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Saying Goodbye To Whitey's Boston — With No Real Nostalgia

On my right sits a retired schoolteacher. On my left a delivery driver from Stoughton. In front of us sits a father with his three teenaged daughters. We are among the spectators filling one of three overflow courtrooms in the federal courthouse in Boston watching via closed-circuit TV the testimony of Stephen J. Flemmi, former partner and henchman of James "Whitey" Bulger, infamous gangster, longtime fugitive, criminal icon and now defendant who potentially faces the death penalty.

Clockwise from top left: Stephen "The Rifleman" Flemmi, in 1974 from the Boston Police Department; James "Whitey" Bulger, in 1984 from the FBI; Bulger, in a June 23, 2011 booking photo provided by the U.S. Marshals Service; Flemmi, on Sept. 22, 2008, as he testified in a Miami court in the murder trial of former FBI agent John Connolly. (AP)
Clockwise from top left: Stephen "The Rifleman" Flemmi, in 1974 from the Boston Police Department; James "Whitey" Bulger, in 1984 from the FBI; Bulger, in a June 23, 2011 booking photo provided by the U.S. Marshals Service; Flemmi, on Sept. 22, 2008, as he testified in a Miami court in the murder trial of former FBI agent John Connolly. (AP)

A stoop-shouldered elderly man, Flemmi describes in a deadpan monotone how he shot, strangled, stripped naked and then used dental pliers to pull out the teeth of his multiple victims, some of whom he once considered partners, friends, lovers, even a child he raised as his own.

When I tell my friends where I've been the last few days, many respond, "Eew... why would you want to do that?"

Various reasons, I suppose. Morbid curiosity, for one. To hear first-hand a man describe in gruesome detail the mayhem and carnage he caused for decades. Watching Flemmi is a bit like seeing a fierce animal caged in a zoo — you know how dangerous he can be, but from where I sit he is harmless.

I nervously laugh with my fellow spectators when Flemmi describes how after each murder Bulger would take a nap or sit off to the side, seemingly exhausted by the excitement or simply unwilling to help out as Flemmi and others dug the grave or disposed of the body.

A part of me wanted see how a real-life gangster measures up to those portrayed in Hollywood productions like "The Sopranos" or "Goodfellas." But Flemmi's testimony obliterates any romantic notions I had of gangsters. These men are not tough guys who live by a code of loyalty but who, underneath it all, are sensitive — if flawed — human beings. No. Here in the real world, men like Flemmi and Bulger are ruthless psychopaths.

This trial takes me back, reminds me of a time when Boston seemed grittier, tougher, more insular, more provincial. I remember that place ... But I don't want to go back there.

But there is something else, something beyond the spectacle of the city's most sensational trial that drew me to this place. Call it nostalgia. I didn't grow up on the mean streets of Charlestown or South Boston. I've only lived here 37 years, moving to Boston in 1976. I got my first job at a local paper in Allston. I steered clear of the neighborhoods where Whitey and his gang ruled for the most part, not because I knew anything about Bulger or his criminal exploits, but because I was an outsider, and I knew that outsiders were not welcome in those places (which I suppose is one reason why Whitey thrived for as long as he did). This trial takes me back, reminds me of a time when Boston seemed grittier, tougher, more insular, more provincial. I remember that place. It's where I became an adult, began a career, started a family and established roots.

But I don't want to go back there.

During a break in the testimony, I sit with the delivery driver in the courthouse cafeteria, with its picturesque view of Rowes Wharf and the harbor. We talk about the case and what we remember from that time. We talk about how much Boston has changed. We agree the city is more international, more diverse, more open-minded. That’s good. The harbor is clean, the streets are safer, things seem to work better, you can walk around at night. Guys like Whitey, we agree, are relics of bygone era.

Good riddance.

Complete CoverageBulger On Trial: The Complete Guide To Boston’s Most Notorious Gangster

This program aired on July 26, 2013. The audio for this program is not available.

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