Mr. Noonan, 50, took the joke as he takes most things, with good humor. In fact, he recounted that he had been on vacation in Panama, without cell phone service, standing in his swimming trunks shouting over the resort's kitchen phone while he put the finishing touches on the deal and the resort staff put the garnish on lunch.

Along with partner Jennifer Schwartzman, Mr. Noonan won for the sale of a 42,000-square-foot building at 31 West 15th Street, in which the dollars exchanged totaled just over $16 million. It looked unremarkable compared to the runners-up: Newmark brokers Barry Gosin and Mark Weiss for the sale of a 250,000-square-foot building on Sixth Avenue, and CB Richard Ellis' Darcy Stacom and William Shanahan for their sale of development rights on 57th Street. But as Massey Knakal investment sales guru Robert Knakal said when presenting the award: "Every so often you read the submissions, and one deal makes you think, 'I wish I'd done that.'"

Three days later, in a conference room at Newmark Knight Frank's Park Avenue headquarters, Mr. Noonan was still beaming from the compliment, as he recounted that the faulty cell phone reception was the least of the challenges.

The former union hall had been kicking around on the market for four years, but the owners needed to sell quickly because the mortgage was in default and they faced pending litigation. They called Mr. Noonan, a New York University law grad, to testify that the offers they had on the table were at market price. "What good is taking an offer to a judge?" he asked them cleverly. "You want to take them a signed deal."

Within two months, Mr. Noonan had indeed got the union, the New York-New Jersey Joint Board, a deal in contract, but not before dueling with Alchemy Properties, the buyer, over air rights, which the developer needed to acquire from the neighboring school in order to build a roughly 30-story building. Alchemy said they had a letter of intent to give them the air rights, which would chill the bidding on the property and force the union to sell at a lower price. Mr. Noonan responded, he said, with "a little bit of cleverness, a little bit of poker."

Alchemy insisted its letter of intent for the air rights was binding and secret, so the Newmark team received a letter of intent from another potential buyer, which they insisted was binding and secret. In the end, they still sold the building to Alchemy, but for the price the union wanted. "We were a little like two boxers," he said. "We gave each other a couple of shots, but in the end we were friends."

LIKE A PERIOD TO Mr. Noonan's sentence, Jimmy Kuhn burst into the conference room. "What can I tell you?" he said, before taking credit for discovering a disillusioned lawyer with a knack for dealmaking, who joined Newmark in the early 1990s. "When I decided to build a capital group, I wanted somebody with a few extra skill levels that I didn't have," recounted Mr. Kuhn, who at the time was also new at Newmark. "David was in our downtown office renting 3,000 square feet or something like that."

Mr. Noonan recounted that his first deal, to sell a garment center building for MetLife, was, in fact, "a series of disasters." MetLife executives were visiting from Atlanta, and at one point, all of them climbed on fire stairs to look at a collapsed ceiling. "You would make me much more comfortable," he told them, "if none of you would step on that landing."

Today he works primarily on the far West Side, where one of his biggest clients is Verizon, which owns a number of parking lots. ("In the bad times they're parking lots; in the good times they're development sites.") But he can walk through the neighborhood and look at former development sites that have become Hal Fetner's Victory project, Jeff Levine's Ohm and David Walentas' project on West 53rd Street, all significant residential towers. "That's kind of fun."

The son of an architect, Mr. Noonan grew up in a suburb of Chicago and now lives in Tribeca and takes his daughters (he has three, ages 11, 17 and 20) to school in a yellow cab. His wife, Susan, works in financial public relations, a profession that gave him the freedom to take a chance on leaving law. He took up the piano in his 40s, and said jokingly that he's "resolved to be mediocre."

One might, perhaps, say that Mr. Noonan has a knack for transforming mediocrity into great success. Middle-market assets, where he works primarily, are a struggle to sell right now. "If you're selling a building for a Vornado, they can pretty much sell the building themselves, with or without brokers," he said. But selling a middle-market building for an inexperienced seller requires a particular combination of patience and ingenuity.

Lest one underestimate the bespectacled broker's competitive edge, Mr. Noonan revealed at the end of the interview that he was an English major at Dartmouth College and wrote his own submission for the Ingenies. Throwing down the gauntlet, he said good-naturedly: "No one could write about my own deal better than I can."

lkusisto@observer.com

In a January 2010 Observer article, he had sounded one of the earliest calls for not holding the 9/11 terror trials in the federal courthouse in Lower Manhattan. Attorney General Eric Holder announced Monday afternoon that the trials will, indeed, be held at the Guantanamo Bay prison (to the dismay of many among President Obama's lefty base). 

The Observer nabbed Big Real Estate's super at the 101 Club on Park Avenue and queried: Was REBNY the first to sound the call? "I do believe we were," said Mr. Spinola with a wide grin.

