Bill Hillsman: Minnesota's Most Dangerous Political Player?

Beneath his altar-boy smile lurks the soul of a '60s radical

By Kevin Featherly

The ad man punched a button on the video player in his Warehouse District office, downtown in Minneapolis. Presently, a blue TV-test pattern appeared on the TV, abruptly replaced by the red, sweating face of Minnesota's Democratic U.S. Senate candidate of 1990--the candidate's onscreen visage the very picture of doleful dissipation, exhausted anxiety. It's all part of a TV commercial you never saw, made late at night on the Wednesday before that year's general election. Then-incumbent Sen. Rudy Boschwitz, seemingly unbeatable mere weeks before, had lately been feeling the heat, had begun attacking his Democratic opponent's wife and daughter in public. The slights felt very personal. After an intense, trying, long-shot campaign in which few had given him a chance, the cheap shots, finally, were too much for Paul Wellstone to bear.

The candidate on the screen speaks: "This is the ad I never thought I would have to make," Wellstone fairly whines before letting loose his list of grievances toward Boschwitz. His voice hitches, his eyes plead, he's quaking, struggling to maintain some kind of composure for the camera in his face, utterly failing. "Rudy Boschwitz will stop at nothing to get elected," the candidate implores. "Don't let him do it."

Ten years later, the images haven't lost any of their power to spell doom. Bill Hillsman flips off the TV, turns to his visitor. He describes the setting: Wellstone had got Hillsman on the phone at 10 p.m. that night, demanding that a rebuttal ad be produced immediately and aired the next morning. Never mind that there was no open studio suitable to the task that late at night. Never mind that the one place they did find in Plymouth had archaic video-production facilities, no suitable lighting, terrible sound. Wellstone, whose inflammable passions had thus far been held in check through the race, was now basking in his own indignation. He couldn't be stopped by mere technical shortcomings, and no amount of reasoning that the ad would spell suicide could thwart the candidate in his mission to let people know just unscrupulous and ruthless an opponent was Rudy Boschwitz: the people simply had to know. It was exactly the sort of emotion-fed miscalculation that causes candidates like Paul Wellstone to self-destruct, and Hillsman, then just 36, knew it, felt it in his guts. He had been forced to film a train wreck.

But he felt under no obligation to air it.

"I probably told Paul I'd run it the next day," Hillsman says now. "And then just never did. In the stretch run of a campaign, the candidate is so busy they don't know what's going on. They're not looking at televisions, they don't see ads. I think eventually he forgot. But if I had done what Paul wanted, if that ad had run, Paul Wellstone never would've been elected.

"Sometimes," the ad man says, "you have to protect a candidate from himself in his own best interests."

In the intervening years, some very important people have come to trust such instincts in Bill Hillsman when he decides that he's right.

Bill Hillsman, owner of North Woods Advertising in, is the maverick idea man behind the most famous, most successful political rebels of Minnesota's past decade. He may have pioneered adding droll wit and sly mockery to political campaign advertising, he has been, perhaps, the guiding force behind what arguably are Minnesota's two least likely election victories ever: Wellstone's 1990 U.S. Senate coup, and Jesse Ventura's startling ascendancy as governor in 1998. Some strongly disagree, others just as strongly concur that Hillsman's image-making talents all but created those victories, as if he sketched them out of thin air and imagination and bull-headed insistence. A few even think that, if he were to point his cameras and microphones at national politics, Hillsman might have the power to become a missionary in the cause of reshaping the entire political landscape of an American nation mired in flat-lined, disconnected, gridlocked two-party politics--a landscape ripe for rebellion.

"He could potentially be huge," says Dean Barkley, the former U.S. Senate Independence Party candidate who lost in battle to the Hillsman-Wellstone team in '96, before hiring the ad man in 1998 to get Ventura elected. "I think up until now, he's been important. I think he could be absolutely critical for a challenge to the existing two-party system, if in fact we can get candidates worthy of his help to come on board."

But who is he? Who is Bill Hillsman? A gifted visionary, the decade's greatest populist communicator? Or merely a cynic, an angry but exquisitely talented mass-media manipulator? Is his a power to shape TV-viewer response, writ so large, that he can in truth single-handedly determine the outcome of the most major elections? Or is just he a clever operative whose chief talent is absorbing credit for the achievements of others? Talk around and you'll get all those viewpoints. Talk to Hillsman himself, and you'll find a rebel with a clue, a confident natural insurgent. You'll also discover a man who, in conversation, is not averse to applying to his own image the same deft spin he's use to polish with varying degrees of success the facades of candidates like Wellstone, Ventura, John Marty, Sharon Sayles Belton and Tony Bouza.

