E . H . Shepard Ernest Howard Shepard ( 10 December 1879 – 24 March 1976 ) was an English artist and book illustrator . He was known especially for his human - like animals in illustrations for " The Wind in the Willows " by Kenneth Grahame and " Winnie - the - Pooh " by A . A . Milne . Career . Shepard was born in St John ' s Wood , London . Having shown some promise in drawing at St Paul ' s School , Shepard enrolled in Heatherleys School of Fine Art in Chelsea . Having spent a productive year there , Shepard won a scholarship to the Royal Academy Schools In 1915 , Shepard received a commission in the Royal Garrison Artillery , an arm of the Royal Artillery . By 1916 Shepard started working for the Intelligence Department sketching the combat area within the view of his battery position . In 1917 whilst commissioned as a 2nd Lieutenant , and acting as Captain , he was awarded the Military Cross for his service at the Battle of Passchendaele during World War I . His citation read : For conspicuous gallantry and devotion to duty . < br > As forward Observation Officer he continued to observe and send back valuable information , in spite of heavy shell and machine gun fire . His courage and coolness were conspicuous . Throughout the war he had been contributing to " Punch " . He was hired as a regular staff cartoonist in 1921 and became lead cartoonist in 1945 but was removed from this post by Malcolm Muggeridge , who became editor in 1953 . Shepard was recommended to Milne by another " Punch " staffer , E . V . Lucas in 1923 . Initially , Milne thought Shepard ' s style was not what he wanted , but used him to illustrate his book of poems " When We Were Very Young " . Happy with the results , Milne insisted Shepard illustrate " Winnie - the - Pooh " . Realising his illustrator ' s contribution to the book ' s success , Milne arranged for Shepard to receive a share of his royalties . Milne also inscribed a copy of " Winnie - the - Pooh " with the following personal verse : When I am gone , < br > Let Shepard decorate my tomb , < br > And put ( if there is room ) < br > Two pictures on the stone : < br > Piglet from page a hundred and eleven , < br > And Pooh and Piglet walking ( 157 ) … < br > And Peter , thinking that they are my own , < br > Will welcome me to Heaven . Eventually , Shepard grew to resent " that silly old bear " and felt that these illustrations overshadowed his other work . Shepard modelled Pooh not on the toy owned by Christopher Robin , Milne ' s son , but on " Growler " , a stuffed bear owned by his own son . ( Growler no longer exists , having been given to his granddaughter Minnie Hunt and subsequently destroyed by a neighbour ' s dog . ) His Pooh work is so famous that 300 of his preliminary sketches were exhibited at the Victoria and Albert Museum in 1969 , when he was 90 years old . An E . H . Shepard painting of Winnie the Pooh is the only known oil painting of the famous teddy bear . It was purchased at an auction for $ 285 , 000 in London late in 2000 . The painting is displayed at the Pavilion Gallery in Assiniboine Park , Winnipeg , Manitoba , Canada . Shepard wrote two autobiographies : " Drawn from Memory " ( 1957 ) and " Drawn From Life " ( 1962 ) . In 1972 , Shepard gave his personal collection of papers and illustrations to the University of Surrey . These now form the E . H . Shepard Archive . Shepard was made an Officer of the Order of the British Empire in the 1972 Queen ' s Birthday Honours . Personal life . Shepard lived at Melina Place in St John ' s Wood , London and Lodsworth in West Sussex . He had two children , Graham ( born 1907 ) and Mary ( born 1909 ) , who each also became illustrators .