The Globe vs. Ray Flynn

Part 2

by Dan Kennedy

Thanksgiving day, 1985. It's 10 a.m. Mayor Ray Flynn, in one of his favorite photo-ops, is dancing with some homeless people at the Pine Street Inn. And he is, according to a then-Globe reporter assigned to cover the event, "drunk as a lord."

Appalled, the reporter told an editor what had transpired and asked why no one was writing about Flynn's drinking. The answer: half the reporters and editors drank with the mayor. "This story is about 12 years too late," the reporter says of last Friday's piece. "The Globe really contributed to the conspiracy of silence."

According to several former and current Globe staffers, the chief conspirator was the late Kirk Scharfenberg, a close friend and drinking buddy of Flynn's who ascended from city editor, to metro editor, to deputy managing editor, to editorial-page editor during Flynn's mayoralty. Scharfenberg also became friends with Flynn's top political operative, Ray Dooley, a veteran of progressive organizing efforts. Sources say Scharfenberg fought to keep negative Flynn pieces out of the paper. One well-placed source says he even enthusiastically backed the transfer of a reporter to the prestigious Washington beat so the two of them would no longer have to lock horns over coverage of City Hall. Then, too, Scharfenberg, Flynn, and Dooley shared a genuine commitment to urban liberalism; at best, that idealism animated the Globe during the 1980s.

The friendship between Flynn and Scharfenberg, who died of cancer in 1992 at the age of 48, was an unlikely one. Scharfenberg was a classic liberal, sharp and well-read; Flynn, as a state representative and city councilor from South Boston, until that time was known mainly for his opposition to court-ordered school desegregation and for the so-called Doyle-Flynn amendment, a notorious piece of anti-abortion legislation. Ray Flynn the progressive populist had yet to be born.

Flynn recalls Scharfenberg's approaching him at a hearing over a proposal to create a home for unwed mothers on the Jamaicaway. Flynn believes Scharfenberg sensed that their shared interest in poverty issues might be a way for them to bridge what seemed, on the face of it, to be an insurmountable gap. After the hearing, they adjourned to Doyle's for a few beers -- the first of many such nights.

"I admired him greatly, and he became a very close friend of mine," Flynn says. "He was very supportive of me. I never really had any kind of relationship with anyone at the Boston Globe other than Kirk Scharfenberg."

Not that Scharfenberg was alone in protecting Flynn. Indeed, no one was prepared to blow the whistle, especially since Flynn always seemed able to handle his booze. Herald political editor Joe Sciacca recalls a night when he, fellow staffer Joe Battenfeld, and the mayor closed down a bar across from City Hall. Sciacca and Battenfeld couldn't make it home, and were painfully hung over the next day. Flynn was at a 7 a.m. event, raring to go. "Trying to keep up with Ray Flynn in terms of alcohol consumption is a mistake," Sciacca says.

Globe columnist Marty Nolan remembers writing a piece in 1991 on a day in the life of the mayor. Flynn ended the day with several beers at Doyle's, and then left at 11 p.m. -- to go running through Franklin Park. (Flynn continues to run at least 10 miles a day, and competes in two marathons a year.) "I was in awe of his capacity," Nolan says.

Slowly, though, the Flynn sheen wore off. There were early signs. The late Globe society columnist John Robinson alluded to his drinking in 1983. So did Howie Carr, in a 1984 Boston magazine profile and in subsequent Herald columns. Globe-staffer-turned-novelist Charlie Kenney, in Globe Magazine profiles of Flynn in 1985 and 1989, raised the issue gingerly, referring in the latter piece to "what is described as Flynn's propensity for dropping by neighborhood taverns."

Meanwhile, Flynn's performance in office was deteriorating. Arguably an outstanding mayor in his first two terms, he displayed indifference and boredom during his third. He fought for the right to appoint the school committee, then shocked supporters by loading it up with cronies. The police department, run by his childhood friend Mickey Roache (now a popular city councilor), was beset by corruption and incompetence. Thus, when Bill Clinton tapped Flynn for the ambassadorship to the Vatican in 1993, the appointment was met by many in the city with genuine excitement for Flynn, combined with relief that he was finally leaving.

Flynn's triumph, though, quickly turned to tragedy and farce. A former aide, Douglas deRusha, was convicted of embezzling more than $200,000 from Flynn's campaign and was sent to prison. A trusted associate, Joe Fisher, went to prison for corruption. Attorney General Scott Harshbarger -- now the frontrunner for the office Flynn intends to seek -- investigated Flynn, a probe that ended inconclusively. Flynn was also hit by accusations that he was too political and raw to be an ambassador (he was reprimanded twice by the State Department for speaking out of turn). And his son Ray Jr. was battling substance abuse problems.

Flynn considered running for governor in 1994, but decided against it in the face of rapidly dropping poll numbers. A headline in the Sunday Globe Focus section that spring read: ONCE MASSACHUSETTS' MOST POPULAR POLITICIAN, RAY FLYNN IS NOW ITS FAVORITE POLITICAL JOKE.

Meanwhile, in Flynn's absence, the culture of the Globe was undergoing a metamorphosis. Under Matt Storin, who was named editor of the Globe in 1993, just as Flynn was leaving, the paper has become tougher and more evenhanded in covering politics than it was back when it was sometimes criticized as a house organ for the Kennedys -- or for Ray Flynn. "I think it's a much more aggressive paper," says Globe alumnus Michael Frisby, now White House correspondent for the Wall Street Journal. "The old ties and the old ways of doing things don't make it anymore."

This change has taken place in a larger media context in which any notion of a zone of privacy has utterly disappeared. Thus, US Representative Joe Kennedy pulled out of the governor's race at least in part because of never-ending media questions about his brother Michael's problems. The Globe and its competitors badger acting governor Paul Cellucci about his personal debt despite lacking any evidence that it's relevant to the way he conducts state business.

It was into this new, unfamiliar media- scape that Flynn naively staggered two months ago.

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Dan Kennedy can be reached at dkennedy[a]phx.com.