Although prohibitions or penalties, related to townsmen who sought to avoid their civic duties by bearing office, were not uncommon, at Reading there may have been particular reasons why some burgesses were reluctant to take on the challenge in the fifteenth century. The borough had been engaged, and would be into the next century, in a periodic battle with its lord, the abbot of Reading, over control of local government.

Reading had been a settlement of some importance since the ninth century, and was recognized as a royal borough in Domesday. But Henry I in 1125 granted the borough, as an endowment, to the abbey he had founded a few years earlier; its abbot thereafter had control over commercial affairs in the town, appointment of the borough executive, licencing of retail activities, and administration of justice, among other powers. The townsmen relied on their merchant gild as a mechanism for organization and self-determination, and the abbot tried to suppress this source of opposition. Their struggle with the abbot to wrest away from him control of such matters was protracted and often violent; in 1253, for example, they were accused of ambushing the abbot's bailiffs and obstructing them from performing their duties, while in the following year it was the abbot's servants who were in hot water for killing obstructive townsmen. The contest erupted periodically at points over the next two centuries.

Around the opening of the fourteenth century, the burgesses had created a mayoralty, the first known officeholder dating to 1302 and, as seems not to have been uncommon when this new office was introduced into towns, apparently holding office for several years. The mayor was essentially the warden, or master, of the Merchant Gild wearing another hat, and the first known mayor was said to have been elected by community assent. This may, or may not, indicate that the abbot's right of annual appointment of the head of the gild, established by a settlement between gild and abbot in 1254, was in abeyance. The abbey's hold over the town may have been waning at this time, for it had financial problems, and in 1302 the burgesses were also resisting the abbot's right (again confirmed in 1254) to impose taxations on the town. In that scenario, the mayoralty could have been created as a direct challenge, as appears to have been the case in some other towns where the burgesses were battling for independence from an overlord. The abbot does not seem to have ever formally recognised the mayoralty per se, preferring the term "warden" for the gild officer and in the fifteenth century heaping scorn on the mayoralty.

In 1351, during one of the periodic legal battles, the community sought freedom from the abbot's overlordship by claiming to have long been a royal borough, and to have been electing a mayor as head of its Merchant Gild since before 1125 (a claim we have no reason to take seriously – the earliest reference we have to the gildhall is ca. 1204-15, although it was no novelty at that date). Control over election of the town constables was another of the key issues at that time. That issue came to the fore again in 1417, with some success for the burgesses, who then proceeded to assert themselves by building a new gildhall. A more combative abbot, Thomas Henley, came into office in 1430, and was able to hold the townsmen in check.

After that abbot's death in 1446, the battle was renewed and continued into the sixteenth century. It was important for those leading the opposition to the abbot to protect their interests and to keep their fellow burgesses loyal to the cause, motivating or disciplining them. Some burgesses at least must have preferred to steer clear of trouble, while possibly among the unenfranchised residents there was some support for the lord of the town against a government over which they had no influence, as was the case at Lynn. We cannot know precisely whether the causes for criticizing the mayor and his government in 1453-54 were political or personal, but they could not be glossed over. The battle with the abbot and perhaps with factions internal to the borough called for stout-hearted men to accept the burden of office. The number of townsmen qualified for office was small; Henrietta Haynes has reckoned that there were fewer than 50 members of the gild around this period ["Reading Borough to 1638", Victoria History of the County of Berkshire, vol.3, 1923]. This difficulty may have been compounded by reluctance among some of the members to take on repeatedly the role of mayor, in those challenging times. The 1474 specification limiting re-election was subsequently annulled – both the enactment and the annulment may reflect difficulty in finding men willing to serve. A small number of names were dominating the nominations year after year.

We do not have a satisfactorily clear picture of the contest, but fortunes on either side seem to have waxed and waned. In the 1490s the abbot refused to appoint any town nominee to the mayoralty. At the election just before Michaelmas 1492, three nominees were put forward, but no-one was confirmed in the mayoralty by the abbot, and the same impasse seems to have continued for the following three or four years. In 1497, the election being delayed until late October, from the three nominees it was the burgesses who were said to choose, by "free election", their leader for the next year; this officer was now referred to as master of the gild, the mayoralty under that title having been abandoned, perhaps as a concession to the abbot if the title "mayor" were seen as an irritant, or perhaps because past changes in title of the gild leader had created legal openings for the abbot's counsel in challenging gild efforts to assert independence. The same occurred the following year, when the burgesses were said to have unanimously agreed that they would obey the master in all things, just as they had previously obeyed the mayor. But after peace was restored between abbot and gild in 1499, the title mayor quickly crept back in. By 1511 the quarrel had exhausted itself, and the abbot had once more been conceded the final election from the three nominees, as well as exercising traditional jurisdiction in the borough. The burgesses had to wait for the Dissolution before they could obtain self-government.