James Baird Thorneycroft Montgomerie, or Montgomery as it was sometime and wrongly spelt, was born in 1894 officially in Galston, but actually by Darvel and Newmilns. His parents were from Ayrshire, his mother from Galston, his father from Muirkirk, a gamekeeper cum Police Constable, who volunteered for the army the evidence for which is that he was in the Imperial Yeomanry and killed whilst fighting South Africa in 1901, a casualty of the two years of the Boer War. At the time the family had moved to Portsmouth but soon returned North, settling in Darvel, where in 1911 Jimmy was a sixteen year-old Grocer's Assistant. 

However, soon after it seems he left for Canada, aged perhaps seventeen, taking his already-honed footballing skills to Montreal. There he played for Montreal Highlanders and in 1915, so aged twenty-one, he was part of the Montreal All-Stars team that lost in the inter-city clash to the Toronto All-Stars. It was also the year, in which he signed up for the Canadian Army, where he was awarded the Military Medal and the Military Cross with bar, rising from the ranks eventually to be commissioned.

It must also meant service in Europe during the The Great War years and time spent in Scotland, indeed in Darvel and its neighbouring village, Newmilns. Certainly, when he married in 1918 he left from his mother's house in Darvel and his bride, Janet Semple, from her family's home on Main St., Newmilns. However, the newly-weds were clearly intent on making their lives back in Canada, indeed Montreal. Being in the military perhaps James had no choice. So in 1919 they crossed the Atlantic, their first two children, two boys born that year and the next, recorded as both Scottish and Canadian. 

Once back in Montreal Jimmy,  now in his mid-twenties and working as aa accounts clerk but still involved with the military, returned to football. He played for the Grenadier Guards, in 1922 winning the Quebec Cup, and in 1924, after a return to the home-country already as Captain Montgomerie and already thirty, he turned professional, joining the then major American team, the New Bedford Whalers, based in the the Southern Massachusetts town of the same name. He was signed as a centre-half, but it would have been as what he knew from his origins, a Scottish, attacking , goal-scoring centre-half, the pivot for seven seasons of a team replete with Scots and playing the Scottish game. With it he would in 1926 win the Lewis Cup and, be runners-up in 1929 and finish in second place of twelve in the American Soccer League in 1926 and 1930, on both occasions losing out to nearest rivals Fall River F.C..