Photos by Dan Bishop

It’s a sunny summer day and Larry Nelson isn’t exactly making a fashion statement.

The Waukesha mayor has come to work clad in khaki slacks, white socks, black Crocs and a lavender polo shirt that stretches over his middle-aged paunch. Nelson looks more like the summer-vacationing teacher he used to be than chief executive of the state’s seventh-largest city.

Nelson is the odd man out, a fish out of water, a ham sandwich at a bar mitzvah. He seems in every way contrary to conservative, Republican Waukesha: an unabashedly progressive, Jewish, union-activist Democrat who once marched for a nuclear freeze and counts among his heroes Mo Udall, Howard Dean and Mahatma Gandhi.

How in the world did Nelson ever get elected? His win in the spring 2006 election stunned the right, angered Republicans, and left Democrats cheered, if a bit mystified. Yet some Republicans are now predicting Nelson could get elected to a second term.

Nelson’s Cinderella story is about many things. A Waukesha that transcends its one-dimensional stereotype. A Democratic Party that may have gotten more strategic. A state with a history of nonpartisan local government, where voters often choose the person rather than the party. And perhaps the decline of polarized, right-versus-left politics.

The underdressed mayor of Waukesha might well be the poster child for all these trends. More than anything, his energy and optimism brings to mind a Minnesota politician who once enjoyed considerable popularity in this state: Hubert Humphrey. Like the former U.S. senator and vice president, Larry Nelson could be dubbed the Happy Warrior. He’s a people-oriented pol who invariably leaves citizens smiling.

“It’s great to be the mayor of Waukesha,” he says, for the umpteenth time over the course of three interviews. He does so with that slightly raspy, gee-whiz voice and a beaming smile he seems to bestow on everyone he greets. Nelson is truly the Happy Warrior of Waukesha.

“Happy days are here again,” blogged sometime Democratic strategist Bill Christofferson after Nelson won. Nelson had upset the favorite, former Republican state Rep. Ann Nischke, though he spent just $13,000 compared to her total of $34,000 –
more than any Waukesha mayoral candidate in history. Nelson also overcame Nischke endorsements by the Journal Sentinel and influential radio talkers Mark Belling and Charlie Sykes, confounding the many experts predicting his defeat.

Commentator Jessica McBride sputtered in her post-election Waukesha Freeman column that Nelson was “a stealth candidate” who “muddied the waters” in the race, somehow confusing voters about where he stood.

But state Rep. Bill Kramer (R-Waukesha), the conservative who succeeded Nischke in the state legislature last November, dismisses that theory. This was a man known for years of activism in the local teachers’ union and the Democratic Party. “It would be hard for me to understand how somebody didn’t know his politics,” Kramer says. Yet they voted for Nelson anyway.

On Larry Nelson’s desk in City Hall arethe souvenirs of a varied life. A whimsical Shakespeare action figure, a tribute to his three decades of teaching middle school English. A photograph with Mo Udall, taken when Nelson was 20 and active in the Democratic congressman’s 1976 presidential campaign. A picture of his father’s high school graduation, the father who died when Larry himself was still in high school.

Nelson grew up on Milwaukee’s Northwest Side. Bookish and reserved, he skipped half of third grade because he read so well, hiding behind black horn-rimmed glasses that at age 7 made him look like a mini Woody Allen.

Nelson’s grandfather founded the Nelson Shoe Store on North Green Bay Avenue. His father, Seymour, ran the store until the changing neighborhood drove away customers and put it out of business. Seymour Nelson then worked selling shoes at Brill’s in Bayshore Mall.

He also read the news voraciously and engaged his son in talk about politics and current affairs. In his senior year at John Marshall High School in 1972, young Larry convinced his parents to vote for George McGovern in the Wisconsin primary. That was one of his father’s last acts. “My father died a month before my high school graduation,” Nelson recalls. “He was 46. I was 17.”

Seymour Nelson had served in World War II and lost a leg to a land mine. He wore an artificial leg thereafter. After 28 years, a blood clot in the remaining stump killed him instantly.

