Managing the Message

Behind the scenes of several campaigns, the latest of which put a First Lady in the U.S. Senate, Howard Wolfson has suffered the slings and arrows of political fortune-always with a greater good in mind.

She called him "Wolffie." And he called her "Hillary." But the road Howard Wolfson A.M. '91 traveled to such intimacies with the First Lady of the United States, as communications director for her New York U.S. Senate campaign, was pitted with potholes from the start.

During his very first one-on-one with her, in June 1999, he was just off crutches from a torn ligament and hobbling badly-right into his White House job interview. Hillary sympathized. That August, he accompanied her to an upstate fair where he scarfed down some peanut butter taffy-forgetting his food allergies-and his trachea slammed shut. "I don't always travel with the president," Hillary Clinton gently chided, as White House medics saved his neck. "You have to be more careful."

He could but try. During a January 2000 appearance at a small college, he sprained his ankle for no good reason. He took some sun at an outdoor press conference last summer and his face peeled like a tangerine. Stress-induced eczema caused him misery last June. He was the butt of jokes about such publicized quirks as his necklace-twisting fetish, which we'll get back to later. And, always, always, Wolfson suffered the slings and arrows of the campaign so hard, so personally, that Joel Siegel of The Daily News once said of him, "If you were a camp counselor, he'd be that kid you just wanted to put your arm around and ask, 'What's wrong?' " Have we mentioned his fear of flying?



Wolfson rallies: high-profile campaign was "a sixteen-month roller coaster" 
Photo: AP Photo/Kathy Willens.



Such pitfalls and eccentricities helped define Wolfson as the lovable neurotic to Hillary's Queen of Control, an accessible Woody Allen to her remote Mia Farrow. They were also dissected and commented on by colleagues: "He has a large number of personal tics that I, and I think many others, have found very amusing," says Neera Tanden, Clinton's deputy campaign manager.

Yet it's conceivable that those tics worked to Wolfson's and, ultimately, to Hillary Rodham Clinton's advantage. Because surely his vulnerabilities drew the candidate-who's taken a few hits of her own-closer to this bear of a man. If nothing else, he was valuable to her merely for being the things she was not: Ethnic. King of the one-liner. A consummate in-your-face New Yorker given to public displays of political passion and shock, shock, at the foibles of Clinton's Republican opponent, U.S. Representative Rick

Above all, Wolfson's biggest strength was this: He's funny. "He was a benefit to her in a very important way," says Duke political science professor David Paletz. "My sense of her was she was very cautious and serious and solemn; humor was something that either didn't come naturally or she avoided it. So it's nice to have someone working for you who can provide that."

Of course, humor was only part of it; Wolfson, who cut his political teeth as chief of staff to Bronx/Westchester Congresswoman Nita Lowey and as communications chief to Brooklyn's Chuck Schumer during Schumer's tough 1998 Senate race against incumbent Alfonse D'Amato, scored points with Hillary's inner circle for his political counsel on policy and direction. "There were literally a handful of people," Tanden says, "who were determinative of our victory, who were irreplaceable-without whom maybe we would have barely slipped by." In fact, Hillary trounced Lazio by twelve points. "Howard had many contributions, and I think Hillary deeply recognizes this."

And Wolfson himself-now considering public- and private-sector employment offers in New York-looks back on Hillary 2000 as a "sixteen-month roller coaster" that was "great and terrifying at the same time." On a rainy Sunday in New York, Wolfson sits down -a rarity from all reports-to say more. He's at the spartan Upper East Side apartment he shares with girlfriend Terri McCullough; it's got books, a couch, and a table, and not much more. Moving up from Washington last winter, McCullough thoughtfully presented Wolfson with a bed to sleep on months after he'd moved in.

