In the introduction to their edited collection of early modern letters, Robert J. Clements and Lorna Levant include the almost warning note that, in reading the collection as a whole, the ‘servility imposed by patrons on their greatest Humanists, writers, artists, and musicians emerges in a disturbing dimension’. The comment forewarns the reader of the shock of seeing, for example, Wyatt’s groveling, self-serving letter to Henry VIII, apparently written immediately after Anne Boleyn’s execution. In the letter, Wyatt claims to have warned the King that Anne was ‘a bad woman’ whom the King should not marry. More shockingly, he then goes on to accuse Anne of likely sleeping with a groom, after leaving her bed mid-tryst with Wyatt himself, and claims that within the same week he ‘had [his] way with her, and, if your Majesty, when you banished me, had permitted me to speak, I should have told you what I now write’. The surprise of the letter, of course, depends entirely on the accepted content of Wyatt’s poetry. Setting aside the general modern exoneration of Anne Boleyn, how to reconcile this damning letter with the content of critical poetry like ‘Who lyst his welthe and eas Retayne’ or even the less political, but still far from servile, ‘Who so list to hounte’? The answer lies in a complex negotiation of simultaneously separating and relating political, personal, and poetic strategies as understood and used by the Henrician court poet.