“Who knows, life is inherently a gamble. You take and accept that risk when you wake up every day. I can’t say I think much of any person willing to live without risk.” — Iain Gerrard in an email to a friend, June 24, 2014

MEMPHIS, TENN.—Iain Gerrard left late on July 14, 2014, after staying up the night before to celebrate the World Cup soccer final with fellow travellers at a hostel in Memphis.

Like he did before each daily journey, he loaded up his 24-speed Brodie Romulus road bike with his patch kit and stove, carefully checking that the straps on his bags were properly secured.

Just before 2 p.m. he called his mom, Jean, in Toronto.

He told her of his planned 50-kilometre ride south that day, across state lines, to Robinsonville, Miss., along the famed Highway 61 — the Blues Highway once travelled by Muddy Waters and B.B. King.

“I’m on my way,” Iain told his mother.

Visibility was good as Iain pedalled along the side of the paved, right-hand lane of the roadway. The temperature hovered around 30 C. Traffic was light.

An hour into his ride, Iain entered a flat portion of the four-lane highway.

Not more than half an hour from his destination, the 23-year-old from west Toronto was struck and killed by a tractor-trailer going 100 km/h driven by a man from Brampton, Ont.

The incident has left Iain’s family and friends devastated, while many questions remain unanswered about a shoddy investigation of the incident by authorities in America’s Deep South.

***

Exactly two months earlier, Jean Gerrard dropped her only child off on Highway 5, near Oakville, Ont. She drove alongside him in the rain for a while. At one point, he stopped to tinker with his gear and remarked to his mother that he was wary of the trucks and cars that generate drag at high speeds.

“I’m not sure if I was happy when he decided he wanted to do the trip, but you would never be able to tell Iain not to do something if his mind was set on it,” says Jean.

For about a year, Iain had been ruminating on the idea of taking a cycling trip through the United States to explore his love of southern American music and the culture that created it. Iain spent months planning a 4,000-kilometre journey that would take him to New Orleans, Louisiana, and back.

“I think in pursuing the roots of North American music he was also trying to find himself and find what he wanted to be for the rest of his life,” says his dad, William Gerrard.

Growing up, Iain was an awkward kid who was picked on, say his friends. He had a learning disability that made it difficult to learn the way most kids do in school — through classroom lessons taught with a blackboard. Iain learned by doing. By working on bikes, making music, engaging in conversation.

He liked to push people’s buttons, to take them out of their comfort zone. His friends and family say he could be rude at times.

“He had very little verbal filter. He would say whatever he was thinking,” says his friend, Willis Klein, 22. “He was a really, really, really loyal friend, if you could deal with how challenging he could be in the beginning.”

Klein and Iain were big into the Toronto music scene. The friends met in 2013 at Solstice, a music and arts festival near Collingwood, Ont. Iain invited him back to his tent to drink homemade moonshine. They stayed up talking until sunrise.

At the Nuit Blanche that same year, the pair found themselves dancing in a mobile rave on a float in the Renegade Parade.

Klein remembers his friend putting his arm around his shoulder: “We’re the cool kids now,” said Iain.

“I think that was a big moment for him because I think he did face a lot of rejection when he was young. But he was unwavering. He didn’t change any of his opinions to fit in,” says Klein.

After graduating from an alternative high school, Iain pursued a diploma in audio engineering at The Audio Recording Academy in Toronto. His bachelor apartment down the street from his childhood home was more like a recording studio with a bed, where he’d hole himself up creating drumbeat loops and electronic melodies.

Iain considered himself a musician but was reluctant to turn it into a career. When his dad asked him why he wanted to take a job washing dishes at an Oliver & Bonacini restaurant, Iain said it was so that he could allow his mind to be elsewhere.

The chance to lose himself in thought while sitting on a bike for hours had a similar appeal.

***

By Day 5 of his journey, Iain had made the nearly 200-km trip to London, Ont., where strangers let him pitch his tent in their backyard.

When he finally hit the Canada-U.S. border at Windsor, Ont., 11 days into his trip, Iain wrote on his blog: “The journey has become real after months of planning I am finally doing it. My life in Toronto has felt pretty stale over the last year or so, but now I have this amazing feeling of accomplishment. I’m so happy.”

In Detroit, where he spent four days visiting cousins, Iain was taken with the Detroit Institute of Arts Museum, home to one of the largest art collections in the U.S.

Curious about a Latin inscription reading “Vita brevis, Longa Ars” above the entrance to the museum’s Rivera Court, Iain phoned his dad to ask what it meant. The literal translation is “Life is short, long is art” and is attributed to the ancient Greek physician Hippocrates. William encouraged his son to look it up for himself.

It was one of the four times a day Iain would call his folks, normally in the morning, at lunchtime, in the afternoon upon reaching his destination, and in the evening to talk to his dad for an hour or so.

“Iain liked to be in touch. He would call and we always knew where he was,” said Jean.

