As Boston’s mayor-elect to succeed Thomas Menino, Dorchester’s Marty Walsh follows in the “green” footsteps of the likes of Patrick Collins, John “Honey Fitz” Fitzgerald, James Michael Curley, Maurice Tobin, John Hynes, John Collins, Kevin White, and Ray Flynn. Walsh captured the office at a time when the city’s changing demographics will in the not-so-distant future make the Boston Irish mayoral choke-hold of the past increasingly unlikely. But as challenging as his hard-fought victory was, it was not as daunting as that of the city’s first Irish mayor, Hugh O’Brien, who was not only of Boston, but also of Ireland itself.

O’Brien was sworn in as the city’s first Irish-born mayor on Jan. 5, 1885. To many of Boston’s Brahmins and Yankees, his ascent to City Hall represented a once-unthinkable development in a region notable for its antipathy toward Irish Catholics. His odyssey to the top of the heap in Boston politics began in 1832 when as a five year old he emigrated from Ireland with his parents. He displayed a considerable intelligence early on, but was yanked from the city’s public school system as a twelve year old to work as an apprentice to a printer at the Boston Courier. A tradesman’s future beckoned the young O’Brien, who felt lucky in escaping the low-paying and insecure street sweeping or dockside work so many of his fellow Irish immigrants were forced to take. But he had set his eyes on a far loftier future – one placed in the rarefied circles of Yankee commerce.

Following his stint at the Courier, O’Brien took a job at the private printing firm of Tuttle, Dennett and Chisholm on School Street, learning the ins and outs of printing while at the same time figuring out how to publish his own paper, the Shipping and Commercial List. His publication proved a smash hit among the Yankee merchants and Brahmin financiers who were always looking for ways to follow the flow of goods and business news across Boston’s docks. It was quite the feat for the ambitious Irish Catholic to make himself indispensable to well-heeled Protestants whose Back Bay and Beacon Hill brownstones generally meant only one thing to immigrants of “the old sod”—back-breaking work as maids or handymen. Grudgingly, Brahmins looked at O’Brien in a different light; these upscale sorts began to view him as an anomaly – one of the “good Irish.”

O’Brien’s business value to New England merchants and moguls notwithstanding, the question of how far the ambitious publisher could rise among what the historian George Potter termed the “Irish-hating ice-cicles of Yankeeland” intrigued the local Democratic leaders who ruled the city’s Irish neighborhoods. In 1875, the forty-nine-year-old O’Brien won election to the Board of Alderman, and the watchful eyes and ears of the Irish community noticed when, over the next seven years, even hard-boiled Yankees lauded his “conscientious hard work.”

The Democratic luminaries of the burgeoning Irish community first put O’Brien’s political palatability to Yankees to the test in late 1883 by nominating the publisher/alderman as the party’s mayoral candidate. In the weeks before voters went to the polls, many Yankees recoiled against the notion of an Irish-born mayor. And on election night, the Irish turned out in force for their candidate, a man whose financial outlook shared more in common with his Protestant and Republican foe, Augustus Man, than with fellow immigrants. But O’Brien lost the election, if by a narrow margin.

A year later, his name once again topped the Democratic mayoral ticket, and enough Yankee voters swallowed their misgivings to help the immigrant poor sweep him into office. O’Brien’s campaign platform of lower taxes and his demonstrated ability as an alderman to back that promise had proven a fiscal siren song too sweet to resist for many Brahmins. He took the oath of office on Jan. 5, 1885, heralding a new political era for Boston and for the region. He wasted little time in keeping his campaign promises of sound spending and lower taxes, worked to improve the city’s parks and roads, and helped to lay the groundwork of the Boston Public Library, a site where even “Paddy and Bridget” would be allowed to read and study. O’Brien held the office until 1889. But it wasn’t until 1903, when Patrick Collins, a resident of Dorchester, won the mayor’s race, that the Irish dominance of the job began in earnest.

Boston has changed greatly in the past two decades as other immigrant groups and minorities began in turn to flex their political muscle in the way that the ward bosses once did. Marty Walsh worked hard to earn their trust and support, just as Hugh O’Brien did with the wary Yankees 130 years before.