Jailbreak, Rivalry and Plot!
The Union of the Crowns
The Coronation of King James VI of Scotland as King James I of England on the 25th July 1603 brought huge change to the British Isles. The new King and his associates now had greater power at their disposal and could implement new policies across these islands. To understand the impact this was to have on life in Ulster we need to go back in time...
East Ulster: Waste and Desolate
For centuries east Ulster had been different from the rest of the Province. The Norman Lord, John de Courcy, arrived in Ulster in 1177 and the Earldom of Ulster (essentially counties Antrim, Down and part of County Londonderry) was established around 1205 with its headquarters at Carrickfergus Castle. 100 years later a branch of the O’Neills advanced from mid Ulster into south Antrim and north Down and laid claim to the areas known as Lower (North) Clandeboye, Upper (South) Clandeboye and the Great Ardes.
Throughout the 1500s Ulster was embroiled in conflict. Queen Elizabeth I intended to tame the Province by sending armies across the water to fight the Gaelic chieftains of the time. Yet these wars weren’t as “black-and-white” as we might imagine today - for a variety of reasons some of those Gaelic chieftains became allies of the English.
Scorched Earth and Failed Settlements in Antrim & Down
In County Down, Sir Brian Phelim O’Neill had been knighted in 1568 for his service to the Crown against Shane O’Neill - yet in 1571 Elizabeth granted a sizeable amount of Sir Brian’s lands to Sir Thomas Smith, to settle the area with English gentlemen. Smith passed the opportunity on to his son of the same name, who shortly after was murdered by one of O’Neill’s supporters. The Thomas Smith settlement scheme had failed.
By 1572 it was clear to O’Neill that he had fallen out of favour and he adopted a “scorched earth” policy, burning the major buildings - Grey Abbey, Movilla Abbey, Newtownards Priory, Black Abbey, Holywood Priory and Comber Abbey - to prevent any incoming English army using them as garrisons. Subsequently, Elizabeth directed the Earl of Essex to sail to Ulster in 1573 with the lofty ambition of taking control of the lands from Belfast to Coleraine. Essex’s campaign was brutal - he captured Sir Brian O’Neill and had him, his family, and their attendants executed in 1574. After yet another brutal massacre - on 26th July 1575 on Rathlin Island - Elizabeth brought Essex back to England. Essex’s settlement plans had also failed.
Across the North Channel, King James VI of Scotland’s own efforts at settlement had also been unsuccesful. He had tried to establish settlements of Lowland Scots in Kintyre and Lewis in 1598 but, under attack from the local clans, many of these settlers fled across the North Channel to seek refuge in County Antrim.
So, for the 34 years between 1572 and the beginning of the Hamilton and Montgomery Settlement of 1606, the east of Ulster was depopulated, wasted and desolate.
Con O’Neill’s “Grand Debauch”
Sir Brian Phelim O’Neill’s lands eventually passed to his son Niall in 1575 and were described by Sir Henry Sydney in that year as “...all waste and desolate...”. Next they were passed on to Niall’s son, Con Niall MacBrian Fertagh O’Neill. In 1586, Con signed his entire estates over to the Queen, who then re-granted them to him in 1587 for his “faithful services and allegiance”. Con lived in the ancient Norman fortress Castle Reagh, also known as Castle Clannaboy, a massive structure 100 foot square, with turrets on the corners, dominating the Castlereagh Hills and overlooking what was then the small village of Belfast.
Around Christmas of 1602, Con held what has been described as “a grand debauch” at Castle Reagh, and when the wine ran out he sent his servants to Belfast for more. As they were returning they quarrelled with some of Sir Arthur Chichester’s troops and had the wine confiscated. Con was furious and sent them back to attack the English soldiers, some of whom were killed in the skirmish. Con was arrested, found guilty of “levying war against the Queen” and was imprisoned in Carrickfergus Castle. Although the conditions of his imprisonment were later relaxed, and he was occasionally allowed to walk through Carrickfergus with a guard, he was ultimately destined for execution - Chichester having generously offered to hang him without trial.
The Carrickfergus Jailbreak
When Elizabeth I died and James VI of Scotland became James I of England, many in Ulster saw this new era as an opportunity. James, the first Stuart on the English throne, angered Chichester by regranting the Gaelic lords of west Ulster their lands; he also lost no time in granting the MacDonnells of North Antrim the territory of the Glens and the Route. James Hamilton and Hugh Montgomery were aware of the opportunities in Ulster and had influence with the new Scottish King. Their time would soon come.
Another who saw an opportunity was Ellis O’Neill, Con’s wife. She made contact with Hugh Montgomery to see if he could use his influence with the new King to secure a Royal pardon for Con. If he succeeded, Hugh Montgomery’s reward was to be half of Con’s wasted lands in County Down. Montgomery agreed. Hugh Montgomery then entered into a plan with his Ayrshire neighbour, Thomas Montgomery of Blackstone, who is described in The Montgomery Manuscripts, the family records, as “...a discreet, sensible gentleman...”. Thomas was owner of a ship (or ‘sloop’) which traded between Scotland and Carrickfergus, and he was to implement a jailbreak plan very similar to one Hugh had used to escape from Holland a few years before.
In July, 1604, Thomas arrived in Carrickfergus and noted the identity of the Provost Marshall, who was also the jailer of the town. He then courted the Provost’s daughter, Annas Dobbin, in order to befriend her father. After an evening of well-planned drunken revelry in the Castle jail, Thomas got a rope to Con, possibly inside a hollowed-out cheese. Con escaped from his cell, used the rope to scale the castle wall, boarded the boat at the harbour below, and he and Montgomery fled to Scotland.
