Boston At-Large Councilors Ayanna Pressley and John Connolly talk to John Flynn, Jr. outside his Cerdan Avenue home before speaking to his mother. Credit: David Ertischek

Before hitting hilly Cerdan Avenue, At-Large Boston City Councilor Ayanna Pressley pulled on some sneakers for some door knocking and coincidental exercise. Fellow sitting At-Large City Councilor John Connolly decided to keep his dress shoes on as the duo hit the West Roxbury neighborhood he grew up in.

Pressley and Connolly recently joined their campaigns as the Nov. 8 election looms. Also all four incumbents, including Council President Stephen Murphy and Felix Arroyo, initially all asked residents to vote for the quartet, in hopes of keeping former city councilor and mayoral candidate Michael Flaherty off the council.

As the two walked they talked about their union and friendship, which dates back at least six years.

“This wasn’t about a white guy trying to get black votes, or a black woman trying to get white voters…” said Connolly.

Connolly said they have cosponsored eight pieces of legislation during Pressley’s first term, more than any other legislation they cosponsored with any of the 11 other councilors.

The two met during Connolly’s first run at City Council and their friendship continued while Pressley was US Sen. John Kerry’s political director.

While knocking on doors the two spoke to residents about how Connolly is about schools and Pressley is about families, two very-intertwined issues. Pressley said strong schools need strong families.

Continually Connolly was saying hello to residents who already knew him, many with Connolly signs on their lawn. “She works on families, and knows the importance of parents and fathers,” said Connolly, or some iteration of that motto repeatedly.

Taking her cue from Connolly, Pressley would then speak about her work with youth, girls, women, and families. The two would then of course ask for the residents’ votes.

“Education is the equalizer and families are the stabilizer,” said Pressley, who has worked on legislation to stop human trafficking, empower girls in schools and strengthen families.

As a part of their recent campaign share, Connolly’s campaign can legally match dollar for dollar of the funds that Pressley’s campaign raises. The sharing of funds started because Connolly has a plush war chest while Pressley’s funds have lagged.

Pressley said door knocking is the best way to learn what’s happening in the neighborhoods. “One on one contact with constituents affirm what’s working and isn’t. We often learn about issues that need to be addressed.”

At one house, a resident complained about Occupy Boston demonstrators downtown. Connolly and Pressley listened carefully to the woman’s opinions. Connolly and Pressley both said they were concerned about the costs of Occupy Boston to the City.

Said Connolly, “If West Roxbury knows (Pressley’s) priorities and what she supports they will vote for her… She’s only been on the council two years and it is hard to know every neighborhood, yet alone your own.”

Sara Smolover asked, “Are you working well with Matt?” referring to District 6 Councilor Matt O’Malley. Both Pressley and Connolly said they were and characterized O’Mallley as someone born to be a Boston City Councilor.

Said Pressley while walking, “The issues never change: jobs, public education, public safety.” She added there are often bullet points under those issues such as housing and transportation.

For resident Larry McDonough, he didn’t need to hear Connolly and Pressley’s pitches, and why they are campaigning as a pair, “It’s a smart move. Brilliant. If you say it’s legit. I believe it.”

City Councilor John R. Connolly has something Ayanna Pressley, his council colleague, covets – an overflowing campaign treasury and strong appeal in some of Boston’s highest voting precincts. Pressley, meanwhile, has something Connolly wants – more pull in minority precincts, more credibility with the full rainbow of the electorate in the city he would like to run someday.

City councilors Ayanna Pressley and John R. Connolly campaigned together…(Jim Davis/Globe Staff)

Together they have something people have said for years that Boston needs – unity. A white politician and a black one, putative rivals, working together. Not just words – common ground, in fact.

It may well be the first partnership of its kind, at least in this town. Connolly and Pressley have agreed to share resources and split campaign costs in a fierce reelection fight. The alliance defies the entrenched norms of politics of Boston, where voting has historically been defined by neighborhood and ethnic loyalties.

The pact was born of necessity: Pressley is in danger of losing her seat just two years after becoming the first woman of color ever to serve on the 13-member City Council. And of ambition: Connolly doesn’t talk about it this way, but he has long been spoken of as a likely mayoral contender, and taking a stand as bridge-builder can only burnish his citywide image.

On the campaign trail, where Connolly and Pressley have been making daily appearances together for more than a week, they describe the partnership as a “natural progression’’ of a longstanding friendship and close working relationship. But they also speak bluntly about the dynamics of an off-year municipal election without a mayoral race to draw people to the polls.