“My father’s death was the worst tragedy I ever had to deal with,” Nelson says. “That was really the turning point in my life, both as a person and politically. I really wanted to make a difference in people’s lives.”

Nelson went off to the University of Wisconsin-Madison in 1972, still too young to vote in that fall’s presidential election. He spent his first year buried in books.

“I didn’t realize it at the time, but I was still severely depressed about my father’s death. The way I dealt with it, I would go to the bookstore and pick out the thickest classic literature books I could find.” It was the literary excursion of many a college freshman: a little Dickens (David Copperfield), a little Ayn Rand (Atlas Shrugged), and plenty of existential angst (Camus’ The Plagueand Dostoevski’s The Brothers Karamazov).

He weighed a major in philosophy or psychology, then settled on English, drawn by the novels of James Joyce, the plays of Shakespeare, the essays of Henry David Thoreau and transcendentalists like Ralph Waldo Emerson. “There were more life answers in literature than in psychology or philosophy,” Nelson says.

In his senior year Nelson attended his first demonstration, for a controversial black studies professor whom the university had denied tenure. When the education writer Jonathan Kozol came to campus, Nelson buttonholed him at a book signing, and later saw the power of ideas even as spoken by a mild-mannered personality. “That night I went to his public lecture. He rolled up his sleeves and gave one of the most impassioned speeches I’ve ever heard about the need for educational reform.”

Nelson joined two UW political groups: the Committee Against Racism and Students for Mo Udall. “Friends in the Udall campaign would ask me, ‘Why are you involved in that Committee Against Racism?’ And friends in the Committee Against Racism would say, ‘Why waste your time in electoral politics?’ It was a good introduction to why the left is usually unsuccessful: They’re so busy fighting among themselves they don’t make coalitions to succeed.”

It was a lesson he’d never forget.

After getting his UW degree in 1976, Nelson got a job teaching English at Morgan Butler Middle School in Waukesha. From the day he started, he would tell students at the end of every class, “Thank you for coming.” Many thought it was corny. But the habit stuck.

Nelson moved to Waukesha and threw himself into the community and social activism. He helped found Wisconsin Educators for Social Responsibility – an anti-nuclear weapons group that evolved to press schools to teach about social issues and current events from multiple points of view. He spent six years on the board of the Women’s Center, which helps battered women. He served on the board of Jobs with Peace and marched in New York City for a freeze on nuclear weapons.

After flirting with third-party politics by backing John Anderson’s 1980 presidential run, Nelson returned to the Democratic fold. In 1982, he joined other teachers in supporting Jim Wood’s failed bid for the Democratic nomination for governor. He attended the Democratic National Convention as a delegate for Walter Mondale in 1984, for Al Gore in 2000 and John Kerry in 2004 – “Although I did support Howard Dean before he imploded,” Nelson notes.

In 1992, Nelson became president of the joint union council serving teachers in Waukesha, Elmbrook and Menomonee Falls. He was building political contacts and skills. And he was getting to know the city of Waukesha in great detail.

Ask outsiders about Waukesha and you’re likely to hear the city conflated with the surrounding county. Waukesha County is the locus of the state Republican Party: conservative, wealthy, suburban, home to staunch Catholics and Evangelical megachurches. For some Milwaukeeans, Waukesha symbolizes white flight, suburban sprawl and an antagonism to urban ideas like light rail.

But if the county is overwhelmingly Republican, the city is more divided, delivering a 60 percent majority to George W. Bush in the 2004 presidential election.

“I’ve never felt the city of Waukesha was that heavily Republican,” says Paul Vrakas, who served as its mayor for two different eight-year stretches. “We’re like a mini Milwaukee. We’re a city with an older downtown, a city with a lot of industry.”

Nor are voters necessarily unwilling to pay for government. Carol Lombardi, a former mayor, boasts of “the quality of the city’s services,” from its emergency response to its public library. The city of 68,000 residents has made efforts to preserve historic old buildings, has a growing number of trendy shops, and cultural offerings, such as an arts crawl several times a year.

“A lot of people paint Waukesha with one broad brush,” says UW-Waukesha political scientist Joe Foy. “But the city tends to be a little more diverse, a little more
working-class.” The city is home to foundry workers and factory employees, including those who work at the nearby General Electric plant. And Hispanics now make up 10 percent of the population.

