By the death of Henry Tudor, complaints against Kildare had evolved in terms of detail, polemic import and sophistication. This literature of decay, long a feature of political commentary on the lordship, was invigorated by protégés of Wolsey. Far more so than his predecessors, the Cardinal cultivated patronage in Ireland and apparently sought, or was at least receptive to such petitions. Most notable in this respect were prelates John Kite, Hugh Inge and William Rokeby. In contrast to the impression given by the archive, criticism of Kildareinduced decay did not originate under Henry VIII much less in the year 1515 as implied in the printed State Papers. A number of Henrician treatises have traditionally been associated with this annus mirabilis that has been seen to mark the emergence of humanist reform rhetoric in the lordship. The summer months of 1515, between Sir William Darcy's indictment of Kildare at Court and the return of Gearóid Óg with favour, seems to have signalled that conquest lobbyists were regarded, in the memorable quip of one leading historian, as the ‘pratlings of Polonius’. The volume and vigour of anti-Kildare reform rhetoric from the late 1520s has tended to divert the attention of historians from the preceding developments and the earliest of these documents. The ‘poletique’ and at times watchful approach of Henry Tudor came to enable diplomatic circles cultivated by Fox but more so Wolsey which offered channels of communication for voices opposed to an ascendant ruling magnate. In 1506, when Henry VII ‘entendythe god willinge to make a viage personall in his most noble personn’, consideration was likely given to the disruption of Geraldine governance and patronage of office. The ‘warr…continued by Ebren [O’Brien] of the wilde irishe’ apparently prompted the king's intention to campaign with a force of 6000 men but the precise motive remains unclear.

As early as the 1480s, Ormond and the city of Waterford, particularly the Wise family, provided the crown with what was considered valuable information regarding circumstances in the lordship. Chief baron of the exchequer John Wyse had been charged to account for the ‘maner of this lande’ and he has been credited with the military ‘Discruption of the power of Irishmen’.