Bailey, Thomas, son of Philip Bailey and Jane Phillips, baptized 31 March 1792, at St. Tysilio’s Church, Parish of Sellack, near the village of Peterstow and the town of Ross, Herefordshire, England.

Thomas Bailey’s military record is available at the National Archives in London (WO 97/361/26); from it we know that he served in Canada with the 39th (Dorsetshire) Regiment of Foot during the War of 1812 at the Battle of Plattsburgh, and then with the 15th Regiment of Foot during times of civil unrest from 1827-40.

Thomas Bailey was a carpenter by trade who attested for the 39th Regiment of Foot at Gosport on 30 November 1813.  He served toward the end of the Peninsular War as a Private from 21 December 1813 – 6 June 1814.  He saw his first action under the command of the Marquis of Wellington in the south of France on 13 February 1814 near the town of Garris, and subsequently at the battles of Orthez and Toulouse.

After the abdication of Napoleon Bonaparte, the 39th Regiment marched to Bordeaux and embarked for Canada on 8 June, arriving on 5 August 1814 at Quebec, from where they marched to Chambly on the Richelieu River.  On 2 September, the 39th Regiment and other corps marched toward the United States in order to cooperate with the naval force on Lake Champlain. The British troops occupied camps abandoned by the American forces on the river Chazy on 3 September.   The first battalion of the 39th Regiment remained at Chazy to maintain communications, while its light company moved forward to Plattsburgh, and two officers and sixty men from the 39th were detached to act as marines on board H.M.S. Confiance.

After the American naval victory at the Battle of Plattsburgh on 11 September 1814, the British forces retired to Chambly where they remained during the winter until 27 May 1815.  The Treaty of Ghent had concluded hostilities on 24 December 1814, and the 39th Regiment sailed from Quebec on 12 June 1815.  While the battalions were still at sea, Napoleon Bonaparte was finally defeated at the Battle of Waterloo.

Thomas Bailey is recorded as having joined the occupying force in France from 26 June 1815 – 30 November 1818, but the battalions only arrived at Portsmouth on 15 July and then sailed for Ostend on 18 July 1815.  After disembarking on 21 July, the 39th Regiment marched to Paris where they remained until the Army of Occupation was formed.   The battalions then marched on 27 December 1815 to take up various cantonments in Flanders, where Thomas Bailey was promoted to Corporal on 1 December 1816.

After the Army of Occupation was broken up, the 39th Regiment returned home from Calais on 30 October 1818, disembarking at Dover and then marching to Portsmouth.  The 39th Regiment embarked for Ireland on 17 December 1818 and was stationed in Castlebar for twenty months before Corporal Bailey was discharged in Dublin on 30 November 1820 because he had fulfilled his seven years of limited service.

Thomas Bailey married Helen Coglan of Ballymote, County Sligo, Ireland, and had a daughter, Jane Eugenia Bailey, on 1 December 1821 in that county.  On 14 October 1823, Thomas Bailey re-enlisted at Waterford, Ireland, as a Private with the 15th Regiment of Foot and was promoted to Corporal on 3 May 1825, and then to Sergeant on 6 November 1826.

A son, John Charles Bailey, was born at Portumna, Ireland, on 17 November 1826.  In May 1827, six service companies of the 15th Regiment sailed from the Cove of Cork and arrived at Quebec on 29 June and 6 July.  The companies proceeded up the Saint Lawrence River and remained ten months at Kingston, Upper Canada, before retiring in May and June to Montreal, until they were stationed at Quebec in August 1828.

A son, William Edward Bailey, was born at Quebec on 3 January 1829.  The Quebec Garrison Anglican Church records indicate the baptism of

“William, son of Thomas Bailey, Serjeant in H. M. 15th Regt. of Foot & of Ellen his wife.”

