Tail-end Charlie – another story by Clarence Simonsen -redux

Always nice to get a feedback from a post…

Thank you for writing/posting this. I’m glad to read that my Grandpa made such a lasting impression that you felt compelled to share this so many years after his death. I love that the story captured his humour and personality.

Again, thank you.


Hello Pierre,

Here is another story on a very special person, rear gunner Doug Penny. During his whole life he did so much for Canada and fellow Canadians, but his WWII history and nose art needs to be displayed.

This 1942 cartoon which appeared in an issue of aeroplane magazine tells the true story.




While most rear gunners were proud of their RCAF slang, they also understood it was the most dangerous of all bomber crew stations, the most detached, and they were the least lucky to survive a night attack. Located in the rear, all alone, they will become the first into the air as the bomber tail lifts off the runway in Yorkshire, England.  Then for the next six to eight hours they search and search the night blackness for any movement or shape which might be a German night-fighter. The “Tail-end Charlie” frequently died in his isolated world, shot to death by a night-fighter he couldn’t even see. This lone man also made the decision that could save his entire crew when he screams out “Corkscrew left or right”, then fires his four Browning machine guns at the shape in the darkness. To fly night after night as a rear gunner, you needed a special kind of courage and sometimes just pure luck to escape a rendezvous with death.  F/L Douglas Richard Penny flew 37 operations as a rear gunner and he told me during one operation, he survived only because of his training and luck.

Doug Penny was born near the Qu’Appelle Valley of Abernethy, Saskatchewan, on 22 December 1923. He applied for the RCAF in the fall of 1941, but was not taken on strength until after his 18th birthday, officially dated 23 April 1942. This delay was caused when he contacted scarlet fever while in training at Brandon Manning Depot and spent two months in hospital. He stated “The rats in the hospital were as big as alley cats.” He was posted to No. 2 Wireless School at Calgary, Alberta, but washed out [29 March 1943] where he was informed his Morse Code was not good enough. He always felt his grades were OK, it was the simple fact they needed “tail-end Charlies”  due to the high gunner loss rate.

Doug was next posted to No. 3 Bombing and Gunnery School at MacDonald, Manitoba, and graduated course #50A as a F/Sgt. and attained his A/G Brevet on 14 May 1943. 

“After the usual embarkation leave [30 days] I ended up in the UK at Bournemouth, just in time to get strafed by a couple of German Me109s, while we were lying around the bowling green. I then went to Operational Training Unit at Stratford and crewed up with Wellingtons. During this training period I was slated to go on a fighter affiliation flight in an old Halifax Mk. II. I had just purchased a new bicycle and was late reporting, missing the instruction flight. During a corkscrew by the pilot, the old bomber broken apart and all the crew and new air gunners were killed. It was my first escape from death but not the last. We were posted to No. 420 [Snowy Owl] Squadron and heading for North Africa [late September 1943] when the campaign in Italy ended.”

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“We were posted back to a Heavy Conversion Unit at Croft and Dishforth, then back to No. 420 Squadron at Tholthrope, where we flew three operations in Halifax aircraft. Out pilot [above center] was asked to go on a trip to Berlin as second “Dicky with another crew and was killed in action.” 

“Our crew headed back to Wombleton-in-the-mud looking for a pilot who would take us.  They would meet a Canadian pilot S/L Maurice William Pettit, DFC, who had completed a tour of 27 operations with No. 128 RAF Squadron, flying Stirling bombers. Penny – “He was a super Canadian pilot, also one of the great beer drinkers in the RCAF.” “I  finished my first tour with him at 432 Squadron, East Moor, Yorkshire, a few trips to Berlin, D-Day, and wrapped it up in early August 1944.”

On 18 March 1944, they began operations with No. 432 [Leaside] Squadron, and received a new Halifax Mk. III aircraft serial LW596, QO-D, call sign “D for Dog.” This inspired the new nose art painting, which had appeared in an issue of Saturday Evening Post magazine.


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This Doug Penny photo clearly shows the gas-operated Vickers”K” nose mounted gun in Halifax Mk. III, LW596 and the early nose art painting before name “Devastating Dog” has been applied, operation number three.

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This was the photo Doug proudly called “Penny, spending a Penny.” The British term for urinating in a toilet was “spend a penny” as the use of a public toilet in England cost one penny. Before each operation Doug Penny would “spend a penny” while holding onto his tail guns, just for good luck. He always left his bed unmade, also for good luck, as he  would make it upon his return from the operation. 

In June 1944, No. 432 [Leaside] Squadron began to received new Handley-Page Halifax Mk. VII aircraft and the older Mk. III Halifax bombers were transferred to the No. 434 [Bluenose] Squadron. Halifax serial LW596 joined No. 434 Squadron coded as WL-Z and possibly flew with the same original nose art “The Devastating Dog.” 

The new Halifax B. Mk. VII, serial NP692, was assigned to the crew of S/L Maurice Pettit and tail-end Charlie, Doug Penny. 

