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Calling the Shots

Boston police are facing a surge in violence, the Suffolk County sheriff's office was disgraced by prisoner abuse, and the state prison system needs a drastic overhaul after the death of a convicted pedophile priest. Is it just a coincidence that all three agencies now have women at the helm, entrusted to bring about change?

On an empty road near the state prison in Concord one night in the 1970s, a shy woman fresh out of college drove home alone from her new job computing inmate sentences. Out of the blackness, two cars pulled fast beside her and roughly veered, slamming her car into a ditch. The attackers peeled off, and she was stranded in the dark with a flat tire, no way to call for help. "I remember being really angry that I had to walk half a mile to a gas station," Kathleen Dennehy says. Earlier that day, she'd reported a prison incident that she considered unfair. "Apparently," she says now, "I had ticked off the powers that be.

She faced a choice, that bookish woman who took the job only because the country was still reeling from recession in 1976 and there was not a lot of opportunity for Phi Beta Kappa government majors: Accept that law enforcement -- especially at a medium-security men's prison -- was no place for a woman, or go right back in as if nothing had happened. Now, 28 years later, Dennehy is commissioner of the Massachusetts Department of Correction, the first woman to head the state's 18 correctional facilities. And her appointment in March by Governor Mitt Romney was just the start of what has quietly become a remarkable moment in the state's law enforcement history.

The month before Dennehy's appointment, Kathleen O'Toole was appointed as the first female commissioner of the Boston Police Department, the oldest force in the country. And then, in September, came the loudest shot signaling the new world of policing: Andrea Cabral, a relatively unknown black woman, trounced a longtime Boston Irish pol to win the race for Suffolk County sheriff.

No place else in the country has women at the top of three of its most powerful law enforcement institutions, and while each is a pioneer within her respective department, together they are a landmark, an unprecedented trio.

Coincidence? All three women were brought into departments in the midst of upheaval. Their performances will no doubt be watched closely and could ultimately be used against them if they should fail, just as their successes will help guide the women who follow them. Cabral took over a department scandalized by cronyism and prisoner abuse. Dennehy came aboard after the prison murder of former priest John Geoghan and longstanding union hostility. And O'Toole stepped in after February's Super Bowl riots, which left one man dead; that was followed by the sharp spike in shootings and gang violence this past summer.

Cabral has her own theory on the timing of this shift in law enforcement leadership. "I think people are much more likely to consider the possibility of a woman taking over the helm to correct things," she says. Perhaps. But most observers say the reason is far more mundane: It was simply a matter of time. It takes about 30 years to grow a CEO of any organization, and it was about that long ago that women began joining law enforcement in large numbers and working their way up the career ladder. These women are an overnight success -- three decades in the making. Today, the emphasis on brains over brawn in law enforcement, as well as the move toward community policing -- working with the public instead of against it -- gives women certain advantages they missed in the days when policing relied more on size and strength.

Still, it's a system that does not always embrace women. The National Center for Women and Policing says reports of sexual harassment, derailed careers, and a lack of support from male leaders continue. Some departments are getting fewer female recruits; and many female cops, trying to balance family and work, are turning down promotions. In addition, Cabral, O'Toole, and Dennehy are "taking on the toughest jobs there are in the system," says Scott Harshbarger, former state attorney general, who led a commission pushing for sweeping prison overhaul.

Dennehy, who never did learn who ran her off the road years ago, doesn't disagree. "If they're going to scare you away," she says, "this is probably not the career for you."

DIANE SKOOG WAS A SINGLE MOM WHO needed a paycheck. But in 1977, with few jobs in Carver, she took the civil service exam for police and scored so high that the town had to hire her, part-time, the first woman on the force. She started on Halloween night, when the chief gave her a uniform but no training and handed her a gun, even though she didn't know how to use it. Don't take it out of the holster, she remembers him saying. And stay downtown. Just walk up and down the street. Where he could keep an eye on her.

Store clerks thought she was a trick-or-treater. "They said, 'What a great costume!' They didn't know there was a woman coming onto the Police Department," says Skoog, who in 1990 became the third woman to head a police department in Massachusetts. "My kids were kind a pissed at me because I got more candy than they did."

