 In 1766 he became a leader in the tenant uprising known as the Dutchess County Anti-Rent War, a revolt against the quit-rents left over from the feudal system left in place by Dutch colonists in the region which made it hard for tenants to eventually purchase their land.It was quelled by troops called in from Poughkeepsie.Prendergast was tried, convicted and sentenced to hang for treason.