In 1889 Cherry became Reid Professor of Criminal and Constitutional Law at Trinity College Dublin, and published two books on criminal law. He was called to the Bar in 1881 and became Queen's Counsel in 1896. His promising career was, according to his family, damaged by his staunch opposition to the Boer War, although this did not prevent his appointment as Attorney General for Ireland in 1905 or his election to the House of Commons the following year. His elevation to the Bench in 1909 was said to be due to his desire to be relieved from the extreme pressure of his work as a Law Officer; possibly he was already suffering from ill-health, although it was not until some years later that he was diagnosed with what was described as "slow paralysis". His illness did not prevent his promotion to the office of Lord Chief Justice; however he served only three years, retiring partly through ill-health and partly because the Government was very anxious to promote James Campbell to the Chief Justice's office. After the Easter Rising he served briefly as Lord Justice of Ireland, entrusted with emergency powers of government. His retirement was as active as his increasingly bad health allowed: he divided his time between his summer house at Greystones, County Wicklow, and his town house at St. Stephen's Green, where he died. He married Mary Cooper in 1886; their daughter Mary published a biography of her father in 1924.
Bodkin's case
As Attorney General Cherry became embroiled in the politically sensitive case of Matthias Bodkin, a barrister and well-known journalist, who was appointed a County Court judge, only to find his appointment challenged on the grounds that he was not, as the law requires, a "practicing barrister". The case eventually settled, but not before Cherry's conduct of it had come in for severe criticism. A M Sullivan, one of the counsel involved, called his arguments "nonsense"; Maurice Healy wrote that his argument that the royal prerogative could not be questioned "would have rejoiced the heart of James I" but did not impress an Irish Court in the early 1900s.
Reputation
Maurice Healy, who had first-hand experience of appearing before Cherry, did not rate him highly. While praising his legal textbooks, he considered him a plodding barrister and a well-meaning but ineffectual law officer and judge: "his knowledge of his fellow men was not extensive, and erred towards charity." Healy allows that he had at least the virtue of courtesy, at a time when many of the Irish judiciary had acquired a regrettable reputation for rudeness and impatience. More recently Hogan in a much fuller account of Cherry's career gives a far more favourable picture: he argues that Cherry's rapid rise in his profession suggests a much greater degree of legal ability than Healy allows, and that his speeches and judgments show him to have been a man of intelligence and originality. Hogan agrees with Healy that Cherry was not an outstanding judge, and was too much inclined to agree with his colleagues, but argues that his few long judgments are of high quality, especially those on land law, on which he was an acknowledged expert.
Personal life
Cherry was noted as an expert bellringer, and he, along with Gabriel Lindoff and Digby Scott, founded the Irish Association of Change Ringers in 1895, and was soon after appointed President of the Association. Cherry also presented two trebles to St. Patrick's Cathedral, Dublin in 1909, making it the first twelve-bell tower in Ireland. He was involved on the first peal on the twelve bells, which is believed to have been the first peal on twelve bells rung outside England.