This day, he's casually dressed. At six feet and "too many pounds over 200," he's a big guy with a small beard, losing his hair. He's remembering back all those years to Duke, where, arriving after his 1989 graduation from the University of Chicago, he was in a hurry to earn a graduate degree in American history so he could get on with doing what he loved best. "I wasn't a bad student," Wolfson reflects. "I was a good student who probably in retrospect had his head elsewhere." Certainly, being far from what he calls the rat race of Chicago and his native Northeast-he was born in Middletown, New York, thirty-three years ago-was a plus. But Wolfson found graduate school "monastic." As he puts it, "My head was not in going to the library and reading for hours and taking notes." So he'd go over to Ninth Street, prowling Poindexter's Records and The Regulator bookstore and indulging at Francesca's ice cream or "the Asian place near the


One thing Wolfson does remember with pleasure are the lively discussions back in that era when, under the leadership of high-profile department chair Stanley Fish, the English department was rethinking the literary canon and approaches to the teaching of literature. In particular, he recalls a class in the American political novel taught by Frank Lentricchia A.M. '63, Ph.D. '66 and Michael Moses. It was there he met Hugo Lindgren '90, who became his buddy and fellow reporter at The Chronicle's then-named "R&R;" arts-oriented section.

"He was a pretty serious journalist. He had those sorts of instincts; I had none," recalls an unduly modest Lindgren, who today is story editor for The New York Times Magazine. "We'd be writing reviews, and one of us would be doing one record and the other would be doing another, and we'd just switch and start writing the other person's review." Lindgren remembers spoofing Billy Joel's "We Didn't Start the Fire." Then there was their political analysis of Cincinnati's 1990 move to censor Robert Mapplethorpe's controversial photos at the city's Contemporary Art Center.

Off-hours were devoted to Wolfson's favorite pastimes, fantasy basketball and East Campus pickup basketball, where he and Lindgren were joined by Timothy Tyson Ph.D. '94, now an associate professor of history at the University of Wisconsin-Madison. "He was not a good athlete, but he was ruthlessly competitive," Tyson recalls. "Good-natured but very competitive."

That competition came out in politics, says Tyson: "He was so gifted at it; he was both interested in politics as a sport, the mechanics of it, and the strategy and combat of it." Wolfson, Tyson says, especially loved political culture. "He could break into a speech or famous bits of political lore. He could quote [Robert F.] Kennedy and Martin Luther King, even bits of lore from the McCarthy hearings." How many people collect political posters? Wolfson had RFK, FDR, and Adlai Stevenson. How many can cite William Jennings Bryan's "Cross of Gold" speech? Wolfson knew it by heart.

He also had a zany sense of humor. Tyson recalls Wolfson, during the Clarence Thomas Supreme Court hearings, imitating South Carolina Senator Strom Thurmond, as the famous "Dixiecrat Democrat" drawled of the black-but-ultra-conservative Thomas, "You have to give this man a chance!" Behind the cutting humor, however, the racism that Wolfson thought he saw in Thurmond's remark was the motivating force. "He had an acute sense of injustice, and he has a temper about those sorts of things," says Lindgren. And, from Tyson: "I think he had a certain moral vision and was very much committed to doing something about it." No surprise that Wolfson's graduate thesis examined the shaping of Martin Luther King Jr.'s public image by the national debate over the King holiday.

Wolfson had missed that era, of course, but as a kid growing up in Mt. Vernon, New York, he made up for it reading everything he could get his hands on about it-Selma, Vietnam, Watergate. He attended the prestigious Fieldston School in the Bronx and engaged in dinnertime debate with his schoolteacher parents. "I came from a very political household," Wolfson says. "My first political memory was watching the first POWs come home from Vietnam after the Americans pulled out." His high school yearbook dubbed him "Most Likely to Discover Watergate." Not that Wolfson was an activist: "He tended to be more pragmatic in his politics," Tyson says, "and he was more interested in electoral politics. Not protest politics, and certainly not sectarian-Left politics."

The mainstream, in fact, was enough to make Wolfson bolt grad school before finishing and head north to work a year reporting for the suburban Connection Papers of Fairfax, Virginia. "There weren't enough firecrackers going off in grad school for Howard," Tyson says. Wolfson says he missed the frenetic pace and camaraderie of his campus newsrooms. He was close enough to the Beltway to taste political life, too. So, after finishing his master's at Duke, he was won over by Washington. He started work on the Hill in January 1992.

