The Chilcot of the Monmouth rebellion had at least two brothers. One Humphrey emigrated to MD in the late 1680's, the other was named James and the land records of MD have many transactions with his Humphrey and a JOhn's name on them...He was sent to Barbados as a slave for his part in the rebellion. This is all well documented in the Bloody Assizes trial records in England. Years ago, in a book in a library in Oregon entitled something to the effect of ship's registries of vessels sailing from Bristol 1600-1840, I found him listed as a 'person of quality' being transported in chains.
FYI the spelling of names were fluid in those days. I found my ancestor's christening records in old Saint Pauls Episcopal Church in Baltimore MD from 1739 with his name spelled Chilcote, while his two siblings were spelled Chilcoat. Land docs listed the same people spelled in a variety of ways.