In 1589 Connill was despatched by the Lord Deputy of Ireland William FitzWilliam with a force of Irish Army troops to the recently established County Donegal.
[1] This was part of the Tudor reform programme in Ireland which sought to replace the Irish clan chiefs with English Sheriffs.
Connill allegedly secured the position by bribing Fitzwilliam with two gold chains that had been recovered from the wreck of the Spanish Armada in Ireland.
Connill backed one of the candidates, Sir Donnell O'Donnell, High Sheriff of Donegal, until his defeat and death by forces loyal to his father at the Battle of Doire Leathan in September 1590.
[6] A criticism of Connill and Willis was that their conduct was similar to the activities of the Irish clan warfare they were officially supposed to be preventing.