This gentleman is of Irish extraction, but was born near Niagara Falls, on the 18th of May, 1806. He was chiefly educated at the Niagara Grammar School, there being no colleges or universities in the country at that early day. He commenced the study of the law with the late John Breakenridge, in the old town of Niagara, then the commercial rival of Little York (now Toronto), and at an early period the capital of Upper Canada. On the death of Mr. Breakenridge, in 1828, Mr. O’Reilly went to Toronto, and completed his legal education in the office of the late Messrs. Baldwin and Son; and was called to the Bar in June, 1830. He is consequently now the oldest practising barrister in Ontario. He very soon acquired a very extensive practice, and became the leading counsel on the Niagara and London circuits. He was always a staunch Loyalist; and as one of the “men of Gore” (as they were then called), he took part in the battle of Vinegar Hill, near Toronto, on the 7th of December, 1837; and at the trial in the following spring, of the 106 prisoners confined in the Hamilton gaol, charged with high treason, Mr. O’Reilly, unaided and alone, defended the whole of them. That was a very exciting period in the history of Upper Canada. The prisoners were tried before that excellent Judge, the late Chief Justice Macaulay, sitting under a special commission; and the late Chief Justice Draper, and Sir A. N. MacNab prosecuted for the Crown. As public feeling (so soon after the rebellion) was still very bitter, and the prosecutions conducted with great ability and zeal, it was considered a very remarkable circumstance that not one of the prisoners was convicted of the higher offence: some of them would undoubtedly have been promptly executed if they had been convicted. The result of these trials, which occupied over two months called forth at the close of the court a most elaborate compliment from the learned judge upon Mr. O’Reilly’s conduct and learning, and placed him in the front rank of his brethren of that day. Mr. O’Reilly describes many thrilling and interesting incidents connected with these trials, the witnesses to which (or most of them) have now passed away. On the 7th of February, 1837, he was appointed judge of the district court of the district of Gore, which then embraced the counties of Wentworth, Halton and Brant, and portions of Waterloo, Wellington and Haldimand. That office, however, did not until 1841 interfere with his practice in the higher courts, which he continued to pursue in the meantime with great success. He resigned the judgeship, however, near the close of 1853, and returned to the Bar, taking charge, for a time, of the legal department of the Great Western Railway Company, whose affairs at that time were somewhat embarrassed, and which Mr. O’Reilly was largely instrumental in bringing back to their subsequent prosperous and satisfactory condition.
As a judge, Mr. O’Reilly was extremely popular; and it is still not uncommon to hear the remark from the older inhabitants that he had the happy faculty of convincing and satisfying both the contending parties. He was appointed Queen’s Counsel in October, 1856, and one of the Masters in Chancery in September, 1871; the business of this latter office soon increased to such an extent that he has been forced practically to withdraw from active practice at the Bar.