“Conventional wisdom says that in this municipal election, traditional voters – code words for white – will not vote for me,’’ Pressley told Connolly supporters last week as they sipped white wine at an intimate South End fund-raiser hosted by one of his former classmates. “I think that’s insulting to me. And to white voters.’’

Pressley needs a boost as Michael F. Flaherty, a mayoral finalist in the last election, is attempting to win back the seat he held for years on the City Council. His presence on the ballot could put the squeeze on other incumbents, with Pressley likely the most vulnerable.

Connolly has a war chest brimming with $245,000, which dwarfs Pressley’s $38,000 and totals almost as much as all the other at-large city council candidates combined. Sharing campaign costs is allowed under state campaign finance laws as long as the expenses are divided equally.

The 38-year-old incumbent has strong support in his home neighborhood of West Roxbury and other predominantly white enclaves of Boston, where voter turnout is traditional higher in municipal elections.

“I take very seriously representing the whole city. I’m always trying to work with people to bring neighborhoods together and people together,’’ Connolly said, dismissing speculation about ambition for higher office. “Ayanna Pressley and I have had very different life experiences, but we share a common vision for a city coming together.’’

The Boston City Council has four at-large seats that represent the entire city. All four incumbents – Connolly, Pressley, Stephen J. Murphy, and Felix G. Arroyo – are running for reelection.

The most substantial challenge will come from Flaherty, who served on the council for a decade before leaving to run unsuccessfully for mayor last year. Two other competitors, Will Dorcena and Sean H. Ryan, will also be on the ballot, though they have been slow to raise money and gain traction.

In Boston, it will be a first for two at-large candidates competing for the same votes to form a team and split campaign costs, said Lawrence S. DiCara, a former City Councilor and longtime watcher of city politics.

“It is ingenious and risky simultaneously,’’ DiCara said. “It’s risky because no one can accurately predict the numerous combinations of votes in a multiple candidate, at large election.’’

Pressley and Connolly seem to be aware of the pitfalls.

“I’d never want to take my own reelection for granted,’’ Connolly told supporters at his South End fund-raiser. “But according to the political pundits [Pressley] is most at risk of losing. That would be a tragedy. I couldn’t look my wife or daughter in the eye If I didn’t do everything I could to make sure that doesn’t happen.’’

Pressley became the first woman of color ever elected to the City Council in 2009, when she captured an open seat by finishing fourth in the at-large race with almost 42,000 votes. She won by a comfortable margin, beating the fifth place candidate by almost 12,000.

But the Menino-Flaherty mayor’s contest drove 111,190 voters to the polls, which represented a citywide turnout of 31 percent. Less than half of that turnout is expected on Nov. 8. The last off-year municipal election in 2007 saw just over 46,000 ballots cast.

Those who show up for low-interest elections tend to be older, white, and more conservative, a dynamic that could hurt Pressley.

Some believe that no matter what Connolly and Pressley do to bolster their collective candidacies, few voters are likely to head to the polls on Election Day. That’s particularly true in communities of color, said Paul Watanabe, a professor at the University of Massachusetts Boston who specializes in ethnic politics.

“In a low turnout election, maybe moving a few votes this way or that may have some immediate impact,’’ said Watanabe. “But the notion of deriving some future political benefits from this, I actually don’t see it.’’

Partnerships between two candidates is most common at the gubernatorial level, where teams often join forces and run simultaneously for governor and lieutenant governor. But it also happens on occasion at the local level, said Jason Tait, a spokesman for the state Office Campaign & Political Finance.

“Joint expenditures are OK so long as the costs are shared proportionally,’’ Tait said.

Connolly grew up in Roslindale. His father served as a state representative and secretary of state. His mother is the chief justice of the state’s district courts. Connolly graduated from Roxbury Latin School, Harvard University, and Boston College Law School. He taught middle school for three years before becoming a lawyer and has made education the focus of his work on the City Council. The last election, he won the most votes in the at-large race.

Pressley, 37, has a very different biography. Born in Chicago, she was raised by her mother because her father struggled with addiction. Pressley has talked publicly about being sexually abused as a child and sexually assaulted as a college student when she attended Boston University. But she went on to work for former US Representative Joseph P. Kennedy II, and ultimately became political director for US Senator John F. Kerry.

