A City on the Edge

A property the size of the Old Port, located on the waterfront, is ready to be transformed into a vibrant urban neighborhood. Is 58 Fore Street the future of Portland? Or will this project be stopped before it even breaks ground?

Picture this: from a trail along the ocean, you look inland and see buildings that rise gradually in height like stairs. Old brick warehouses, converted into modern lofts and storefronts, sit easily alongside playful examples of contemporary architecture. Narrow streets wind between the beguiling blend of old-meets-new. Cars cruise slowly alongside bikers and pedestrians, and a smattering of trees lends leafy green shade to the afternoon. Music pours from the open window of a coffee shop and commuters stop on their way home from work to listen. As you walk away from the water, the city rises with you, leading you rapidly to the top of the hill. Turn back and gaze down. Blue water stretches out, dotted with green islands and the graceful white forms of sailboats.

This scene could be from a European novel, a story set on the shores of the Mediterranean. It could be a pipe dream, an idealized urban landscape that will never quite exist. Or it could be Portland.


Casey Prentice, one of the would-be builders of this vision, sits behind a conference table at the CPB2 office on the Portland waterfront. He flips through slide after slide of maps, state permits, and construction plans, speaking quickly and confidently, pausing rarely to laugh or make a casual aside. He has an audience of one, but the 29-year-old developer informs me that he’s given this presentation many times before—he’s talked to state officials, to potential investors, to historical preservation groups, and to environmentalists. “It’s been an extremely complicated deal,” he admits. “I was just young and naïve enough to try it. Other developers would have walked away long ago.” Not Prentice. Since 2009, he’s had his sights fixed on 58 Fore Street. Despite his considerable accomplishments—Prentice is the founder and president of the Prentice Organization, which, along with his family, owns and operates Chebeague Island Inn, Five Guys Burgers and Fries, Evo, and other Portland properties—he’s retained enough youthful optimism to keep working toward this “extremely challenging” piece of land. 58 Fore Street is his moonshot, his white whale.

The property in question is a 10.5-acre parcel of land located on the northern edge of the Old Port, directly southeast of Munjoy Hill. Right now, it is remarkable only in its decrepitude. Overgrown with weeds, it’s accessible via the Eastern Promenade Trail and the Narrow Gauge Railroad. Unless you’ve walked along the water from the Old Port to the Eastern Promenade, you might not have had a reason to visit this narrow, undeveloped strip of Portland. And if Phineas Sprague Jr. had held onto his inherited land, you probably wouldn’t be reading this right now, much less considering the possibility of an entirely new urban neighborhood blossoming on the corner of the peninsula.

This alternative future very nearly came to pass. “Phineas Sprague had some very specific thoughts about what would happen to the property. He talked to a lot of prospective buyers, but he didn’t feel comfortable with them,” says Tony McDonald of the Boulos Company. McDonald first started working with Sprague back in 2008, but it wasn’t until 2012 that Sprague finally decided to sell 58 Fore Street to CPB2 for an undisclosed amount. The deal took so long partially because it was so complex. Not only did Sprague require his potential buyers to find him a place on the peninsula where he could relocate his boatyard—a stipulation that led Prentice and his group to purchase, and sell again, a 26-acre parcel on the western Portland waterfront—he also wanted a say in what came next. “The land had been in his family for a very, very long time, and he considered himself the steward of the property,” explains McDonald. “He wanted to see a world-class project built there that would be a tribute to the City of Portland. He wanted to see something his grandkids and great-grandkids would be proud of.” Big hulking condo buildings and aboveground parking garages wouldn’t cut it. That wasn’t the legacy Sprague wanted for his name; it wasn’t the dream he had for his Portland.

