CAPE ELIZABETH — Ask Cynthia Dill about her elementary school days, and the first thing she recalls is a fistfight.

The bully was a bigger, older boy. He had been relentlessly taunting a severely disabled girl, who used a wheelchair, on the playground of her Barrington, R.I., elementary school. Dill, a fifth-grader at the time, says she told him to stop. He wouldn’t, and when pushes turned to punches, she stood her ground.

“She was being tortured by him,” Dill recalls today. “I was always the kid to stand up for the kid who was being bullied.”

In the decades since, Dill has continued standing up to the big kids, from the bar owner she sued in college for demoting her on account of her gender to the major corporations she took to court as a young attorney, to going head to head with Maine’s governor as a freshman state senator.

Now she’s running for U.S. Senate, taking on the sitting secretary of state and a popular and wealthy two-term governor. Those who have known her through the years say if elected, she’d remain the person she’s been since grade school: fearless, outspoken, ambitious and not one to pull her punches in defense of principle. Her detractors wonder whether her stridency – which has propelled her in just six years from being a freshman town councilor in a small, affluent suburb to the Democratic nominee to one of the most prominent and powerful lawmaking bodies on the planet — has doomed her party’s chances of winning the three-way race.

A respected family

Her story starts in Carmel, N.Y., a leafy town of 30,000 just over the border from Westchester County and near the far end of the commuter rail lines to Grand Central Station. She was born there Jan. 6, 1965, the fourth of five children of the scion of a successful family business and an Italian-American nurse from Rhode Island.

The Dills were a respected and influential family in Carmel. Cynthia’s grandfather, Fred Dill Sr., had come to the area as a penniless young man at the height of the Great Depression and built a thriving regional chain of lumber and home improvement stores. As she was growing up, Fred Dill was founding community organizations and a local bank and chairing the local chapter of the United Way. There is a nature preserve named after him; it incorporated land he had donated to the town for that purpose.

“He got all the different organizations in the community to get together and work together and help one another,” says Alfonso Lotrecchiano, a close friend of the family patriarch who serves as historian of the local Rotary Club. “He didn’t look for accolades, but he loved to see people succeed and helped a lot of people, unbeknownst to the public.

“He never got involved politically, but he had a lot of clout; and if he said something, people listened,” Lotrecchiano adds.

The Dills — including Cynthia’s father, Fred Dill Jr., who managed the business with his brother — were Republicans of the old Yankee sort, Cynthia says, and their experiences as small-business owners and community leaders shaped her worldview.

“I didn’t grow up with the idea that government was the enemy. I was brought up with ‘you serve your community, you work hard, and you give back through public service’ — and to me, that’s what government is,” she says.

Cynthia’s parents divorced when she was 9, and she moved to her mother’s hometown, Barrington, a comfortable suburb of Providence. She and her siblings continued to spend weekends, holidays and a chunk of their summer vacation in Carmel with their father and stepmother. “He remarried Carol Brady and she had four kids, complete with Peter Brady, so we became a mixed family of nine, a Brady Bunch,” she recalls.

An independent childhood

In Rhode Island, her mother worked long hours as a respiratory therapist, and her grandmother helped take care of the children while working night shifts at a nearby rubber plant.

Dill says she had a remarkably independent childhood, catching buses to Providence, Newport, Carmel or her grandmother’s home in Bristol, “a little house with Italian food and a beach nearby.”

From age 14 she worked, and she did well in school without trying very hard.

“I was a free agent, because I was a good girl and did well in school,” she says. “My grandparents had instilled confidence in me, and my father really encouraged all of us kids to take measured risks.”

“Her father and grandfather were very strong men and very confident, and they played a big role in her life; and both really impressed her in those ways,” says Mary Katherine Pyle, who became best friends with Cynthia in second grade. “She’s a very brave person and a fighter, and when she sees situations where people are in an unfortunate circumstance, she’s going to do what she can to help them.”

She finished high school and started college a semester early. A high school boyfriend led Dill to attend college at the University of Vermont. The Air Force posted him in Plattsburgh, N.Y. The university was in Burlington, just across Lake Champlain.

“It was definitely a party school. A lot of people went there because they liked skiing and the outdoors and the Grateful Dead,” says college friend John K. Kane, now a partner at Jones Day, a New York law firm. “Cynthia took part in a lot of that stuff. She liked the outdoors and skiing and she did party and was a Grateful Dead fanatic.