When the alderman serving the Sixth District – where Nelson lives – resigned in 2000, then-Mayor Lombardi encouraged him to seek the office. Lombardi, a moderate who has never identified with either political party, says Nelson’s politics were different from her own. But he was someone she’d gotten to know as an administrative employee in the Waukesha School District, and she was impressed by his skills. “We have the same values. We care about this community,” she says.

Nelson decided to take a shot. “I watched a couple of council meetings and I thought I could do it,” he says. Appointed to fill the vacant term, Nelson then won a 2001 special election against a 19-year-old challenger. He was re-elected the next year, unopposed, to a full three-year term. In 2005, he ran for his second three-year term and faced his first serious challenger.

“It was the first time I did a campaign brochure, the first time I did doors, lawn signs and calling people,” he says. Nelson won with 53 percent of the vote, even as a school-funding referendum went down to defeat the same year.

Along the way, Nelson got married. His first marriage, in the early 1990s, had ended in divorce after five years. Nelson dated around and asked a close friend whether she knew any romantic prospects for him. She mentioned a cousin of hers, but warned, ‘You two don’t have anything in common.”

And that’s how he met Dawn Borowski, a travel supervisor living in Mequon. After a telephone conversation, he dropped by her home one day on the way to a get-together with his own family. “Do you like Willie?” he asked her. Borowski was puzzled. “Willie who?” “Willie Shakespeare.”

Well, she did actually. So they made a date. After brunch at Trocadero on Milwaukee’s East Side, they drove out to Spring Green and saw the American Players Theatre’s production of Taming of the Shrew,then back to Mequon. At 14 hours, “it was a very long first date,” Borowski – now Dawn Borowski Nelson – recalls.

“I was scared to death to go on a date that went from 10 in the morning till 1 a.m. But both of us were talking nonstop the whole time. I loved his personality. He was very interested in what I had to say – he was a good listener.”

He also couldn’t help being a teacher. While she, too, tends to vote Democratic, she was no political junkie. “Whenever anything came up involving politics, he’d give me articles on both sides and make me read them,” she says. “He wanted to have a discussion. I have my points of view and he’s fine with that – as long as I can back them up. Because of him I have to learn about all the issues.”

The cousin who had made the match once told her, “You know, some day he’s going to be mayor of Waukesha.” Replied Borowski: “Yeah, right.”

Nelson’s 2005 victory in his aldermanic race gave him confidence to enter the February 2006 mayoral primary. He faced six rivals, including Nischke. When he launched his campaign, “I gathered all the political lists and identified 850 of my closest family and friends.”

Nischke’s win in the primary was no surprise. Her assembly district covered the city, giving her strong name recognition and the experience of twice running a citywide race. Moreover, she seemed likely to gain the supporters of the losing candidates, who were all conservatives as well. Pundits were already writing Nelson’s political obituary.

But not everyone in the Nischke camp was so confident. “The day after that primary I told that campaign they were in for the fight of their life. They thought I was nuts,” one Nischke activist says privately.

The underdog’s secret weapon was his history in the schools. “Thirty years of parent conferences turned out to be a surprising hidden strength of support from the thousands of parents and students I got to know,” Nelson says. Coupled with his affable demeanor and a hard-working campaign that stressed his experience in city government as well as the schools, he targeted Nischke as too removed from the nitty gritty of local government.

Most handicappers, particularly conservatives, took their cues on the race from the special election for Waukesha County executive, held six months before the mayoral campaign. That race, also nonpartisan, pitted Republican state Rep. Dan Vrakas – son of the former mayor – against Jim Dwyer, chairman of the Waukesha County Board. Vrakas, running on a campaign supporting a state-imposed property tax freeze and cutting the size of the county board, trounced Dwyer, who had opposed both.

Nischke (who now works for a personnel firm and declined to comment for this story) and her campaign strategists read her race the same way. Nischke touted her role as co-author of a statewide proposal to require local referenda to raise property taxes in local jurisdictions.