Fortunately, Prentice had a leg up on the other bidders. He had been talking to Sprague since 2009, laying the groundwork for the deal, and in the process, building a lasting friendship with the seasoned boatman and lifelong Mainer. While other developers were pitching plans for condo units, Prentice came to the table with another idea. “I realized that other developers were looking at the property the wrong way,” he says. “The challenges of the site are so extreme that it called for a creative solution. The hillside is an 88- foot sheer drop. So how do you make that part of the city? How do you connect it to Munjoy Hill and make this one continuous cityscape? Who builds like that?” The answers, he decided, could be found by looking across the Atlantic, particularly at the Italian coastline community of Cinque Terre.

Inspired by old European settlements that build with the curve of the land rather than on top of it, Prentice and his group drafted up a plan that would turn the 58 Fore Street property into an entirely new neighborhood, complete with alleyways, mixed-use streets, small plazas, and urban parks. “The phrase I kept coming back to during my talks with Phin was ‘world class.’ He wanted something spectacular and I want to make something spectacular. I want to create a district that is popular enough and beautiful enough that it becomes an economic driver for the city,” he says. “Other developers simply saw this as a condo project, and because of that, they couldn’t justify the price.” Instead of building single-use structures, Prentice wanted to see restaurants and shop fronts, boutiques, and national retailers. He wanted to bring in coffee shops and art galleries—all the things that make a neighborhood unique. His plan includes high-end housing, and it also includes retail and office space, pedestrian-only brick streets, and a meticulously preserved “historic core.”

This out-of-the-box thinking not only impressed Sprague, it also attracted investors. Prentice recalls taking potential investors to Middle Street and spreading his arms wide. “Ten years ago, if you could buy all this, would you?” he asked them. They always answered yes.

However, building a new neighborhood isn’t as simple as buying some land and throwing down bricks. There were many more hoops to jump through before CPB2 could break ground, and there was one particularly pressing issue: the land wasn’t zoned for mixed commercial and residential use. In 2000, the city had started the process of rezoning Sprague’s property as part of the Eastern Waterfront Master Plan, which detailed the City of Portland’s vision for construction and investment in the area. (“The Master Plan envisions new development in the area to be an amenity and an asset to neighborhood residents, the greater city, and the visiting public… An integrated Master Plan allows the City to support the working waterfront, promote economic development, and enhance and protect our residential neighborhoods,” reads the preamble from the 40-page document). At the time, 58 Fore Street had a special designation found nowhere else in the city of Portland: “waterfront special use zone.” At first, Sprague was fine with the idea of rezoning his property, until he realized that changing its zoning would raise the value, and thus dramatically effect his taxes. In 2004 (and again in 2006—the city tried to rezone the area twice) he asked to keep his special designation, which he humorously dubbed the “waterfront Sprague useless zone” since it ensured that this property could continue to operate as a boatyard (but wouldn’t allow much else).

“In 2012, we went to the City and told them that we were ready to have them finish what they started,” explains Prentice. At this point, the team at CPB2 had solidified, with Prentice, Jim Brady, and Kevin Costello acting as co-managers. They wanted the City of Portland to finish the rezoning process, which would enable them to turn 58 Fore Street into a bustling city neighborhood. They were told the rezoning process would take about four months. It took over a year, but in the end, the rezoning amendment received a unanimous recommendation from the city planning board, and a seven-to-two vote in favor from the City Council. As of June 2015 it appeared that everything was finally in order. Sprague was happy, the City of Portland had approved, and CPB2 had the early drafts of a plan that, he believed, would turn the property into an attraction on par with the Old Port or the Arts District. And yet, another roadblock soon arose, one that could still stop CPB2 from moving forward entirely. “I would have never envisioned that there would have been any opposed to fulfilling the Eastern Waterfront Master Plan,” says Brady when asked about the Soul of Portland, a group that has banded together to stop the development of this particular corner of Portland through a referendum. “It was very well received when the plan was done. We saw this as a very easy, no-opposition thing to do. We thought we were doing exactly what the city wanted to have done with the eastern waterfront. I’ve been surprised that certain folks don’t agree with that vision.”

