This poem never mentions Charles Stewart Parnell or Hugh Lane by name, although these two men were both regular topics of Yeats's work in general. However, "To a Shade" is deeply engaged with these men's lives and, to an even greater extent, with their downfalls. Yeats uses the poem as a space to express his admiration for Parnell and Lane, and to express anger and disappointment at the circumstances that thwarted them. Through apostrophe, the speaker directly addresses Parnell's ghostly form, noting that he was harmed by widespread cruelty and myopia from the people he intended to help. The speaker then describes another man, implied to be Lane, who is harmed by the same forces in the same city. Through these descriptions, Yeats parallels the two figures, describing them as Irishmen who deserve to be seen as heroic, despite ingratitude from Dubliners.
Parnell was an Irish nationalist of the late nineteenth century. He was elected to the Irish parliament in 1875, while Yeats himself was still a child. He joined parliament as a member of the Home Rule Party, which supported Irish sovereignty. Three years later, he became the chairman of his party, and in this leadership position he expanded the party's power in parliament immensely and moved its policies in a more radical direction. Parnell also led the Land League, which advocated for the rights of tenant farmers. In 1881, Parnell was arrested as part of a crackdown on nationalist activism, specifically because of his protests on behalf of the Land League, though he was released on the condition that he use his influence to calm violent backlash in Ireland. In 1887, Parnell risked a political downfall when he was accused of involvement in the Phoenix Park Murders, wherein several politicians opposed to home rule were killed. Several letters from Parnell, apparently in support of the murders, were produced—however, these were proven to be forged, and Parnell was able to retain and increase his power until 1889. That year, his political ally and fellow parliamentarian William O'Shea filed for divorce, revealing that his wife and Parnell had carried on a years-long affair. The scandal ended Parnell's leadership period, in large part because of the protests of the clergy. He died powerless in his forties, though he remained widely beloved.
Hugh Lane, meanwhile, worked not in politics but in art. Lane was of Irish descent but raised abroad, and became a successful art dealer in London. Yet even from England, Lane began delving into Irish culture and politics, developing an affinity for the Celtic Revival movement, in which Yeats himself was a major player. He developed a goal of opening a municipal gallery in Dublin, which would, in Lane's vision, specialize entirely in modern art. He worked tirelessly to display and promote modern art around Dublin in the hope of garnering funding and support for his gallery. Though he commissioned an architect and obtained a temporary space for the municipal gallery, he struggled to find a permanent home for his project. This was partially due to a lack of support in Dublin, where the gallery was viewed by some as a frivolous expense during a time of limited funds. While waiting for the gallery to be founded, Lane, who expressed resentment over Dubliners' lack of enthusiasm for the gallery, loaned a number of paintings to London's National Gallery. He also left these paintings to London's National Gallery in his will. Lane died aboard the ship Lusitania, which sank in 1915, after which a codicil to his will was found backtracking on his previous statement and instead requesting that the paintings be displayed in Dublin. However, the codicil was technically not legally binding, since it had no witness. The paintings, therefore, remained in London, but with controversy hanging over them.
Yeats was a vocal supporter of both Parnell and Lane in his poetry. Among Yeats's more famous tributes to Parnell, in addition to "To A Shade," are the works "Come Gather Round Me, Parnellites" and "Parnell's Funeral," as well as the short, striking couplet "Parnell." Much of his writing, furthermore, does not refer to Parnell directly but nonetheless references Irish political life and activism in the aftermath of Parnell's leadership. Meanwhile, Yeats was already prominent during Lane's campaign for the municipal gallery, and the two were acquainted with one another. In addition to his role in the Irish revival that inspired Lane, Yeats wrote a series of poems advocating for the gallery and decrying its detractors.
Through the device of the shade, returning from the dead to see a modernized Dublin, Yeats allows Parnell and Lane to encounter one another in this work. This allows him to draw links between them, despite their differences—Parnell's popularity and Lane's general lack of it, Parnell's political work and Lane's art-world dealings, Parnell's prominence in the late nineteenth century and Lane's in the early twentieth. Parnell and Lane, in this telling, are unified by a selfless and visionary desire to make Ireland a better place to live, liberating it politically and elevating it culturally. Both are thwarted by personal vendettas and parochialism, though, Yeats suggests, they may eventually be fully redeemed posthumously.