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.

 

Mr. Wolfson is a partner at the Washington-based firm the Glover Park Group. The firm has lost a significant amount of its influence in New York. It has closed its entire creative department, and senior partner Gigi Georges has reduced her client workload as she does a public policy fellowship at Harvard. But in the city, Mr. Wolfson still matters, and several insiders expect him to start something on his own. Over a recent lunch at Nobu, though, where he knew the menu well enough to order without looking at it, he insisted that he’s staying put.

"If I were a candidate, I would hire Jef to do polling, Josh to do media," said Mr. Wolfson. It went without saying that Mr. Wolfson would hire himself to do the communications.

Mr. Wolfson served as communications director for Hillary Clinton’s Senate and presidential campaigns. During the selection process to replace Mrs. Clinton in the Senate after she left to become secretary of state, he informally advised and promoted Ms. Gillibrand, whom he helped elect to Congress in 2006. Glover Park will work on the reelection campaign of Nassau County Executive Tom Suozzi, who is expected to run for attorney general when Mr. Cuomo runs for governor. Mr. Wolfson’s only official business now is a $40,000-a-month-before-bonuses gig as communications director for Mr. Bloomberg’s reelection campaign. (The fee is paid to Blizzard Communications, Glover Park’s campaign arm.)

Mr. Pollock’s Global Strategy Group, which has generally thrived on business outside of the Schumer and Clinton orbit, has recovered from the inglorious departure of Mr. Spitzer by acting as an adviser and pollster to Ms. Gillibrand and Mr. Cuomo, who may also use Global if he runs for governor.

Mr. Pollock worked for Freddy Ferrer in the last two mayoral elections, and in the presidential campaign, his firm worked for John Edwards. His firm now counts Mr. De Blasio, Ms. Katz and Manhattan district attorney candidate Cy Vance Jr. as clients. Global has never advised Israeli leaders but they are active in South America. Mr. Pollock was once hired to modernize government polling practices in Kazakhstan.

Sometimes the three compete. Often, they overlap.

In 2003, Mr. Pollock and Mr. Wolfson worked together on the effort to kill a referendum in favor of nonpartisan elections in New York. In 2006, they both found themselves being screamed at by Rahm Emanuel, who was urging them, forcefully, to do more to get Ms. Gillibrand elected to the House.

Mr. Pollock and Mr. Isay have worked together for Mr. Stringer, City Council Speaker Christine Quinn and several other candidates and unions.

But the most astounding thing, for many political insiders in the city, is that Mr. Isay and Mr. Wolfson are now working together, sometimes in the same closed office, for Mr. Bloomberg.

"We talked about it," said Bradley Tusk, Mr. Bloomberg’s campaign manager, referring to a conversation he had with Mr. Isay before bringing on Mr. Wolfson. He said that Mr. Isay told him, "You’d much rather have Howard working with you than against you."

 

At one time, it seemed only natural that the two would go into business together.

Mr. Isay, an Upper East Side native, was Mr. Schumer’s chief of staff on Capitol Hill, and Mr. Wolfson worked as a press secretary for Representative Nita Lowey. Mr. Isay dated a friend of Mr. Wolfson’s. The two sports fans (Isay, Mets; Wolfson, Yankees) talked on the phone all the time.

They bonded even further when Mr. Isay, who was Mr. Schumer’s campaign manager, called on his friend to come aboard Mr. Schumer’s 1998 Senate campaign as communications director.

"He gave me a huge opportunity," said Mr. Wolfson. "We had a lot of fun on that campaign."

In the end, Mr. Schumer outmaneuvered fellow Democrats with more famous names (Green, Ferraro) and beat Al D’Amato, a Republican institution, to get to the Senate, where he is now the most powerful legislator the state has seen in a generation. Mr. Wolfson went back to the Hill, as Ms. Lowey was expected to run for Senate herself. But when Mrs. Clinton entered New York politics with the force of a rare comet, Mr. Wolfson attached himself to her, and became one of the most trusted aides in her 2000 Senate campaign.

