The Middle English dream-vision Wynnere and Wastoure (modernized as Winner and Waster) has perennially been of acute interest for literary critics. Insofar as it has been seen as one of the earliest works of late medieval alliterative poetry, this poem has featured prominently in many literary-historical models, and its lively debate about post-plague economics has appealed to literary critics and historians alike.

In “Winner and Waster” and Its Contexts: Chivalry, Law and Economics in Fourteenth-Century England, W. Mark Ormrod offers a valuable contribution to the study of this poem. With a goal of critiquing early arguments that the poem dates from 1352–53, Ormrod seeks to show both the rationale for, and the benefits of, placing the work's composition well into the 1360s. Featuring sustained analysis of both the poem and its political and economic social context, while also including a modernized and insightfully annotated text of the poem, Ormrod's volume will be valued by both literary critics and historians of late medieval Britain.

In the introduction, Ormrod demonstrates how deeply Israel Gollancz's 1920 framing of Wynnere and Wastoure as a highly topical poem likely composed in 1352 or 1353 has influenced scholarship, even after critics such as Stephanie Trigg revealed the “reductive” nature of Gollancz's editorial historicization (9). After announcing his intention to move away from such a narrow dating of the poem, Ormrod clarifies that his reassignment of the poem well into the 1360s allows the possibility of “wider meanings of the poem” (13) missed due to the problematic influence of Gollancz's edition.

In the first chapter, focused on “chivalry and internationalism” (15), Ormrod spends considerable time analyzing the poem's opening to make a case for the poem at the very least post-dating 1358. While recognizing that his argument that the poem's opening encounter may have drawn “inspiration” (25) from the 1358 Order of the Garter feast held at Windsor could be seen as no less “reductive” (24) than Gollancz's reading, Ormrod amasses considerable thought-provoking evidence about the unusually public nature of this event very possibly having influenced the poet's vision.

In the second chapter, Ormrod compellingly critiques some critics’ insistence on placing Wynnere and Wastoure within the immediate wake of the 1352 Statute of Treasons, while also making a strong case for seeing the poem as a debate within members of “landed society” (39). Ormrod convincingly undermines efforts to see the poem directly echoing the Statute of Treasons, and instead places the conflict between the allegorical figures of Wynnere and Wastoure within the broader concerns of law throughout the 1350s and 1360s. Similarly, Ormrod demonstrates how the poem's “past tense” (48) references to Chief Justice William Shareshull could refer to legal proceedings stretching out at least until his term ended in 1361, if not well into the era of his successors. Ormrod establishes that Wynnere and Wastoure being “foreign-born” is in no way in conflict with their being “servants” (49) of Edward III, whose court had significant international roots. Ormrod also persuasively treats the dispute between the poem's allegorical competitors as governed by a principle of royal “arbitration” (57) rather than a trial by force. By analyzing royal “arbitration” as a process oriented towards “compromise” (56), Ormrod helps us better understand the dream-vision's trajectory towards an adjudication in which each member of the process receives judgment and compensation, rather than one being declared the winner (no pun intended).

In the third chapter, Ormrod is especially successful in steering the poem's dating into the 1360s, while also convincing in its presentation of Wynnere and Wastoure as conducting an internal debate within “Landed Society” (61), rather than a conflict between commercial and landed interests. Offering an excellent survey of recent criticism of the “middle class” (62) appearing suddenly in the fourteenth century, Ormrod argues against Wynnere being seen as a “merchant” (64) embodying the nouveau riche. After surveying the turbulent economic situation throughout the 1350s, Ormrod suggests that the poet reveals a “conservatism” (70) derived from a conviction that landed powers could contribute significantly to negotiating the social and economic chaos of the post-plague era. Ormrod shows that the poet could easily be placed later than 1353, examining records that reveal various efforts to deal with economic instability throughout the later 1350s and early 1360s. Ormrod is especially convincing in linking the poem's discussion of concerns about clothing and class to the sumptuary legislation of 1363.

In the fourth chapter, Ormrod explores the considerable interest among scholars in “Edward III's household management and war finances” (83). Building on both his critique of arguments seeing Wynnere as representative of the “bourgeois elite” (84) and his suggestion that the poem is best seen as post-dating the era of English peace (with France, at least) inaugurated in 1360, Ormrod suggests that the poem's debate is focused more largely on broader issues of government than merely on wartime spending (though Ormrod allows that the poem is dealing with concerns about a sudden return of war concerns throughout the 1360s).

In the fifth chapter, Ormrod situates Wynnere and Wastoure within the broader context of both complaint poetry and alliterative verse, while also offering some intriguing speculation that the poem's author may have been a person from “one of the great households operating in England during the 1350 s and 1360s” (122) who was keenly interested in providing “articulation of current political topics of debate” for a courtly audience (128).

In a final, brief chapter, Ormrod reflects on the way that the poem's topicality may have “limited its appeal” (133). Ormrod also offers an intriguing suggestion that the “severe turbulence” (135) of the Northern economy in the 1430s and 1440 may explain Robert Thornton's having been drawn to this work: this editor may have been especially sympathetic to another member of the “gentry” (134) dealing with a socioeconomically disrupted realm.