“She was a hardworking and energetic and very mature person. That struck me early on,” Kane adds. “In a school that had a lot of privileged upper-middle-class kids who maybe weren’t the best at taking care of themselves, she was the opposite. She would cook brown rice for herself in one of those crock pots and paid a good number of her bills herself.”

During her junior year, Dill gave up waitressing to take a better-paying job as a bartender. Less than an hour into her first day, the owner walked in and, displeased to find a female behind the counter, demoted her to cocktail waitress. She protested. He fired her. She sat crying on the curb. She had no idea how to meet the rent, until one of her professors happened by, learned what had taken place and advised her to sue for employment discrimination. She did and ultimately won.

“I had no idea there was this system in place. It was a whole new window for me,” Dill recalls, adding that it was a formative experience.

“I think it brought it home to her personally, the issues women face in the working world,” Kane says. “I think it had some relationship to where she wound up going in her legal career.”

According to Dill, she was also drawn to law school by spending two weeks traveling with a Eurail pass in France, Spain, Italy and Switzerland. “It was an eye-opening experience,” she says. “I had traveled, and I think I had my sights set on this international business law career, that that would be an opportunity for me to make a difference.”

From business to civil rights law

Dill attended Northeastern Law School and in 1990 moved to Portland, taking a job with a medium-sized law firm, Thompson, McNaboe, Ashley & Bull.

“I did a lot of transactional work, closing loans for banks and doing some work around Canadian free trade,” she says. “You’d just sit down with a pile of documents and you’d have to read through and negotiate terms. It was incredibly boring.”

Former colleagues remember Dill in her mid-20s as competent, brave and spirited in her political views. “She was always driven and was clearly smart, dedicated and represented her clients well,” says Adrian P. Kendall, one of her peers at the firm. “We’d have spirited conversations about social and progressive issues.”

“She was very focused, a quick study, and one thing that struck me very early on is that she’s courageous,” says Ed Ashley, who was a firm partner. “She’s pragmatic and focused on what she wants to get done. … I think what you see is what you get with Cynthia.”

One day in 1991, Dill was assigned to litigate a civil rights case involving a disabled veteran and the Old Orchard Beach Police Department.

“It was the first litigation case I had on my own, and I just loved it,” she recalls. “I remember feeling so exhilarated, that this is what I really wanted to do.”

Soon other cases alleging civil rights violations by southern Maine police departments were coming her way, some of which she settled for significant amounts, placating her superiors at the firm, which didn’t normally focus on such work.

In 1994, Dill struck out on her own, setting up a solo legal practice out of rented offices on India Street. She had some business clients and real estate closings, but a review of court documents confirms her primary work was civil rights and employment discrimination litigation in federal court. Often she was in a David-and-Goliath situation, representing clients against the U.S. Postal Service, Rite Aid, the Navy, KeyBank and Hartford Insurance.

“It’s very exciting,” she says of going head to head with the U.S. attorney or major law firms such as Pierce Atwood. “I work really hard and am almost always underestimated. It’s also a big financial risk, so I would spend a lot of time really evaluating a case before taking it on.”

Her friends weren’t in the least surprised when she made the move. “I’d been surprised (earlier) when she said she’d joined the big law firm,” Kane says. “I’d always expected her to take up to the fight of the underdog and to make sure they aren’t run over by the overdog.”

A modest windfall, a political debut

She had married Tom Clarke, a teacher at Thornton Academy in Saco, in 1990 and had the first of two children in 1995. In 1996 they made two real estate purchases that would pay off — a modest South Portland home on Bowers Street and a 1,500-square-foot home on D Street, near Legion Square, which they converted to offices and where she moved her law practice.

On the campaign trail, Dill has touted herself as a middle-class person sticking up for “the 99 percent” against the peers of wealthy rivals such as Angus King. She recently released tax returns back to 2002 that substantiate that she and Clarke have had modest incomes, but they did benefit from the sale of their South Portland properties in 2003-2004 for $297,900 more than they had bought them for.

This windfall allowed the family to move to a home in Cape Elizabeth so their children could attend its well-performing schools. While their Shore Road address evokes the shorefront mansions of neurosurgeons, corporate lawyers and wealthy heirs, the Clarke-Dill home is at the road’s terminus in the town village, just inside a commercial zone. Dill’s law firm — and now her campaign headquarters — is located in the walk-in basement. They bought it for $477,000 in the fall of 2003 and invested in a nearby $185,000 condominium unit two years later.

