When Ayanna Pressley ran for City Council At-Large in 2009, six other Dorchester residents were on the ballot. Pressley, a Chicago native and former aide to John Kerry, had moved into the neighborhood the previous November, after living in other parts of the city like the Fenway and Back Bay.

In all, fifteen candidates ran for four at-large slots that year, a stampede prompted by the departure of two at-large councillors – Michael Flaherty of South Boston and Sam Yoon of Fields Corner – who left hoping to knock Mayor Thomas Menino off his perch. Of the Dorchester seven, and only Pressley grabbed one of the slots.

Four years later, she is one of two at-large incumbents, along with Stephen Murphy, a Dorchester native now living in Hyde Park, running for reelection. (Councillors are on a different municipal election schedule than mayoral candidates, having to run every two years instead of four.)

As was the case in 2009, two councillors at-large, John Connolly and Felix Arroyo, are giving up their seats to run for mayor, although Menino will not be on the ballot. This year, 19 at-large candidates have answered the bell, a number that includes five Dorchester candidates: Pressley; Annissa Essaibi-George, a high school teacher and local yarn shop owner; local political activist Catherine O’Neill; former City Councillor Gareth Saunders, and perennial candidate Althea Garrison.

The other candidates are from the North End, Charlestown, the South End, Mission Park, Jamaica Plain, East Boston, Roxbury, Hyde Park, and West Roxbury, to name just a few neighborhoods.

For Pressley, incumbency certainly has its advantages, like the ability to appear with Attorney General Martha Coakley and team up on a campaign called Eliminate DEBT (Deceptive Education Business Tactics), which is targeting the marketing that some for-profit schools create in a bid to lure low-income students.

On a recent Tuesday, Coakley stood with Pressley in a sun-soaked room inside the Reggie Lewis Center in Roxbury, and praised the councillor. Pressley, Coakley said, is a “force of nature on her own.”
After the meeting, Pressley noted that she is “DBC” – Dorchester By Choice. “This is the biggest neighborhood in the city, debatably or arguably the most civically engaged, and also the most diverse,” she said. “So oftentimes, you know, my daily experiences in Dorchester directly influence how I go about trying to effect change.” For example, the neighborhood she lives in, Ashmont, has restaurants that are economically vital to their communities, like Tavolo and Ashmont Grill, she said.

“And that directly informed my push for liquor license reform,” she said. “When I need examples of youth leaders and activists, I think of the B.O.L.D Teens in Codman Square. When I need an example of the difference that open space can make in our community, I think about Dorchester Park.”

Having topped the ticket in 2011 – Pressley received over 37,500 votes and campaigned across the city with West Roxbury’s Connolly – she is widely expected to be among the final eight candidates who emerge after the Sept. 24 preliminary to face off in the Nov. 5 final election.

“All of the at-large candidates, we joke that we should be car-pooling,” said Essaibi-George, the yarn shop owner who considers East Boston a second home – she has spent 12 years working there as a high school teacher. She also spends a lot of time campaigning in other neighborhoods in a bid to broaden her campaign’s reach, including Allston Brighton, South Boston, Roxbury, and West Roxbury, she said.

Essaibi-George, who was raised in Dorchester and married a neighborhood native, Doug George, displayed an early interest in politics: She was elected to her school’s student council and later served as an intern with US Sen. Max Baucus (D-Montana). Public safety and education remain the top issues voters want to chat about the most, she said, and she hopes to focus on improving high school education due to her background. She notes that she is the “only mother” – she is the mother of an 8-year old boy and 7-year-old triplets – and the only Boston teacher in the race.

“The benefit of having so many Dorchester candidates is that it really builds a lot of excitement in Dorchester, because there are people interested in stepping up and representing the city as a whole,” she said. “It signifies a good talent pool in Dorchester and an intensive activism.”

Catherine O’Neill is one of those intense activists, having worked for various politicians over the past decade, from Michael Flaherty to state Sen. Linda Dorcena Forry. A playwright as well, O’Neill, who was born and raised in Lower Mills, has lived in Savin Hill since 1998. “I understand what it’s like to live in Dorchester when you’re dodging bullets and I understand what it’s like to live in Dorchester when you’re buying sushi and a latte,” she said.

She plans to be an “independent” voice who thinks the Boston Redevelopment Authority, the city’s top planning agency, should be “blown up” and she opposes the East Boston casino. Her base is in Dorchester, she said, but she also is seeking voters in West Roxbury and elsewhere in the city, including South Boston and Mattapan. “I think those neighborhoods, those communities, they know me,” she said.

Senior citizens also remember her cable access interview show. “I had a woman come up to me at an event and she said to me, that she would do anything she could to help me because her recently deceased father loved my television show. I almost started to cry,” O’Neill said. “So I have those intimate connections with a lot of people.”

Gareth Saunders is another person hoping to leverage the connections he has forged, particularly when he was the councillor for District 7. “I provide proven experience,” said Saunders, when asked what differentiates him from the 19-person field. A pro-life Democrat, his path to victory, Saunders said, runs through Roxbury, parts of Dorchester, Jamaica Plain, and “people of faith.”

Saunders has lived in Dorchester for four years, and previously lived in Roxbury and Mission Hill. He was born in the Bronx and moved to Boston after he served in the US Air Force. He currently works on licensing policy at the Registry of Motor Vehicles.

Garrison, who frequently runs for various public offices, first tasted life as an elected official when she won a race for state representative. A self-described conservative, Garrison recently told Boston magazine that she will be calling for an independent municipal audit of the city’s finances while she referred to her potential colleagues as “rubber stamps.”

Even if most Dorchester candidates don’t make it, and most won’t, if history is any guide, there is life after an unsuccessful run for office, which was particularly so after the 2009 race: Tito Jackson ran for district city councillor and won, replacing Chuck Turner in District 7; Jean Claude Sanon, a Haitian-American activist, is running for the District 5 City Council seat, which Rob Consalvo is giving up in the hope that he’ll land in the mayor’s office; Ego Ezedi, former executive director of the Roxbury YMCA, is a reverend at New Empowerment Christian Church; Robert Fortes is a consultant; Hiep Nguyen is helping Connolly in the mayor’s race; and Bill Trabucco, a Boston EMT, has stayed involved in his local civic group.

As for the current crop of Dorchester at-large candidates, “they’re all working hard,” according to state Rep. Marty Walsh, the longtime Dorchester lawmaker who is running for mayor. “Certainly anything can happen.”

He’s sympathetic to the at-large candidates’ struggle to break through and reach out to voters who are perhaps fatigued by the constant electioneering that hasn’t stopped since last year, the trial of gangster James “Whitey” Bulger, and the aftermath of the Boston Marathon bombings. “There’s just so much happening,” Walsh said. “I’m running for mayor and it’s difficult to get the message out.”