With so much experience under their belts, Mr. Wolfson and Mr. Isay often discussed going into business together, though they never had any formal arrangement.

In January 2000, Mr. Isay left Mr. Schumer’s office for a brief stint as the Silicon Alley lobbyist for the Web advertising firm DoubleClick. In early 2001, Mr. Wolfson joined the DCCC as its executive director. In the spring of 2001, Mr. Isay returned to politics to work with his mentor, Hank Morris, on Alan Hevesi’s 2001 race for mayor.

Then, an opportunity presented itself.

With a governor’s race on the horizon, Andrew Cuomo, fresh off a résumé-building stint as Bill Clinton’s director of housing and urban development, wanted to run, and he was hungry for talent.

He called Dan Klores, a public-relations man who was an old friend and drinking buddy. Much of the exploratory work for Mr. Cuomo’s campaign was done within Mr. Klores’ Park Avenue South offices, where Mr. Cuomo said he wanted to put together an aggressive, battle-tested campaign team. Jonathan Prince, who had worked in the Clinton White House and knew Mr. Cuomo from his time at HUD, signed on. He suggested his friend Mr. Wolfson, an idea Mr. Cuomo liked.

According to several people involved with the negotiations, Mr. Wolfson was torn. He told Mr. Klores and Mr. Cuomo that his original plan had been to go into business with Mr. Isay, whom they did not know well. Most people involved at the time remember that Mr. Wolfson suggested to Mr. Cuomo, Mr. Klores and Mr. Prince that they meet with Mr. Isay. Mr. Wolfson ultimately decided to return to Washington and the DCCC. Mr. Isay, according to several sources, also expressed his reluctance about joining the firm.

Soon after, though, an incredulous Mr. Wolfson caught wind that Mr. Isay, unbeknownst to him, had decided to go for it after all. He became a founding partner of the firm of Isay, Klores, Prince, with the intention of working as campaign manager for Mr. Cuomo.

Mr. Wolfson called Mr. Isay to see if the rumors were true.

They were.

Mr. Wolfson told Mr. Isay that they would never speak again.

And for a very long time, they didn’t. The two men were married within days of each other in June 2002—Mr. Isay to Cathie Levine, a former Schumer operative and a publicist at ABC News, and Mr. Wolfson to Terri McCullough, now the chief of staff to House Speaker Nancy Pelosi—but they didn’t attend each other’s weddings. Their wives didn’t speak. Their friends got caught in the crossfire.

For an elite circle of consultants and political insiders, the feud has provided an unmissable subplot to many of the city’s races. One consultant said that it was a cross between a "soap opera and the Bloods and Crips."

"It’s ancient history," said Mr. Wolfson. "I’m thrilled to be able to work with him now. For my part, I certainly regret what happened, and if I could do it differently, I would, and I blame myself."

"I regret what happened and wish that we could get back the years that we were not friends," said Mr. Isay. "But we have a long time to make up for it, starting with this campaign, and I know that we both want to."

 

As it turned out, the Cuomo campaign was an unmitigated disaster, and the new firm quickly disbanded. Mr. Prince became more interested in John Edwards, for whose 2004 presidential campaign he played a key role. Mr. Klores, bitten by the film bug, began concentrating on making documentaries. Mr. Isay stayed, and he suffered for it.

Despite having been frozen out of important decision-making relatively early on, his burgeoning reputation as a political tactician took a serious hit.

He started over. Partnering with Micah Lasher, then a 20-year-old senior at N.Y.U. who had done field work for Mr. Cuomo during the campaign, he formed Knickerbocker Partners, and started calling prospective candidates all over the city and state.

Their first client, Ken Bishop, who was running for Congress, was referred to them by, of all people, Mr. Wolfson at the DCCC.

(Several people with knowledge of the feud viewed the help as a peace offering. It didn’t work.)