In January 2005, Dill ran for elective office for the first time, taking on a conservative Republican in a special election for a seat on the Cape Elizabeth Town Council.

“George Bush got elected for the second time, and I was just beside myself,” she says of her motivation. She lost by six votes, but ran again in the regular November election that year and won.

 

Taking on Augusta

Dill had served just one year when she ran for and won a seat in the Legislature, defeating another conservative Republican, Jennifer Duddy, by 144 votes. For two years, Dill served in both positions simultaneously, allowing her law practice to go largely dormant.

Several councilors who served at the same time as Dill declined or did not respond to interview requests for this story. News accounts suggest that the highest-profile issue was a proposal Dill backed to defray the costs of maintaining the popular, town-owned Fort Williams Park by imposing a $5-per-vehicle admission fee for nonresidents. Town voters untimately overturned it.

In Augusta, Dill drew attention by taking provocative stands. She refused to follow tradition and vote in support of the Republicans’ choice for House speaker, Bob Nutting, because of his having owned a pharmacy that overcharged MaineCare by $1.6 million and still owing the state $1.2 million when it went bankrupt in 2003.

She sponsored measures to allow the recall of the governor and to prohibit nepotism in state government (both in response to actions by Gov. Paul Le-Page). She boastfully blogged of having won re-election in 2010 without having knocked on a single door, instead connecting with voters using a laptop purchased with Clean Election funds.

She also spearheaded the creation of the “three-ring binder,” a recently completed expansion of broadband Internet in rural Maine, and helped obtain millions in federal grants to make it happen.

“I was new in the Legislature and was just foundering around, trying to figure out what my role was. I wasn’t doing my law and I wasn’t the chair of a committee, and I wanted something to do.” A colleague told her: Pick something and become an expert in it. Dill noted that the federal stimulus package had money for expanding broadband and researched and promoted the issue wholeheartedly. “In the Legislature, I was like Mrs. Broadband,” she says.

Dill handily won re-election to the House in 2008 and 2010 and, in May 2011, a special election for a vacated state Senate seat. She also unsuccessfully challenged Emily Cain, D-Orono, for House minority leader.

She’s a vocal proponent of the creation of a North Woods National Park and in August founded a group, Friends of the North Woods, to further the effort. Burt’s Bees co-founder and philanthropist Roxanne Quimby, who wants to donate land for the park, has donated $12,000 to Dill’s leadership political action committee and another $2,500 to her U.S. Senate campaign.

“For people who follow Maine politics, she has a reputation for being tenacious, scrappy, willing to say what she is thinking and to let the chips fall where they may, even if they rub her own party the wrong way,” says political scientist Jim Melcher of the University of Maine at Farmington. “She has a strong profile as a liberal, and there are parts of the state where she might be seen as representing a southern Maine point of view that they don’t care for, particularly concerning the national park issue.”

She has tangled regularly with LePage in public, but says in person they get along well.

“I have a good relationship with the governor, and when I was elected to the Senate, we had fun and he gave me a big hug,” she says. “We have no similar views when it comes to politics, but I don’t hate him.”

Melcher says Dill and LePage are similar in some respects. “They’re mirror images of each other, in that they both say, ‘I’m going to say what I’m going to say, and if you’re going to be offended about it, that’s too bad,’ ” he says. “They are both farther from the middle than the average person in their parties, and there are parts of the state where they don’t play very well.”

Reaching for Capitol Hill

Early this year Dill, a half-term state senator, took the most audacious step of her political career, announcing she was running against popular three-term incumbent U.S. Sen. Olympia Snowe, who Dill felt was moving too far to the right.

When Snowe subsequently announced her surprise retirement, Dill was briefly elated.

“I ran out to the car and my heart was pounding,” she told the Portland Press Herald in May. “It lasted about an hour before the reality hit that now everyone would be getting in.”

When King jumped into the race, he cleared the field of many of Dill’s strongest potential primary rivals, including U.S. Rep. Chellie Pingree, D-1st District, and former Gov. John Baldacci.

She went on to win her party’s four-way primary by 9 points, but has been well behind King and Republican nominee Charlie Summers in polls. The national Democratic Party hasn’t endorsed her, and all of the television ads in support of her candidacy were paid for by Republicans seeking to weaken King’s left flank.

Pyle, Dill’s childhood friend, hopes she can defy the odds. “She’s an honest person with a lot of integrity who really values trying to make this world a better place to live in,” she says. “I think we need more Cynthia Dills in this world.”