How former liberal operative Josh Isay became the default paid-media guy to the New York establishment

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On February 16, Josh Isay’s current and former clients dominated the local news. New York governor and former client Andrew Cuomo was threatening to usurp the duties of Attorney General Eric Schneiderman, a more recent client. The New York Times ran a 1,400-word article on Connecticut governor Dannel Malloy, who was elected in 2010 with Isay's help. Analysts debated Deutsche Boerse’s proposed purchase of another Isay client, the New York Stock Exchange.

Asked later that day about the Malloy and Schneiderman stories, Isay, a 41-year old political and media consultant, evinced a disinterest at odds with his reputation as a detail-obsessed image-broker, brushing off Malloy and claiming not to have read Schneiderman closely.

Most likely, Isay was just being guarded. Though he has worked for Michael Bloomberg, Christine Quinn, Bruce Ratner, Scott Stringer, Joe Lieberman, Charlie Crist, Caroline Kennedy, the New York Stock Exchange and Benjamin Netanyahu—or maybe because he already moves in such powerful circles, and no longer feels the need to market himself—Isay has become a private person, loath to appear on television or at political events, reluctant to take interviews and, usually, entirely uninterested in discussing himself. It may, as his friends and family say, derive from a natural shyness, but that’s a shyness he’s only in recent years begun to indulge, as he expands his professional roster to include corporate clients, many of whom might consider a regular slot on NY1 to be more liability than asset.

“I think there’s something between glad-handing and J.D. Salinger, and I’m probably somewhere in between,” said Isay.

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JOSH ISAY SELLS ADVICE TO NEW YORK POWER BROKERS from his place of business at the end of a labrynthine hallway on the fifth floor of a building on Broadway, between Houston and Prince streets. The offices have the feel of a genteel law firm in the days before mass corporatization forced American workers into sterilized beige cubicles. The walls are decorated with old political posters, the conference room floor sprouts a shabby red white and blue rug, beneath a glass table, next to a clanging radiator.

Isay is a slight, hirsute man with a runner’s build and a face that, though not unattractive, would send a caricaturist’s pen into spasms of delight—the furrow between his eyes, the dimpled chin, big ears, prominent nose, slightly wayward teeth. He lives with his wife, the former Schumer aide Cathie Levine, and two children in a $3 million apartment on West End Avenue.

He speaks quickly, and obliquely, issuing generalities about the importance of hard work and good staffing.

“The company would not be where we are if it wasn’t for putting together a really good team,” said Isay. “The trick to success in business is to do a really good job with the clients you have and then more clients come in.”

In 2006, the firm hired Stefan Friedman, a former New York Post reporter and the son of former HarperCollins CEO Jane Friedman. Since then, the firm’s corporate clientele has come to comprise between 30 and 40 percent of SKD Knickerbocker's business. In 2007, Isay brought on Jennifer Cunningham, a powerful union lobbyist who is the ex-wife of Attorney General Schneiderman and a close confidant of Governor Cuomo.

“This is the only place I considered,” said Cunningham, who was previously executive vice president of the most politically powerful union in New York, 1199 SEIU.

In addition to NYSE, the firm has been hired by a host of corporate and union clients, including Thor Equities, the firm that sparred with the city over the redevelopment of Coney Island; the Rudin family, which controls some 14 million square feet of real estate in New York City; Genting New York, a subsidiary of the Malaysian gambling giant that won state approval to install slot machines at the Queens Aqueduct; and Education Reform Now, the Joel Klein creation that’s battling teacher unions in New York. (Anita Dunn, Isay’s partner in D.C., is advising a group with a similar agenda: Michelle Rhee’s StudentsFirst.)

Meanwhile, Isay seems to have worked at one time or another with all of the best-known politicians in New York City, many of whom have competed for the same office, and, at times, for their consultant's attentions: Stringer and Quinn, who both want Bloomberg's job; TLC commissioner and former councilman Yassky, who was beaten in a brutal congressional primary by another Isay client, Yvette Clark; longtime Manhattan DA Robert Morgenthau and his protege-turned-bitter challenger, Leslie Crocker Snyder.

Most of the time, it seems, Isay's work in opposition to onetime clients has not been held against him.

