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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:

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