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Scott Walker entered a crowded Republican field for an open Assembly seat in spring 1993 as a 25-year-old college dropout and newcomer to the district who had already lost one election and had little fundraising prowess.

An aide to former Rep. Peggy Rosenzweig, who won election to the state Senate, had the inside track to win the Assembly seat, but she entered the race late and didn’t realize Walker had already connected with hundreds of conservative voters while previously campaigning for Rosenzweig. In retrospect, Mary Jo Baas realized it had been a mistake to underestimate Walker.

“We were completely caught off guard at how intelligent and forceful his campaign really was,” Baas said. “He is one of the few people in politics who knows exactly who he is, what he stands for and what his goal is, right from the beginning.”

Walker’s official announcement entering the 2016 presidential election this week marks the culmination of his long, steady — and at times serendipitous — rise in Wisconsin politics.

Be it winning the five-way Assembly GOP primary with more than 44 percent of the vote, becoming the first Republican Milwaukee County executive, exiting the 2006 gubernatorial election only to emerge as the 2010 front-runner, or enduring the protests and subsequent recall over his signature Act 10 collective bargaining law, Walker has made plenty of savvy political moves to arrive at this historic moment — as the first sitting Wisconsin governor to run for president.

But Walker also benefited from fortuitous timing and circumstances outside his control, such as Rosenzweig’s decision to run for Senate, a Milwaukee County pension scandal that swept out the county executive, and a Great Recession that whetted the public’s appetite for a governor promising bold tax cuts and job-creation goals.

It was a job he had long coveted.

In 1997, after a day of touring Texas prisons holding Wisconsin inmates, Walker was knocking back Miller Lites and noshing nachos with fellow GOP Rep. Dean Kaufert, now the mayor of Neenah. Talk turned to how long they planned to stay in politics.

“I’m going to be governor,” Walker told Kaufert.

Every state legislator wanted to be governor, Kaufert thought, but here was someone who might have the gumption to do it.

“He just had that persona, that will to do his job, to get what he wanted,” Kaufert said. “He had a drive to excel and to move up the ladder. He was very confident about himself.”

Walker, who is set to announce his presidential campaign Monday evening at the Waukesha County Expo Center, declined to be interviewed for this story.

Son of a preacher

Born in Colorado Springs, Walker spent several of his early years in the farming town of Plainfield, Iowa, a part of his biography he mentions as often as possible in the state that hosts the first nominating contest of the 2016 cycle.

In 1977, parents Llew and Pat, a Baptist minister and a bookkeeper, moved to where Walker honed his speaking skills from his father’s pulpit at the First Baptist Church of Delavan.

“It was a fishbowl,” Walker told the State Journal during his 2010 gubernatorial run. “Everyone knew my father. And everywhere I went, they asked me to lead them in prayer.”

The confidence and speaking skills came in handy in the summer before his senior year at Delavan-Darien High School when Walker attended the prestigious Badger Boys State summer leadership program.

Walker, an alternate from his high school who got a chance to attend when another student backed out, so impressed his counselors that he was one of two delegates chosen to attend the Boys Nation program in Washington, D.C. Ronald Reagan, who was president at the time, remains his political hero.

Tom Skrenes, a Lutheran bishop in Marquette, Michigan, who was a Badger Boys State counselor in 1985, recalled Walker earning the trip to Washington because counselors recognized his leadership potential, positive attitude and for being “articulate, energetic and eager.”

“There’s no doubt about it, he did stand out,” Skrenes said. “As a young man, he had a good poise and a good sense of who he was.”

A conservative star

In 1995, Republican Gov. Tommy Thompson thought he had a deal. He had cobbled together enough votes among minority Democrats and majority Republicans in the Senate to push through a gas tax hike. The Republican-led Assembly had a healthier margin of control and wouldn’t be a problem.

But Walker and a handful of his fellow Assembly conservatives weren’t ready to go along with a tax hike, snubbing Assembly Speaker David Prosser and Majority Leader Scott Jensen. Walker’s opposition was clear, and unequivocal, and the emergent conservative media loved him.

“He was asked to explain his rationale and a star was born,” Jensen said.

In addition to making the rounds on talk radio, Walker was a frequent guest on conservative talker Mark Belling’s weekly TV panel program.

