...in 1885, Hugh O'Brien, the first Irish immigrant elected mayor of Boston, took the oath of office. A new era was beginning. For several decades, the Roman Catholic Irish had outnumbered the native-born Protestants, who were now forced to give up their long domination of Boston politics. As a well-spoken, mild mannered, successful businessman, O'Brien defied all the Yankee stereotypes of Irishmen. During four terms as Mayor, he widened streets, planned the Emerald Necklace park system, and built the new Boston Public Library in Copley Square, all the while cutting taxes. Popular among both native- and Irish-born Bostonians, Hugh O'Brien paved the way for the better known Irish mayors who would follow him— "HoneyFitz" Fitzgerald and James Michael Curley.
O'Brien, Hugh (1827-1895) — of Boston, Suffolk County, Mass. Born in 1827. Mayor of Boston, Mass., 1885-88. Catholic. Irish ancestry. First Irish Catholic mayor of Boston. Died in 1895. Interment at Holyhood Cemetery, Brookline, Mass.From the Irish Heritage Trail - As Boston's first Catholic Irish-born mayor, Hugh O'Brien (1827-95) helped usher in a new era of Irish participation in the city's government. He and his family immigrated to Boston when he was five years old. He left school at age 12 to work in the newspaper business, and had a successful career as a publisher, launching the widely read Shipping and Commercial List. A member of Boston's Board of Aldermen (1875-83), O'Brien challenged Republican mayor Augustus Martin in 1884 and beat him by a margin of 3,124 votes. His victory represented the city's passage from a Yankee plutocracy to a more democratic and accessible political environment that quickly inspired other Irish to run for office. He served four consecutive terms (1885-1888) as mayor and quickly allayed Yankee fears by demonstrating strong leadership, fiscal responsibility and vision for Boston's future. He was a strong advocate of public parks: during his administration Frederick Law Olmsted developed the city's famed Emerald Necklace park system. O'Brien laid the cornerstone of the new Boston Public Library in 1888, and was viewed as a champion of workers. He was an active member of the Saint Vincent's Orphan Asylum, the Charitable Irish Society and the Catholic Union of Boston. His funeral mass at Holy Cross Cathedral was attended by the city's leading citizens. According to the Republic Newspaper, "The largest and most conspicuous delegation was that from the St. Vincent's Orphan Asylum, 200 little children all dressed alike, who sat immediately behind the family." American sculptor John Donoghue (1853-1903) created the bust of Hugh O'Brien in 1888.
And, finally, the Mayor's obit in the NYT.