The Mechanic

Before he was a leader in the New York commercial real estate market, Howard Nottingham was a Chevrolet dealer in Indiana, a career that, he says plainly, he was happy to scrap.

Besides a few perks here and there—like being invited to take a sponsored pace car for a whirl at the famed Indianapolis Motor Speedway, home to the Indy 500—he has no regrets about a career change that has led him along the circuitous highways of Indiana, Ohio and New York before finally ending at Studley in midtown.

“Honestly, I’ve been happy every day I’ve been out of it, but I’m a pretty happy guy, in general,” Mr. Nottingham said. “All I know is I didn’t like the car business. Not in the least.”

But if the automobile industry was not the key to success Mr. Nottingham had hoped it would be, it did provide the father of four with an astute sense of salesmanship that has served him well over a 27-year real estate career.

Indeed, since being hired as a broker at LaSalle Partners and later Cushman & Wakefield before winding up at Studley as an executive managing director, Mr. Nottingham has been at the helm of many of the most complicated deals of the past decade.

With a client roster that has included Chase Manhattan Bank, MetLife and Cablevision’s Rainbow Media Holdings, Mr. Nottingham has netted an estimated 12 million square feet in transactions—and that volume is expected to increase in 2010, thanks to a number of deals currently shifting around the city’s proverbial pipeline.

“Right now, I’m as busy as I have been in a long time,” said Mr. Nottingham, 56, during an interview last week at Studley’s Park Avenue offices. “People still need to figure out what they need to do about their real estate needs. In some cases, they have too much, and in other cases, what they have is antiquated and they need out of it.”

Nowhere was the latter problem more obvious than in 2003, when the dean of New York Law School hired Mr. Nottingham and fellow Studley executive managing director Woody Heller to address limitations of the institution’s century-old Tribeca complex, which, as enrollment grew, was busting out of its seams.

The deal spanned four years and involved zoning variances, rent-controlled tenants and complicated tax-exempt bond grabs—all while the residential market was softening and project costs at the site were soaring.

In the end, the $136 million sale of a development parcel on Church Street and the subsequent construction of a state-of-the-art school building nearby earned Messrs. Nottingham and Heller the Real Estate Board of New York’s “Ingenious Deal of the Year” award.

Since then, Mr. Nottingham has been tasked with increasingly complicated deals, including one on behalf of Time Inc. in 2007 that placed Lehman Brothers in a 200,000-square-feet sublease at 1271 Avenue of the Americas, where the media company leases most of the property. A year later, of course, Lehman collapsed, and now, like Peter Turchin at CB Richard Ellis, Mr. Nottingham and his team have been tasked with leasing prime space recently abandoned by Lehman.

“It didn’t turn out well,” said Mr. Nottingham of the 200,000-square-feet Lehman space he’s trying to lease. “Hopefully, with any luck, we’ll have that space cleared up by next year.”

The Mechanic