Is this a man committed to the causes his ads champion? Or is he one whose commitment is to his own talent, his own insatiable drive to push the media that is his personal canvas, to see just how far he it can go in twisting malleable public perception? These are perhaps the most enigmatic questions about the man.

"I donÕt know that there's a succinct answer to that," says Pat Forceia, a long-time Hillsman friend who also helped deliver Wellstone to Capitol Hill as a political consultant, before moving on with Hillsman to market the Minnesota North Stars hockey team. The two are back together again working on Democrat Mike Ciresi's current U.S. Senate bid. "Bill does have a gift for understanding what motivates Americans, what irks Americans. And he happens, I think, to be fortunate enough to be living in an era when there are powerful mediums available to him to deliver his message. He understands how to tell stories. And having a medium available to him like television really plays to his strength."

Former Boschwitz campaign manager Tom Mason, now editor of the Twin Cities Business Monthly, thinks questions about Hillsman's true ideology are almost too na•ve to consider. "Media people have to present the world through the eyes of the candidate and not through their own," Mason says. "To suggest that he's trying to do something that propels a message that's his own is a real insult to him."

But as he so often does, Hillsman himself confounds such conclusions. "I think I'm right on the issues," he says. "I would not take the work we do if I didn't think was the right thing to do. We know when we're getting into (a campaign), most of the time, that we're on the right side."

Child of the Sixties

Few would argue that Hillsman is less than a product of his age. He grew up in Chicago, which for a time in 1968 became ground zero of a nation in flames. Hillsman recalls, as a teen, attending the Jefferson Airplane concert there that ended in rioting. He was around for the disastrous Democratic National Convention that erupted in a downtown police rampage. These were, Hillsman notes today, radicalizing forces, though he didn't consider himself radical. Still, he says, he did manage to get passed over for National Honor Society commendations as a teen, because everyone at his Jesuit academy thought he was a Communist.

"I didn't even know what that meant then," he insists.

What it meant was that it was about time to leave town. Hillsman tried signing up for Harvard, but he applied too late. So he tried Carleton College in Northfield, Minn., because it was, he says, the next hardest school to get into. He was accepted and began attending.

Carleton at the time was a place where the students almost all had older brothers or sisters or high-school friends attending schools like Harvard, Columbia, Berkeley, the hot beds where student-led protests were grabbing national headlines. Spurred on by a radical professor named Paul Wellstone, the kids at Carleton tried to emulate their big-city peers. But to Hillsman, who watched it all from the empty athletic fields where he liked to drink beer with his buddies, it was all so much worthless posturing. "We were in Northfield, Minnesota. Come on, the whole world was not watching, man," he says. "It just all seemed so futile. The more I saw it, the more I realized how futile it was."

Nonetheless, Wellstone did leave an impression on Hillsman, for the prolific organizational skills that would come to serve him so well politically. And both men, despite their differences, shared one pivotal nascent influence--long-time Chicago community activist Saul Alinsky, the man who once, at an exact appointed time, got hundreds of followers to commandeer every single O'Hare Airport toilet stall to protest a housing shortage, while refusing to vacate them. And they threatened to do it over and over again until Alinsky's group was included in city talks. In short order, Alinksy had a seat at the bargaining table.

Two other Sixties figures also left a lasting impression on the young Hillsman, who would soon begin channeling his wild creative energies into the field of marketing and advertising. They were Yippie agitators Jerry Rubin and Abbie Hoffman, two media-savvy radicals whose extreme guerilla-theater tactics got them a lot of attention, and generated some hatred, in the chaos of the late '60s. "The first rule of advertising is to get people's attention," Hillsman says. "They were great at that. I made fun of them at the time, but I give them credit in retrospect."

Dean Barkley isn't surprised to hear of such affinities. "I think he's got the same thing that I've got, the same thing that Jesse has, probably the same thing that Wellstone had," Barkley says. "You can call it populism. But you can also say that it's a distrust of the establishment. · His motivations are honorable. He really does believe that the underdog, grass root person needs to be heard. And he helps bring that message.

"He is a catalyst for political change in a political process that desperately needs change."