By Day 37, Iain had reached St. Louis, Mo., where he checked into the Huckleberry Finn Youth Hostel, and befriended Aurora Laybourn-Candlish, 21, a student in town from Oregon to present a paper at a philosophy conference. She proved to be a much-needed sounding board for the lonely traveller. The two ended up wandering the streets all night looking for greasy food and discussing life and “all the taboo things, everything that no one wants to hear,” recalled Aurora.

“Don’t censor yourself,” Aurora told Iain. It was advice that Iain was grateful for and he wrote about it in his blog.

“When I said goodbye to Aurora at the train station this morning and she repeated the advice she had been giving me all weekend … I appreciated that someone took the time to review my circumstance and actually tell me something that comes from a perspective based in critical thinking,” he wrote.

The two stayed in contact during the ensuing weeks, sometimes emailing and calling each other several times a day.

Aurora flew from Oregon to Iain’s funeral in July 2014.

***

On July 3, Iain rolled into Memphis on schedule and in time for the Independence Day celebrations. The city, its people and culture were to have a profoundly spiritual impact on him. He titled the last chapter of his blog “Born again on the Fourth of July.”

His mother, Jean, says Memphis was Iain’s “idea of heaven.”

He threw himself into tourist mode, partying his way through the Fourth of July, touring Elvis Presley’s Graceland, checking out the ducks in the fountain at the Peabody Hotel, and visiting the famed Sun Studio, where Presley, Jerry Lee Lewis and Carl Perkins recorded songs that defined Rock ‘n’ Roll. He also visited the Lorraine Motel, where Martin Luther King was assassinated in April 1968.

But it was the relationships he formed with the staff and his fellow travellers staying at the Pilgrim House, a hostel operated by the First Congregational Church in the heart of Memphis, that were to affect Iain most deeply.

A self-described “secular thinker,” Iain wrote in his blog of being moved almost to tears by a service he attended at the First Congregational Church, affectionately known by the locals as “First Congo,” next door to the hostel. He was struck by the sermon, which centred on the story of Apostle Paul and the blessing of the thorn from 2 Corinthians. In it, Paul describes his “thorn in the flesh,” a metaphor for living with humility and grace while suffering.

“I was moved by it in the most secular way possible,” Iain wrote. “Once you remove the religious aspect of the sermon (which isn’t difficult to do) you are left with what is essentially a superb life philosophy.”

Iain made friends with the hostel’s manager, Danny Grubbs, who recalled that the young Canadian had a knack for making friends quickly, sometimes in the unlikeliest of places.

Grubbs advised Iain to stay away from the convenience store down the street due to its location bordering one of Memphis’s poorest and most crime-ridden neighbourhoods.

Within a couple of days of his arrival, Iain knew the store’s attendant by name.

“I’d gone to that gas station for six months at that point and never had bothered to learn that dude’s name, but yet, he and Iain had connected in a matter of two days,” Grubbs said.

Before he left, Iain hung a Team Canada hockey jersey over a chair and told staff that every Canadian who stayed at the hostel needed to sign it.

On July 13, the day before he died, Iain delayed his journey southward to join his fellow hostel guests watching Germany defeat Brazil in the World Cup soccer final. Soccer had always been one of Iain’s passions; in every photo of Iain on his Facebook page, he is clad in his green-and-white striped jersey of his beloved Celtic Football Club.

The next afternoon, Iain made his farewells, called his mom, remarked about the heat, put on his bike helmet, and headed out onto Highway 61.

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Back in Toronto, Jean Gerrard was expecting a call from her son around 5 p.m. The call never came.

“I thought, well, that’s happened before. His phone has run out of money or he’s run out of battery … I thought, no, it’s OK,” Jean recalled.

By early evening, the Gerrards still hadn’t heard from their son.

Then, shortly before 8, the phone rang.

Jean picked it up. It was the coroner in Desoto County, Miss.

Jean shouted for her husband, William, to pick up the phone.

“Just tell me something,” Jean said. “Has my son been injured?”

“Ma’am,” the coroner said. “Your son is dead.”

***

Just before 3 p.m. on July 14, 2014, an 18-wheel transport truck hauling a shipment of foam cups and office furniture was heading south on Highway 61. The truck hit Iain.

The 59-year-old driver, Atma Gill of Brampton, Ont., maintains that Iain was cycling the wrong way on Hwy. 61, towards traffic. He has told this story to the state trooper, an insurance investigator and a Star reporter. Gill says that the young cyclist turned in front of his tractor trailer and that it looked as if Iain was trying to kill himself.

“I don’t know, I think he committed suicide,” Gill told the insurance company investigator assigned to the case.

Yet a driver who witnessed the crash said he saw Iain cycling southbound — in the same direction as the transport trailer.