His mild words don’t quite express the frustration that the partners of CPB2 are feeling at this point. For the past two years, he has been negotiating with a number of different interest groups to get his plan for this site approved. He has consulted with historic preservation groups, urban planners, architects, Portland Trails, and Greater Portland Landmarks. Now, a single city vote could undo all that hard work.

The November referendum put forth by the Soul of Portland will establish a new “scenic zone” law that would prohibit landowners from building above a certain height in designated areas, which would be identified by a “Scenic Viewpoint Task Force.” The language of the document is disturbingly broad, defining a scenic viewpoint as a “discrete place or area from which the public may see a significant number of scenic resources within a scenic area of regional, state or national significance.” It would also give the City the right to enter onto private property to trim any vegetation that the Task Force deems overgrown, obscuring public views. In addition, Prentice points out that, if this law had been passed years ago, many of Portland’s most iconic structures never would have been built.

“I think the referendum is a tragedy,” says McDonald. The restrictions put in place for the proposed scenic zones would dramatically limit the options of any developer looking to build in downtown Portland—including, but not limited to, CPB2. Because several of the founding members of the Soul of Portland are Munjoy Hill residents with homes overlooking the property, the opposition to 58 Fore Street is subject to charges of NIMBY-ism (that is, their motivating sentiment is understood to be “not in my backyard”). For them, it’s their view that’s in danger. These homeowners could lose sight of the water. But the development’s advocates argue that, in opposing the growth of Portland, they’re really losing sight of the big picture.

“This referendum is a symptom of what is wrong with the system. You can get a group of people together with no experience and sign a petition and all the sudden you have a referendum in front of you that entirely undermines years and years of work done by qualified professionals, planners, architects, civil servants, with so much public interest,” says McDonald. “It’s scaring people away from wanting to do business in Portland and it has got to change.”


It should be clear by this point that I support the development of 58 Fore Street. I live in Portland and I want to see the city grow; I want to see housing prices go down on the peninsula, not skyrocket like they have in other highly desirable places to live. By building housing, CPB2 could help even out the cost of rent for many Portlanders. “I’m a big believer in the laws of economics and supply and demand,” says Brady. “One of the reasons that housing has become so expensive in the city of Portland is that the demand is outpacing supply. If you add more housing, all housing will lower in cost.” According to Brady and Prentice, CPB2 plans to build a diverse range of units. These condos and apartments should appeal to a wide swath of people, from small-living supporters and young, single professionals to retirees seeking to downsize and simplify. Although it is too early to tell exactly what will happen with 58 Fore Street, Prentice makes it clear during our conversation that he wants to see it become a “diverse, vibrant, beautiful” place to live. To him, “world class” isn’t an exclusionary phrase, but rather a way of articulating his high hopes for the property.

The idea that one small group of people could stop the city from growing in new, innovative ways seems wrong—and I’m not the only one who sees it this way. “It shouldn’t be so hard to do the right thing,” says Brady. “I never would have expected that people wouldn’t see this as the right thing.”

Prentice echoes these statements. For him, this project is the chance of a lifetime. It’s a massive commitment of time and energy (so far, it’s dominated the better part of his twenties, and should the plan go forward, it will take at least another decade to secure tenants, finalize building plans, and finish construction). He views 58 Fore Street as a way to create a lasting legacy, as do all the players at CPB2. But even now, as he waits for the vote that could decide everything, as he faces this unexpected hitch in his carefully laid plans, he claims he wouldn’t do anything differently.

“If we were a developer who wanted to make a quick profit, maybe we should have gone in asking to build 20 stories high, something that would terrify the neighborhood, and then we could settle in the middle,” he says, reflecting on the long road that brought him here. “But instead,we went to the city with what we really thought was best. We’ve already made all the concessions we could. From a business perspective, did we do the right thing? I don’t know. But from a moral perspective, I know we did.”

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