Looking for opportunity for advancement, Montgomery came into contact with the wife of Con O'Neill, a landowner in Ulster, who was imprisoned at Carrickfergus Castle for instigating rebellion against the Queen. Montgomery and Ellis O'Neill (the wife) made a deal that the O'Neills would give half of their land to him if he could free Con and secure for him a royal pardon. Montgomery sent a relative to Ireland to lead the jailbreak, which was successful. At this point, James Hamilton interfered with the negotiations with the King, securing for himself a share of the land in question with the resultant shares being one-third each for Hamilton, Montgomery and O'Neill, who gained pardon. (Montgomery also secured for his brother George, his staunchest political ally, title as Bishop of Derry and Raphoe.) Montgomery and Hamilton recruited Scots of many families and trades to populate their settlement. In May 1606 the first wave of settlers arrived. Montgomery settled at Newtownards and soon established a trade route between Donaghadee in Ireland and Portpatrick in Scotland. In 1613, Montgomery, along with Hamilton, represented the settlement to the Irish House of Commons. At Donaghadee he built a large stone quay to accommodate vessels ferrying between Scotland and Ireland from 1616 onwards. On 3 May 1622, Montgomery was made Viscount Montgomery. Montgomery may have been given a Scottish State funeral in Newtownards on 8 September 1636. Montgomery’s coat of arms (a fleur de lis and hand above a crescent) survives today as part of the crest of Ards Borough Council, and in the school badge for Regent House Grammar School, Newtownards. His sons included: