What Does Seth Pinsky's Wife Know About Real Estate? A Lot, It Turns Out.

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Mayor Bloomberg arranged the office in City Hall as a large bullpen with everyone sitting at open workstations. His was, and still is, at the center of the room. Ms. Pinsky sat near the periphery, but the layout avoided isolation and permitted everyone in the room to feel within the fold of the office’s work.

“You could hear what the mayor was talking about on the phone and you always had an awareness of what was going on,” Ms. Pinsky said. “There were no silos. That was one of the great things about the administration—it was transparent.”

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She remembers Mayor Bloomberg as having a photographic memory and a talent with data. “Numbers are part of his body,” Ms. Pinsky said. “But he was also very instinctual. The mayor would do the research and then trust his gut.”

Mr. Doctoroff, who left city government in 2007 to become the chief executive of Mayor Bloomberg’s financial information company, Bloomberg LP, was more analytical. “Dan wanted analyses down to the penny and he would ask you little details to see if you knew about a project inside and out,” Ms. Pinsky said.

Ms. Pinsky grew close with Mr. Doctoroff. She said he still checks in on her. “I had a very strong attachment to Dan,” Ms. Pinsky said. “I was young and had a lot to learn. I was timid. Working in that situation makes you learn about decision-making. I grew up a lot in that role. Dan still calls all of us. He’s very protective.”

Mrs. Pinsky stayed on when Mr. Doctoroff left, maintaining her position as a chief staffer for Bob Lieber, a former Lehman Brothers executive who was hired as Mr. Doctoroff’s successor in the role of deputy mayor of economic development. Mr. Lieber was less of a visionary than Mr. Doctoroff, according to Ms. Pinsky, but had a clear talent for negotiating deals, skills that Ms. Pinsky would also soon come to appreciate.

One of the first issues they handled together was what to do with Off Track Betting. The parlors were oozing red ink, Ms. Pinsky said, largely because the city and state took money out of its total revenue rather than its profits. “OTB expenses were rising and there was nothing to compensate it for that,” Ms. Pinsky said.

Mr. Lieber helped devise a solution in which the city and state would share a cut of OTB’s profits only, an approach that would pad its bottom line. He worked hard to align various interests in the state that would permit the idea to be implemented. But the negotiations bogged down and eventually he retreated, arranging a deal that would allow the state to take control of the organization. A year later, it was shuttered.

Mr. Lieber’s efforts had paid off in one sense; the city was no longer on the hook for OTB’s $500 million of pension and other liabilities. Still, it was demoralizing to see how such a common-sense solution could meet defeat when OTB’s inevitable demise had been so widely predicted.