For nearly a decade, there has been talk of transforming the city’s last undeveloped stretch of lakefront, between 79th and 92nd Streets, into a “neighborhood of the future.” But last October, something besides talk actually happened: Crews completed work on a $64 million extension of Lake Shore Drive that provides direct access to the 596-acre site. Now the Chicago developer Dan McCaffery is assembling an unlikely power portfolio—politicians, urban planners, and public intellectuals —to help get the estimated $4 billion, 50,000-resident community off the ground. If a model of new urbanism on a swath of vacant industrial land sounds far-fetched, remember that this is the same city that plopped Millennium Park onto a grimy rail yard.

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Illustration: Chicago Lakeside Development

A. The Lakeside plan establishes a series of neighborhoods, each built around a “center” with restaurants, a school, a dry cleaner, and boutiques.

B. A proposed site for an Obama presidential library

C. A 1,500-boat marina and harbor

D. Planners incorporated a recreational lagoon for rowing and canoeing.

E. The long-term plan imagines an offshore wind farm and other renewable energy components.

The Boss

Few details, however small, get past Chicago developer Dan McCaffery (No. 84), who in 2005 entered into a joint venture with the site’s legacy owner, U.S. Steel, for terms that were undisclosed. From that point on, McCaffery lobbied
hard for the Lake Shore Drive extension, most of which was paid for by a capital construction program ($46 million) overseen by Governor Pat Quinn (No. 50). “LSD being complete was as essential as the sun coming up tomorrow,” McCaffery says.

The Master Planner

The director of urban design and planning at architecture giant Skidmore, Owings & Merrill, Douglas Voigt spent two years drafting his vision for a city within a city: by 2040, 50,000 residents, 13,575 new housing
units, and more than 17 million square feet of retail and commercial space bisected by boulevards and bikeways.

The Bureaucrats

Before he left City Hall, Richard Daley made the area a tax increment financing district, and the City Council’s finance committee, chaired by Ed Burke (No. 39), greenlighted a $98 million subsidy for streets, lights, and other infrastructure projects. (McCaffery’s firm has donated $38,000 to Burke and various committees he controls since 1997.) By all accounts, Rahm Emanuel (No. 1) is also a supporter and helped kick $3 million in local transit dollars to the LSD extension.

The Geeks

One of the anchor tenants of the site could be a gigantic state-of-the-art data center, says the venture capitalist Amy Francetic, who is helping recruit participants. This vision (and the need to build a high-tech fiber-optic network to support
it) has piqued the interest of the Computation Institute—a multimillion-dollar joint initiative between the University of Chicago and Argonne National Laboratory.

The Engineer

Plenty of consultants said the site’s rock-like slag base would be impossible to work with—akin to trying to put a sewer system on the moon. But Bill Loftus, president of the Rosemont engineering consultancy Spaceco, says this
porous foundation—a byproduct of the site’s steel-manufacturing roots—could be harnessed to funnel storm water into Lake Michigan. This plan would eliminate the need for an expensive sewer system and be a regional model of sustainability.

The Sports Enthusiast

The Italian expat Emanuele Bianchi, founder of the Chicago-based pet product retailer PetEgo, is trying to raise $45 million to build an Olympic-size velodrome designed by the Loop
architecture firm RTKL.

The Conservationist

A fifth of the development’s acreage is intended for parkland. Figuring out exactly how to convert a brownfield into green space is a task for John Marlin, a researcher at the Illinois Sustainable Technology Center in
Champaign. Since the early 2000s, this river restoration expert has overseen a program called Mud to Parks, in which sediment is dredged from the Illinois River near Peoria (to help clear the way for barge traffic) and redistributed for topsoil. Multiple sediment shipments have been sent by barge to Lakeside; trees and prairie grass have already begun to sprout.