It wasn't until 1972, when Title VII of the Civil Rights Act was extended to include government agencies, that the first generation of women in law enforcement was hired under the same terms as men. "And so police departments were dragged kicking and screaming into hiring women," says Dorothy Moses Schulz, a professor at John Jay College of Criminal Justice in New York and author of Breaking the Brass Ceiling: Women Police Chiefs and Their Paths to the Top, due out next month.

Women had worked in policing in the United States since the mid-19th century (although the Boston Police Department didn't hire a woman until 1921), Schulz says. But they were limited to handling matters involving women and children, and forbidden from uniformed street patrols, which meant no promotions. But until the 1970s, the percentage of women in these fields never rose above 5 percent and usually hovered around 1 percent. In the corrections field, women had been around even longer as matrons of female prisoners and could rise to management as wardens at women's prisons.

When the law changed, money beckoned. Blue-collar work in traditionally male fields paid much better than pink-collar jobs, and women were eager to enter the world of sirens and badges. Those who stuck it out are finally reaping the rewards. Today, out of 18,000 police departments in the United States, 200 -- slightly more than 1 percent -- have women chiefs. In the past year, in addition to Boston, women were named for the first time to head departments in Detroit, Milwaukee, and San Francisco (it also has a female fire chief). Women lead 30 of the country's 3,000 sheriffs' departments, and nine states have women heading correction departments.

Schulz, who interviewed more than 100 female police chiefs and sheriffs, found striking similarities among them: They began their careers in the late 1970s or early '80s; they had strong mentors; they usually have no more than two children; and they are better educated than their male colleagues (in departments with more than 100 officers, almost every female chief has a master's degree or higher).

All three women here fit that profile almost perfectly. O'Toole and Dennehy, both 50, joined their respective organizations in the 1970s. Cabral, 44, started her career as a prosecutor in 1986. O'Toole is married with one child, Dennehy is married with no children, and Cabral is unmarried. Dennehy has a master's degree in public administration; both O'Toole and Cabral have law degrees. O'Toole counts former Boston police commissioner William Bratton as her mentor; Dennehy was guided by a fellow corrections specialist from another state; Cabral credits her mother as her mentor, but her career was largely groomed by Harshbarger and by former Suffolk district attorney Ralph Martin.

The women differ in personality and style. But each is from a tight-knit family where both parents stressed public service and believed their daughter could achieve anything. All three say they see their work as a calling and favor Fortune 500-style management principles. Dennehy and O'Toole describe themselves as apolitical, and until the September election, Cabral had never run for office. They insist on transparent departments, open to the public and the media, and, as record numbers of inmates return to the streets after serving their terms, these women say they are committed to improving prisoner reentry programs to keep the public safe.

"I think if there were ever three women that understood and empathized with each other in this state, it's us," says Cabral. "Because we all understand what it's like to be a woman in charge in this arena."

No one seems surprised that Massachusetts is the first state to have three top-ranking women in policing. It also ranks first among the 50 states in the percentage of women appointed by the governor to policy-making positions, according to a new study from the Center for Women in Government and Civil Society at the University at Albany, State University of New York. Other law enforcement leaders include Paula Meara, Springfield's police chief; Martha Coakley, Middlesex district attorney; Maureen Walsh, chairwoman of the state parole board; and Jennifer Franco, head of the state Sex Offender Registry Board.

"Boston is a city that doesn't look at gender, we look at the most qualified," says Mayor Tom Menino, who appointed O'Toole police commissioner. "That's why we have these three women. We tend in Boston to be more open-minded than most places. We always look at the best."

TOM DEROSA STANDS 6 FEET 6 INCHES TALL and weighs 320 pounds. He has small, deep-set eyes, fleshy features, a huge head, and a crew cut. When he plants his feet and crosses his arms, he makes a fine roadblock. If you were casting a prison film and needed a scary guard, you'd call DeRosa. "No, no," he says, sounding slightly hurt at this analogy. "Common sense. I treat the inmates with respect.

"DeRosa is a deputy sheriff at the Nashua Street Jail, where he's worked for 10 years. On a September night at the Hampshire House in downtown Boston, he's celebrating the election of Cabral as the first woman sheriff of Suffolk County. It's a victory for everyone eager for an end to political favoritism, who believes a hardworking woman obsessed with professionalism could effect a sea change. Cabral's themes of reform and accountability struck a nerve, and not just with the communities of color, the so-called new Boston. On this night, there are plenty of florid Irish faces in the crowd, and, like DeRosa, the people are heartened.

