Family Despatches

Jamie Leonard digs through his family history and recounts the part that both his grandfather and great uncle played in the Second World War as Despatch Riders.

Words: Jamie Leonard. Photos: As Specified


In Confederation Square in Ottawa there stands a granite arch, rising up from a stone pedestal in the middle of the square. Twenty-two figures all in all march through this arch, each representing one of the varied branches of our military, representing those who have fought in our wars and lived and died wearing our uniform.



A Lewis gunner, a sailor. Cavalry, artillery and others have all served in our names.

At the left rear, however,  strides one figure in goggles and cap, his sheepskin all-weather coat belted around him. He is invisible in almost all of the photos taken of the monument; his is a story less told – and yet it is a story no less important than the others.

He is a despatch rider — a volunteer — whose duties include everything from mail delivery to guarding POWs. A despatch rider faced danger from simple traffic, road conditions, the whims of weather, and from shells and bullets, too.

I’m proud to say that not only my grandfather but my great uncle as well served as despatch riders in the Second World War.



Jack Leonard.
Photo: unknown

My grandfather, Jack Albert Leonard, was known for many things.

At various points in his life he’d been a chimney sweep, a firefighter, and a lumberjack – the latter being back in the days of axes and saws, and long road trips into distant lumber camps.

He loved anything mechanical, and could fix or build almost anything he set his mind to. This even extended to a penny-farthing bicycle – which is a rather tall 19th century contraption with no brakes, fixed pedals and a terrifying riding position. This he rode in no fewer than 54 Victoria Day parades, much to the amusement of onlookers.

These are the things most people knew about my grandfather.

What they didn’t know was his life as an army despatch rider. A job that involved riding on bombed out roads, through mud deep enough to swallow vehicles whole – at night … without lights. All the while being a prime target for snipers, airplane strafing — or even just run over by a truck — also running without lights.

My earliest memories of my grandfather involve him sitting on the stone shelf that surrounded his fireplace. He’d gesture me over, poking at the fire and slowly start into a story, sharing with me some of the things he’d seen and done while despatching.


Jack and his wife Joan.
Photo: unknown

He became a DR after arriving in England in 1940, and was stationed near Oxted, Surrey, where he met his future wife Joan.

There happened to be a great need for despatch riders and when his unit was lined up and asked if they had any motorcycle-riding experience, he spoke up. What he had neglected to explain, however, was that his “experience” consisted of two brief rides on a borrowed motorcycle, back home in British Columbia.

Not that it mattered, he soon found out that he was a natural.  Eventually he became a motorcycle instructor, and a bit of daredevil from all reports – regularly jumping his Indian motorcycle during training.  Apparently it isn’t wise to tell a DR “You can’t jump that thing that high.”

In the early days of the war, Canada scrambled to outfit the increasing numbers of troops and he was subsequently issued a holster, but no pistol.

Joan remembered that she still had her father’s pistol out in the back garden shed –  a WWI-era Webley revolver and a box of shells with the brass turned green, which she gave to him.


Jack soon realized that he was a natural on a bike.
Photo: unknown

Undeterred, my grandfather took his cleaning kit, oiled and cleaned the pistol, cleaned each bullet until it gleamed with brass polish, and placed the pistol in his newly issued holster. Job done.


Army issue riding outfit.
Photo: unknown

His first chance to use the Webley came about on a moonlit night, while making a delivery on his motorbike, when he spotted a pheasant off to the side of the road. At the time, according to my grandfather, the rations were positively horrible. He thought that if he could bag a pheasant for the regimental cook to serve, he’d end up the hero of the day.

Switching off the bike and gliding to a stop he gently slid the sidestand down and pulled out the Webley. Moving slowly so as to not startle the bird, hearing only the tick of the cooling engine, his breathing and the slow crunch of his steps on the dirt of the road, he aimed carefully.