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Flight/ Sgt. Doug Penny in his new office, which had a better rear turret heater.

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Halifax B. Mk. VII, serial NP692, “D for Dog”  received the same nose art and name as LW596.

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NP692, The Devastating Dog at her hardstand after thirteen operations. 

On 28/29 July 1944, Doug Penny was flying his 33 operation, and this attack on the German city of Hamburg involved almost the entire force of 234 aircraft from No. 6 [RCAF] Group. The bomber stream was allotted a four thousand height band between seventeen and twenty-one thousand feet over the target city. This would prove to be a night the Canadians would never forget as the night-fighter attacks were intense over the target, then the German fighters continued to attack the bombers on the homeward journey. The bombers of 6 Group would have twenty-two aircraft shot down, including Halifax LW596, [The Devastating dog] flown by F/O I. Alexander and crew in No. 434 Squadron, all killed in action.

 Doug Penny recalls -“It was a long stressful trip home in total darkness, then I felt the most welcome slow descent and I knew we were approaching the English coast and home.  As we approached four thousand feet, I began to relax, removed my oxygen mask and reached forward for my thermos to have a cup of hot coffee. Suddenly, in the blackness I saw a movement, dropped my thermos and fired my four machine guns. At the same time the darkness was alight with the return fire of a German night-fighter. The German fighter had followed the Halifax bomber across the English Channel and both Penny and the German pilot had opened fire on each other at the exact same instant. The German shells missed Doug Penny by six feet, but Doug scored a direct hit on the Ju-88 fighter, which dove straight into the sea, witnessed by several bomber crews. In the morning light, F/Sgt. Doug Penny looked at the damage on his Halifax wings and realized he had escaped death by pure luck, combined with his skill as a rear gunner.


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The Halifax tail wing damage caused by the German night-fighter [Ju-88]  on 29 July 1944. [Doug Penny]



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 Damage caused to Halifax NP692 main wing, almost reaching the fuel tanks. [Doug Penny]


For his actions in saving his crew, Doug was promoted to Flight Lieutenant and received the Distinguished Flying Medal. He returned to East Moor and instructed gunners in No. 432 and 415 Squadrons on combat and night vision tactics. During this time he also completed four more operations with Wing Commander J. K. MacDonald who was the C. O. of No. 432 Squadron, finishing his tour in early October 1944. He continued to train new gunners until the spring of 1945. 

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After completing 37 operations, F/L Douglas Penny arrived at Gransden Lodge, Bedfordshire, in April 1945, to begin his second tour flying with No. 405 [Vancouver] Squadron, under No. 8 [Pathfinder] Group of the RAF. The C.O. decided he had not been screened long enough and he was ordered to Canada and 60 days leave. During his leave, the war in Europe ended and he was sent to instruct at No. 7 Bombing and Gunnery School at Paulson, Manitoba. Doug – “That’s where I lounged until September 1945, when I was discharged from the RCAF.”” I left the service an older and wiser Air Gunner, then returned to finish my schooling in Regina, Saskatchewan.”“I was only 22 years of age.”

On 8 October 1949, Doug began a career in the oil and gas industry as a salesman for Imperial Oil Ltd, in Edmonton, Alberta. From 1952 to 1955 he served as Adjutant with No. 418 [Auxiliary] “City of Edmonton” Squadron, flying the North American Mitchell Mk. II and III aircraft. He was a member of many service organizations, including the Masonic Lodge, Associated Canadian Travellers, and a member of the Royal Canadian Legion for over sixty years. He served as National President of the Air Gunners Association, spending his personal time and money visiting members in the United States and Canada, acting as M.C or Speaker for many of the National Reunions. He always presented himself in a manner which made him most popular with all membership. Doug was big supporter of the first formed Lancaster Museum of Nanton, Alberta, now named the “Bomber Command Museum of Canada. 

After a lengthy battle with cancer, F/L Douglas [Doug] Richard Penny passed away at the Sarcee Hospital [Calgary, Alberta] on Friday, 9 February 2007. 

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My first meeting with Doug Penny occurred in the summer of 1980, when he drove to my farm located six miles east of the village of Acme, Alberta. Doug introduced himself and during our chat he ask if I would paint his nose art for him. That began a friendship that last until 2004, when I ask him to autograph this third replica painting of his Halifax nose art. Today this hangs in the nose art section at the Bomber Command Museum at Nanton, Alberta, however it contains little information of the two RCAF Halifax aircraft that carried this nose art or the man who flew as the “Tail-end Charlie” in both.

In 2009, I attempted to create a section in Nanton Museum that would tell this history and honour the forgotten WWII men who painted nose art during the war. The Directors of the Bomber Command Museum of Canada took a vote and said – “NO”. 

This story was created to honour Doug Penny and record the history of the nose art painted on the two Halifax bombers he flew rear gunner in World War Two. 


 written by Clarence Simonsen