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Jason Horowitz: The Ballad of Josh, Jef and Howard

In 1998, Josh Isay recruited his best friend and fellow Capitol Hill operative, Howard Wolfson, to return to their native New York and work on the long-shot U.S. Senate campaign of his boss, Representative Chuck Schumer. Around the same time, Jefrey Pollock, then a 27-year-old Philadelphia transplant who tried to mask his pubescent appearance with phony glasses, crunched poll numbers for an attorney general candidate, Eliot Spitzer, a virtual unknown who had suffered a pummeling in a primary four years earlier.

The stunning victories of Mr. Schumer and Mr. Spitzer are now the stuff of local political lore. But those campaigns also heralded the arrival of the three unknown operatives who would become the consultant kings of New York. (These days, if you’re an A-list politician, you’re almost certainly employing at least one of them.)

"I wouldn’t advise running without them," said Manhattan Borough President Scott Stringer, who has employed both Mr. Isay and Mr. Pollock. "They are rewriting once again how to get elected in New York City. Right now they are the best."

"The three of us obviously occupy space in lots of campaigns," said Mr. Pollock. "People are looking to our firms to be the leading voices."

But the three men, all Jewish, all vaguely nerdy, all Democrats—though of varying degrees of liberality—have distinct personalities, expertise and, more often than not, clients.

Mr. Isay, 39, whose increasingly reclusive behavior has come to remind many insiders of his shabbily dressed former consultant-mentor Hank Morris, is widely considered the most effective media consultant in town.

Mr. Wolfson, 42, a strategist who also comes with his own package of quirks—a fear of flying, obsessions with baseball statistics and indie rock, a near-fatalistic approach to campaigns—is the most sought-after communications guy.

Mr. Pollock, 37, a likable, natural entrepreneur—and a onetime protégé of Republican consultant Frank Luntz, even though he is arguably the most progressive of the three—does polling for the top Democrats in the state.

They all work for different firms, but their careers paths in New York have repeatedly converged and parted, sometimes dramatically, and sometimes in very personal ways.

Mr. Isay and Mr. Wolfson, in particular, have been actors in a quiet feud—or, more accurately, holders of a meticulously observed grudge—for nearly seven years. Once best friends, they don’t speak. Neither do their families. And while there are signs of a thaw, thanks in part to the magical power of Mayor Michael Bloomberg’s billions to bring them together in the same office of his reelection campaign, Mr. Pollock has essentially taken Mr. Wolfson’s place as Mr. Isay’s best political pal. Now it is those two who eat at each other’s houses. Now it is their wives who work out together.

But the real competition between the three consultants, is, of course, for business.

Name any major officeholder in recent years, and chances are they have at one time or another employed the firms of some or all of the three consultants.

Mr. Isay, a former chief of staff to Mr. Schumer, runs Knickerbocker SKD, which he founded in 2002 and made a fortune from after scoring Mr. Bloomberg as a client. They also have counted among their clients Mr. Stringer; District Attorney Robert Morgenthau; a handful of City Council candidates; and unions, including the powerful 1199 SEIU. Mr. Isay did campaign mail for Barack Obama in New Hampshire and North Carolina during the general election. In 2006, he worked on Joe Lieberman’s general election in Connecticut, and in 2008 made television spots for Benjamin Netanyahu in Israel. This year, his firm counts as clients Manhattan district attorney candidate Leslie Crocker Snyder (who Mr. Isay’s former client, Mr. Morgenthau, despises) and comptroller candidate David Yassky, whom Mr. Isay helped crush in a 2006 bid for Congress when he worked for Yvette Clarke, now a representative.

"He’s an enormous asset to any campaign," Mr. Yassky said.

When he loses, the intense Mr. Isay loses hard.

Like, for example, when he ran Andrew Cuomo’s disastrous 2002 campaign. These days, multiple sources familiar with their relationship say, the two can’t stand each other and would never work together again. (Mr. Isay says the relationship has improved. Not coincidentally, perhaps, Mr. Isay has hired seasoned labor operative Jennifer Cunningham, who is considered a close ally of Mr. Cuomo.)

And the increasingly distant attitude of Mr. Isay, a former press secretary, toward the members of the media was decidedly not helpful during his botched public rollout of Caroline Kennedy as a candidate to replace Hillary Clinton in the Senate.

The Senate seat has been bad luck for Mr. Isay altogether. News that he was informally advising Mr. Stringer and Carolyn Maloney during the posing phase of their ultimately aborted primary challenges resulted in his former boss, Mr. Schumer, a supporter of Kirsten Gillibrand, brushing him back...
Read entire article at PolitickerNY.com