In West Roxbury on Friday, Ann Sullivan, 78, said she votes for Connolly “every time’’ because she meets him in her neighborhood so often. Connolly was there again that day to talk to Sullivan and a few dozen other seniors at a turkey, stuffing, and gravy lunch at the Roche Family Community Center. This time he appeared with Pressley and actively urged the seniors to give her one of their four votes.

“I’ll think about it,’’ Sullivan said with a shrug after the candidates were out of earshot.

But then Pressley took the stage. She told the seniors about her tough upbringing, her work with Kennedy and Kerry, and quipped that as the only woman running for reelection, “Somebody, ladies you know this, has to keep these men in line.’’

Sullivan laughed. So did others. And they listened as Pressley outlined her efforts to combat poverty, teen pregnancy, and stabilize families.

“I like her,’’ Sullivan said.

But City Councilors Tito Jackson and John Connolly are looking to change that and continued their fight yesterday to raise the eligibility age for school-ditchers from 16 to 18.

“We … allow a 16-year-old to put a low ceiling on their future by leaving school,” said Connolly during a city council meeting.

Efforts to file a home rule petition at the state level to make the changes moved forward yesterday, and a hearing on the proposed bill was scheduled for next week.

Jackson said city officials could to change the lives of young people in Boston and give them a good start to life.

“We live in a city with 34 colleges and universities and 150,000 college students and we want [BPS] kids to have the opportunity to land in one of those universities,” he said.

But Councilor Bill Linehan, having been a troubled student himself, doesn’t think the city should mandate a law to keep kids in class, he said.

“[BPS] will have very destructive students … with all the other good, matriculating students for two more years. One student in a class of 30 can make a mess of [that class].”

Councilors will discuss ways in which city government can make Boston a healthier and more environmentally friendly place to live and work. Topics of discussion will include ways to ensure that government processes have fewer negative impacts on the environment, how Bostonians can involve themselves in government activities to encourage the City to adopt green initiatives, and how Boston City Council’s vision of greener neighborhoods will shape these efforts across the city in years to come.

Connolly is the former chairman and O’Malley is the current chairman of the council’s Committee on Environment and Health. Both councilors are committed to making Boston a healthier and greener city and have worked with West Roxbury Saves Energy on numerous green initiatives in the Parkway.

Boston GreenFest 2011 is taking place on City Hall Plaza from Thursday, Aug. 18 to Saturday, Aug. 20. The event is expected to draw thousands of people from Boston and its surrounding areas to celebrate and advocate green practices in everyday life and in city policies.

Councilor At-Large John Connolly with Cate Arnold, a resident of West Roxbury and faculty advisor to the Boston Latin School Youth Climate Action Network, and the Co-President of BLS Youth CAN, Eshe Sherley at a Youth Green Jobs program organized by Dorchester Bay Youth Force and BLS Youth CAN.

City Councilor At-Large John Connolly gets ready to set off on the first day of the Hubway program.

Fellow incumbent Stephen Murphy, who also is serving as City Council president, fell short, receiving 10 votes, six votes shy of the number needed for an endorsement. Arroyo received 20 votes and Pressley and Connolly both received 19 votes.

The endorsements followed the city’s first at-large candidates’ forum, attended by six of the seven candidates running for the four City Council At-Large slots. A summary of candidates’ remarks is available here at Universal Hub. See this week’s Dorchester Reporter on Thursday for more on the forum, which was moderated by the Boston Phoenix’s David Bernstein.

Pressley was unable to attend the forum. In a letter to Ward 5 Democrats, Pressley apologized and wrote that her mother Sandra is “fighting for her life.”

“My mother has been hospitalized for weeks and she’ll likely remain there for the foreseeable future,” Pressley wrote. “Her condition is grave and it’s not hyperbole to say she’s facing a life or death battle. For now, I need to spend most of my time at the hospital with my mother. I serve as her medical proxy and the seriousness of her condition requires me to make decisions about the course of her treatment, day and night. But watching my mother fight her illness has only strengthened my resolve to win reelection in November. My mother would have it no other way.”

The breakdown for those who did not receive the Ward 5 Democratic Committee endorsement includes: Former City Councillor At-Large Michael Flaherty (8 votes); Jamaica Plain’s Sean Ryan (6 votes); and Hyde Park’s Will Dorcena (4 votes).

State Rep. Martha Walz, a Back Bay Democrat who is a voting member of the ward committee, cast her votes for Arroyo, Flaherty, Murphy and Pressley.

Joshua Dawson, Ward 5 chairman and executive director of the Steve Grossman Committee, declined to cast a vote.