Mordecai Lee, a UW-Milwaukee political science professor and former Democratic lawmaker who appeared with Walker on that show, was struck by how effectively Walker could espouse the same conservative views as the host without sounding so bombastic.

“He had his formula long before he ran for governor,” Lee said. “He sounds less conservative, less ideological, less close-minded, more seemingly fair-minded and open-minded, much less threatening and much less off-putting by the lack of anger. Rush Limbaugh couldn’t get elected to anything, and yet Scott Walker can get elected to anything, and there’s practically no difference in their views.”

Belling agreed that Walker was typically the most conservative of his guests, yet “so soft-spoken that he doesn’t remind people of prominent media conservatives.”

“He was always calm and unflappable,” Belling said. “In that respect, it was similar to how he handled the virulent protests during the Act 10 period and the recall. Walker never lost his temper and was always calm. This style is his hallmark.”

Spreading his wings

Thanks in part to his media savvy, Walker’s political star was rising. He had also taken the lead in passing a state law that would ensure convicted criminals served the time prescribed in their sentence, a reform dubbed truth-in-sentencing. There were calls for him to challenge the more moderate state senator he had helped elect, or perhaps run for lieutenant governor.

Instead, he announced a bid for county executive in heavily Democratic Milwaukee County. Some fellow Republicans were astounded. Although the post is nonpartisan, no Republican had been elected to the position. But Walker saw another opportunity.

Residents were in an uproar over the county board approving seven-figure, lump sum pension payouts for top county officials. County Executive Tom Ament resigned, rather than face a recall election.

Walker had amassed a campaign war chest having faced token opposition in winning five elections in a solidly Republican district. He also benefited from close ties to Citizens for Responsible Government, the conservative activist group that collected about 182,000 signatures to recall Ament.

Orville Seymer, one of the group’s organizers, had first met Walker during an Assembly committee hearing on the death penalty several years earlier. Seymer, who suffered the loss of two family members to murder, remembered Walker being sympathetic to his call for legalizing the death penalty, a position Walker wouldn’t take publicly until years later. Seymer worked on Walker’s Assembly campaigns and his county executive campaign.

“They were some of the most well-organized campaigns I have ever seen,” Seymer said. “Everything went off like clockwork.”

Walker won the county executive election decisively, aided by an influential endorsement from Seymer’s group. In pamphlets and campaign ads, he asked voters to put his list of three promises on their refrigerators and hold him to them. They included cutting his own pay by $60,000, making the county board part-time and forcing department heads to re-apply for their jobs.

A year after his victory, Walker gathered representatives for all of the county unions in his conference room and laid out a proposal to reduce their workload to 35 hours per week. The measure was needed to close a multimillion-dollar budget deficit without layoffs, he assured them. The employees were stunned, and said the move violated the terms of their contract. A few months later, Walker laid off more than 200 employees instead.

“I don’t think there was a civil moment that we had from that point on,” said Dave Eisner, who at the time was president of the local county employee union. “We were just at war.”

Walker also clashed with the County Board, seeking property tax cuts each year, only to have the board rewrite his proposal with tax increases and then override his vetoes. His decision near the end of his term to impose furloughs on county employees ended up costing county taxpayers more than $4 million for back pay after he left office.

“He had aspirations to go to higher office,” Eisner said. “This was some place he could spread his wings and do some damage and move on to something else. He’s always been like that.”

‘Timing is everything’

In January 2005, a year into his first full term as county executive, Walker launched his first campaign for governor.

But within a year, he was being advised to drop out of the race. Margaret Farrow, a former lieutenant governor and state senator who knew Walker as a young activist, took him aside at an event and laid out the reasons why he should get out: He was young, he hadn’t spent enough time in the county executive office and he would be much more successful in the future.

“Timing is everything,” Farrow said.

In exiting the race, Walker cited eventual nominee U.S. Rep. Mark Green’s superior campaign cash reserve. But Walker’s announcement at an event in the heart of Republican Waukesha County helped build his own political capital, according to Jim Klauser, who was Tommy Thompson’s campaign committee chairman for all four of his gubernatorial elections.