To the Manner Borne

Hillsman began making a mark as a commercial ad man long before he turned his talents to politics. He was part of what he regards as the Minneapolis-led TV-advertising renaissance of the 1970s; he and his peers at the Kauffman Stewart ad agency and their equally capable local competitors were among the first to break away from staunch TV-advertising conventions that demanded, for instance, that a product's name be repeated ad nauseam during the duration of a 30-second TV spot.

Hillsman credits himself and his cohorts with helping to "revolutionize" (he loves that word) the marketing of banks, HMOs, professional sports franchises and shopping mall--it was Hillsman, for instance, who gave the Mall of America its motto, "There's a place for fun in your life." His North Woods Advertising firm was launched as a side business, a way to deal with all the freelance work his waxing reputation as a marketing wizard was generating.

While political advertising now appears to supply the bulk of his income, it is not a political campaign--at least not in the strictest sense of the word--that Hillsman says represents his company's greatest work. But it does have all the hallmarks of his greatest election hits.

"The best job we ever did was the Northwest Airlines campaign, taking the side of the pilots against the airline in a labor dispute," Hillsman said. "Northwest Airlines spent $5 million saying that the pilots were greedy. We spent $1 million, saying that the pilots helped save the company, so whereÕs ours? We framed it as a matter of fairness. That's something that anybody can understand." After a months-long media war and a 14-day strike, the pilots ratified a favorable contract.

He also takes great pride in the victory of Sharon Sayles Belton over John Derus for Minneapolis mayor in 1993, a race he, perhaps uncharacteristically, takes frank credit for winning. "Derus looked like every machine politician I'd ever seen in Chicago," Hillsman said, noting that in debates, Derus had the early edge, scoring big against Sayles Belton with lines like, "You can't social-work with someone who's climbing into your bedroom window."

"We had a huge perceptual problem," Hillsman said, describing the difficulty of turning public opinion of a race in which a large, powerful white man who appeared to be unstoppable was taking on a petite, shrill-voiced black woman in a mostly white city. The gap was overcome through use of a humorous late-campaign ad that called into question Derus' crime-fighting expertise, ridiculing him as more a soap salesman than a crime fighter.

It's a version of the facts that Steven Schier, a political science professor at Carleton Colleges finds revisionist and highly dubious. "That might have been true in 1973. But it wasn't true in 1993," Schier said. "The Minneapolis electorate had changed enough. But any political operative is going to tell you how important they are to the outcome of an election."

It had been the Wellstone campaign in 1990, and its whimsical "Where's Rudy?" and "Fast-paced Paul" TV spots that made Hillsman a hot political property. The two-minute "Where's Rudy" spot, which parodied the "Roger & Me" documentary by tracking Wellstone in hopeless pursuit of an elusive, debate-avoiding Boschwitz, so impressed the critics that it was chosen by Campaign magazine as the greatest political ad in history bar none, though some still dispute its message.

"That 'Where's Rudy' ad was really fraudulent in its substance, but it got them some free media coverage," says Mason, who always has questioned the real importance in that race of Hillsman and his team of writers and video producers, especially given the many variables marking perhaps the wildest election year on record. "Afterward, he did further ads, some of which were critical at certain times," Mason says. "But to give him credit for Wellstone's election in 1990 is just folly."

Still, even Mason is something of a Hillsman convert now. "I think that he has gone a long way toward solidifying the reputation that he's had, a long way since I first commented on him way back in the wake of the Boschwitz 1990 loss," Mason says. "I was not convinced at that time. I think I pretty well am today. He's a very smart political operative."

Presumably the change of heart has something to do with the Jesse Ventura campaign in 1998 that earned Hillsman media-oracle status. Though there were about as many variables in the Ventura race as there had been in the Wellstone victory in 1990, many people credit Hillsman's ironic "Governor Action Figure" ad, and his revelatory, haunch-flashing "Jesse The Thinker" ad, with pushing The Body Politic into the governor's mansion.

Here Hillsman stops short of saying as much himself; he once even gave credit for the victory to numbers-crunching campaign consultant Ed Gross, whose spreadsheet analysis identified, precinct by precinct, where Ventura's potential voters lived and could be targeted. Still, Hillsman does note, "In a race that close, our work is usually worth 3 to 5 percentage points." Ventura, of course, beat Norm Coleman by a 37-34 percent margin, with Skip Humphrey trailing the pack with 29 percent. Through a spokeswoman, the governor declined to comment for this article.