In 1830, a detachment of one hundred men was moved to the Isle aux Noix and Saint John’s on the Richelieu River.  On 3 May 1831, the 15th Regiment was moved to Montreal, where they were called to arms on 21 May 1832 to suppress a riot after a contested election.  Three supporters of Daniel Tracey of the Parti Patriote were killed, and for ordering the shooting Lt. Col. MacIntosh and Captain Temple of the 15th Regiment were arrested, but later absolved.

In June of 1832, the 15th Regiment lost 37 men to Asiatic cholera at its barracks in Montreal, but the epidemic subsided after they moved to an encampment on Saint Helen’s Island.  The regiment moved in 1833 to Kingston, from where it sent detachments to Brockville, in aid of the civil power, and to Cornwall, to help with construction of some public works.

A daughter, Helen Charlotte Bailey, was born at Kingston about 1834.  Later this year, the 15th Regiment moved to the newly incorporated city of Toronto, Upper Canada, and sent detachments to outposts at Fort George, Amherstburg, and Penetanguishene.  On 13 September 1835, Thomas Bailey was promoted to Colour Serjeant.

A son, Thomas James Bailey, was born at Toronto in 1837.  During this year, the 15th Regiment was withdrawn to Quebec to serve in the suppression of the Lower Canada Rebellion.  In May 1838, the 15th Regiment proceeded to Chambly, then in November, under command by Lt. Col. Charles Wellesley, to Saint John’s, and began a campaign to disarm rebel insurgents in the neighborhood of Napierville before the corps returned to Chambly.

In December, the headquarters moved again to Saint John’s and then to the Isle aux Noix with two companies posted at Napierville until they were withdrawn to Montreal in 1839.

Thomas Bailey was discharged at Saint Helen’s Island, Montreal, on 31 May 1840, due to chronic rheumatism and dyspepsia, with conduct and character deemed “most excellent.”

The service companies of the 15th Regiment returned to England on 25 June 1840.  The next month the Act of Union created Canada West and East from Upper and Lower Canada. On 9 September 1840, Thomas Bailey was awarded his pension for service of 23 years 231 days, and he received it at his home in Toronto until his death from paralysis on 2 August 1862.  His son William Edward died of inflammation of the lungs on 14 July 1854 and was buried at Saint James Anglican Cemetery in Toronto.  The gravestone inscription

“Sacred to the Memory of William Edward, second son of Thomas and Helen Bailey, born at Quebec January 3rd, 1829, died at Toronto July 14th, 1854, We Will Meet Again,”

marks the burial place (Section F, lots 5 and 7) of all the men in the Bailey family.  Although the grave marker identifies only the burial of one son, the Saint James Cemetery records indicate that Thomas Bailey and other family members are buried alongside him at the same site.

Helen Bailey and the two daughters are buried in the O’Keefe family plot at Saint Michael’s Roman Catholic Cemetery in Toronto.  The gravestone for Helen Bailey begins:

“Sacred to the memory of Helen, relict of Thomas Bailey.”

The 1861 census of Toronto confirms that the Bailey family members who were residing in Toronto at that time were Protestant men and Catholic women.  The family home, constructed for Thomas Bailey in 1856, was located at the corner of John and Wellington streets; prior to that time, Toronto directories indicate Thomas Bailey lived at the corner of Jarvis and Gerrard streets.

In 1844, Jane Eugenia Bailey married David Stark Layton, who was appointed surgeon to the Indian Department at Manitowaning, Manitoulin Island, and was signatory to the 1862 treaty with some of the island’s First Nations people.

John Charles Bailey and Thomas James Bailey became civil engineers, and both independently worked to build numerous roads and railways in Canada and parts of the United States.

In 1862, Helen Charlotte Bailey married Eugene O’Keefe, who established the O’Keefe Brewery in Toronto and financed many philanthropic projects including the construction of Saint Augustine’s Seminary in Toronto.

An early settler in Toronto, Thomas Bailey defended Canada from invasion and insurgency, and his family pioneered the exploration and economic expansion of Canada into Confederation.  Numerous descendants of Thomas Bailey served Canada in major conflicts during the twentieth century.