It all began with a simple premise: If you could ask the city’s biggest, most powerful commercial real estate owners 15 questions, what would they be, and what would that list look like?

Sure, it would include market predictions and boilerplate real estate stuff, like views on Midtown South’s dramatic uptick in popularity and its ongoing trendiness among tech upstarts. But it would also feature more intimate questions about politics and family, art and personal achievement. In short, it would be our platonic ideal of a night out with some of the most successful businessmen in New York.

And to our surprise, real estate owners responded enthusiastically and, in many cases, with a level of candor previously unseen in an industry where owners often play their cards close to the vest. Indeed, real estate titans like Anthony Malkin, Jason Pizer and Donald Trump let down their guard—if only for a moment—to share a lifetime of personal wisdom, market predictions and some strongly held convictions, from the outcome of November’s presidential elections to a dollop of property tax angst.

As much as possible, we viewed this, our First Annual Owners Inquisition, as an opportunity to include the city’s diverse array of landlords, from real estate investment trusts like SL Green and Vornado—who together command in excess of 50 million square feet of property in Manhattan—to smaller, nimbler companies like RXR Realty, Newmark Holdings and a host of other players whose well-known names dot the borough’s skyline. The only requirement, in fact, was that the submissions come from owners boasting property in Manhattan rather than the outer boroughs, which hundreds of additional landlords call home.

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BY DANIEL GEIGER

Every real estate investor dreams of the moment when, through diligence, smarts or luck, he or she finds a building whose potential is at once dazzling and wholly unrealized. Such discoveries can lead to deals that make fortunes, even careers.

It is not a surprise, then, that a steady procession has taken place over the years to a slumbering behemoth located in a onetime hinterland that has recently resurfaced as a new frontier for development. 550 Washington Street, a building more commonly known in real estate circles as the St. John’s Terminal Building, is the archetype of a diamond in the rough.

Sprawling more than three city blocks, the property, with its 1.3 million square feet spread between only four levels, has the notable distinction of having Manhattan’s largest floors, the kind of cavernous open space coveted in modern office layouts.

“It’s like you took the Empire State Building and laid it down on its side,” said one top investment sales broker in the city.

Even before the nearby commercial office neighborhood known as Hudson Square blossomed into a popular destination for tenants or a pocket of blocks just east of 550 Washington Street was recently rezoned to allow residential development, owners and developers have for years quietly come to the building in the hopes of trying their hand at unlocking its tantalizing possibility.

“Everybody has looked at it,” said one prominent owner who has invested in buildings in the neighborhood.

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BY DANIEL GEIGER

Christopher Milito, who is 37, joined the law firm Morrison Cohen almost a year ago and quickly got swept up in one of the most prominent real estate deals of the year: the Domino Sugar factory. Mr. Milito represents the Katan Group, which owns the Domino site in partnership with the Community Preservation Corporation, and he has led the company’s efforts to block CPC’s efforts to sell the site—including a deal with Two Trees—for what it claims are below-market prices. Mr. Milito spoke to The Commercial Observer about why winning in the courtroom isn’t always the goal of a good litigator and his time learning the ropes of litigating while starting out in the Manhattan District Attorney’s office.

You’re the lawyer representing the Katan Group on the Domino Sugar Factory site. That turned into a huge story. What has that done for your career? Well look, part of it is luck, I was the attorney put on it here. There is an element of luck in any success professionally. I would like to think we’ve handled it well.

It seemed like Katan lost in the first round of litigation that you launched earlier this year. What is the status now? It’s not over yet. The status is there is a motion pending for a preliminary injunction enjoining the sale to Two Trees.

So, stopping that transaction? Yes.

When do you find out if you get it? Hopefully soon.

A week? A day? No, I would hope in two weeks. The closing is set for October 15.

If you get the preliminary injunctions, what do you want to do? Break up the sale to Two Trees and do a better deal? That’s exactly right.

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BY DANIEL GEIGER

Commercial leasing brokers often earn a reputation for being proficient in a particular neighborhood, whether it be Midtown, Downtown or one of the more popular office destinations outside Manhattan, such as the New Jersey waterfront.

“It’s definitely a more specialized business these days,” said Mark Ravesloot, a leasing broker at CBRE.

Even in a city where top brokers are often prolific and versatile, Mr. Ravesloot’s career is distinguished by the apparent ease with which he has done sizeable deals across Manhattan and its ancillary submarkets.

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