The player

Politically connected lawyer Cheryl Cronin is a consummate Democratic insider -- and a high-powered woman in what's still a man's world

by Michael Crowley

Cheryl Cronin didn't want this story to be written. As a fabulously wired lawyer and adviser to the stars of Massachusetts Democratic politics, Cronin prefers to stay out of the public's eye. Unlike the brand of top-tier politicians she advises and represents, Cronin first responds to a reporter's call not with enthusiastic self-promotion, but by making a vigorous case for her own irrelevance. Genial but forceful, she protests that she's not important enough to be the subject of a profile, that calls around town will prove her insignificance. "People might say, `Cheryl who?' " she warns.

Resigned to the coming scrutiny, however, Cronin quickly recasts herself. Out goes the anonymous ingenue; in comes an ultraconnected power player. Cronin ticks off a list of references that amounts to a who's who of state Democratic politics: former congressman Joe Kennedy, outgoing Democratic National Committee chairman Steve Grossman, House Speaker Tom Finneran (D-Mattapan), state treasurer Shannon O'Brien, Boston mayor Tom Menino.

Cronin's clever maneuverings are a fitting introduction to a woman who, far from being an unknown, is one of Boston's most sought-after sources of political advice, legal counsel, and media strategy. Although Cronin may be all but unknown to the public, she is a consummate behind-the-scenes player and one of the most influential figures within the inner circles of Massachusetts politics -- "an insider's insider," as one insider puts it.

"She knows most of the central participants," says John Sasso, chief of staff to former governor Michael Dukakis. "People who are at the core of public-policy debates in this state seek her advice and her help."

"She moves at the highest level," says Finneran.

Yet while the back rooms of local politics overflow with advisers, consultants, and all-purpose fixers, Cronin occupies a niche of her own. She is a lawyer with an almost unrivaled mastery in that most perilous of political minefields: campaign-finance law. But Cronin is known for combining her courtroom expertise with a rare feel for the more political court of public opinion. She has thus become the counsel of choice for bigtime politicians who find themselves in trouble, and for those who want to avoid it. With a client list that has included Finneran, Kennedy, state senator Dianne Wilkerson, former Boston mayor Ray Flynn, former Senate president William Bulger, and the state Democratic Party, Cronin is to Boston what Robert Bennett or David Kendall is to Washington.

"She's one of the few lawyers who really understand both the law and politics," says Democratic consultant Mary Anne Marsh. "If you want to stay out of trouble, call Cheryl. And if you want to get out of trouble, call Cheryl."

Cronin, 44, has been known for years to the usual suspects of state politics, but her influence over public policy has only now reached its pinnacle. Having played a key role in Tom Reilly's campaign for attorney general, Cronin was the newly elected official's choice to chair the transition team that guided his inheritance of the office from Scott Harshbarger this winter. Although Cronin turned down an official post in Reilly's office, the AG calls her "one of a small group of people" to whom he turns for advice. And Cronin has just assumed a critical role for which she was selected by her pal Tom Menino: chairing a citizens' advisory board that will evaluate a controversial $300 million hotel and entertainment complex proposed for the Back Bay by New York-based Millennium Partners.

All the more remarkable for being a successful Jewish woman in a clubby arena of Irish and Italian Catholic men, Cheryl Cronin serves as a window into the behind-the-scenes world of local politics, in which a small group of low-profile but highly influential insiders run campaigns, advise candidates and officeholders, manage public images, and forge the alliances and networks that can be even more relevant than the ballot box itself. Politicians come and go with every election, but the Cheryl Cronins of the world endure. People might say, "Cheryl who?" -- but not the people with political clout in Boston.

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Time and again, people who know Cheryl Cronin say the key to her success is an ability to combine mastery of arcane campaign-finance law with a keen sense of public relations -- a rare pairing that makes her invaluable to ethically challenged pols who fear the media's verdict as much as a jury's.

"Bill Clinton is a great example," Cronin says, "A politician client is never going to feel satisfied if the disposition of a case works for them legally but has enormously adverse political consequences."

"Sometimes when there's a case with a lot of publicity involved, there aren't many people to turn to," says Cronin's partner, criminal lawyer Thomas Hoopes. "There are not five lawyers in Boston who really understand how publicity affects a case."

