Simon was Leonard Cheshire’s pet poodle, apricot in colour and purchased in 1941 whilst Leonard was on leave from his RAF squadron with his crew in London. The pet shop was behind Berkeley Square. On the same trip, Leonard’s wireless operator Jock was left for a while to look after Simon at the Mayfair Hotel. Leonard later said, ‘When I came back, Jock was not alone. He said he had never had so many beautiful girls come up to him in all his life, and figured out that the passport to success was to buy a poodle puppy.’
A portrait photograph of a standard poodle dog

Simon the poodle

Simon appears in Leonard Cheshire’s books and also in his biographies by Russell Braddon and Richard Morris. From these we have a good idea of his favourite activities. They included: chewing shoes and stealing caps, digging up the flowerbeds, chasing hens and following Leonard on his ritual tour of the base after every successful raid.

Two men in RAF uniform crouching down. One on the left with a cigarette in his mouth is petting a large standard poodle. The man on the right has an alsatian.They are outside on the grass

Flight Sargeant Len Sumpter, left with Simon the poodle and another airman with an alsatian dog at the Petwood Hotel, Woodhall Spa in 1944.

Three women with a standard poodle, centre, stood in the gardens of a blacka nd white building

WAAFs wearing their waitressing uniform outside RAF Woodhall Spa Officer’s mess, the Petwood Hotel. Kitty McQuillan and Simon stand centre 1943/44.

Leonard was often away, and during his time as Wing Commander of RAF 617 Squadron, Simon was left in the care of the WAAFs who walked him in the grounds of the Petwood hotel. When Leonard was posted to India and the USA in 1944, we believe Simon was left in the care of WAAF Kitty McQuillan.
A woman outside in WAAF uniform, crouching down with two dogs, Simon the poodle is on the right. A blacka nd white building is behind her and the weather is snowy

WAAF Kitty McQuillan with Simon and another dog in the grounds of the Petwood Hotel, the RAF Officer’s mess at Woodhall Spa, Winter 1943/1944.

A poodle posed on a garden plinth in a spring garden outside a black and white building

Simon posing majestically in the gardens of the Petwood Hotel, RAF Woodhall Spa’s Officers Mess, in the Spring of 1944.

We have photographs of Simon in our photograph collection at the archive; he is a very popular subject. However we were surprised to receive an enquiry a few years ago from someone whose father had looked after Simon at RAF Mildenhall. The photographs we were sent show Simon in June 1945 being walked around Mildenhall in Suffolk. Unfortunately we don’t know much more about how Simon had got there, or who he was living with, but in the photos it is obvious that he was well cared for and somewhat famous for being ‘Leonard Cheshire’s Poodle’.
A man and a poodle walking into a cafe

Simon being walked at RAF Mildenhall, Suffolk in June 1945. He is about to enter Morley’s Café. Photo thanks to Shaun Russell.


Two men posing outside a large building with a standard poodle sat centre, panting

Simon with two RAF airmen at RAF Mildenhall, June 1945. Photo thanks to Shaun Russell.

Further reading