Yeats asked John to make his portrait for an etching to illustrate his Collected Poems. John visited him in Ireland, and did some drawings and this painting as studies. He returned to London to make the etching, using a different study. Yeats however rejected it, and chose one by Sargent instead. John wrote privately that Yeats, although he was then aged 42, wanted to look like 'the youthful Shelley in a lace collar'.
This was the first of John's many portraits of writers, and his first commission for the portrait of a celebrity.