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Pickersgill graduated from Kelvin High School in Winnipeg. Holding an English degree from the University of Manitoba and a Masters degree in Classics from the University of Toronto, Pickersgill had originally set out to cycle across Europe, and then returned to Europe in 1938 to work as freelance journalist for several Canadian newspapers. During his travels he met with Jean-Paul Sartre, whose work he had hoped to translate into English though the oncoming war distracted his labours.
He served the first two years of the war in a labour camp as an enemy alien; he escaped by sawing out a window in the now-clichéd style of a hacksaw blade smuggled into the camp in loaves of bread. Once he was safely back in Britain, Capt Pickersgill rejected the offer of a desk job in Ottawa, and instead requested a commission with the newly created Canadian Intelligence Corps.
Along with fellow Canadian, John Kenneth Macalister, he was parachuted into the Loire Valley in occupied France on June 20, 1943, to work with the French Resistance. The two men were picked up by the SOE agent Yvonne Rudellat and the French officer Pierre Culioli. Their vehicle stopped at a German checkpoint and after Rudellat and Culioli were cleared, they decided to wait for the two Canadians to come through. Minutes later at the checkpoint, their cover was blown and Culioli tried to speed away, but the Germans opened fire hitting Rudellat in the head and Culioli in the leg, causing the car to crash. Both Rudellat and Culioli survived the crash. In March 1944, Pickersgill tried to escape the Parisian Fresnes Prison where they were being held, attacking a guard with a nearby bottle, and throwing himself out the second-storey window. He was shot multiple times in the escape attempt and recaptured; Pickersgill was interned with other agents at a Nazi-camp at Ravitsch 25 miles North of Breslau until on August 27 he was shipped with members of the Robert Benoist group to Buchenwald concentration camp.
Pickersgill was executed at Buchenwald by the Nazis on September 14, 1944, along with 35 other SOE agents, including Canadians Roméo Sabourin and John Kenneth Macalister. Though there are conflicting reports about their death, the men are commonly thought to have been hung on meat hooks and strangled with piano wire, a painful death typically reserved for traitors and spies. Their bodies were incinerated.
Posthumously, the government of France awarded him the Legion of Honor, and as one of the SOE agents who died for the liberation of France, he is listed on the "Roll of Honour" on the Valençay SOE Memorial in the town of Valençay in the Indre département. Captain Pickersgill is also honored on the Groesbeek Memorial in the Groesbeek Canadian War Cemetery in the Netherlands, and the University of Toronto designated a Pickersgill-Macalister garden on the west side of the "Soldiers' Tower" monument. Later the plot was rededicated "in memory of those tho gave their lives for peace and freedom", though there is still a plaque saying it was originally dedicated to Macalister and Pickersgill.
- The Pickersgill Letters, written by Pickersgill during the period 1934-43, were published by George H. Ford (1948).
- His letters were republished in 1978 by McClelland & Stewart as The Making of a Secret Agent: Letters of 1934-1943 by Frank Pickersgill. The book expands on the original publication and includes a new introduction by George H. Ford.
- In 2004, two of his letters, sent to his family from Central Europe in 1939, were published in Charlotte Gray's acclaimed book "Canada: A Portrait in Letters".
- His story, and that of Ken Macalister was retold in Unlikely Soldiers: How Two Canadians Fought the Secret War Against Nazi Occupation, by Jonathan Vance (HarperCollins, 2008). This book uses recently made available material from SOE files to tell a more complete story of their endeavours.