Existing evidence pertaining to Ireland’s Nine Years’ War (1594–1603) strongly lends itself to the impression that the majority of Old English Palesmen, at least those of higher social status, chose to support the English crown during this conflict rather than their co-religionist Gaelic Irish countrymen. Loyalties, however, were anything but straightforward and could depend on any number of cultural values, social concerns, and economic incentives. Nevertheless, James Fitzpiers Fitzgerald, a ‘Bastard Geraldine’ who served as sheriff of Kildare, seemed to have been driven by a genuine sense of duty to the English crown and establishment. With the outbreak of hostilities in the 1590s, Fitzpiers proved to be a devout crown servitor, risking life and limb to confront the English queen’s Irish enemies. But, in late 1598 he suddenly, and somewhat inexplicably, threw his lot in with the Irish confederacy, defying the government he had once championed. During the ensuing investigation, the Dublin administration accumulated much damning evidence against Fitzpiers, including a patriotic plea from rebel leader Hugh O’Neill which urged Fitzpiers to defend his Irish homeland from the oppressions of English Protestant rule. Yet, at the very same time, a counter case was made by Fitzpiers’s controversial English friend, Captain Thomas Lee, which argued that Fitzpiers’s actions were more loyal than anyone could have imagined. Through an examination of Fitzpiers’s perplexing case, this paper will explore the complicated nature of allegiances in 1590s Ireland and how loyalties were not always what they seemed.