"Sheriff Cabral promotes you on your merit, not on how much you contribute to her," DeRosa says.

Cabral, who had previously headed the domestic violence unit in the Suffolk DA's office, was appointed by then governor Jane Swift in 2002 to the unfinished term of Sheriff Richard Rouse. His office had been disgraced: A lawsuit ended in a $10 million settlement for women illegally strip-searched after being arrested, and a female inmate who had sexual relations with several guards was found to be pregnant. Cabral's first step was to invite the state Department of Correction -- a separate agency -- to audit the department and make recommendations. She welcomed the media, including 60 Minutes and MTV, to film segments at the jail, so the public could see what went on.

"She's a very stand-up woman. She knew where she was going. She set it out to us," DeRosa says. "And she comes out and explains her mission -- everybody loves that. She's bringing everybody back together again."

Well, not everybody. On a September morning two weeks before the primary, at the Suffolk County House of Correction in Boston, there are at least four vehicles in the employee parking lot sporting stickers for Cabral's opponent, City Councilor Stephen Murphy. A black SUV with two Murphy stickers is parked right next to the front door.

"It doesn't bother me in the least," Cabral says firmly. Really? "Nope. Nope. It doesn't bother me because I know why I'm here, I know the job I'm doing, and I said from the day I walked through the door, I am not playing to the people who like the status quo, who thrive on chaos, who don't like change because they flourish in a system that's politically driven and laden with patronage. I'm not here for you. I'm here for everybody else."

She is a large presence, usually one of the tallest people in any room, and broad. High-energy, Cabral clears a space, physically and psychically. She manages to dress both tastefully and with flair: One day it's a bright-green flowing jacket, a long string of pearls, hair pulled into a tight bun, a bit of eye makeup and lipstick. She's a gifted speaker, with the rolling cadences of a good trial lawyer. Where the columnists and political insiders got Cabral wrong was in quickly tagging her as a naif. "I probably understand better than most people exactly how it works," she says of the system she wants to change. "The fact I don't agree with it and don't accept it is a separate issue."

Several allegations popped up just before the primary: The Boston Retirement Board accused her of shortchanging her employees' retirement fund by $1.3 million, and a nurse at the Suffolk County House of Correction said she had been fired by Cabral's administration after it learned she was helping the FBI look into inmate abuse. "Those allegations were 100 percent ridiculous," says Steve Tompkins, the sheriff's spokesman. "That's why you haven't seen any follow-up [after the election]." Cabral was also accused of refusing Iraq war veterans their vacation benefits and firing two whistle-blowers, including the nurse. Cabral says the allegations were all politically motivated. One of the so-called whistle-blowers was a former guard who testified to covering up inmate abuse.

"He is not getting back in here," she says. "It is just that simple." As for the veterans, they had already taken vacations after their service, and to give them more, she argued, would bankrupt her already cash-strapped department. Still, it looked bad. Why not take the savvier step and give in? "Making these decisions because they're politically expedient -- and this is the irony -- is exactly what got the department in trouble before," she says. Later, she adds, "It is really easy to do the wrong thing for the right reason. Then it's just a hop, skip, and a jump to doing the wrong thing for the wrong reason."

Faced with a funding crisis, her predecessor, Rouse, had laid off 130 employees. Cabral paid off Suffolk County's $5.2 million share of the $10 million settlement arising from the strip-search suit without losing a single worker. Her approach has garnered powerful allies, including Barbara Lee, wealthy patron of women in politics, and Senator Edward Kennedy, who taped phone messages to voters supporting Cabral. These days, Cabral, who switched from Republican to Democrat last year, is stumping hard for John Kerry, and she gave a thunderous speech at the Democratic National Convention before a group Lee started, the Revolutionary Women.

"More is always expected of us," Cabral told the cheering crowd. "We must exceed those expectations. Be agents of change. Lead the rebellion. Fight for and empower each other."

IF THERE'S ONE THING the Boston police commissioner hates, it's questions about herself. Not that Kathleen O'Toole minds reporters. She'll talk to them all day long if the topic is public safety. But unlike former commissioner William Bratton, now the Los Angeles police chief, who never saw a TV camera he could resist -- "Like a moth to light," O'Toole says jokingly -- she abhors any appearance of self-promotion.

