The 2013 trial of James “Whitey” Bulger stirred memories of South Boston, better known as “Southie,” once a landmark neighborhood of Irish America. I lived there from 1987 to 1990.

The 83-year-old Bulger, former leader of the notorious Winter Hill Gang, was convicted on 31 of 32 counts of murder and racketeering. He ruled Boston’s Irish underworld from the 1970s through the early 1990s from a Southie bar called Triple O’s. He skillfully leveraged his FBI contacts against the city’s Italian Mafia and other criminal gangs.

The other big Irish-American figures in the neighborhood included Whitey’s younger brother, William, president of the Massachusetts state Senate; and Raymond Flynn, the Boston mayor. Then, the city’s busing crisis was finally drawing to a close. Most of the court battles and violence had focused on South Boston High School, a block from my apartment. (See Stephen Burke’s blog/novel The Chieftains of South Boston.)

It was impossible to walk the streets of Southie without hearing stories of the Bulger brothers; Whitey, the gangland criminal who allegedly handed out Thanksgiving turkeys to the poor; and Billie, the intellectual lawmaker who hosted an annual St. Patrick’s Day Breakfast that became a televised, must-attend political roast.

I enjoyed the working-class grittiness of Southie, a stub of peninsula jutting into Boston Harbor. There is a great waterfront park called Castle Island (a variation of the Kerry town) and dark fingers of ship channels and industrial slips. The park was a great place to go for a run. In the winter I exercised at a community center named after former Mayor James Michael Curley, an Irish-American legend.

Aer Lingus flights swooped low over Southie to land at Logan International on the other side of the harbor–East Boston, or “Eastie.” The Irish tricolor was as ubiquitous in Southie as the stars and stripes; the shamrock as common as the stylized “B” font of the Boston Red Sox.

I loved the Irish Catholic feel of Southie, with three parishes within a few square miles: Sts. Peter & Paul; St. Monica/St. Augustine’s; and Gate of Heaven — “Gatey,” as it was affectionately known — where I attended Mass. If you whispered a “Hail Mary” each time you passed a statue of the Blessed Mother in the small front yards and porches of Southie, the prayer would stay on your lips for the length of any walk through the neighborhood. Of course, that was before the 2002 Boston Globe investigation that uncovered widespread clergy sexual abuse of children throughout the Archdiocese of Boston.

There was a joke in Southie that most of the people who lived there were in the CIA: Catholic, Irish and alcoholic. Booze, drugs, and Whitey Bulger fueled a lot of crime in Southie, especially its public housing projects. A mural painted on the wall of one tenement showed the Notre Dame Fighting Irish mascot with the middle finger extended on one hand, a clenched fist in the other. The Irish republican math equation “26 + 6 = 1” was common graffiti.

Many of the alcoholics and drugs addicts in the neighborhood were striving for sobriety in places such as Answer House and Gavin House, which taught the fundamentals of 12-step recovery. David Foster Wallace immortalized Boston A.A. in his 1996 book, Infinite Jest.

Southie was a place of police sirens and church bells, of shouted rage and hearty laughter. The neighborhood was full of cops, firefighters, longshoremen, teachers, pressmen, iron workers, and commercial fishermen. There were kids on every corner. Many of their moms were not too far from childhood themselves.

Whitey Bulger fled Boston in 1994, about the same time U.S. News and World Report reported Southie had one of the highest concentrations of white poverty in the nation. But young urban professionals, or “yuppies,” had already begun to discover the neighborhood. By the time U.S. Sen. John Kerry of Massachusetts was nominated for president at the 2004 Democratic National Convention in Boston, the transformation was nearly complete. It became a topic of media commentary.

Bulger and his girlfriend were finally captured in 2011. During his trial, the AP observed:

Triple O’s, a hole-in-the-wall bar where Bulger allegedly collected unpaid loans, is now a sushi bar. Across the street is a Starbucks.

Even the City of Boston said this about Southie:

Once a predominantly Irish-Catholic community, in recent years South Boston has become increasingly desirable among young professionals and families who are attracted to the neighborhood’s strong sense of community and quick access to downtown and public transportation.

My wife and I traveled to Boston in March 2013, a few days before the annual St. Patrick’s parade and a month before the Boston Marathon bombing. We stayed at the Seaport Boston Hotel in a section of Southie near downtown. What used to be the hard-scrabbled industrial waterfront was now filled with upscale hotels, condos, restaurants, and shops.

I didn’t get to see too much of my old neighborhood during our short stay. But it didn’t really matter. The Southie I remembered had changed a long time ago; for good, for ill, and forever.

(This piece was revised on Oct. 30, 2018, after the 89-year-old Bulger was murdered in a federal penitentiary. It was modified again on July 14, 2024, when I removed links from the original post. I’ve made several trips to Boston since 2013. I usually make a pass through Southie. MH)