bandit. The company promptly rescinded the offer. Rather than admit defeat, he let his family go on believing that he still had a job. He needed to perform the lie every day.

Meanwhile, Brett and Kristen were planning their wedding for September 16, 2016, right around the anniversary of their first date in 2011. They were going to be married at Ancaster Mill, a rustic creekside venue near Hamilton, with $100 plated service per person. Brett planned a bachelor weekend in August with some friends at Mont Tremblant. The couple hoped to move on from their tiny condo after the wedding. They’d enlisted the help of a realtor and started looking at houses.

Brett was making his mother proud. Sue often bragged of his successes to their neighbours. She told them about his university degree, his good job, his condo downtown, his upcoming wedding. At the same time, he was relying more heavily on her for help. With so many financial demands on the horizon, he pressed her for more paid jobs around the house. Sue did what she could for him. She was grateful he’d come so far.

Even with his mother’s help, Brett’s situation was becoming dire. Less than a month before the wedding, after a year of piling lie upon lie, Brett finally followed his psychologist’s advice: he told his mother the truth about what was really going on. He knew he had to get a job, but he needed her support until that happened. Instead of a bailout, he received an ultimatum: tell Kristen everything or Sue would do it herself. She’d give him no more money until he came clean.

For Brett, telling Kristen the truth was the worst possible scenario. She might leave him, and then he’d be forced to return home to the little house on ­Lawndale with his mother and brothers. He’d be destitute, reliving a history of failure that he thought seemed terribly unfair for a nice guy who always did everything for others. He was too close to achieving his dream life. He wasn’t going to allow his mother to drag him down. He was going to kill her.

Brett needed a weapon. The conditions of his sentencing made it illegal for him to acquire a firearm, so he decided to buy a crossbow, which doesn’t require a licence and can be purchased by anyone over the age of 18. He chose a Barnett Recruit Youth 30, one of the cheapest and lightest crossbows available in Canada. Designed for teenage hunters, the Barnett shoots at 140 feet per second. On Amazon, it costs around $288, but Brett bought his second-hand in order to avoid leaving a potentially incriminating record of the purchase.

In the days after the ultimatum, Brett continued to visit his mother’s home to work on renovation projects. During one of those trips, he stashed his crossbow in the garage behind some tools on a top shelf. He and his brothers had recently renovated their mom’s kitchen, and the garage was a mess, with old flooring heaped up in the centre. No one was going to be poking around the clutter.

August 25, 2016, was a sweltering day, with high humidity and thunderstorms. In the morning, Brett and Kristen got ready for work—she at her physiotherapy practice, he at his imaginary job at a tech company. The sun was pouring through the floor-to-ceiling windows when Kristen left at 7:30 a.m. Once she was gone, Brett got to work building a device that he hoped would provide an alibi if he was ever accused of the crimes he was about to commit.

First, he opened his laptop and propped it against the wall with two five-pound weights. Then he duct-taped a wooden spoon to a black cylindrical oscillating fan and placed it so the tip of the spoon lined up with the laptop’s enter key. He plugged the cord into a digital timer, like the kind used for Christmas lights. When the timer activated, the fan would turn and the spoon would click on a cursor hovering over an icon that would open YouTube.

Next, he took two more portable fans, also plugged into digital timers, and screwed them to a wooden board, which he placed on the granite countertop of the kitchen island. He taped styluses to the casings of the fans. Then, Brett screwed a smartphone and a tablet to another wooden board, so that the screens faced the fans. When the timer went off, the fans would turn, the styluses would tap the phone and tablet, and each would send out pre-typed messages: one thanking a friend for a real estate tip and the other about home repair. The ­timers were rigged to go off at various points throughout the afternoon, and the devices were set so they wouldn’t go to sleep while he was away.

Brett designed all of this to leave a digital trace that the police would triangulate to his home. No matter what happened that day, he would be able to say that he’d stayed at home the entire time, watching YouTube and sending emails—the perfect alibi for the digital age.

Despite the blistering heat, Brett put on two pairs of jeans before leaving the house. He packed his gym bag with a ­familiar disguise kit: some spare clothing, a wig and a bucket hat, just like the kind he’d worn for his bank robberies. He threw in a few broadhead bolts for the crossbow.

In order for his elaborate alibi to work, Brett needed to leave his condo building without showing up on any of the security cameras in the elevators, lobby and parking lot. That left him only one route: 14 flights down the stairwell and out through the back alley. There were a few cameras out there too, but he’d eyeballed where they were pointed and planned a path to duck them. When he left the alley, he headed to the GO terminal, took a train to Eglinton station and walked 10 minutes to his ­mother’s home. He arrived at 10 Lawndale Road around 10 a.m. Sue wasn’t expecting him to show up that morning; she’d just cancelled her plans to go to the CNE with her neighbour Marie. She had a cold.

Brett hoped Sue might be able to see his perspective. But she held her ground, promising to tell Kristen everything if Brett didn’t. The argument got heated, and Sue called her eldest son, Chris, on her cellphone, asking him to come over to help her handle his brother. Brett quickly realized the situation was getting away from him. He marched out the back door and headed straight for the garage. Sue followed him.

Crossbows are difficult to load, and with only a few steps between the house and the garage, Brett didn’t have time to cock the string and fit a bolt in place before his mother entered the garage. Instead, he grabbed a broadhead bolt, with three sharp serrated blades that form a point, and stabbed her in the cheek and the ear. Then he wrestled her to the ground, behind the pile of hardwood flooring left over from the kitchen renovations. As she struggled, some of the flooring fell on top of her. He took a piece of yellow nylon rope and strangled her with it until she died.