“Anyone else think the Waukesha mayor’s race is just the county executive race redux?” asked McBride in her Waukesha Freeman column less than six weeks before the mayoral election. After casting Nischke in the Vrakas mold and noting Nelson’s Democratic party membership, McBride finished on a patronizing note: “So who do I think will win the Waukesha mayor’s race? I give the Democrats credit for trying.”

Nelson met the Nischke strategy with a canny series of counter-maneuvers. He framed the so-called Taxpayer Protection Amendment as a move by state legislators to strip power from local officials. “I’m for local control,” Nelson said again and again.

Commentators framed the nonpartisan race as a de facto contest between the GOP and the Donkey, but Nelson invited to his campaign independents and Republicans as well as Democrats. He recalls telling them that he wanted “to be mayor of everyone.”

After he was elected, he took to characterizing his followers as “Democrats, independents and open-minded Republicans.” Says Nelson, “I pride myself on having a cordial relationship with people of both parties. That comes from 30 years of teaching middle school.”

At one debate, Nelson pointedly corrected talk radio host Jeff Wagner, who had said the alderman was running with the Democrats’ endorsement. But while the party didn’t formally back him, Nelson did tap into its network of campaign activists, according to Rick Congdon, who was party chair at the time of the race. (Congdon says he stayed out of the race himself.) Nelson also enlisted the help of the Wisconsin chapter of Progressive Majority, a liberal group specializing in grass-roots campaigns. The group aided him with research that targeted Nischke’s legislative record and public statements, and with advice on how to craft brochures and handle yard signs.

With a much smaller war chest, Nelson was forced to campaign frugally. He designed his campaign brochure to be used in the primary election, and then, with a sticker that covered the original election date, reused it in the general.

When the dust cleared on April 4 and Nischke had lost by 500 votes, the surprised were not only in her camp. “It’s a pretty tough area for a progressive or a Democratic-leaning individual,” says Democrat and attorney Steve Schmuki. Nelson’s victory helped cement Schmuki’s own plans to run as a Democrat for the state Assembly in 2006. (He lost to Republican Kramer.)

But for some, Nelson’s win was no surprise at all. Nischke “kept talking about the
taxpayer’s amendment instead of what she would do for the city of Waukesha,” says Congdon. “She was getting advice from her Republican colleagues who were pushing a certain agenda that had nothing to do with Waukesha’s problems.”

James Wigderson, a conservative blogger and Waukesha Freeman columnist, says Nischke was weakened by the legislature’s failure to pass the Constitutional amendment limiting property tax increases. “If the amendment had passed, she would have been able to tout that as a success,” he says. “Because of her failure, all of her touting of it was a reminder to people why they didn’t like Madison.”

Another mistake: copying the Vrakas playbook, down to his proposal to cut the County Board. “At one point she even floated a trial balloon of reducing the number of aldermen,” Wigderson complains, “not understanding that people look at their aldermen and county supervisors in a completely different way. Aldermen are personal.”

The Nischke campaign, he adds, “just stumbled along with this sense of inevitability that a Republican would win over a Democrat. Nelson hit the doors a lot harder than she did.”

By Nelson’s own account, his greatest crisis as mayor came shortly after he took office. News broke that Glen Savoie, the man appointed to fill the Sixth District seat after Nelson’s election as mayor, had been charged in 1994 with soliciting sex for pay from two girls, ages 12 and 14. Savoie initially refused to resign, but later did so under pressure from Nelson and two aldermen. Nelson vowed to require police background checks of subsequent appointees to the Common Council.

The new mayor also stumbled after a Dec. 1 storm blanketed the area with 10 inches of snow in less than 24 hours and the city was slow in digging out. “He learned his lesson not to let the snow pile up again,” says Wigderson.

But despite these missteps, “he’s done very, very well,” says Bill Huelsman, a downtown Waukesha developer whose wife, Jody, is a former GOP legislator. Huelsman, whose work leads him to attend frequent meetings of the Common Council and the Plan Commission (which Nelson, by virtue of his office, also chairs), says Nelson is a skilled parliamentarian. “He’s both fair and balanced in how he runs a meeting – gives everybody a chance but still keeps it focused on the issue at hand.”