Arriving at the coastal town of Largs in Ayrshire, in the shadow of the Montgomery clan castle of Skelmorlie, they were met by a welcoming party led by Hugh’s brother-in-law, Patrick Montgomery, and they all travelled to the castle home of Hugh Montgomery, the Sixth Laird of Braidstane. The Montgomery Manuscripts say that Con “...was joyfully and courteously received by the Laird and his Lady with their nearest friends. He was kindly entertained and treated with a due deference to his birth and quality, and observed with great respect by the Laird’s children and servants...”
When the deal - a Royal pardon for O’Neill (with half of his lands going to Montgomery as a reward) - had been finalised at Braidstane, Con and Hugh travelled to London to win the King’s approval.
James Hamilton Intervenes
But little did O’Neill and Montgomery realise what was about to happen. In August 1604 James Hamilton discovered their plan.
Hamilton’s close associate, Sir James Fullerton, was an advisor to the King and had been granted Olderfleet Castle, near Larne, in September 1603. He convinced the King that O’Neill’s lands were much too large to be split between O’Neill and Montgomery alone and that it would be better if they were divided into three portions - with one third for James Hamilton. The King agreed to the new plan; after all, settlement had never worked before and he had nothing to lose by allowing Hamilton and Montgomery to invest their own finance and energy in the wasteland of east Ulster. When O’Neill and Montgomery arrived in London, the King presented them with the new scheme. Montgomery, realising what had happened and no doubt outraged, kept his composure and agreed to the revised plan.
On 31st April, 1605, the tripartite deal was agreed, but Hamilton’s actions seem to have united Montgomery and O’Neill for a time. Even though Con’s life had been spared and his Royal Pardon had been granted, and Hugh Montgomery had secured substantial lands in County Down, they had both lost out on their original deal. The Hamilton Manuscripts, the Hamilton family’s record of the settlement, state that O’Neill and Montgomery left London together, travelled back to Edinburgh and Braidstane, and then across to Ulster. Con returned to a hero’s welcome in Castle Reagh.
Before leaving London, Montgomery had renewed his relationships with some of the King’s advisors and in doing so created an opportunity for his brother George to benefit in some way. George had been made Dean of Norwich by Elizabeth I, and after her death he was appointed as King James’ personal chaplain. Six weeks later, as a direct result of Hugh’s influence on the Royal advisors, George Montgomery was made Bishop of Derry, Raphoe and Clogher on 13th June 1605 – the first Scottish bishop in Ireland. His portrait can be seen in Clogher Cathedral.
Hamilton, delighted by his own success, travelled to Dublin to present the outcome to Sir Arthur Chichester, “the most important Englishman in Ireland”. Chichester was aghast at the amount of land which had been granted by the Scottish King to his fellow countrymen Hamilton and Montgomery - perhaps because he wanted O’Neill’s lands for himself? If Chichester’s offer to Queen Elizabeth I (to hang O’Neill without a trial) had proceeded, he would have been in a prime position to confiscate all of O’Neill’s lands for himself. However the Queen was dead, and he had now been sidelined by the new King and his ambitious Scottish associates.
The relationship between Hamilton and Montgomery from this point on has been described as “mutual hatred”. These two Ayrshire neighbours, the minister’s son and the Laird’s son, who had grown up only five miles from each other, were now bitter rivals for supremacy in Ulster. Perhaps their rivalry and determination were factors in the unprecedented success of the settlement.
Three-way negotiations and the Gunpowder Plot
With the agreement signed, O’Neill, Hamilton and Montgomery began to trade and sell with each other in a complex set of transactions from June 1605 until May 1606. Half way through this period, back in London, one of the most famous events in world history took place - the Gunpowder Plot. Guy Fawkes and Hugh Montgomery had fought on opposing sides during the wars in Holland in the late 1500s; Fawkes was there from 1594 - 1604 and held a post of command in the Spanish army when they seized Calais in 1596, and Montgomery was Captain in a Scottish regiment under William I of Orange from circa 1582 - 1587.
On 5th November, 1605, Fawkes’ Gunpowder Plot was foiled and he was arrested. An emergency session of the King’s Privy Council was held early that morning, and Fawkes was brought in under arrest. When questioned by the King and the Privy Council (all of whom had originally been with James at his court in Scotland) as to how he could conspire such a hideous treason, Fawkes replied that his intentions were “...to blow the Scotsmen present back to Scotland...”.
Fawkes and the other conspirators were found guilty and were hung, drawn and quartered in London in January 1606. If the Gunpowder Plot had succeeded in killing the King and replacing him with a new monarch, the Hamilton & Montgomery Settlement may never have happened at all, and neither would James’ Plantation of Virginia in 1607, his Plantation of Ulster in 1610, and his Plantation of Nova Scotia in 1621. The course of modern history would have been radically altered.
The Settlement Begins
The trading continued through late 1605 and early 1606; Hamilton passed the Masserene area of Antrim over to Chichester, and acquired lands around Coleraine as well as the lucrative fishing rights to the River Bann, which infuriated Sir Randal MacDonnell of North Antrim. By April, 1606, Hamilton had sold off all his interests in County Antrim in order to concentrate on County Down.
King James’ “Union of the Crowns” policies continued, and on 12 April, 1606, he issued a proclamation announcing a new flag for his combined kingdoms.
With their new areas now assigned, Hamilton and Montgomery sent communications to Scotland to find willing tenants to farm the lands. Both men convinced their extended families to join them in the settlement scheme and, in May 1606, the first waves of settlers - farmers, stonemasons, builders, carpenters, textile workers, merchants and chaplains - sailed across the narrow channel of water and arrived in Ulster to form the backbone of the new Ulster-Scots community there.
(This article was originally published in The Ulster-Scot, March 2006)