The aspect of the political economy that has attracted the most enduring attention of scholars working on the social meanings of W&W relates to Edward III's household management and war finances. The idea that the poem provides a commentary on the financing of the Hundred Years War goes back to a short article by Gardiner Stillwell published in 1941. Stillwell argued that Wynnere's opening speech represented Wastoure as the personification of the state, unjustly extracting hard-earned resources from its subjects to finance its own proud ambitions:

Convinced by Gollancz's dating of the poem to 1352–3, Stillwell compared this passage to the formal record on the parliament roll of 1352 of the grant made by the Commons to the king of a three-year fifteenth and tenth (the standard form of taxation that had been in place in England since 1334). This schedule included a statement that ‘le commune people de la terre fut molt empovery, sibien par la pestilence mortiele qe nadgairs avient en la terre come par autres soviers taxes, taillages et plusours autres chevances qe les ont survenuz’ (‘the common people of the land [are] greatly impov¬erished, as much by the deadly pestilence which they recently suffered in the land as by the frequent taxes, tallages and many other levies which have befallen them’). This was apparently enough to convince Stillwell that the passage in W&W just cited was a veiled allusion to public discontent with the unreasonable economic burden that the king's wars placed on the coun¬try at precisely the moment that the Commons made their tax grant in 1352.