It is said the citizens readily admitted him within the walls of Dublin. His chief attack was from Ship Street, but the Constable of the castle getting the thatched houses there set on fire, the besiegers fell back into Thomas Street.
Lord Offaly having been obliged to commence hostilities against Ossary, the siege was not carried on with much heart. Many of the arrows sent into the castle were headless, and others bore letters saying some of the besiegers were really in sympathy with the King’s party.
Upon the rumour of help from England, the citizens closed the gates and made prisoners of the attackers.
Lord Thomas hurried back, and at once laid siege to the city itself, but his force was too small to have any effect.
As he had seized the Dublin children who had been sent to outlying villages on account of the plague, the citizens agreed to liberate his party if the little ones were restored. This was done, and shortly afterwards aid from England quelled the rebellion.
Several exciting escapes have been made by prisoners from the castle. In 1587 Hugh O’Donnell was confined in one of the gate towers for three years, when he and a companion managed to escape on to the drawbridge by a rope. He was, however, treacherously sent back to Dublin by O’Toole of Castlekevin, upon whose hospitality he had thrown himself. At this time a partly dry and partly wet moat surrounded Dublin Castle, and O’Donnell was now imprisoned in the Wardrobe Tower round which the Poddle flowed. He, however, escaped again the next year through the water, and, arriving after much hardship at Glenmalure, eventually reached the North in safety.
In 1697 Lord Delvin was imprisoned in one of the gate towers for taking part in a conspiracy against the King. The Lord Deputy hearing that he meditated escape, desired Tristram Ecclesten, Constable of the Castle, to remove his prisoner from the upper to a lower storey. Not only did Ecclesten neglect to do this, but he allowed Lord Delvin to have visitors, who managed to convey him a rope, by which he escaped. Next year he surrendered himself and was pardoned.
Law Courts and Parliaments have at different times been held in the castle.
In 1689 King James made a State entry, and stayed one night there after the battle of the Boyne.
In 1783 St. Patrick’s Hall was built. In 1784 the Viceregal Lodge was bought, and since then the State apartments of the castle have only been used during the Dublin season.