The question launched development of Lakeshore East, a $4-billion fully integrated community of residences, retail, hospitality, schools and parks, all sited on 28 acres along Chicago's lakefront.

The development's 82-story Aqua, designed by MacArthur Genius Fellowship winner Jeanne Gang, principal with Chicago-based Studio Gang Architects, ranks among the most acclaimed high-rises to join the city's skyline in decades.

"The concept," says Carlins, "was to construct a self-sufficient village in the heart of the city." Its six-acre park opened in 2005—Carlins says he wanted it completed first so residents of planned high-rises wouldn't live adjacent to a construction site—followed by The Lancaster, the first of several residential or mixed-use high-rises including The Shoreham, 340 on the Park, The Coast and the Aqua.

Today, the Lakeshore East development remains a work in progress. In addition to town homes, a supermarket, a hotel and the first of a pair of private schools, Magellan has completed 11 of a planned 19 residential high-rises, some containing condominiums, others apartments and some both.

In December, it announced it was re-teaming with Gang on Tower No. 12., a $900-million, 88-story condominium and hotel it is undertaking in a joint venture with Chinese developer Wanda Group.

When completed, the structure will stand as Chicago's third tallest, Carlins points out, and contain 390 condominiums, 250 guest rooms and 9,000 sq ft of retail space.

Skeptics wonder if the Chicago market, flush with new residences, can absorb what will be downtown's largest condominium to join the skyline since the start of the recession.

Others contend Lakeshore East, whose recently completed Coast achieved 90% occupancy, is a market unto itself. Aqua achieved considerable success during the depths of the recession.

Every new venture presents unique challenges, Carlins acknowledges. "I'd rather attempt something new than do the same thing over and over," he says. "I've never been afraid to do something new and fail.