After Brett stabbed and strangled his mother to death, he set about cocking the crossbow. He knew his brother Chris was on his way, and he needed to be prepared. He braced the crossbow nose-down on the ground and inserted the ball of his foot into the stirrup to hold it in place. Then he prepared a simple ­cocking device: two hooks that attach to the strings on either side of the barrel and small handles just above the hooks for pulling the string up to the firing mechanism.

A crossbow is a simple implement. Anyone can learn to shoot with reasonable accuracy with the help of a YouTube video and a few minutes’ practice. When Chris came into the garage, Brett stepped up quietly behind him and fired at very close range, so that the three blades went through Chris’s neck and lodged in his mouth. Brett barely had to squeeze the trigger; all it needed was a light touch. His brother died immediately.

By this point, the gravel-and-sawdust floor of the garage was muddy with blood. Brett grabbed his brother’s body and stacked it on top of his mother’s behind the heap of hardwood flooring, then draped a tarp over them. If he’d had time, he could have stuffed his bloody outer jeans into his gym bag and donned the wig and Gilligan hat he’d packed for this scenario. But before he could do any of that, his younger brother, A. J., came home.

Brett exited the garage and met A. J. on the walkway to the back door. He was carrying another crossbow bolt in his fist. By this point, he realized he’d gone too far down this night­marish path not to see it through. They grappled, and Brett stabbed A. J. in the neck. He collapsed onto the driveway.

Brett’s third brother, Leighland, had been napping in his bedroom. He heard the altercation and went outside to see what was going on. When he saw his youngest brother bleeding on the ground, he ran to the phone to call 911. Brett followed him into the house and attacked him. What ensued was a ghastly struggle for survival. The two brothers stumbled chaotically through the house, down the hallways, into two different bedrooms, fighting and kicking over furniture as they went. They snapped an end table and threw each other against Leighland’s bedroom door. Brett was soaked with the blood of his family members; Leighland sustained a head wound and bled profusely. As they fought, they left a trail of blood on the walls, the floors, the ceilings.

Meanwhile, A. J. crawled down the driveway toward the street. He’d made it as far as the front of the house when ­Leighland escaped from his brother and ran outside, where he found A. J. still alive, bleeding in the driveway. With Brett in pursuit, Leighland ran across the street to get help from his mother’s friends Warren and Marie. He hammered on the door. When Warren answered, Leighland tumbled into his arms. “Call 911,” he told them. “My brother’s bleeding in the driveway. Make sure the police come. Make sure the police come.” After relaying his message, ­Leighland promptly passed out.

Defeated, Brett got a bottle of water from the fridge. He didn’t bother shutting the fridge door as he returned to the front stoop. He was waiting there calmly when the police arrived. A. J. was still alive when the first responding officer came to the scene, but he died before the paramedics arrived. “I should have driven him to the hospital,” Brett told the police. “The guys in the garage are dead. Crossbow to the head. It was me.”

Shortly after Brett was apprehended, Toronto police entered Kristen’s condo on Queens Quay and discovered the homemade alibi devices. Unsure what to make of them, they evacuated the building and called the CBRNE team—chemical, biological, radi­ological, nuclear, explosive—who unplugged the fans and removed the styluses before the timers were activated. They say the devices were functioning properly and would have worked if they hadn’t disassembled them. Their report contradicted Brett’s version of events: he told prosecutors that he’d experienced a change of heart after assembling the alibi devices and that he hadn’t activated them before leaving the house to confront his mother.

Brett hired John Rosen—the Toronto criminal lawyer known as Mr. Murder who has a long track record of defending accused killers, including Paul Bernardo and members of the ’­Ndrangheta organized crime family. Brett waived the standard preliminary inquiry and pleaded guilty. He was convicted of second-degree murder in the death of his mother—he claimed that during their argument, he went to get the crossbow from the garage to threaten her, not kill her. He pleaded guilty to first-degree murder for Chris’s death, since he’d hidden and waited for his brother to arrive before executing him. And for A. J., he was convicted of second-degree murder, since the victim had shown up unexpectedly.

At his sentencing, Brett addressed the court. He sniffled through his tears, his voice wavering. “I can only begin to say how sorry I am for what I’ve done.” He said he was “sick with grief,” though he couldn’t imagine what his friends and surviving brother were going through. “The time now doesn’t belong to me, but I’ll make the most of every opportunity I’m afforded,” he promised. “To everyone, for all of this, I’m very sorry.”

As Justice John McMahon outlined the reasons for his sentencing, he expressed admiration for Brett’s presentation in court. He complimented his elocution, sincerity and willingness to be accountable for his deeds. He determined that Brett was not just the author of this tragedy, but one of its victims—a good man who’d done something extraordinarily heinous. Brett had been caught in “a simple web of lies,” McMahon concluded. “I have no hesitation that Mr. Ryan is remorseful for his actions.” Brett received concurrent life sentences for each of the murders, plus 10 years for the attempted murder of Leighland. He will be eligible for parole in 2041, by which point he’ll be 60 years old.

Leighland Ryan, Brett’s sole surviving brother, declined to be interviewed for this piece, but he told the court what it was like to see his entire family slaughtered by his brother. He described a life shattered by trauma. He now suffers from severe anxiety. He struggles to leave the house at all. He can hardly sleep or concentrate. Above all, he thinks about his little brother A. J., taking his last breaths, bleeding out on the driveway.

This story originally appeared in Toronto Life magazine. To subscribe, for just $29.95 a year, click here.