Present day Dorchester lays claim to being the biggest part of Boston, in terms of land mass and population. But, big as it is today, Dorchester was once much, much larger.

At its height, the town of Dorchester nearly reached the Rhode Island border. It included parts of present day South Boston, Hyde Park, Roxbury, Foxboro, Dedham, Wrentham, Canton, Sharon, Raynham, Mattapan, Quincy, and the entire towns of Milton and Stoughton.

What if Dorchester had maintained those historical borders? What if Dorchester had, as one resident from the Boston annexation period was recorded saying by William Dana Orcutt in his book, Good Old Dorchester, “a few feet more depth of water along the ten miles of shore which formed her sea boundary?

Would we be living in the City of Dorchester, with Boston as one of our neighborhoods?

Earl Taylor, President of the Dorchester Historical Society and a resident of Ashmont Hill notes:”I’m not sure it’s a desirable state of being to be separate from Boston. I doubt that we have the taxpaying infrastructure. We don’t have huge businesses, the downtown [area] has a lot of big commercial property, whereas Dorchester is nearly all residential.”

A City of Dorchester would thus require a greater involvement amongst Dorchester residents. All the human resources that are there would make it work if it could, I just don’t know if the monetary resources are there” to support the public services Dorchester would lose from the City of Boston.

Kevaughn Arthur, 27, of Grove Hall, agrees with Taylor.

“It’s great to have Dot pride, but it takes a lot more than that to be a successful city. I don’t believe it would succeed unless there was already a full infrastructure in place, which there really isn’t.”

Carla Poles, 24, of Neponset believes such a city “would succeed.”

“The intrinsic diversity of Dorchester provides the cultural and intellectual wealth necessary for success in the maintenance of a city,” Poles said, although, for the record, much of Dorchester’s diverse population settled here after the annexation into Boston. But, if Dorchester had a viable harbor, many of these immigrants might have settled in Dorchester rather than Boston proper.

As the populace grew, bits of Dorchester segued off to become their own towns. Once the City of Boston claimed South Boston and later annexed Roxbury, it became clear to the residents of Dorchester that annexation of their town would be next on the agenda of the governments of Boston and Massachusetts.

Dorchester annexationists promoted a union with Boston and on June 22, 1869 - in a vote held on the site of what is now the Great Hall in Codman Square - approved an annexation into Boston by a vote of 928 to 726. The next year, Dorchester ceased to exist as an independent town and became the biggest part of the City of Boston. By the 20th century, the neighborhood accounted for 20 percent of the population of Boston.

Over the past few years, Dorchester has experienced a revival with new construction occurring all over the neighborhood and up scale restaurants and shops opening up in nearly every area. Young professionals have flocked to Dorchester thanks to below average rent and home prices, compared to the general Boston area. In 2007, Business Week named Dorchester one of Americaâ’s “Next Hot Neighborhoods.”

Vincent Baker, 46, and Louis Baker, 51, brothers from Savin Hill, exemplify the local business owners that have cropped up in Dorchester over the past decade. The Bakers own the Domestic Boot shop on Dorchester Avenue and are proud lifelong residents of Dorchester. Vincent thinks a City of Dorchester “is not doable right now. The infrastructure is in place already for the whole city. Creating a new city would be a logistical nightmare.”

Louis countered that the new city could save by “not paying for school buses and sending kids to local neighborhood schools within walking distance. Even with any savings the new city might realize, Vincent strongly emphasized “we would need more local businesses. It would happen on its own and tax incentives would encourage new businesses.”

The gentrification Dorchester is experiencing today is something supporters of the Mandela Initiative, a movement by Roxbury activists to form a new city composed of Roxbury, Mattapan, and parts of Dorchester, the South End, Jamaica Plain and the Fenway, sought to avoid. The City of Mandela would have cordoned off roughly a quarter of Boston’s mass and population into a new 12.5 square mile city of approximately 150,000 residents.

The Mandela Initiative was voted down on a 1986 state ballot and once again on a 1988 city ballot. The mayor’s office stated that the proposed city would likely face immediate bankruptcy. The loss of tax revenues from commercial properties in the downtown area would have left a shortfall of $100-135 million, according to the Mayor Flynn’s administration. A smaller secession measure in South Boston was likewise rejected by the voters in 1992.

Even with the influx of new businesses and residents, Dorchester would likely face a similar budget shortfall if it chose to secede today. Dot pride and the working class ethic would be its two biggest assets. But these assets would not be enough, according to Corrine Tobias, 24 of Clam Point.

“Dot Pride is great, but it doesn’t bring in the tax dollars necessary to run the neighborhood, the roads are already bad enough,” she argues.

Since 1904, on the first Sunday of June, Dorchester residents have joined together to celebrate the creation of Dorchester in 1630. Dot pride is on display in full force during the annual parade that travels across the entire neighborhood, from Lower Mills right to the edge of the Polish Triangle. That pride is expressed daily too. From Dot stickers to bloggers touting the diversity and energy of Dot to the lifelong inhabitants who could have moved to greener pastures but decided the grass is plenty green right here.

Already home of the first free public school in the USA, the first community health center, the first settlement in Suffolk County, and the first government run by town hall meetings, could Dorchester become the first neighborhood to successfully secede from the City of Boston?

Some of the men who initially pushed annexation back in the 19th century would surely oppose such a move. A pamphlet written by N.W. Coffin counseled: “And by annexation we shall avoid a great evil - the possibility of a city organization of our own, to be delivered from which every good citizen should constantly pray.”

Even then, the Dorchester annexation supporters knew that the management of a city would require far more resources than Dorchester possessed. Stephanie Simpson-White, 24, of Adams Street, agrees with the sentiment.

“Frankly I would love to see the people of my city spend their time and effort on fixing the problems we have instead of worrying about whether to become a separate entity or not. The quality of living in Dorchester has been on the rise for the past few years. What would happen to that progress if we lost support from the City of Boston”

Roseanne Foley of Codman Square adds: “Without a few more university juggernauts, and with most of our fertile agricultural land now covered by development, it’d be tough to find a successful niche in which to succeed on our own, although maybe the “green” economy might be our ticket.”

Andrew Binns, 25, of Uphams Corner provides perhaps the most compelling argument against an independent Dorchester.

“I love being from Dorchester, but I also love being from Boston. Growing up in Dorchester and Boston has given me exposure to a hugely diverse world. Seceding from the City of Boston would harm that exposure as Dorchester would become cut off from the rest of the city.”

Adam Pieniazek is a lifelong Dorchester resident who owns his own web consulting company, The 42nd Estate, and who blogs at his site http://www.adampieniazek.com.