The Fiery Enigma

If you look at him from the correct angles, you can see in Bill Hillsman a prism of contradictions. Though arguably he is one, in the main, he dislikes hired-gun political consultants, thinks they are part of the disease that makes so much of what happens politically so unbearable. He clearly is coming to trust the established parties less and less; but he is working for a Democrat in the current U.S. Senate race. He thinks there's too much money in the system; yet Mike Ciresi is one of the richest men in Minnesota and most people think he will have to spend at least $6 million to win the race against Rod Grams this year.

If there is one thing that Hillsman clearly believes in his guts, it is this: he hates pollsters and media consultants, thinks they are, as a genus, complete idiots. "Campaigns are robbed blind," he says. "And the parties are in league with the pollsters. It's bad for voters, it's bad for the parties. So who the hell is it good for? It's good for the pollsters, and it's good for the consultants."

"This to me is a sign of Hillsman's weakness," says Schier. "When you believe that you are on a different plane from every other practitioner in the field, you are falling victim to potentially fatal arrogance. I don't believe that all political consultants are idiots. Some are, and some aren't, right? And if you operate on the premise that everybody else is an idiot, you're more likely to put too much faith in your own judgment at some point and blow it."

But Ed Gross won't argue with the ad man. "I do not have good relationships with media consultants," Gross says. "Media consultants are arrogant, they don't put any kind of stock in a serious analysis, like the numbers analyses. It's not very sophisticated marketing. If they had to market a product, they wouldn't survive. ItÕs almost a closed society. Bill is smart enough to understand that you can take it to a level of sophistication. That's where Bill and I have come together. Because Bill likes the numbers." He is, after all, a marketing whiz first.

Those close to Hillsman, and even those distrustful of his influence, seem to find a lot to agree about. Many, even Steven Schier, are willing to call him brilliant, perhaps the best in the United States at conveying to the disaffected masses a sense that there are at least a few would-be leaders out there who feel just as dissatisfied.

Tim Penny, the former US Representative who left office in 1994 out of disgust with the system, is not particularly close to the ad man, but is at least conditionally among the believers. "At some level," Penny says, "he's just got an innate sense of where the average folks are at and how to construct a message that will be noticed by those folks. I think that, with Hillsman, he trusts his instincts and goes with that. And more often than not, he's right."

But there are flaws, as well. There is occasional wrath, his friend Forceia says, and at times an apparent joy in discomfiting people around him. "He is certainly one of the most strong-willed people I've ever had a chance to work with; it's his greatest strength," Forceia says. "(But) his strength is something that makes him a hot potato to deal with at times. He regularly tells people what he feels, good or bad. And he seems to almost relish at times in passing that bad news along, in a very blunt style."

To Schier, this is the hallmark of the Hillsman style. Far from being a possible force for liberating, populist social change, what he detects in Hillsman is a mix of "toxic emotions," the power of which, when communicated with humor through the mass media, serve only to make the disaffected even more so.

"I think what he has is mainly hostility to politics in general, and a belief that politics as it's been conventionally practiced in America is essentially bullshit, so let's shake it up and try something else," Schier said. "I suppose you could call that populism, but if so, it's sort of a negative populism, as opposed to an affirmative populism."

Schier says Hillsman seems to approach politics from the vantage point of an deeply angry man, one who believes that most politicians are idiots. "The point is that I think a lot of the public shares that attitude," Schier said, "and I think that is at the root of a lot of his effectiveness." It's also at the root of what makes Hillsman potentially a destructive force, Schier suggests. "Itâs part of this relentless negativity in politics," he said. "I don't blame Bill Hillsman for this, he's just part of it. And the whole environment drives people away from politics. So if you want politics without any citizens, this is a great tactic to get that."

Tony Bouza, the renegade 1994 Democratic candidate for governor who Hillsman calls his favorite political client ever, takes a different view. "Hillsman is rather an extraordinary character," Bouza said. "He's the very antithesis of (former Clinton spin doctor) Dick Morris. One is just a hired gun and a very talented prostitute. But Hillsman is a man who brings with him two things - talent and integrity."

Penny has worked with Hillsman several times over the years, most closely in 1998, during the campaign by Penny's friend, former State Sen. Tracy Beckman, to take back Penny's former First District U.S. House seat from Republican Gil Gutknecht. Penny himself recently dropped out of the U.S. Senate race against Rod Grams; had he not, he might have had to go through Hillsman and the wealthy, high-powered attorney-turned-candidate Mike Ciresi, plus a lot of cold, hard cash, to get there.

