Career
He took his surname from the parish of Holywood (also spelt Hollywood), near Balbriggan, County Dublin. He was a Remembrancer of the Court of Exchequer (Ireland) in 1356 and in 1359 was charged with the defence of Leinster. He was appointed Chief Baron in 1363, superseded the following year, but reappointed in 1367.
In 1376 he finally stepped down as Chief Baron.
In 1361 he received a royal pardon for purchasing land without royal permission, which as a rule was strictly forbidden for Crown officials. This may refer to his purchase of Artane Castle, of which he was the first recorded owner and which remained in his family for several centuries (unlike most judges of the time he was not in holy orders).
In 1367 he sat on a powerful commission to determine whether or not the manor of Rathkeale was Crown land, but it apparently never reported, since an identical inquiry was launched in 1374. Ball notes that while many of his fellow judges exposed themselves to the dangers of going on on assize, Holywood preferred the security of Dublin.
Christopher became a distinguished soldier, and in 1413 was appointed one of the commanders of the King"s army in Ireland.