That's a consensus opinion, and it's why top Massachusetts pols who find themselves in hot water repeatedly turn to Cronin. When Tom Finneran faced questions in 1997 about his role in legislation favoring a semi-public agency that was a client of his law firm, it was Cronin who argued successfully on his behalf before the state ethics commission. When state senator Dianne Wilkerson (D-Boston) saw her political career jeopardized by her failure to pay federal income taxes for several years, Cronin helped keep her out of jail and in the Senate. When former Boston mayor Ray Flynn's campaign finances were the subject of a long investigation that jailed two of his aides, Cronin helped get Flynn off the hook.

"Part of it is word of mouth," says Democratic consultant Jim Spencer, breaking into a Mametesque dialogue to illustrate his point: "Someone says, `God, I've got this . . . ' and it's like, `Go talk to Cheryl Cronin.' "

"She doesn't put some magic fix in," Spencer adds. "She just knows the law really well." Indeed, some say Cronin understands campaign-finance law even better than the state's own regulators -- and that that has been her ticket to the nerve center of state politics.

Born in the Washington, DC, suburb of Silver Spring, Maryland, Cronin came north to attend Boston University -- she transferred and graduated, summa cum laude, from UMass Amherst -- and then Boston College Law School. In 1982 she took what she calls "a formative job" as general counsel in the state's Office of Campaign and Political Finance (OCPF), where she shaped and mastered complex laws regulating money in politics.

Cronin left OCPF in 1987 to have the first of her three children, and worked briefly for former attorney general Jim Shannon. But she soon began employing her expertise in campaign finance -- a field that was growing increasingly baffling and hazardous for politicians by the 1990s -- to carve out a legal niche for herself. She signed on with the prominent downtown lawyer Tom Dwyer in 1989; soon after, then-state Democratic chairman Steve Grossman enlisted her to advise the party on campaign-finance matters, which she has done pro bono ever since. In early 1996, she opened a practice with Tom Hoopes, where she now handles a mix of political, corporate, and criminal clients.

Cronin's move from the public to the private sector raises some hard questions about the integrity of the state's legal and regulatory process. Her transition from writing campaign-finance laws to helping politicians navigate those same laws is just the sort of thing that feeds public cynicism about politics and government, playing into a perception that it's all a game rigged by a cabal of insiders.

"As is so often the case when people are moving in and out of government and then are moving to lobby or represent people in government cases, it oftentimes gives the appearance that there's a revolving door," says Ken White, executive director of Common Cause Massachusetts. "There may be no evidence of wrongdoing, nor anything illegal or unethical" -- and in Cronin's case there is absolutely none -- "[but it's] simply the case that it does tend to erode public confidence."

State ethics regulations, however, require only a one-year "cooling off" period, during which former government employees are forbidden from appearing before the state in connection with matters that were under their authority. And even White is quick to add: "You can't ask someone to download all the knowledge they've gathered when they leave the door."

Cronin, for her part, is unapologetic about switching to the private sector. "It's the world we live in," she says. "There's a benefit to people moving in and out of the public sector," she adds. "The reality is that I do think I'm a more skilled lawyer dealing with government agencies, having been in government, because I do have an understanding of how the system works and how a regulator would tend to think."

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In person, Cheryl Cronin is neither the steely poker ace nor the slick power yuppie one might expect a high-octane political lawyer to be. With bright eyes, a shock of curly black hair, and an eagerly youthful smile, Cronin comes across as warm and personable. But it's impossible to miss a meticulous, even obsessive, quality to her. Friendly but wary, Cronin asks constantly what others are saying about her, negotiates the conditions under which she will allow herself to be photographed, turns over the papers on her desk before allowing a reporter into her spartan downtown office.

Cronin makes no secret of the fact that her guardedness derives in part from having watched the press disembowel her clients. "The bottom line is that the press is just very unnecessarily unkind," she says. "I mean, I'm not sure it's necessary to be so vicious and so unkind in order to cover a story adequately."

Yet Cronin maintains that above all, she simply doesn't see herself as worthy of scrutiny. "I think of myself as the mother of three kids," she says. "You know, I go home every night and change diapers."

On the contrary, Cronin's motherhood only makes her all the more intriguing. Powerful females are still rare in Massachusetts politics. Cronin is one of a small group of women -- and an even smaller group who are Jewish -- to enjoy real respect from the boyos of local politics.

"This is still an old boys' game, and she has gone in and beat [them] at their own game," says Jim Spencer. "It's not easy for any woman to be accepted. Politics is still that white-male bastion, and she has made herself a respected inside player."

Her partner, Tom Hoopes, goes a step further: "In some ways I think she's twice the lawyer a lot of guys are," he says. "I've seen her work here until five o'clock, go home, deal with supper, put the kids to bed, and then get up at three in the morning and work."