Then, in 2005, they landed Mr. Bloomberg as a client. Since then, Mr. Isay’s firm has become one of the biggest in town.

Also, Mr. Isay changed.

As a young consultant, he was sociable and talkative and emotional. (His mother was the author of Walking on Eggshells: Navigating the Delicate Relationship Between Adult Children and Parents.) Now he’s reluctant to speak the press, on the record or off. He has quit smoking and lost weight. He eats salads.

 

Raised in a suburb of Philadelphia, where his father owned pharmacies and his mother was a lawyer, Mr. Pollock interned for Representative Charlie Rangel when he was in high school, and then attended the University of Pennsylvania, where he enrolled in a class taught by the Republican operative Frank Luntz called Candidates, Consultants and Campaigns. (He now teaches a similar course at Columbia University.)

After class, Mr. Luntz and his best students would go to drink at Smokey Joe’s, a bar where Mr. Luntz, an Oxford-trained debater, would argue just about any side of any issue with them. At 2 a.m., when the bar closed, Mr. Luntz and his acolytes would head to the local IHOP, where they’d talk about polling. Mr. Luntz always ordered himself a steak.

Mr. Pollock was enthralled.

In 1992, as a senior in college, Mr. Pollock and other students accompanied Mr. Luntz to the New Hampshire primaries. During the campaign, Mr. Pollock was hoping his mentor would set him up with a job with Bob Shrum, a guest lecturer at the campaign class and a Democratic legend, but was instead farmed out to work as a pollster for Ross Perot. Mr. Perot dropped out, and Mr. Pollock finished school. After graduation, he took a job with Mr. Luntz, with the understanding he not work on any Republican campaigns.

In 1993, Mr. Luntz worked on Rudy Giuliani’s campaign with David Garth, the city’s most successful and powerful consultant. After Mr. Luntz wrote the "Contract With America" with Newt Gingrich, Mr. Pollock left the firm and started doing more work back in New York with Mr. Garth, and moved in with his girlfriend, Deborah Brown, at Columbia University.

There, he started his own firm, called Strategic Research Team. (The stationary he had printed read "Stragetic Research Team." He was the team’s only member.)

He had a single client, which he inherited from Mr. Luntz: Pedro Rossello, the Puerto Rican governor. In 1995, as he polled for Mr. Rossello’s re-election campaign, he was introduced to John Silvan, who also had business in Puerto Rico and who had started Global Strategy Group in the rent-controlled Washington Square Village apartment of his recently deceased grandmother. The two businesses merged.

They were successful right away, helping Bill Murphy, a candidate for district attorney in Staten Island, defeat beloved Republican Guy Molinari. They helped elect Carolyn McCarthy to the House, and in 1997, they started getting business from Freddy Ferrer.

Then in 1998, Mr. Pollock’s last-minute polls correctly predicted that Mr. Spitzer would beat Dennis Vacco by about a single percentage point.

"At that point, we certainly became a much more well-known commodity," said Mr. Pollock.

These days, Mr. Pollock’s firm has a local and national presence. Through a merger with consultant Harrison Hickman, they worked on John Edwards’ 2004 and 2008 presidential campaigns. They have polled for Chet Culver in Iowa and, recently, for Arlen Specter in Pennsylvania. They have also been at the vanguard of the Democratic retaking of Albany, first with Mr. Spitzer, and now that he is gone, with Mr. Cuomo, who hired Global for his 2006 attorney general’s race.

"I used to say, ‘Andrew, you are winning by 25 points,’ and he’d say, ‘It’s not enough.’"

On a personal level, Mr. Pollock is now close to Mr. Isay. They take their kids to synagogue together. Their wives climb steps and exercise together in the morning along Riverside Park. Their children play together.

At Mr. Pollock’s birthday party a couple of years ago, Mr. Isay stood up and made a surprise announcement. His family intended to move just down the block from Mr. Pollock on the Upper West Side.

"What a wonderful friend and wonderful family," Mr. Isay said. "And we’re going to be neighbors."