Huelsman is one Waukesha insider who professes not to have been surprised by Nelson’s victory. “Larry has a lot of friends and a lot of people that have been in his classes over the years,” he says. “He’s very likeable and he campaigned hard.” Even Nelson’s tenure as union leader worked in his favor, the developer adds. “It was a period of labor peace. People could sit down and discuss the issues and work out problems. I think that’s much to his credit.”

Council members also seem warmly disposed to the new mayor. “It’s good to get a mayor that comes from the council. You know what the issues are,” says Alderman Emanuele Vitale. Nelson’s liberal reputation is no secret, Vitale adds, but “I don’t believe Mr. Nelson has injected any of his political leanings when it comes to issues that affect the city. I’m a conservative individual. I don’t belong to any political party. But I also believe in progress. You can’t vote against anything that might come down the pike just because it might cost a few bucks.”

As for Dan Vrakas, he may not be Nelson’s political soul mate, but he speaks highly of the mayor’s first year in office. “Mayor Nelson’s worked hard to reach out to people that supported both him and his opponent, which is a sign of good leadership,” says Vrakas, who meets frequently with Nelson. “The mayor and I don’t agree on everything but we’ve got a good working relationship.”

Alderman Joan Francouer, who sits on the city’s Plan Commission, says Nelson has made some thoughtful appointments to the body. “Those new members have brought a different perspective,” she says. “He’s trying to run an inclusive administration.” It’s a record in keeping with his tenure as alderman, she adds. “His approach was to have a relationship with everyone on the council.”

The Waukesha Chamber of Commerce doesn’t endorse candidates. But Brian Nemoir, owner of a communications firm and volunteer chair of the chamber’s governmental relations program, says it’s no secret the business community generally backed Nischke. That stemmed from her years of backing business-supported legislation in Madison and her work as a real estate broker in the community.

With the election over, though, “Larry and I get along real well,” says Nemoir. He praises Nelson’s work to secure a city subsidy for a major downtown hotel development, the Clarke Hotel and Black Trumpet Restaurant. “He ran on the fact he’s going to revitalize downtown Waukesha,” says Nemoir. “That hotel and restaurant are smart steps. That took a lot of courage.”

But Nelson’s top challenge is the water issue. “That’s an issue where he gets put in the crosshairs of the folks who elected him,” Nemoir says.

Under orders from the state Department of Natural Resources, which is enforcing a federal mandate, the city must reduce radium levels in its water supply. Nelson supports, “as a last resort,” an approach using eminent domain to condemn and acquire 42 acres near the Vernon Marsh Wildlife Area in the adjacent Town of Waukesha. There, the city would establish several wells of radium-free water, which it would blend with its existing supply in order to meet the federal mandate.

An alternative solution involves a much larger chunk of land. Under that proposal, Fiduciary Real Estate Development Co. would donate 198 acres of town wetlands to the county and the state. The city would annex another 90 acres and rezone it for residential development, and Fiduciary would give the city access to a parcel of land with space for two more wells. For the plan to work, the city Plan Commission would have to change its land use plan for the area to be annexed. The Plan Commission, though, has nixed that idea, fearing the current level of city services couldn’t handle the new development.

Nelson prefers the second option, but both proposals have caused friction with his political base, gaining the opposition of the Waukesha Environmental Action League. The group’s president is Steve Schmuki, the same person who was encouraged to run for office by Nelson’s victory.

Still, Schmuki is conciliatory. “We understand the mayor has inherited that issue,” he says. “It may be the League and city are going to have to agree to disagree. But I give the mayor credit, because he has reached out to the Environmental Action League and other groups. My real hope is that somewhere in the mix of solutions we can all come to a compromise.”

A tougher battle looms over the future of the Great Lakes Water Compact, which governs access to water under the purview of the eight states bordering the Great Lakes. A proposed agreement would give each state absolute veto over access to that water by any communities – including Waukesha – not in the lakes’ immediate basin.

