Two seemingly unrelated news items from the last month: The tunnel boring machine digging the extension of the number 7 subway line completed its task, leaving the new project on target for a late 2013 opening. And the Downtown Brooklyn Partnership, a quasi-public development corporation formed to oversee the reconstruction of a 22-block swath of downtown Brooklyn, was reported to be short of cash and threatened with being reduced to "a shell" of its former self.

The tie that binds these two stories: Dan Doctoroff, who as deputy mayor for economic development spearheaded both the 7 train extension and the downtown Brooklyn rezoning, along with numerous other development projects that marked Mayor Bloomberg's first two terms in office. Initially brought in to oversee development tied to Bloomberg's ultimately fruitless bid for the 2012 Olympics—Doctoroff's previous job was as director of the city's Olympic bid committee, NYC2012—the former investment banker became a familiar visage on the city scene, with his Albert Brooks grin and ubiquitous Powerpoint presentations. ("You use Powerpoint the way Picasso used a brush," then-Councilmember Eric Gioia once enthused at a City Council hearing.)

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Neil deMause
Neil deMause
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It's been almost three years now since Doctoroff departed city government for the top job at Bloomberg LLC. In that time, both the city's finances and its real estate have entered uncertain waters, but the projects set in motion during Doctoroff's time at the helm continue to shape the city's future. Here's a look at some of Doctoroff's most notable projects, and how his development legacy—and Bloomberg's—look now.

  • Hudson Yards
    The Plan: Doctoroff first concocted plans for a redevelopment of the airspace above and land surrounding the rail yards west of Penn Station in 1999, when he was still running NYC2012. The plan for a combined Jets and Olympic stadium fell apart after state Assembly Speaker Sheldon Silver, using his veto power as a member of the Public Authorities Control Board, blocked it in June 2005. But rezoning of the site lived on, as did a city-funded $2.1 billion project to extend the 7 train to 33rd Street and 11th Avenue.

    What Happened: The 7 extension is on schedule to open in 2013, but for now it will still lead riders to a giant hole in the ground because the above-ground redevelopment is in limbo. After several years of disarray—original anchor tenants Morgan Stanley and Goldman Sachs both dropped out—this May the Related Companies, run by Doctoroff's old real estate business partner Stephen Ross, signed a 99-year lease with the MTA for the 26-acre railyard site for $1 billion, though it won't have to pay up (or begin construction) until the real estate market improves. (Running the project for Ross: Jay Cross, formerly in charge of the Jets' stadium push.) The city, meanwhile, has run through most of the payments by real estate developers slated to pay for the subway line and other infrastructure, and is facing nearly $100 million a year in debt payments on the project starting in 2011.

    Glass-Half-Full View: "I'm banking on the fact that the stars are finally aligned. ... It's possible for us to start at the beginning of 2012 or late 2011. ... We're sort of coming out of hibernation." -Jay Cross, president of Related Hudson Yards