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I Spent a Terrifying Day Trying to Keep Up with a Bike Messenger

Many bike couriers don't do their jobs for the money, they do it for the death-defying thrills.

Allan Shaw. Photos by the author

"Brutal. Fucking brutal, man."

It's the third time today that a driver has taken the liberty of fully sticking his head out of his window to verbally berate me.

The reason the driver's losing his shit is understandable: I unintentionally cut him off while very intentionally blowing through a red light in the middle of rush hour in downtown Toronto. I'm attempting to keep up with Allan Shaw, a Scottish expat who, in the lore of the local bicycle messenger's community, is one of the fastest riders.


I met Shaw that morning, just three hours before nearly getting run over by that very angry driver. He's crossed the continent from New York to Vancouver by bike, and has been a bike messenger in Mexico City, Vancouver, and now Toronto. At 26 years old, he's got the calves to show for it, along with a gnarly mustache and tattooed legs that give him the kind of ragged look that has become a bike courier stereotype.

I'm following Shaw around Toronto because I wanted to figure out whether everything I've heard about bike messengers is just an exaggeration or the real deal. Most of what I've learned comes from bragging friends, the rest of it from the film Premium Rush, a slightly cheesy flick where Joseph Gordon-Levitt plays a cute but hardcore NYC bike messenger. And then there are always the rumours about crazy messengers who'll smash a driver's side mirror if they get cut off. For the record, I definitely didn't witness any of that.

Cycling in Toronto is dangerous as it gets in North America: While there are bike lanes – some of which are even separated – the bike lane network itself is entirely patchy. Despite a growing number of cyclists, they still don't have the critical mass to be on the forefront of a driver's mind, like in some European cities. Streetcar tracks are a built-in booby trap, and cycling in the winter is reserved for those with nerves of solid ice. Despite that, bike messengers are pushing the limits on how fast you can ride on Toronto's unfriendly streets. The danger, speed, and urgency gives the job a sense of romanticism that doesn't exist for your average UPS driver.


From the moment I met Shaw, I'm told that bike messengers don't do this for the money. (Depending on whether they're getting paid hourly or by the delivery, their rates can range from $12-$17 [$9-$13 USD] an hour.) Instead, they do it because they love biking in all its various permutations. One courier I met was into mountain biking. Some, like Shaw, are into long distance riding. Curiously, some others are into bike polo, a brutal sport that's basically regular polo on bikes.

Two hours into following him around Toronto, Shaw's living up to the hype. He leads me in between idling cars, through tiny gaps within crowds of pedestrians, inching close enough to moving vehicles that the messenger bag dispatch handed me for comedic effect bounces off multiple side mirrors.

It took Shaw some convincing once we get out of dispatch to ride like he usually does. He tells me that riding with others makes him nervous – not only because I might hold him up, but also because I'm not as adept as dodging cars and people as he is.

In the next hour, we don't stop at a single red light. A lot of our riding is spent simply on the wrong side of the road and Shaw weaves between and in front of cars seamlessly. It's the kind of riding I was hoping to see, but I can see why it would make him nervous to have me try to follow.

Any calculations he's making when it comes to how much space is available – where gaps will appear and how long the'll remain open – are for his bike alone. I'm struggling to get creative and make it through the tiny gaps he's found in traffic as those opportunities close and space runs out.


What catches me off guard though, is when Shaw does something I assumed you only see in the movies: Biking down the congested thoroughfare of King Street, Shaw grabs onto the side of a moving truck for about 15 seconds to take a moment of rest and get a quick boost of speed. He says it's referred to as "skitching," and it's actually quite common.

"Some people skitch by grabbing onto the wheel hubs of cars or the sides of moving trucks," he casually explains as we bike on. "I like to grab onto door handles of cars, but you have to be careful not to pull too hard, or you'll open their door. I've done that by accident once."

I'm trying to imagine the horror of looking in your rearview mirror and seeing what probably looks like a hitman about to hijack your car. Shaw tells me that sometimes he'll catch a glimpse of a driver's eyes in the mirror.

"The moment you make eye contact, you can tell if you can keep holding on, or if you're going to have to let go," Shaw explains. The worst situations can be when a driver fully freaks the fuck out and slams on the brakes or starts swerving wildly.

In places like Chicago and New York, Shaw tells me that skitching is more "accepted" and commonplace, and you can skitch for entire streets. He keeps encouraging me to give it a shot, but I'm not particularly convinced (although door handles are always calling my name when I'm biking now).

Between grabbing onto cars and flying through reds, the end result is that bike couriers are unfathomably quick. Three hours into Shaw's work day, I challenge him to race me from Parliament Street to Roncesvalles, a length that covers almost the entirety of what you can consider "downtown." A quick Google search would tell you that during rush hour, it's a 30-minute drive, and 25-minute trek on the subway.


Now that he's freed from having to slow down, I've lost sight of him within the first set of traffic lights. Without him, I'm not brave enough to rush through red lights on my own. The amount of skill it takes to fly through intersections sinks in.

After what feels like endless pumping, I finally gasp my way to Roncesvalles, a whole 22 minutes later. It took Shaw only 12 minutes, less than half the time it takes to drive the four mile stretch.

Biking like this feels like real-life Need for Speed. It can come with some costs though, especially in Toronto. Shaw tells me that he's gotten two hefty traffic violation tickets in Toronto, more than he's gotten in every other city combined.

When reached for an interview, Mark Pugash, the Toronto Police Service's Director of Corporate Communications, put the cop's perspective of messenger riding quite simply.

"We regard anyone who rides a bicycle unsafely as a threat to public safety," Pugash said in an email. In regards to targeting bike messengers, Pugash went on to say, "we don't target groups. We target those who endanger public safety, whether they are drivers, pedestrians, bicycle riders, motorcycle riders, e-bike riders, and so on. We have regular enforcement initiatives as well as officers who enforce the law year-round."

For Shaw, dealing with the cops is something that comes with the territory.

"I'm very passive with the cops, I don't pick fights." Shaw says. "If you wanna give me a ticket, you can give me a ticket. I don't pick fights, I'm not interested in that at all."

The greater cost though, can be your body. In Toronto, there's an average of 1271 bike accidents per year, as reported by the Toronto Star. Despite that large number, there have only been three reported fatal accidents as of June 2015. In 2009, bike messenger Darcy Sheppard died after being run over by Michael Bryant, a prominent political figure at the time. Criminal charges were laid against Bryant, but many news outlets were quick to paint Sheppard as an "angry, aggressive road warrior," despite eyewitness accounts that pinned Bryant as the main aggressor in the altercation. The charges against Bryant were eventually dropped, but the issue remains controversial and still receives media coverage even in 2015.

Despite what can be dangerous riding at times, Shaw reckons that mile to mile, bike messengers get into very few accidents when you consider their sheer daily mileage. On our five hour ride, we easily covered about 25 miles. Shaw's never been in a crash, but he's had a lot of eye-opening close calls. Close calls that could have even been fatal.

"I know that the next big accident is coming. It will happen. Seeing these skilled riders that I know get into accidents that aren't their fault, you have to assume that it's part of the job," Shaw says. "You just ride the way you ride, and can't live in fear."

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