third-floor apartment, the Conleys’ home did not have much of a view. They looked out onto the asphalt parking lot of the telephone company building that occupied the entire block from East Broadway to the side street—H Street. The far side of the parking lot actually rose uphill, an incline leading to the back entrances of some retail businesses on East Broadway. Kenny Conley called the tiny hill Tar Hill. In the winters after a fresh snowfall, he and his pals used it for sledding. The “trail” began atop a sliver of grass, ran under an iron railing, and then across the asphalt lot. The chain-link fence at the sidewalk served as a safety net, stopping their sleds from shooting out onto the street.
The Conley homestead was only 3.8 miles from where Mike Cox and his family were living in Roxbury—but the two neighborhoods were a world apart. Southie was overwhelmingly white and Irish—and had been since after the Civil War when the first wave of Irish immigrants moved into the area.
In the other three-decker apartments and row houses surrounding the Conleys lived families much like their own, where the breadwinners mainly worked in the trades, the public utilities, Gillette, “the T,” or the police and fire departments. The median family income when Kenny was a toddler was $11,200 annually, and the majority of grown-ups never went to college. It was blue-collar through and through.
In the beginning, meaning back to the American Revolution, the grassy and hilly peninsula jutting into Boston Harbor was ideal for grazing livestock. In March 1776, the Colonial forces, led by General George Washington, used it as a base from which to drive the British out of Boston. By the early 1800s, South Boston formally became part of Boston, connected to the downtown by the new Dover Street Bridge.
Given its geography—nearby but separate and isolated—Southie became a convenient location to build the city’s prisons, hospitals for the mentally ill, and poorhouses. Iron foundries, machine shops, and shipyards on the waterfront all sprang up.
The potato famine from 1845 to 1850 that devastated Ireland triggered a massive exodus to the city, first to the tenements of the North End and then, in the decades following the Civil War, to Southie. The Irish eagerly took jobs in shipbuilding and along the waterfront unloading freight ships. The women traveled across the bridge where they cleaned the homes of the Brahmins on Beacon Hill. Life revolved around work, family, and the many new Catholic churches opening throughout a neighborhood that was only 3.1 square miles. In time, it was said that Southie was a “state of mind.”
“For those born and raised there, South Boston was a warm, friendly, comfortable community where people knew one another, shared the same values, enjoyed the same pastimes, and were safe from outside contacts and alien influences,” wrote the historian Thomas H. O’Connor, a history professor at Boston College. “Southie pride” became a powerful force embedded in the clannish, tight-knit neighborhood—an us-versus-them mentality between the neighborhood and the rest of the city, or world for that matter.
Kenny Conley quickly came to embody that pride and the neighborhood’s cultural emphasis on staying put rather than breaking away. “I did see myself growing old, sitting right down here, in South Boston. I’ve always said, and I think it’s the sentiment of everyone around here, Why leave God’s country?” From early on, in addition to working as a police officer, he’d say his dream was to marry and have a family. And his idea of making it was to find a house in the densely built neighborhood that actually had a garage and a driveway. “You know, something I could take a snowblower to.”
Kenny was nine years old when his parents realized their owndream and became Southie homeowners. His father paid $10,000 in cash for 78 H Street—the third in a cluster of six row houses they could see
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