He squeezed the trigger, the hammer fell with a click, the Webley gave out a slight “pop,” and the bullet slowly tumbled out of the pistol and fell into the mud a few feet from the end of the barrel.

He tried again. Pop. The result was no better, if a little louder – just enough to scare the bird away. The almost 30-year-old ammunition was … less than functional.

Turned out that the powder in each bullet was an inert lump after the years of sitting in the shed, with just the primer going off to make the “pop.” The pistol he’d gotten to protect himself while riding alone along the treacherous wartime roads, was only useful for scaring away birds. And even then it took at least two shots.


An unidentified DR riding a Norton motorcycle, England, 11 January 1943.

I don’t know if he ever had reason to fire his pistol again after that (generally he spent more time riding through enemy fire than returning it) but it was a moment he certainly never forgot.

My grandfather passed away in December of last year – and I wish I had more of his stories.


My great uncle Lennox Andrew Martin Booth was born in Quebec in 1918.

With the outbreak of the Second World War he volunteered and joined the Royal 22nd Regiment of the First Canadian Division.


Great uncle Lennox.
Photo: unknown

In fact, it wasn’t an easy task to get accepted as he suffered from flat feet, and the army at first didn’t want him as it would limit his ability to march. However, after much insistence he was offered a spot as a despatch rider, where it was felt his inability to march would not be as much of a factor.

Like many a veteran there were certain things he didn’t talk about. For example he was part of the rescue forces after the disastrous Dieppe raid.

Asked one time to speak about it (and introduced as a “hero”), his reply was simply “I’m not a hero. All we managed to do was to get close enough to get some of the wounded out.” And that was all he would say.

He would talk however about his duties as a DR and his various run-ins with authority.

In England, during training, he was assigned to drive a colonel around in a Jeep, in addition to his other duties. On one occasion, while returning the colonel to base in a jeep, he found the road temporarily blocked. Rather than waiting for the road to clear he decided to take a “short cut” up a steep bank.

Gunning the motor, he slewed his way up the steep slope – sliding up and around with the colonel bouncing haplessly in the rear seat. The colonel was somewhat less than amused by this. That was the first time he lost his corporal’s stripes.


firing_guns.jpgInfantrymen of The Regina Rifle Regiment and a despatch rider firing into a damaged building, Caen, France, 10 July 1944.  


One particular day in Italy, while riding his army-issue Norton motorcycle, he was handed a package and ordered to deliver it to the front lines straight through the firing line. Riding at breakneck pace along damaged roads all the while dodging bullets and shells, he finally came to the officer to whom the package was addressed.


Despatch riders were also trained in field repairs and frequently would have to modify or repair their machines to keep them running under extremely rough riding conditions.

The officer opened it in front of him, revealing it to be a simple can of fly spray. Upon seeing this, Lennox used some rather strong language, having risked his life to deliver this “priority package.” Needless to say, he ended up losing his corporal’s stripes for the second time.

There’s a bond that inevitably develops between man and machine, especially under such extreme circumstances. My uncle’s Norton was his for most of the war but was at one time deemed too damaged to repair. So he asked for, and received, a few days off which he spent feverishly repairing it himself, rather than seeing it retired so that he could be issued a new one.

There are stories of DRs stealing officers’ bikes, stripping them for parts, and then disposing of what remained in a handy canal, though I’m sure this wasn’t my uncle’s style …


Throughout the Second World War, the DR was essential to carry out a variety of duties. They were, of course, responsible for communications (since there were only so many radios available) and proved to be a priceless source of information on both allied and enemy troop locations.


Despatch rider Frank Shaughnessy of the 2nd Anti-Tank Regiment, Royal Canadian Artillery (R.C.A.)

But delivering despatches was only one part of the job, they frequently rode out to locate missing or lost units and would regularly be assigned to lead convoys as many of the drivers had no maps or navigational experience, and most of the roads lacked signs.