As early as December 2009, Mr. Spinola (pictured) met with Bill Rudin, the landlord and Association for a Better New York chair, in his office. Initially, Mr. Spinola spoke with then-White House deputy chief of staff Jim Messina, Homeland Security Secretary Janet Napolitano and presidential adviser and policy wonk David Axelrod. The board at first kept a low public profile on the issue to resist offending the administration.

But Mr. Spinola was getting an earful from REBNY members, as The Observer noted a month after the meeting with Mr. Rudin, more than he had gotten on any single issue since he took over the board in the mid-1980s: "They're saying to me, 'You've got to stop this, you can't let it happen.'" To hold the trial downtown, they said, would disrupt traffic and create security concerns that could drive out tourists and office tenants, plummeting the downtown economy to post-9/11 lows.

The real estate board, one of the most powerful lobby groups in the state, has had an impact on other issues like property taxes, but none with quite such national resonance. In other words, the board took on the president of the United States and won. 

During his Monday evening recap with The Observer, Mr. Spinola also gave credit to Community Board 1 for helping. Victory, Mr. Spinola said, was not surprising (rumors of the administration's reversal surfaced this past January). "We assumed it would not be in New York," he said. "We're very happy." 

lkusisto@observer.com 

CB Richard Ellis led all comers with four nominees, notably a deal for Mercedes Benz' new flagship dealership at 770 Eleventh Avenue that did its part to revitalize Manhattan's autoabahn alley and Proskauer's eye-grabbing 400,000-square-foot, anchor lease deal at 11 Times Square.

Meanwhile, Newmark Knight Frank was nominated for three deals, including for Local SEIU-32BJ's office space at 620 Avenue of the Americas and the sale of 31 West 15^th Street.

"These awards are the most coveted honors that REBNY presents to its commercial members who have demonstrated their creativity and skill through these remarkably ingenious deals," said REBNY President Steven Spinola. "These awards are particularly meaningful in these trying economic times, when deals have been ever more complicated and difficult to get done. We commend all who submitted their most creative and challenging transactions and we look forward to announcing the winners on April 4."

The entire list of nominees is below:

• 100-104 Fifth Avenue office condos, Woody Heller & Will Silverman, Studley
• 250 East 57^th Street, Darcy Stacom & William Shanahan, CB Richard Ellis
• Cabrini Medical Center, 227 East 19^th Street, Vincent Carrega, Grubb & Ellis
• 31 West 15^th Street, David Noonan & Jennifer Schwartzman, Newmark Knight Frank
• 770 Eleventh Avenue, Michael Laginestra & Michael Geoghegan, CBRE
• 620 Avenue of the Americas, Robert Eisenberg, Barry Gosin & Mark Weiss, Newmark Knight Frank
• 333 West 34^th Street, Josh Kuriloff & Robert Lowe, Cushman & Wakefield
• 605 Third Avenue, Andrew Roos, Colliers International
• Susquehanna International Group, 140 Broadway, Chris Helgesen, UGL Equis
• Capital One, 90 Park Avenue, Lee Brodsky & Ross Perlman, Newmark Knight Frank
• Proskauer, 11 Times Square, Stuart Eisenkraft, Michael Geoghegan & Stephen Siegel, CBRE
• 4 New York Plaza, Bradley Gerla & Howard Fiddle, CBRE

jsederstrom@observer.com

Every year, around this time, in a closely watched nomination process, the Real Estate Board of New York selects the most inventive of the bunch and awards them a Most Ingenious Deal of the Year award, or, put more succinctly, the Ingenies. This year, 15 deals were nominated. Only three won.

At a cocktail party on Tuesday night at the 101 Club, REBNY gave the most coveted first-place honors to Cushman & Wakefield’s Paul N. Glickman and Mitchell L. Konsker, who, in a rather extraordinary feat, managed first to convince the Hakimian Organization to stop its residential conversion of 636 11th Avenue and to redevelop it as commercial space; then, in an arguably even bigger coup, the duo lured advertising firm Ogilvy & Mather from the far more convenient Worldwide Plaza into a 560,000-square-foot lease in the hinterlands of the far West Side.

CB Richard Ellis’ Darcy Stacom and William Shanahan came in second—an unusual spot for a team accustomed to preeminence—for the sale of the portfolio of buildings once belonging to Harry Macklowe, and ultimately turned over to lender Deutsche Bank, including the GM Building at 767 Fifth Avenue, 540 Madison Avenue, 125 West 55th Street and 2 Grand Central Tower.

The third-place finish was awarded to Ackman-Ziff’s Shawn Rosenthal for the financing of 650 Madison Avenue in credit markets that, like Lake Erie in winter, had gradually frozen over.

REBNY’s president, Steven Spinola, took note of the unusually harsh climate in a statement: “Navigating the complexity of the real estate market in New York City is difficult, especially in uncertain times, but as these complicated deals demonstrate, when an experienced REBNY broker is involved, obstacles can be overcome.”

drubinstein@observer.com

The winners of the Real Estate Board of New York’s Most Ingenious Deals of the Year Awards will be announced on April 28 at the 101 Club, the Kodak Theatre of city real estate.