"It certainly does take women longer, and maybe even a Jewish woman might take a little longer to break into that [world]," Cronin says, noting that her attempts to talk sports with men are met with looks that say don't even bother. Rather than adopt a posture of combative resentment, however, she takes more of a grin-and-bear-it approach. "I think it's important for women who are going to be working in that world not to have an edge about it . . . to basically take some punches. I guess the thing I would say is not to overreact, not to think that every hit that comes your way is based on gender." That formula might not fly for some of Cronin's female colleagues, but it's certainly worked for her.

That's not to say Cronin is afraid to play hardball. Some who have crossed paths with her say she can be prickly and overbearing. And despite her aversion to publicity, Cronin has been willing to inject herself personally into some heated public battles.

For instance, Cronin was a lawyer for Billy Bulger when the then-Senate president was fending off a 1994 coup attempt by a rebel group of state senators led by Bill Keating. The struggle veered into a debate over anti-Semitism when Keating suggested that Bulger and his allies were making an issue of the fact that Keating's political consultant, Michael Goldman, was Jewish.

Cronin responded to the charge with outrage. In a letter to Keating, which Bulger quotes in his 1996 autobiography, she wrote: "Michael Goldman is no `victim of anti-Semitism,' and asserting that he is in this matter is a grave dishonor to the all too many true victims of anti-Semitism. . . . Most tragically these victims include people like my 87-year-old aunt, who has spent the last fifty-one years of her life alone since her husband was killed by the Nazis at Auschwitz. Such exploitation to advance your own political agenda is nothing less than shameful."

Usually, though, Cronin likes to operate more discreetly. Asked what her first piece of advice is for panicky pols who've landed in trouble, she says: "Don't talk to anyone. Don't do anything. It's tempting, particularly when something's in the paper, to want to offer people the facts. But it's very important to just sort of shut down at that point."

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Although she may try to downplay her influence around town, Cheryl Cronin has never been more visible or influential than she is today.

Cronin's chairmanship of the Citizens' Advisory Committee (CAC) for the Millennium Partners project, for instance, is her first undertaking of major public responsibility since her days at the OCPF, and it puts her in a hot seat. Back Bay neighborhood activists have vehemently protested the project's design, raising concerns about size, shadows, and traffic.

And some have come to eye Cronin warily, wondering whether her close ties to the mayor will prevent her from being an impartial arbitrator. Peter Catalano, an outspoken neighborhood activist and a regular critic of development projects citywide, charges that Cronin has shown an early bias in favor of the Millennium proposal. "There are troubling signs," Catalano says. "I don't think it was wise for such a politically connected individual to be appointed with, so far as I know, no background in urban planning or design or community activism."

Cronin says she is well-qualified for the CAC, arguing that the panel was not designed to review the Millennium project on urban-design or architectural grounds. "I think it's really intended to review the impact of the development on the people who live in the abutting communities as well as on the city as a whole," she says, noting that she's been a Back Bay resident for 15 years. As for charges of pro-developer bias, Cronin suggests she has simply tried to maintain balance. "An enormous amount of time has been spent at the meetings listening to public comment, and much of that comment has been negative about the proposal," she says.

Although her seat on the CAC is more visible, Cronin probably enjoys even greater influence through her close link to the state's new attorney general, Tom Reilly. A long-time Reilly friend, Cronin played a key advisory and fundraising role in his 1998 campaign. In December Reilly tapped Cronin to chair his transition team, but couldn't persuade her to give up a lucrative private practice. "It would have been better if we could convince someone of her caliber to join this team," Reilly says. "She certainly is someone whose friendship and opinions and judgment and advice I value a great deal."

Both Reilly and Cronin say they see no reason to be concerned about the fact that Boston's top political-corruption lawyer enjoys such a cozy relationship with the attorney general, the public official charged with prosecuting political corruption.

"Cheryl knows that her clients are not going to be treated any different than anyone else's clients," Reilly says. "She's not alone. I've been a practicing trial lawyer for all my career and there are many people I know, and they know where the line is and they would never cross that line. And particularly Cheryl -- she has the highest ethical standards."

Cronin says the question is one that could be posed to "hundreds of other people" in state politics. "Everyone has connections to certain people," she adds.

It's certainly true that, in the incestuous world of Massachusetts politics, everyone may have connections to certain people. But, as Cheryl Cronin illustrates, a few certain people seem to have connections to everyone.

Michael Crowley can be reached at mcrowley[a]phx.com.