His first real job was media work for Indiana Congressman Jim Jontz. But Jontz got dumped by voters that November. "Not an auspicious way to begin a career," Wolfson quips. He moved on to Sacramento, California, Congressman Bob Matsui, then jumped ship in early 1993 to his hometown Congresswoman, Nita Lowey. He admired her "compassionate-progressive" stance, her identity as the "go-to" person on abortion rights and head of the Women's Caucus. He credits her with saving public TV during Newt Gingrich's "Contract with America" era. "I feel proud that I was a part of that process-people fighting on the ramparts, beating those folks back. It's something I will tell my kids about."

Wolfson moved up-first becoming Lowey's press secretary in May of 1993 and two years later becoming her chief of staff. Then, in August 1998, he was loaned out to help Schumer defeat incumbent senator Al D'Amato. It was shortly after that victory that New York Senator Patrick Moynihan announced he wouldn't run again and all eyes, including Wolfson's, turned to Lowey. He insists she was ambivalent-though the conventional wisdom is that she was pushed out by the Greater Force of Hillary. Whatever the reality, Wolfson's star was rising; he was recruited for the press slot by no less a light than Hillary's campaign chairman and former White House deputy chief of staff Harold Ickes.

What do you say to an offer like that? "You say yes," Wolfson responds, laughing. "I knew that working for her would be the opportunity and adventure of a lifetime." His hire was announced June 26, and Wolfson was shortly sucked into the Hillary Hysteria Machine, with a cell phone and pager that didn't stop, even late at night. Days on the road for Clinton's "Listening Tour" began with dawn breakfasts and ended with an exhausted sleep in some heretofore unknown upstate town. His fear of flying made things worse. New York is an enormous state and he'd drive as far as Buffalo and back in one day to avoid the campaign plane.

Then, from last summer on, Wolfson, who'd been promoted to communications director, manned the New York "war room" in shabby quarters near the garment district, shooting e-mail to reporters, dealing with the gulf between the campaign and White House staffs, answering criticisms about the obvious splintering within the Hillary ranks.

En route, he says he was amazed by the extreme passions she engendered. In typical press-rep fashion, he deflects a question about hate toward the Clintons. "There was some reporting about the passion in favor of her but not as much as the passion against her." To illustrate, he produces a photo of Hillary surrounded by admirers in Queens.

This was Wolfson's job: to channel the emotion for and against Hillary back into the Message, the Issues. Events, however, kept getting in the way. She was "banned" by Crown Heights' ultra-orthodox Jewish council for reaching out to ex-Mayor David Dinkins, who was disliked for the way he'd handled the Crown Heights black/Jewish riots. In the fall of 1999, her stock sunk even lower with Jews when, on an official White House trip to the West Bank of Israel, she embraced Suha Arafat, right after Arafat's wife charged in a speech that Israel was poisoning Palestinian children. There was more: President Clinton's offer of clemency to Puerto Rican nationalists was seen as a sop to his wife; then there was an allegation of an anti-Semitic slur. And this past fall, the campaign twice embarrassed itself, obtaining 1,400 names from a White House visitors list and accepting money from a Muslim group advocating armed force against Israel.

Wolfson could be glum at such down times, says Tanden, the deputy campaign manager. ("I'm not known for my optimistic streak," Wolfson allows.) And he was downright disappointed when Mayor Rudolph Giuliani withdrew, putting to rest the "race of the titans." But Congressman Lazio polled in the 40-percent range with Hillary, making for a neck-in-neck race that had to be exciting enough, and giving Wolfson ample opportunity to unleash that New York emotion of his. Reacting, for instance, to a Giuliani ad describing the mayor's "compassion," Wolfson shot back that Giuliani was prone to "breaking up families by taking homeless children away from the parents," and added, "If that's compassion, I'd hate to see him on a bad


When Giuliani canceled a Rochester appearance to attend a Yankees game, Wolfson rushed Hillary upstate. "I heard some people around here were hoping to meet a Senate candidate," he gushed to the crowd. Nor was he above stunts. He had an "Uncle Sam" figure trail Lazio on the campaign trail and even showed up himself to toss the opponent copies of Hillary's New York property tax bills (Lazio had said he'd release his fifteen minutes after Hillary did).