“The Most Ingenious Deal of the Year awards are seen as the highest marks of distinction in the industry and the most coveted accolades that a REBNY member can receive,” said REBNY President Steven Spinola in a statement. “And given the climate of the market over the past year, these deals are all the more impressive.”

We can’t argue with that.

And, without further ado, we give you the nominees:

SALES

“Miracle on 83rd Street” – Redeemer Presbyterian Church, 150 West 83rd Street. Brokers:  David Lebenstein & Nicola Heryet, Colliers ABR, Inc.

“The Granddaddy of Historic Preservation – The JV of Cobble Hill Towers, 419-35, 445 Hicks St., Brooklyn, New York.” Broker:  Kenneth S. Freeman, Massey Knakal Realty Services

“The Sale of the GM/Legacy Portfolio – Honoring the Family Name” – 767 Fifth Avenue, 540 Madison Avenue, 125 West 55th Street, 2 Grand Central Tower. Brokers:  Darcy A. Stacom & William M. Shanahan, CB Richard Ellis, Inc.

“Sale of 231 and 180 Bowery” – 231 Bowery and 180-82 Bowery. Broker: Robert Burton, Massey Knakal Realty Services

LEASES

“PNC Financial Group Regional Headquarters & First New York Branch” – 340 Madison Avenue. Broker: Robert T. Tunis, FirstService Williams

“Three Clients. Three Requirements. One Firm. One Deal.” – 395 Hudson Street. Brokers:  Josh Kuriloff, Jonathan Serko & Joseph Cabrera, Cushman & Wakefield, Inc.

“Colgate-Palmolive’s Long-Term Commitment to New York City” – 300 Park Avenue. Brokers: Brian Given, Robert Freedman & Mark Jaccom, FirstService Williams

“Burberry” – 444 Madison Avenue. Brokers:  David Goldstein, Daniel O. Horowitz & Jeffrey I. Peck, Studley, Inc.

“Pioneering a New Frontier: The Hakimian Organization’s Redevelopment of 636 11th Ave. & 560,000 – SF Lease to Ogilvy & Mather.” Broker:  Mitchell L. Konsker & Paul N. Glickman, Cushman & Wakefield, Inc.

“Mission Impossible – The Leasing of 380 Madison Avenue to the United Nations.” Brokers:  Edward Goldman, Stephen B. Siegel & Bruce Weinberg, CB Richard Ellis, Inc.

“Viacom’s Coup at 1515 Broadway.” Brokers:  Scott L. Gottlieb, Michael R. Laginestra & Andrew Sussman, CB Richard Ellis, Inc.

FINANCE

“400 Avenue U Condo” – 400 Avenue U, Gravesend, Brooklyn, New York. Broker: John Lama, NY Urban Real Estate Services, Inc.

“650 Madison Avenue.” Broker:  Shawn Rosenthal, The Ackman-Ziff Real Estate Group LLC

“250 Hudson Street.” Brokers:  Scott A. Singer & Jeffrey C. Moroch, The Singer & Bassuk Organization

“Carlton’s $630 Million Equity and Debt Recapitalization” – 666 Fifth Avenue. Broker: Howard L. Michaels, The Carlton Group

On Tuesday evening, after The Observer went to press, REBNY presented its annual Most Ingenious Deal of the Year Awards at the 101 Club on Park Avenue. The Ingenies are, as one real estate insider put it, “something you’ll refer to probably for your entire career.”

The Observer got the award winners’ names in advance of Tuesday evening’s event.

And so the 2008 Ingenie winners, selected from 39 nominees in 21 deals in 2007, are …

Mary Ann Tighe and Gregory Tosko of CB Richard Ellis won first place for “Adding Color to Grey: The Winding Road to Grey Group’s 370,000-square-foot anchor lease at 200 Fifth Avenue.” This year, just as the market was starting to struggle, Ms. Tighe and Mr. Tosko brokered a deal that will move Grey Group, an advertising firm, from its Third Avenue headquarters into the Toy Center building.

Moshe Sukenik and David Noonan of Newmark Knight Frank won second place for “The Land Swap that led to the new Lincoln Square Synagogue,” a sale and leaseback deal that REBNY described as “one of the most complex land assemblages in Manhattan.” The deal will create “the largest new synagogue in Manhattan since Temple Emanu-El in 1927.”

Andrew J. Singer and Kathleen McSharry of the Singer & Bassuk Organization took third place for the finance deal “50 Murray Street.” REBNY said the deal “enables World-Wide Holdings, the ground lessor of 50 Murray Street, to arrange replacement permanent financing for the luxury rental housing development.”

Who will take home the coveted Most Ingenious Deal of the Year Award? Last year it was Woodie Heller and Howard Nottingham of Studley.

Here's a list of current nominees. See you there!