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

“At one point, D’Amato put an ad on the air and in the same day they had a response ad,” recalled Oliva. “In other words they’d already predicted the ad. At the time, that was revolutionary at a statewide level.” Following Schumer’s win, Isay became his chief of staff. He established himself as a hard worker, and a reluctant shmoozer.

“Every night in the Capitol Hill office buildings, some lobbying group or some trade association or advocacy group would have a cocktail function,” recalled Yassky, who was then on Schumer’s staff. “He was never one to go hang out at the social functions. First of all, he works unbelievably hard.”

By 2000, Isay’s star had risen so rapidly that he turned down offers from both Al Gore and Hillary Clinton to instead become a lobbyist for DoubleClick. But soon the dot-com bubble collapsed and Isay returned to politics, joining Hank Morris’ firm, Morris, Carrick & Guma. Isay worked as a spokesman for Hevesi, who was running for mayor in the 2001 Democratic primary against Bronx Borough President Freddy Ferrer and Mark Green.

At the time, Isay was a visibly aggressive advocate for his clients and for himself; he maintained a regular presence on television and in the papers.

(“He used to do a little television on NY1, and he was always very boring,” his mother said.)

Following Hevesi’s loss, Isay set out on his own, joining forces with Dan Klores and Jonathan Prince to form Isay, Klores, Prince. Their first client was Andrew Cuomo, who was making his disastrous first attempt for the governorship, running in the primary against Carl McCall. It was an ugly race on many levels, including in the papers.

(One delightful example: "I'm not going to say a bad word about Carl McCall," Isay told The New York Times in 2002. "He gets himself in enough trouble as it is." "In order to be elected, you have to be liked,” countered Hank Sheinkopf. “His negatives are very high. Carl's are not—because people like Carl.")

Following Cuomo’s defeat, Isay’s firm disbanded, and he founded a new company called Knickerbocker Partners with a young prodigy named Micah Lasher, then a 20-year-old NYU student who worked against Isay's candidate, for Mark Green, in the 2001 mayoral campaign. Isay began building his firm in earnest. In 2005, Knickerbocker Partners merged with Squier Knapp Dunn in D.C., a group headed by three powerful political operators, including former White House communications director Anita Dunn. The same year, Isay scored Bloomberg as a client, in addition to Morgenthau and Stringer. In mid-2006, he joined other Bloomberg operatives to help embattled senator Joe Lieberman beat back Democratic nominee Ned Lamont in the Connecticut general election.

The same year, Isay began his pursuit of the corporate class, hiring Friedman to spearhead the effort. Isay acquired yet more firepower with the addition of Cunningham. Today, they are the three principals, in partnership with Bill Knapp, Hilary Rosen and Anita Dunn in D.C, who together employ about 40 members of staff, dividing their time between political campaigns and non-political clients like AT&T, Microsoft, Time Warner and Pfizer.

The corporate part of the business is what they call "strategic consulting," which essentially means helping to formulate messages that enable their clients to navigate potentially tricky political, regulatory or media terrain. Both the corporate and the political clients ostensibly benefit from the same essential asset: Isay’s knowledge of how reporters, politicians and regulators process information.

“We come up with a good plan, we’ll tell you how we think we should execute it, we’ll execute it, we’ll be patient and when the normal sturm and drang happens, we will try to stay focused on what our goals are,” said Isay. “We will not deviate from our plan unless we really learn new information that makes us. I think there’s kind of a calmness under pressure. But also, really executing and delivering.”

Isay is said to take his clients' losses very personally.

“Because he’s so into his clients, meaning he’s so deeply in, when they suffer failures, he suffers with him,” said Jefrey Pollock, president of Global Strategy Group and a good friend of Isay. “When he was doing a really rough campaign this year, the Charlie Crist campaign, he became really close to Crist. When the campaign wasn’t going well, you can see Josh suffering along with him.”

IF THERE WAS EVER A TIME JOSH ISAY could be neatly categorized as a "Democratic operative," that time is over. He is now the guy who could represent Quinn or Stringer or some other Democrat if those are the choices for mayor in 2013, but who is just as likely to represent the next Bloomberg, if and when one surfaces, if that candidate is the one he likes best, and has enough money, and looks likely, with some expert help with messaging, to win.

Certainly, he will not feel constrained by any sense of partisan duty.

(As one of Isay's consultant friends put it, "Josh is highly motivated by making profit, which is fine.")

When the Democratic primary electorate rejected Joe Lieberman in Connecticut, Isay (like Schumer, and other Democratic senators) helped Lieberman beat the Democratic nominee in the general. Isay did his best to help Crist, the former Republican governor of Florida, who became an independent only when it became clear that he was going to lose his Senate primary. Outside American politics, Isay has worked for Netanyahu and Israel's Likud Party, which is increasingly explicit about its ideological alligment with the U.S. Republican Party. (There was a tradition, dating back to the Bill Clinton era, of top Democractic consultants working for Likud's opponents; Netanyahu's first American guru, by contrast, was Arthur Finkelstein, the reclusive archconservative who masterminded the rise of former governor George Pataki and the Senate campaigns of Al D'Amato.)

Isay describes himself, in the context of Israeli politics, as “a bit of a hawk, actually.”

“It is hard to apply our domestic left-right views on to the politics of Israel,” he said. “I think that basically there’s only one country, one side that truly wants and can bring their people a peaceful settlement at this point. That’s Israel. I don’t see a partner for peace. If you don’t have a partner for peace, it’s hard to argue with Netanyahu’s position, for me.”

As far as American politics is concered, Isay said, “I consider myself kind of a, what is Koch’s expression? A liberal with sanity. I think that’s Koch’s expression.”

(It is.)

It's difficult from the outside to calculate precisely how much the firm takes in these days, and Isay declined to say anything specific about revenue. But it has grown, since Isay started it less than a decade ago, into a serious money-maker. To cite one example of the profit taken in from just one client (albeit a big one) in one election cycle: The New York City campaign finance database indicates that, in the 2009 election, Bloomberg's campaign paid Squier Knapp Dunn $61.4 million for mailings, TV ads and consulting. Assuming the standard 10 to 15 percent cut of a media buy applied here—and assuming every bit of the rest of that money actually went out the door in the form of salary and expenses, which it almost certainly didn't—SKD would have taken in well upward of $6 million.

Even if the mayor never runs for public office again, that type of revenue is unlikely to dry up for Isay and Knickerbocker anytime soon.

“He’s always my first call when I’m looking to hire someone to do ads,” said Bradley Tusk, a prominent consultant who, like Isay (and Wolfson) is a former Schumer aide who went on to a big payday for Bloomberg.

Isay will likely get a piece of President Obama’s reelection campaign in 2012, perhaps playing a bigger—and proportionately more lucrative—part than in 2008, when Knickerbocker SKD handled mail in the northeast, and television in the west.

“I don’t know how they’re going to organize it for the next presidential,” said Isay. “But Anita [Dunn] was communications director for the White House and will certainly play a role in whatever they want to do.”

He didn't say anything explicit about what his own role would be. But then, as usual, he didn't really have to.

Correction: Dannel Malloy's campaign for governor was not "managed" by Isay, as the original version of this article said. Isay was a paid consultant. Malloy's official campaign manager was Dan Kelly.