Through intensive study, combined with the careful guidance of Henry Tonks, Augustus John had already achieved a remarkable technical ability by the late 1890s. William Rothenstein, who became his earliest and most enthusiastic patron, was one of the first to recognise this. Rothenstein was a few years older than John, and had been at the Slade briefly in the early 1890s, before the arrival of Brown, Tonks and Steer had raised the dynamic of the school. Having spent time studying in Paris, Rothenstein returned to London in 1893, which is when he first met John. As he recorded many years later,

[John] brought me his drawings, which were truly remarkable; so remarkable that they put mine […] into the shade. Here was someone likely to do great work; for not only were his drawings of heads and of the nude masterly; he poured out compositions with extraordinary ease; he had the copiousness which goes with genius, and he himself had the eager understanding, the imagination, the readiness for intellectual and physical adventure one associates with genius.

To Rothenstein’s surprise, John found it hard in his early years to sell his work, and he was frequently very poor, changing his lodgings around London frequently as his money ran out.

For a while in the 1900s Rothenstein was effectively John’s dealer. He showed his drawings to more established artists such as John Singer Sargent, Charles Conder and Charles Wellington Furse. The latter, who had been a scholarship student at the Slade in the 1880s, selected a number to buy, though was taken aback when John asked £2 for each of his nudes. Rothenstein considered this price ‘modest … but Furse hadn’t expected a student to ask so much.’ In fact, and to his surprise, Rothenstein often initially found it hard to persuade collectors to buy any of John’s drawings. ‘It was not so much the indifference of the critics, of artists and collectors that angered me,’ he later recalled, ‘as their constant assertion that John couldn’t draw, that his work was “ugly.” These lovely things badly drawn and ugly! Were people blind? So John often needed his friends’ help’.

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In London sometime in late 1902 or early 1903 John met a beautiful, rather enigmatic young woman, Dorothy McNeill. He renamed her Dorelia, and she became his mistress and muse, and for a while she lived with John and Ida in a ménage à trois. This pencil drawing was made around the same time as several other three-quarter-length drawings, one of which was inscribed with the date: 1908.