The witness, Milton Scarborough, a retired man from Mississippi, told the insurance investigator he, his wife and granddaughter were driving south on Hwy. 61 when they passed Iain. Scarborough said Iain was cycling with traffic on the rocky shoulder. As he looked back in his rearview mirror, Scarborough said he saw Iain now cycling on the road with the tractor-trailer coming up behind him.

“And then, all of a sudden his body just went up in the air, his bags just come off, everything,” said Scarborough. “I told my wife, oh my God, he done got hit.”

Scarborough stopped the car and his wife, a minister, went back.

“She put her hands on his legs and prayed for him.”

Back at home, in shock at the news, parents Jean and William Gerrard booked flights and arrived in Memphis the next day to claim their son’s body. They were alarmed by what authorities were telling them. Iain was a stickler for the rules of the road and would never ride against traffic, they thought.

It just didn’t make sense that Iain had been hit head on. When the Gerrards saw Iain’s body, they noticed their son’s face had just one small cut, below his eye where his glasses had been.

“I said ‘There’s something wrong here.’ He looks perfect. He looked alive. There was even a smile on his face,” said William. “And I put my hand behind his head and I just felt the back of his head was just crushed in.”

Footage of the crash scene filmed from a helicopter by a local news channel showed Iain’s bike lying on the grassy roadside, its back wheel mangled. The front of the bike was intact.

Despite this information, the Mississippi State Trooper who investigated, Officer Gerald Cooper, filed a report that mirrored truck driver Gill’s account. The coroner made a similar conclusion and listed the probable cause of death as “multiple trauma.”

In a telephone interview with the Star, driver Gill said he has been driving trucks for three decades and was not distracted when he hit Iain.

He maintains that Iain was cycling the wrong way and that the cyclist turned in front of him.

“Before he’s ride on the right-hand side of the line but suddenly he come close to truck and he come front of my truck (sic),” Gill said.

“Like you know, nobody want to accident right? I’m a driver … So this is bad. No good. Feel sorry for that, but this is not my mistake.”

When Iain’s parents visited the crash site the day after their son was killed, they were stunned to discover many of Iain’s belongings lying by the side of the road. They found his eyeglasses, sunglasses, bike helmet and rearview mirror. They later learned that Iain’s bike had been handed over to the Mississippi Department of Transportation as garbage.

When the Gerrards tried to get answers out of Officer Cooper, the investigating officer, he treated them like they were an “inconvenience,” the parents said in an interview. They said the officer told them they could pick up the police report for a fee a week later.

The Gerrards also wonder why no one seemed to question why it took an ambulance more than half an hour to arrive on the scene.

The family, haunted by what they were being told, was at a loss about what to do until they received a letter about a week and a half later, on the day of Iain’s cremation, from an organization called Bike Walk Tennessee. The organization, which works to improve safety for cyclists and pedestrians, said it had heard about Iain’s death and was concerned that statements made by the Mississippi Highway Patrol appeared to illustrate a misunderstanding of cycling laws.

At Bike Walk’s suggestion, the Gerrards hired Charlie Thomas, a lawyer in New Orleans who specializes in bike law and the personal injury of cyclists.

Thomas hired a private investigator and an accident reconstruction expert, who came to the conclusion that Iain was hit from behind and that the truck driver would have had at least 14 seconds after seeing Iain to change lanes and pass safely.

In Mississippi, vehicles are required by law to leave a minimum of three feet when passing a cyclist.

“This is a result of the driver of the 18-wheeler, who’s either wilfully distracted, he’s choosing to be distracted in the cab. He’s choosing not to give three feet to the cyclist he’s overtaking,” Thomas, who has been representing the family in a now-settled civil suit, said in an interview.

After repeated attempts, Thomas finally reached Officer Cooper and convinced him to take another look at the facts of the case.

After examining Iain’s bike, which he found in a Ministry of Transportation locker, Cooper amended the police report. The new report says Iain was cycling in the direction of traffic and that the trucker “failed to yield right of way” when passing him.

In an interview with the Star, Cooper said Gill was “following too close” but called the incident an “accident.”

“We determined it was just an accident and that’s why we haven’t done any criminal charges or anything like that. It was just an accident,” said Cooper.

He said his initial interpretation of what witnesses saw was a “misunderstanding.”

Cooper told the Star that despite amending his report to show that Gill failed to yield, the Highway Patrol will not lay a charge — or even give the trucker a ticket — because he did not witness the incident.

“I still have to be there to physically witness, because I’m the one that has to sign for the affidavit that I physically witnessed this happen,” Cooper told the Star.

Lawyer Thomas says Cooper’s understanding of the law is mistaken, but not unusual.

“This is a practice across Mississippi which has resulted in a loophole to where people aren’t going to be ticketed unless an officer actually sees the infraction,” he said. “We think that’s a very bad practice that should be addressed.”

Earlier this year, the Gerrards settled a civil suit with the trucker’s insurance company. They are still angry with how their son’s death was handled by authorities and continue to question why the investigation was conducted so haphazardly. The terms of the settlement are confidential.