Another of Wolfson's coups was David Letterman. The talk-show host had called Wolfson a "pantywaist" for not booking Hillary to appear on Late Night. When Letterman actually phoned him-on-air-Wolfson dished back, inquiring whether the Carnegie Deli delivered to the green room. Letterman played peeved. "I do the jokes here," he said. "What's his name? Buddy Bobson?"

Wolfson chalked up other points with the press. Sure, writers chided him for quirks like his, well, limited wardrobe. "I'm giving you two," a Secret Service agent had said, handing Wolfson two identification pins. "One for each of your suits." And of course there was that bizarre need he had to handle jewelry any woman wore within arm's length of him: Tanden, the deputy campaign director, enjoyed tormenting him with her long Indian necklaces. There was also the fake "feminist fund-raiser" that prankster-reporters kept asking a befuddled Wolfson about; the fictional event was geared to a saucy show in New York called The Vagina Monologues. But Wolfson had those reporters' respect. "He was totally honest and totally reliant," says one top New York City reporter, citing professional conflict as a reason to remain anonymous. "He was a true believer, which is

His own camp echoes the assessment. "He was very smart, very creative, very cautious," says statewide field coordinator Marc Lapidus A.M. '87. "There was so much scrutiny, you needed people who dotted their i's and crossed their t's, then went back to make sure the i's were dotted." Tanden tells how Wolfson influenced the campaign's agonized decision to decline any endorsement from New York's Independence Party. Reason: Its presidential ticket, Pat Buchanan and Lenora Fulani, was considered anti-Semitic in some circles. Wolfson also was responsible for convincing insiders that Hillary should maximize her exposure, to overcome doubts about her character. "He was really forceful with Hillary opening up more and doing more interviews," Tanden says. She credits Wolfson for the Letterman and Leno appearances and the stand-up show Hillary did for the state press corps last summer-where she dragged on stage a huge carpetbag to mock her detractors' concerns about her short-term New York residency. Wolfson's work to warm up the First Lady's image was crucial, Tanden believes, because "she has had horribly bad press relationships and her relationship was just a critical, critical issue for her."

In turn, the First Lady warmed up to Wolfson personally. She declares herself "very lucky" to have employed Wolfson. "His communications expertise, political insight, and sense of humor were invaluable to me on the campaign trail. I couldn't have done it without him," "I was surprised at how funny she is," he says. "She is very funny, very quick-witted; and she loves to laugh." He was impressed when she left a message on his home phone wishing his girlfriend, Terri, good luck in the 2000 New York Marathon. ("There are plenty of bosses who couldn't care less that your significant other ran in the Marathon.") And he tells how, when he had to fly home-despite his terror of airplanes-on Air Force One from Los Angeles after the Democratic Convention, Hillary came back to sit with him, without making a big deal of her gesture. "A lot of people wouldn't have handled it as gracefully."

Wolfson was able to fly in other ways. He describes the Gay Pride Parade in New York last summer as a highlight. "The response she got from the crowd was so overwhelming-cheering and screaming and laughing and calling her name, a tremendous outpouring of affection-it was such a feeling of joy." The joy was infectious: Press reports had Wolfson and his staffers dancing their way down Fifth Avenue.

Another highlight was Hillary's appearance at a Harlem church after Mayor Giuliani released the arrest records of N.Y.P.D. shooting victim Patrick Dorismond. "There was a tremendous feel of anticipation, of energy, because people were so enraged by what the mayor had done," Wolfson says. Hillary arrived as the chorus swung into The Battle Hymn of the Republic. "Everyone was on their feet cheering and singing. And she gave probably the most powerful speech of the campaign. There was a moment where you could feel what the power of words really is, where you could watch a speaker's ability to really transform a crowd."

It must have all come together that evening for Wolfson. His "moral vision" that Tyson described against racism and other injustices. His fascination with the machinations of electoral politics. His skill at revealing the humanity of a candidate previously scorned. Asked if "making a difference" is the heart and soul of his political vocation, Wolfson hesitates. "I'm not sure it's a calling in the same way that becoming a rabbi or joining the priesthood is," he says. "It's certainly more than a business. And it is a way to make a difference if you care about these issues." For a kid who collected political posters while schoolmates collected baseball cards, clearly it's the only way.

Oleck is a staff editor at Business Week magazine in New York.


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