Walker continued to build his political profile in the Milwaukee suburbs via talk radio and around the state on an annual county-sponsored motorcycle ride that critics complained was a thinly veiled political tour.

In 2008, Democrats swept into power in Madison and Washington just as the financial meltdown was creating a fiscal crisis for state budgets across the country. The federal stimulus package provided a short-term patch, but by the time Gov. Jim Doyle left office, he left the state with a more than $3 billion deficit.

Walker won his third Milwaukee County election, and soon after launched another bid for the governor’s mansion. He sought to tap into voter concerns about the economy with ads featuring his brown-bag, ham-and-cheese lunches, a promise to keep property taxes in check and a pledge to help create 250,000 jobs in his first term.

He defeated a wealthy primary challenger and his Democratic opponent handily. Weeks before taking office, he began floating plans to address the budget deficit by having public employees contribute to pension and health insurance premiums, but he had not yet laid out what would soon become his signature law.

Act 10 and aftermath

When Walker first presented his plan for dramatically altering public-sector collective bargaining, later known as Act 10, to the Assembly Republican caucus, the room on the fourth floor of the State Capitol was full of young, conservative legislators, eager to make their mark.

Though members had many ideas of their own, none were as ambitious as Walker’s proposal, recalled Assembly Speaker Robin Vos, chairman of the Legislature’s budget committee at the time.

“Almost to a person, everyone in the room was taken aback, in a positive way, that Gov. Walker was willing to swing for the fences,” Vos said.

Act 10 elicited massive protests in Madison from organized labor. Fourteen Democratic state senators fled the state to deny majority Republicans a quorum, dragging on the debate for weeks. Eventually, protesters gathered more than 900,000 signatures to trigger a recall election in June 2012.

Walker won by a larger margin than his 2010 election. In becoming the first governor in U.S. history to survive a recall, he developed a national following among conservative activists.

Vos first met Walker when they were both delegates at Badger Boys State in 1985. He knocked on doors for him during his Assembly and county executive campaigns and endorsed him for governor in 2006.

At each stage, Vos said, Walker took a bigger political risk and it paid off. Oftentimes he wasn’t the odds-on favorite to win, Vos said, “but he showed that he was the one who could get the job done, and it could be the same in the presidential run.”

As Walker embarks on a presidential campaign this week, he is taking the ultimate test of his ability to make the right political decisions at the right time.

Walker remains a polarizing and controversial figure in the state. He has so far navigated a minefield of political scandals, from the conviction of his Milwaukee County aides who were campaigning on taxpayer time within feet of his office to an unresolved investigation into his fundraising tactics during the 2012 recall election. More recently, the State Journal revealed that his top cabinet secretary pushed for taxpayer funds to a well-connected, millionaire campaign donor’s struggling company.

Seymer, the conservative activist, attributes those issues to what he considers Walker’s biggest political weakness — “he tends to trust people who don’t always have his best interest in mind, or the best interests of the state.”

Eisner, the former Milwaukee County union president, calls Walker “the Teflon man.”

“No matter what happened or what he was attached to or what went bad, it just slid off him,” Eisner said.

Though he won re-election last fall by nearly six points, his popularity in Wisconsin has taken a hit as he spent the first six months of this year exploring a presidential bid while Republican lawmakers were left to clean up what one described as a “crap budget.”

Walker’s proposed two-year spending plan cut K-12 and higher education funding, neutered a board that oversees the Department of Natural Resources and put a new Milwaukee Bucks arena on the state’s credit card — items the Legislature scaled back or removed. Walker’s office also helped craft widely reviled language gutting the state’s open records law, which was ultimately pulled from the spending plan.

Even Thompson, who won four gubernatorial elections, ran for president in the 2008 cycle and served as federal Health and Human Services secretary, acknowledges Walker’s budget has taken its toll on his standing in the state.

“After this budget, he’ll have a more difficult time getting re-elected,” Thompson said.

Still, Thompson, who has been courted by multiple presidential candidates but has yet to make an endorsement, views Walker as a credible national candidate.

“Scott Walker is one of the most driven individuals,” Thompson said. “He picks a path and continues on with it, and I think it’s served him well to date. He has got a great opportunity to do well in the presidential sweepstakes.”

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Matthew DeFour covers state government and politics for the Wisconsin State Journal.