Conservative Republicans want the state to torpedo the agreement unless it can be loosened. “Michigan has already stated it will veto any water diversion request,” notes Nemoir, a pact critic. Meanwhile, Illinois has virtually no limits on its access to the water. “This veto clause is a killer.”

Nelson supports the compact. “Under the current policy, governors can veto [access to water] with no standards,” he says. “With the compact, they’ll have veto power with standards.”

Once the compact is fully implemented, Nelson wants Waukesha to test it. “We would submit an application that, if successful, would show the Great Lakes Water Compact is working.” His proposal has many facets: strong water-conservation measures – something the city already implemented and that Nemoir calls “an untold success story”; a change in billing (also already under way in Waukesha) that charges heavier water users a higher rate; a promise to treat and return the water to Great Lakes tributaries in order to ensure little or no net loss of Lake Michigan water; and working with the DNR and governor to show the city is following the compact’s rules.

It’s the sort of stance that puts Nelson’s optimism on display: “We would make it extremely hard for any governor to veto it,” he says. “The city is going to make decisions that are good for the city, but also good for the environment and for the Great Lakes.”

Although Nelson may not have made enemies as mayor, he does have skeptics. Chris Lufter, president of the conservative Waukesha County Taxpayers League, is one. Lufter did battle with Nelson when she served on the Waukesha school board and he headed the teachers’ union back in the 1990s. (The union helped defeat Lufter at the polls.) She says Nelson deserves credit as a city booster, but not for much else.

Lufter and conservative critics point to Nelson’s support of a referendum to increase tax revenues for the Waukesha School District, where he remains on leave. (No referendum has actually been scheduled.) And state Rep. Kramer says Nelson’s 2007 city budget, passed last November, “was terrible.” While the budget held the tax rate to a 3 percent increase, Kramer focuses on the 5 percent hike in the overall tax levy. “I don’t know that he can raise taxes over 5 percent again and not pay a political price.”

Nelson counters that the city managed to gain $700,000 in savings from city unions by negotiating with them to increase the deductibles on their health insurance. He points to public hearings at which “the vast majority spoke against further service cuts.”

That’s part of Nelson’s political skill, says Wigderson. “He’s very good at making it sound like any cut in taxes would make it necessary to cut services.”

To date, Nelson hasn’t generated serious, credible opposition on the common council. His political strength is such that business insiders and even logical rivals like Dan Vrakas won’t go on the record with criticism, knowing they have to work with the guy.

Nelson may be aided by the relatively weak role the mayor has in Waukesha’s city budget process. The city’s appointed administrator draws up the spending plan, and the Common Council amends and passes it. “When it comes to campaign time he could probably distance himself from it,” says Wigderson.

Then there’s his seemingly tireless campaign style. “If Larry works as hard for re-election as he did to get elected,” Wigderson predicts, “I don’t think there’s any candidate that can beat him.”

So is Nelson a model for other Democrats running in GOP-leaning districts to follow? Yes, and no, says state Democratic Party Chairman Joe Wineke. He compares Nelson to U.S. Sen. Russ Feingold, who has managed to garner respectable support from independent and even conservative voters. “They think he’s honest and stands for something.”

But Feingold and Nelson have a likability that not every Democrat (or Republican) can pull off. “Larry had a message that came across as really optimistic, a
can-do attitude that people bought into,” says a former Nischke supporter.

Even Democrat Rick Congdon says some fellow party members have “overblown” the Nelson victory as one that could be duplicated across the state. He believes that the real victor was nonpartisan politics.

“Lesson No. 1 is, work hard,” Congdon says. “Lesson No. 2 is, make sure the message is a good one – not manufactured from the Madison Republican organization.”

Lesson No. 3 may be this: Enjoy it. Nelson sure does. With a broad smile and an ebullience that old Hubert Humphrey himself would admire, Nelson compares what he does now to his lifetime career.

“When people ask me if I miss teaching, I feel like as mayor I’m teaching on a much bigger stage. You can’t be a successful middle school teacher for 30 years if you aren’t by nature an optimist and see the cup as half full.”

Freelance writer Erik Gunn is a frequent contributor to Milwaukee Magazine. Write him at letters@milwaukeemagazine.com.