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This essay picks up a cold trail in the search for the author of Piers Plowman: the name ‘William called Long Will’, without surname, that Michael Bennett discovered among the names of elite associates of Sir John Holland, half-brother to Richard II, indicted for aiding (or not preventing) Holland’s killing of Sir Ralph Stafford in 1385, can be further traced in plea rolls of the case before the King’s Bench. Bennett argued that this eccentric name not only parallels the poet’s only explicit self-identification but identifies the poet at a late point of his life. The newly discovered and edited records serve as occasion for refuting recent objections to Bennett’s claim and for investigating further the figures involved, revealing new reasons to think the poet had a relationship to Holland and others in this group by 1385. Holland, for example, was a major landlord in London’s Cornhill area, where the narrator situates himself in the C text; those properties were managed by another of the figures indicted. Moreover, some novel legal stratagems for land transfers used earlier by the Essex and Suffolk priest, William Rokele, currently the most promising candidate for authorship but whose traces vanish after 1369, were adopted by Holland and his agent soon after the events of 1385. Both the legal and poetic evidence is consistent with the theory that the poet went by varying surnames in earlier periods and for different purposes. This essay thus extends the known documentation of the events of 1385 while adding prosopographical information, comparative examples, and discussion of the poem’s focus on adopting or relinquishing surnames to confirm the possibility that this William called Long Will could have been the poet of Piers Plowman, and to articulate some of the implications for his career and the poem.