1. Heading north to Grand Lake Stream
The fate of the
Portland waterfront
comes to a vote
October 2015
FRESH WATER CATCH
CITY ON
THE EDGE

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3. A CITYON 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?
by KATY KELLEHER
Photographs by NICOLE WOLF
Casey Prentice walks through “building three” on the property at 58 Fore
Street. While some of the buildings on this site are too dilapidated to save,
Prentice and his team are committed to honoring the historic integrity of the
neighborhood by restoring what they can.

5. 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.
PICTURE THIS:

6. Although Prentice and his team plan
to develop the stretch of land along
the eastern side of Portland, they
have no desire to cut off access to
the waterfront—or to interrupt the
Portland Trails system.

7. 94 maine | themainemag.com
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
58 Fore Street
is his moonshot,
his white whale.

8. Opposite: The view inside “building two.” This page: Prentice
has been working on this project since he was in his early twenties.
Now, at 29, he’s ready to start building his legacy in earnest.

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10. October 2015 97
Opposite: The iconic Portland Company building is one of the few landmarks located
inside the 10-acre oceanfront property. This page: CPB2 provided sketches and computer
renderings of their proposed development on the waterfront.
photocourtesyofCPB2

11. 98 maine | themainemag.com
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.
“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.”

12. October 2015 99
Getting the big picture view: CPB2 co-manager Kevin Costello on the roof of “building one.”
“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.”
Jim Brady stands on the SailMaine dock at the waterfront.

13. 100 maine | themainemag.com
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.”
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.

14. October 2015 101
Opposite: If the November referendum passes, the sketches
will likely never come to much, leaving this parcel of land
undeveloped and underutilized. This page: Years of neglect
have taken their toll on the buildings in this property. Here, we
see inside “building one.”