First Canadian Infantry Division had an exciting start to Operation Husky — for certain values of “exciting” — as told in Mark Zuehlke’s Operation Husky: The Canadian Invasion of Sicily, July 10-August 7, 1943:

Every day [during the convoy to Sicily], Major General Guy Simonds and Lieutenant Colonel George Kitching performed the same macabre ritual. Kitching would take a hat filled with equal-sized chits of paper on which the names of every ship bearing Canadian personnel and equipment was written and hold it out to the divional commander. Simonds drew three chits and those three ships were declared lost, victims of torpedoes from a German U-boat — the scenario at times being that about one thousand men aboard the fast convoy had drowned and burned in oil-drenched seas, or hundreds of trucks, tanks, guns, radios, and other equipment in the slow convoy had plummeted to the bottom of the Mediterranean. All lost, gone. Kitching and his staff would then sit down and coldly “examine the effect the loss of these three ships would have on our projected plans.”

On July 3, Simonds pulled from the hat chits for three ships travelling in the Slow Assault Convoy — City of Venice, St. Essylt, and Devis. The coincidence was chilling, for it was aboard these vessels that equal portions of the divisional headquarters equipment — including all the trucks, Jeeps, radio sets, and a panoply of other gear that kept a division functioning — had been distributed. Were one or even, God forbid, two of these ships sunk, the headquarters could function almost as normal. But lose the three and the division was crippled.

Kitching considered the “chance of all three ships being sunk as a million to one”. Deciding there was no point in studying the implications of such a wildly remote possibility, he asked Simonds to draw another three names from the hat, which the general did.

As you’ve probably already figured out, the one-in-a-million situation turned up on schedule. City of Venice took a torpedo during a submarine alert, with Royal Navy escort ships dropping depth charges on a suspected U-boat position. The convoy instructions were for damaged ships to be left behind and for the undamaged ships to carry on, as the danger was greater if the whole convoy slowed or stopped to aid the stricken ship(s). City of Venice could not be saved, and ten crew members and ten Canadian soldiers were killed, but the other 462 men on board were transferred to a rescue ship. A few hours later, two more ships from the convoy were lost: St. Essylt, and Devis.

While the loss of lives aboard the three torpedoed slow convoy ships was relatively small, the amount and nature of equipment and stores sent to the bottom of the Mediterranean was serious. A total of 562 vehicles were lost, leaving 1st Canadian Infantry Division facing a major transportation shortage. Also lost were fourteen 25-pounders [gun-howitzers], eight 17-pounders [heavy anti-tank guns, equivalent to German 88mm guns], and ten 6-pounder anti-tank guns that would significantly reduce the division’s artillery support. “In addition to the above,” the divisional historical officer, Captain Gus Sesia, noted in his diary, “we lost great quantities of engineers’ stores and much valuable signals equipment.” The biggest immediate blow was the loss of all divisional headquaters vehicles and equipment, including many precious wireless sets — precisely the nightmare scenario forecast and rejected by Kitching as infeasible when Simonds had drawn these ships by lot a few days earlier.

Equally serious was the loss in equipment and lives suffered by the Royal Canadian Army Medical Coprs personnel attached to the division. Due to a loading error, instead of No. 9 Field Ambulance’s vehicles being distributed among several ships, fifteen out of eighteen were on Devis. Accompanying the vehicles was a medical officer and nineteen other ranks and medical orderlies. Four of the other ranks were among the fifty-two Canadian troops killed and another four suffered injuries. The other field ambulance, field dressing station, and field surgery units assigned to the division were largely unaffected. No. 5 Field Ambulance’s vehicles had been distributed correctly so only two of them and a ton of medical supplies went down with St. Essylt. City of Venice had just one medical officer, Captain K.E. Perfect, aboard and he escaped uninjured. But Perfect was overseeing safe passage of nine tons of stretchers and blankets, which all went to the bottom.

[…]

A fully accounting of the losses would not be completed for days. Even on July 7, reports were still coming in that City of Venice remained under tow and bound for Algiers. Finally, at 1900 hours on that day, its sinking was confirmed. The report also stated that most of the surviving Canadian troops had been loaded on a Landing Craft, Infantry in Algiers and were en route for Malta. From there, they would eventually rejoin the division.

Compounding the loss of so many vehicles was the fact that the division had left Britain with a smaller than mandated number due to lack of shipping capacity. Once the seriousness of the situation was appreciated, Lieutenant Colonel D.G.J. Farquharson, the division’s assistant director of ordnance services, and his staff “tried to make [the losses] good … by emergency measures, improvising and obtaining what could be obtained buckshee from the Middle East.” They soon had commitments for some vehicles, but these would not be available until after the initial landings. The fact that every vehicle to be found locally was a Dodge posed “a considerable ordnance problem, because what spare parts we had were based on Ford and Chevrolet makes.” Improvisation would be the order of the day.