In 2009, the ward committee endorsed Connolly and Pressley, a former committee member who now lives in the Ashmont area of Dorchester.

Councilors John Connolly and Tito Jackson said that they believe that 16-year-olds are too young to understand the dire consequences of quitting school and that a roughly century-old state law that allows them to do so is outdated.

They point to research that shows that high school dropouts make significantly less money than college graduates and are more likely to depend on welfare or go to jail.

“We don’t let 16-year-olds vote or buy alcohol, but we allow them to decide not to stay in school; it doesn’t make sense,’’ Connolly, chairman of the council’s Education Committee, said in an interview yesterday. “We don’t want a 16-year-old closing off his or her future by making a hasty decision.’’

The push is being made as a similar effort to raise the state’s dropout age from 16 to 18 has sputtered on Beacon Hill, though some legislators continue to advocate for the idea.

During yesterday’s City Council meeting, the two members filed an order to hold a public hearing on raising the city’s dropout age, the first step needed to gain the council’s backing in pursuing a home-rule petition in the Legislature.

Connolly and Jackson said that Massachusetts needs to take action quickly and that the proposal they are developing could serve as a test case for increasing the compulsory school age statewide.

“The clock is ticking,’’ Jackson said in an interview. “We refuse to give up on our young people. Raising the age raises the expectations on young people.’’

Over the past decade, a handful of states have increased compulsory school ages to either 17 or 18. New Hampshire raised its dropout age to 18 at the start of the last school year, and its dropout rate that year was cut nearly in half, to slightly below 1 percent.

Matthew Wilder, a spokesman for Boston’s School Department, said that Superintendent Carol R. Johnson and the School Committee are looking into the idea and have not yet taken an official position.

But Wilder said: “We feel the dropout crisis is an important issue that we are working hard to remedy. We are proud we have a dropout rate that has been the lowest in nearly three decades, but too many students are dropping out.’’

Last year, 6.8 percent, or 1,196, of the city’s 17,498 high school students dropped out, compared to 2.9 percent statewide, according to the state Department of Elementary and Secondary Education.

The Boston School Department has made a number of changes to keep more students in school, such as expanding online courses and tracking down dropouts to persuade them to return to school.

In September, the Legislature’s Joint Committee on Education will hold a hearing on bills filed to raise the compulsory school age across the state, including one by Representative Martha Walz, a Boston Democrat, that calls for a variety of intervention programs.

Connolly and Jackson said their home-rule petition, like Walz’s bill, would also call for the creation of new programs or the expansion of current programs that are getting results.

Donna Walker, 17, of Dorchester, said raising the dropout age is a good idea. Walker recently returned to school, enrolling at Dorchester Academy while taking courses at the district’s re-engagement center.

“I left school for a period of time, and that was the biggest mistake I made,’’ said Walker. “You can’t do anything without a high school diploma.’’

A motion filed by City Councilors John Connolly and Tito Jackson to raise the high school dropout age from 16 to 18 was met with enthusiasm by their colleagues who said the city needs to send a message to local students and their families about the importance of staying in school.

“A college degree is the key to economic and social mobility in our society,” Connolly said at Wednesday’s Council meeting. “Raising the age to 18 sends a signal to our young people that we’re not just talking about college, we think it should be a reality.”

In the 2009-10 school year, 5.7 percent of high school students enrolled in Boston’s public schools dropped out. Raising the age at which a high school student can choose to leave school would help lower that number, Jackson said.

“It’s really an opportunity to give the superintendent as well as the school system another tool,” he said Wednesday. “This is about us helping our young people to have the opportunity to really make a good life for themselves and their family.”

A Northeastern University study conducted in 2007 found that high school dropouts make up 70 percent of jail and prison populations in Massachusetts. In addition, the average high school dropout ends up costing state and federal taxpayers almost $275,000, the study found.

If Massachusetts were to raise the dropout age, it would join twenty other states that already require students to stay in school through the age of 18. New Hampshire recently raised its compulsory attendance age and has seen a “dramatic decrease” in its dropout rate, Jackson and Connolly wrote in an order submitted to the Council.

Councilor Charles Yancey expressed wholehearted support for the measure, which would bring the state’s educational system into the 21st century, he said.

“When we established 16 years of age as the age [at] which young people can decide their future it was a totally different context than what we have today,” he said. “I could not be more enthusiastic in my support of this.”

The matter was referred to the Council’s Committee on Education.