"I wish I knew him better," says Penny. "I do come away with the sense that he may be a bit of a gun for hire. It's just that you don't really know, when you're working with him, how much of it is genuine interest in the candidate and the message, or just the excitement and the enthusiasm about the ways that we can make this message heard. There always seems to be more of a connection to tactic and the technique than on the substance of the candidate."

Hillsman himself, talking about his affinity for marketing, seems to agree with Penny, at least peripherally. "I like doing stuff that's never been done before," he said. "Most of the time in advertising, you live and you die on how many more market share points can you get for the product. I don't really care. If you're going to do this business, you might as well do it in a way that has an impact on the industry you're working with."

Moth to a Flame?

There are indications that it won't be for much longer that Hillsman remains Minnesota's worst kept political secret. During the current presidential race, Hillsman was courted by hopefuls including right-wing Republicans Gary Bauer, John Kasich and Steve Forbes, as well as the liberal's liberal, movie star and political flirt Warren Beatty. In the end, he worked for none of them.

Barkley was in on the ritzy confabs with the movie star. "Bill and I were talking together with Beatty for about a month," Barkley says, adding that their discussions focused on fielding a presidential candidate who could continue the insurgent, third-party-styled success achieved by Ventura. "We were trying to figure out who in the hell can we get into this thing that could do what (Republican John) McCain kind of did here for the last month. We knew it was there, and we knew the formula. For the life of us, we just couldn't find anybody who could come in and fulfill the role."

If there is any indication that Hillsman is the real thing as a dyed-in-the-wool rebel who genuinely wants a third party to emerge, it might lie in his latest project, a Web site called Overthrowthegov.com he has helped create, using mercurial Republican columnist Ariana Huffington as pitch person. The site, which would seem to offer little by way of financial reward, contains an 11-point manifesto for dismantling the system and recreating it in a more moderate, socially responsible mold. It espouses ending poverty. It urges volunteerism, activism, a healthy diet. It hawks campaign finance reform and the abolishment of soft money. "The system is broken," the Web site says. "And it cannot be fixed by the same political class that is benefiting from it."

The Web project may be a further indication that Hillsman is being attracted to the bright lights of the national political stage. If so, his old opponent Mason suggests, it might be a rare tactical mistake for Hillsman. "He could play in presidential level politics if he wanted," Mason says. "I just don't think that advertising plays a huge role in presidential politics. It's important, but the journalistic media is far more important in that arena than it is at a U.S. Senate level or below. I think he's better utilized at a state level or below."

"I can see Hillsman's problem," says Bouza. "Hillsman's problem is that he is so talented, and so much in demand, that I can see him being pulled in a variety of directions."

Forceia too thinks there might be a place for Bill Hillman in national politics; he has all the talent he needs to become as successful as legendary party operatives like Lee Atwater and James Carville, though Forceia sees little desire in his friend to be anything like those two. "If this is what he wants to do, I'd love for him to be as successful, in terms of positively impacting elections," Forceia says. "If he chooses to become a significant national participant in the world of politics, he will succeed. But he will also succeed in a way that will make people who have known Bill for years proud of him."

But Barkley sees something else entirely in the Overthrowthegov.com side of Bill Hillsman, and it's not national political ambition. To Barkley, the Web site and its mission might in truth represent the purist in Hillsman, and might be the closest that the ad man has ever come to showing his truest personal political colors.

"Overthrow the establishment, the government. That's the culture he grew up in," Barkley says. "That's the Boy Scout in Bill Hillsman. He wants to change the world."

Originally published in Minnesota Law & Politics, May 2000

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Kevin Featherly, a former managing editor at Washington Post Newsweek Interactive, is a Minnesota journalist who covers politics and technology. He has authored or contributed to five previous books, Guide to Building a Newsroom Web Site (1998), The Wired Journalist (1999), Elements of Language (2001), Pop Music and the Press (2002) and Encyclopedia of New Media (2003). His byline has appeared in Editor & Publisher, the San Francisco Chronicle, the St. Paul Pioneer Press, Online Journalism Review and Minnesota Law and Politics, among other publications. In 2000, he was a media coordinator for Web, White & Blue, the first online presidential debates.

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Copyright 2004, by Kevin Featherly

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