There are no exact numbers for how many riders were lost, through either enemy action or the dangerous conditions in which they operated.

Nor can we really understand the conditions in which they rode – on heavy, balky and often less than reliable motorcycles. Riding at night, lightless, on a damaged road – alone in a dark place, without ever being quite sure just how far away the enemy was at any point.

All volunteers, with no extra glory, no extra pay, no extra recognition. They were farmers, mechanics, workers of every stripe. Fathers, sons. Family we all can be proud of. I know I’m proud of mine.

As a memorial to my grandfather, who passed away last December at the age of 89, I will be driving my Ural sidecar motorcycle from Toronto out to Victoria, B.C., 4,500 km one way on a cranky, heavy, old-school machine, but at least there’ll be no-one shooting at me.

And Grandpa Jack, I think he’ll be right there – laughing at the stories I’ll be making along the way.



Prior to the First World War, riders were encouraged to use their own machines to save expense.

2012 will be the 100th anniversary of the Canadian Military Motorcyclist. Prior to WW2, Canadian Forces fell under the British military, and the first unit to receive official permission to use motorcycles (there was some “unofficial” use of private motorcycles for errands and some duties prior to this) – was the Royal Engineer Signal Territorial Force in England in 1912.


Royal Engineers DRs at Gallipoli.

However, after the First World War Canadian forces consisted of self-financed militia with no AA guns, tanks, or armoured cars until 1938.

Yet motorcycles could be found in virtually every unit of any size (due not so much to their abilities, but to their relatively small expense).

The numbers would grow explosively (as with the rest of the army) after war was declared, with a need for new machines to replace the odd lots of different makes (prior to the war riders were encouraged to use personal machines to save on expensive – frequently without any compensation for doing so).



Further Reading


  1. “The Winged Wheel Patch” by Max Burns and Ken Messenger (out of print, but check your area library)
  2. “The Dispatch Rider” by Harry Watts (self published chapbook – available at
  3. The Memory Project – stories of Canadian participation in the second world war.
  4. “Adventures of a despatch rider” – public domain book about a DR during WWI


  1. Hi Johnston
    The Canadian Dispatch Riders M.U. is also Canadian wide asso one Unit in Fairfax Virigina ran by an expatriate, they collect food for the Captial FoodBank in DC. We support the homeless and those looking for a warm meal by collecting non parishable food for soup kitchens and foodbanks.
    Check us out at

    Chris Graham aka Sarge
    Founder/ National 1st Officer
    Canadian Dispatch Riders M.U.
    Kingston, Ontario

  2. Thanks Brian…the green patch is what I have seen. I saw them at the Ride for Dad last year in Hamilton and also at Americade.

  3. If you are talking about the green patch on the back of leather vests with the dispatch rider and motorcycle this is the patch of the CAV. Which stands for Canadian Army Veteran’s. This is a Canadian wide organization made up of both veterans and supports who all ride motorcycles.

  4. Hi Jammie,

    Just want to thank-you for this article mentioning my Dad Lennox Booth. My sister Pat came accross this on the 12th of May. Miss both Dad and my Mom.
    Good Luck on your journey !!!!

  5. Great article.
    I love reading anything about these guys as my uncle was a DR in London during the blitz. He’s passed now but the picture of him on a Harley WR is still hanging proud!

  6. Great article, and a fitting tribute to your grandfather and great uncle. As an aside, I would love to get a copy of that recruitment poster. Any ideas where I could buy one?

  7. This is a very enjoyable article. Thanks!

    My parent are immigrants so I can’t say I have any Canadian connection to military motorbikes but my old man was a military police in Holland and rode an old H-D Sportster. Was one of the lucky ones, his father before him rode a horse doing the same job and HIS father before that rode a bicycle, also as an MP I know it seems backwards but they’re Dutch so what can I say?)


  8. Thank you for that article.

    I’ve seen the DR as a club patch on some riders. Is there an organized group related to this peice of history?

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