Just persuading her to sit for an interview turns into a two-month courtship, her public relations staff acting like go-betweens in an elaborate mating ritual. A story about three women in law enforcement? We'll get back to you. Weeks pass, more phone calls. The other two women have agreed? Then she'll do it.At the last minute, O'Toole cancels. Her PR person apologizes profusely. "It makes her very, very uncomfortable," the woman says. More frantic phone calls, more intercessions. All right, no personal questions. But tell the commissioner she can't hide from her role in this historic moment.

The day arrives. Expect the worst: an uptight, suspicious O'Toole, sullenly barking one-word answers. Instead, she sweeps into the conference room at Boston Police Department headquarters in Roxbury, offering a broad smile and warm handshake. It feels like landing a private audience with the pope, she's told.

"Oh, no, I'm not that holy," she jokes, turning to the door and making as if to walk out. She's kidding. Then she apologizes for her reluctance. "It's the only part of the job that feels uncomfortable to me. I'll get up at press conferences, but I get kind of embarrassed when people recognize me and approach me on the street."

Maybe she's an introvert. "I'm not shy," O'Toole says. "Nobody will tell you that." For two hours, she talks easily and openly, lingering longer than promised, joking, answering every question. She's in a black dress, low heels, pearl earrings, and a dressy blue sweater. Brown hair in a neat bob, no makeup. Smart, as the British would say, and tonight she has a dinner at the British Consulate.

"I love my job," she says. Her blue eyes crinkle up. "I absolutely love it. I'm delighted to be here. It's as good as it gets."

O'Toole's father was a teacher in Marblehead who was thrilled she found a career she adored. "God, I can't even explain it," she says. "First of all, there's incredible camaraderie. When it comes down to it, especially in the field, your lives depend on each other. But also, and I just don't want to sound corny, whether you're the police commissioner or a police officer in the field, you have an opportunity to make a little bit of difference in someone's life."

But when Menino offered O'Toole the top position, she pretended to agonize over the decision. She didn't fool her husband -- a retired Boston detective -- or college-age daughter. They knew her heart has been with the force, from when she joined in 1979 as a patrol officer, and over the past 25 years, as other opportunities -- state secretary of public safety; first female head of the Metropolitan District Commission police; serving on a panel on policing in Northern Ireland -- kept her away. Her best memories are as a street cop.

"This morning I was at an event, and people said, 'Didn't you face all these difficulties as a woman?' The thing is, I haven't!" O'Toole says. "When we received our academy assignments and I was sent to work in East Boston, I was petrified. I thought I would get up there at roll call and some guy would say, 'I'm not working with a woman.' Much to my surprise, they were incredibly receptive and very decent."

But she recognizes her experience may be more the exception. With no mentor, Springfield's Chief Paula Meara endured years of legal battles to get and maintain her promotions, and faces a mayor who wants to remove the position from civil service in order to replace her. "I look at someone like Paula Meara, and I'm so thankful I haven't faced all those challenges," says O'Toole. "There were no obstacles that I recall in any way related to my gender." She worked hard to gain credibility, doing the grittiest of police work, and established a cooperative style of leadership.

"I guess when I hear some of the experiences women had, it makes me appreciate the support I've had from my colleagues," she says, adding, "I really believe the Boston Police Department was more welcoming to women in '79 than most others."

This year, on the Police Department's 150th anniversary, women make up 14 percent of the force. O'Toole, dismayed to hear the numbers may be falling, says she wants the force as diverse as the people it serves. It's early, but so far, she has gotten high marks for her outreach to unions, front-line police, and the community. Some credit women for the rise in community policing; O'Toole says she was an early advocate but enlightened men also were strong supporters. In the 1980s, the Boston department was a pioneer of community policing, she notes, in a radical shift from the "us vs. them" mentality toward the public. When the city's murder rate began to rise this summer, just as the Democratic National Convention was about to arrive, O'Toole asked federal and state police to stay after the convention ended. Together, they launched Operation Neighborhood Shield. Some critics have said it didn't go far enough. O'Toole says that, so far, homicides have dropped 50 percent compared with the month before the convention.

The reason the convention was such a success could be, in large part, because of O'Toole's nonconfrontational approach, which she honed during her work in Northern Ireland. Instead of the 2,000 arrests predicted for the convention, there were six. And instead of riot gear, officers responded primarily on mountain bikes.