“It makes a big difference when he’s on your side,” said Yassky. “He’s been on my side and he’s been on the other side, and it’s a 180 degree difference.”

Some attribute Isay’s current, oversize presence in New York to having won a war of attrition, picking up pieces after erstwhile competitors, like Glover Park, Global Strategy and Dan Klores, for various reasons, left space in the local campaign-and-advocacy-messaging market as they pursued other, more convenient revenue-generating activities.

Now, as a friend and fellow consultant put it: “He’s the preeminent media guy in New York."

As is often the case with these sorts of things, Isay's access to power has begotten more access to power. So, for example, the fact that he came up with Schumer, and has kept that relationship in excellent repair has been all the credential he's needed with countless Democrats; the fact that he became a go-to media guy for Bloomberg opened up doors outside the party, and outside politics entirely.

“Certainly, his relationship with the mayor put him out there in the corporate world in a way he wasn’t before,” said Ken Fisher, a former councilman and borough president candidate who is now a lobbyist.

Isay, unsurprisingly, thinks that analysis is reductive.

“I don’t think there’s a Bloomberg campaign stamp of approval,” said Isay. “Our firm has worked for the Obama campaign, senators and governors and mayors, and we obviously have a credibility as a firm with the clients that we work for that I think companies respect.”

JOSH ISAY HAS BEEN A POLITICAL ANIMAL since he was four, according to his mother, Jane Isay. His family history makes that somewhat less surprising than it sounds.

Isay’s maternal grandfather, Abraham Franzblau, was an psychiatric consultant to the surgeon general during World War II, according to Jane Isay, and his best friend was an adviser to Franklin Roosevelt.

As a child, Isay was fascinated by the Nixon impeachment trial, in part because the revered constitutional scholar Charles L. Black was writing a book about the impeachment that was being published by Josh’s mom.

“Charles was in and out all of the time, and those conversations sparked Josh’s passion for politics and government," she recalled.

“It was during the Nixon impeachment era, if he said something naughty, we said, ‘Josh you shouldn’t talk like that. And he’d say, ‘Erase that from the tape,’ referring to the missing tape.”

Isay, one of two brothers, grew up on the Upper East Side, and attended Friends Seminary, where he was, by all accounts, a mediocre student. Even so, he squeaked his way into Washington University, in St. Louis, where he majored in political science.

After graduation, he took a job in then New York Attorney General Robert Abrams' press office. When Abrams unsuccessfully took on Republican Senator Al D’Amato in 1992, Isay acted as his press secretary. (Nearly ten years later, when Isay briefly defected to the corporate sector, working as head of government relations for Doubleclick, he hired Mr. Abrams to advise the firm on privacy issues.)

“I knew then that he was an extraordinarily bright guy who was destined to go far,” said Abrams recently. “He was the low man on the totem pole in the campaign, and he sat in a room diligently reviewing clips, writing memos, and from time to time I was briefed by him. I was always impressed with how sharp he was, how crisp, how his analysis was on target.”

From 1994 to 1996, following a stint working in the public advocate's race for Mark Green, Isay joined then-congressman Chuck Schumer's office as press secretary. Then, in 1996, Isay went to Robert Toricelli’s campaign for U.S. Senate, working under Robert Shrum.

The following year, Isay had his first experience with client-list awkwardness, signing on as a spokesman for Schumer in his underdog campaign to unseat D’Amato. One of Schumer's primary opponents was Isay's former boss, Mark Green.

“When he started working for Schumer, there was a lot of resentment,” said political consultant Michael Oliva, who worked for Green at the time.

Hank Morris, then considered something of a behind-the-scenes guru of New York political consultancy—a spot Isay seems to be growing into now—led Schumer’s political strategy. In 2002, Isay told The New York Observer, “Hank is my mentor and one of my closest friends, and will remain so," he said. "I consider him the smartest person in New York politics and maybe anywhere."

Last week, Morris was sentenced to up to four years in prison for selling access to New York’s pension funds, controlled by his client, former comptroller Alan Hevesi.

The race against D’Amato was both nasty and innovative. Schumer’s team—which paired Isay with another young up-and-coming operative named Howard Wolfson, with whom he later fell out—won plaudits for pioneering the use of rapid- response TV advertisements at the state-wide level.