The emphasis in this grant is not on the delegation of authority or jurisdiction so much as the leasing of revenues in return for an annual lump sum payment. The collection of these revenues entailed jurisdiction. Revenues and jurisdiction were two sides of the same coin. A community sought jurisdiction in order to have more direct control over matters that affected its self-interests, well-being, and prosperity. As towns grew, their industry and commerce flourished, and immigrants were attracted, jurisdiction offered the prospect of increased revenues. If the community could acquire the jurisdiction-revenues for a fixed annual payment, it could capitalize on the growing profit margin, channeling some of those profits into community improvements and strengthened self-government.

After the death of Simon de Montfort, earl of Leicester, at Evesham (1265), the king gave the lordship of Leicester to one of his sons, and it thereby became part of the earldom of Lancaster. As they had in the thirteenth century (see Origins of some customs at Leicester), the burgesses of the fourteenth century town continued to chip away at their obligations to their seigneur, negotiating on matters such as pasture rights, customary payments, revenues due the lord from the fair (stallage, fair court fines), and various market tolls. These negotiations met with mixed success.

New negotiations with John of Gaunt were on a more ambitious scale, with the burgesses seeking to farm a group of revenues and jurisdictions from the duke. This was hardly ambitious on the scale of general urban development, however, as most towns of comparable size and importance had already obtained that degree of self-government through fee farm grants, typically including the right to elect administrative officers. Because of the restricted nature of his lordship over Leicester, however, John of Gaunt was unable (even had he been willing) to give his burgesses of Leicester a grant of perpetual fee farm. Instead the burgesses acquired, during a ten-year lease, direct control over the borough courts and market, and the revenues issuing from them. This included the right to elect the town bailiffs who were responsible for administration of the same, although the duke made it clear that the bailiffs remained essentially answerable to him, by clothing them in his household uniform.

Whether this arrangement was actually to the fiscal advantage of the town is open to question. At this period the mayoral government, to cover its operating expenses, was relying on a small but growing number of rents, a very modest profit from fines for infringements of borough ordinances or the assize of bread, and (primarily) on fees for membership in the merchant gild, supplemented by the occasional local tax imposed when need required, which was often. The mayor was the accountant; but, apparently as a result of the 1375 grant, chamberlains took over this responsibility – whether they were new officers, or the gild's financial officers in an expanded role is more difficult to say – and the mayor focused on accounting for the revenues that had to address the annual farm.

The only such account for the farm to have survived to us is that of 1377/78. Already it refers to substantial arrears due from the very first term under the lease; perhaps the burgesses had not yet been able to take advantage of prospective new revenues from building new shops, for in 1378/79 the mayor and portmanmoot ordered the bailiffs to do their best in finding tenants for the shops. The account also shows that the burgesses had already broken the terms of the lease, with regard to escheats: they had taken revenues from properties that ought to have escheated, and now owed over £10 to the duke, who had presumably learned what was going on and insisted on his rights – but there were perhaps mitigating circumstances (lack of new rents?), as the duke subsequently forgave them the full amount. Nonetheless, at the end of this account they continued to owe the duke the original arrears, although were able to pay the full £80 for 1377/78. In the years that followed, there seem to have been further adjustments in the borough's accounting system, but precisely what is hidden by a disappearance of financial records from this period.

It does not appear that the burgesses obtained a renewal of the farm in 1385. We know only that in 1404 they obtained from his son, as Henry IV, a 20-year lease on slightly more restrictive terms and for £90 a year. In 1423 Henry V's widow renewed the lease for ten more years, at the original £80. Other surviving evidence suggests that in the 1390s and 1440s there was no lease in effect.