"Anarchists were saying, 'Wow, that's pretty cool," O'Toole says with a chuckle.

THE OTHER DAY, a priest called Kathleen Dennehy to leave a message: His parish was praying for her. "I thought, 'This is good. Ramp it up," says Dennehy.

A nationally respected leader in corrections, Dennehy has taken on a $400 million budget, a 10,000-person inmate population, and a daunting list of problems. The murder of convicted child molester John Geoghan in August 2003 brought scrutiny on the department, and a subsequent commission headed by Harshbarger wants top-to-bottom change, including less leave time for corrections officers (they average 52 paid days off per year). Predictably, the union response was swift and hostile and aimed right at Dennehy.

And so another message was recently relayed to her from a top-ranking officer at the Massachusetts National Guard, whose headquarters in Milford her office shares. "She's up to her ass in alligators," he said. It made her laugh.

Harshbarger and others say Dennehy was the perfect pick to do the toughest job -- a career insider dedicated to overhaul. Her long span with the state Correction Department gives her credibility. "If you're going to confront the status quo, you have to be prepared to fight for your life," says Secretary of Public Safety Edward Flynn, Dennehy's boss and ally. "I call it 'bending granite,' in law enforcement."

Dennehy looks like the least likely person to clean up a prison system. She's softspoken, and wears Ann Taylor and dainty jewelry: a gold-and-black necklace on one occasion, a charm bracelet on another. She is meticulous and brainy. She looks and acts like an executive in a high-paying corporate job, which is just how she's running the department. For the first time, it has a value statement, which employees helped write. She created two management positions -- one for inmate reentry, one for strategic planning -- without hiring people. When Harshbarger's study came out this summer, Dennehy had 30 days to draft an action plan and wrote a 115-page response.

"I don't know how you could have done a national search and found someone more equipped to play the change agent role and yet maintain the best in the department," Harshbarger says.

It's a perfect fit, odd considering Dennehy never meant to make a career in corrections. She would have enjoyed being an architect. But she developed an expertise in computing sentences, then rose up the ranks in such diverse fields as training and health services. In the 1980s, corrections was a growth industry, and women and minorities were sought for management positions. When she was named the warden of the state prison for women at Framingham in 1992, she had an epiphany.

"I loved Framingham. I know that sounds bizarre, but I loved it in the sense I thought there was real value and purpose to the work. And the people who worked at Framingham are so committed," she says. It became a vocation. There was the time a middle-aged woman arrived at the front gates on a stretcher, catatonic. "And I was just standing there, thinking, good Lord, where do you begin to address the needs, much less the risk to recidivism, with a woman who can't even communicate?" she says. And the time a Vietnamese woman, eight months pregnant, leapt onto a sink, crying and motioning that she would jump. They found a translator; the woman wanted a tuna sandwich. They got her one, and both the woman and her baby survived.

Her critics -- mostly union leaders -- have tried to portray Dennehy as soft. "People should not confuse niceness with weakness," she says. "I'm not the type of person to take the first punch. But if you take a shot at me, I'll knock you out -- particularly around issues of social justice."

Dennehy has insisted on zero tolerance of prisoner abuse, and she says she admires the courage of corrections officers and prisoners who report it. "I think a lot of it has to do with the way I was raised and a real focus on responsibility," she says. "I saw my mother say the rosary first thing in the morning and last thing at night. It has had a profound effect on me."

On a recent trip to MCI-Walpole to encourage a guard who had reported misconduct, she says she heard something surprising. "He said, very respectfully, 'You know, ma'am, there are a lot of people afraid of you in there.' And that's good. It means you got the message. If I'm hearing people are afraid of being held accountable, then people are doing their job."

When Dennehy makes a move the unions don't like, they accuse her of being soft on crime. She adds, "The unions will say, 'It's hugs, not lugs.' I'm not about hugging inmates, I'm about holding people accountable." The lax approach to corrections of the '70s -- when she started at MCI-Walpole, a prisoner taught her how the security system worked, while others lounged in the lobby -- struck her as preposterous.

On the other hand, the state's prisons aren't like Oz, the fictional HBO series that depicts beatings and rapes in prison. "I look at that and I say, 'Mother of God!' If you ran a prison like that, you'd have the job for 24 hours."

Elaine McArdle is a freelance writer. Her e-mail address is

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