So Milwaukee County Executive Scott Walker made a “very special announcement” this week to no one’s surprise. He’s running for governor, again, and hitting the road in a taxpayer-funded statewide trip on the back of a Harley-Davidson, again.

But a few things have happened in the past four years that will make Walker’s 2009 campaign much tougher than his previous run for governor.

First, Walker’s reputation has changed from a no-new-tax squeaky-clean tightwad to an irresponsible naysayer. In 2006, Milwaukee voters already knew that Walker was an ideologue who was more interested in image than substance. But voters outside of the county probably didn’t have enough facts about Walker’s record to make an informed judgment.

Well, Walker’s been working on that, for better or worse. He’s raised his profile by refusing to submit a “wish list” for federal stimulus funds—then backtracking on that promise, pushing it again, and backtracking. Finally, county supervisors had to step in and compile a list of necessary projects to benefit the county.

It’ll be interesting to see Walker stump around the state and try to explain why he thought more infrastructure spending in Milwaukee was such a bad thing. If he had been governor, he would have opposed the stimulus money for the entire state. Think about it: As Scott Walker travels around the state trying to justify his Sarah Palin-esque stand of refusing stimulus funds, he’ll be confronting new projects fueled by the stimulus funds that are employing people throughout the state. The Obama administration is helpfully branding all such projects with an easily identifiable logo. Walker may want to duck them—and the New Deal-era projects that still stand today, such as the planned village of Greendale, and the construction of roads and buildings in Whitnall, Red Arrow and Brown Deer parks, in addition to improvements to other county parks, waterways and Lake Michigan.

What’s more, job losses are hitting everyone across the board—urban, suburban, professional, service and factory workers are vulnerable. Many of these displaced workers will be losing a job for the first time in their careers and are no doubt grateful for the safety net provided by the stimulus funds (and the job opportunities provided by the package, which can be found at jobcenterofwisconsin.com). Walker’s natural constituency—white suburban and rural voters—may be hit hard by the economic downturn and begin to realize that the worn-out ideology of an unfettered free market ended up costing them their jobs. These folks may be less willing to cast a vote for a hard-liner on the recovery package.

State voters will also get a whiff of Walker’s mismanagement of the county. Over Walker’s objections, Milwaukee County voters approved a referendum to raise the sales tax 1% to provide property tax relief and support necessary services and neglected county assets. The state had to take over the county’s public assistance programs that the Walker administration mismanaged—and is now charging the county $3.5 million a year to manage it. Congress had to resolve the longstanding stalemate over transit funds between Walker and Milwaukee Mayor Tom Barrett. Walker’s leadership never looked so weak.

Challenges from the Left and Right

Perhaps most troubling for Walker, the state’s mood has changed, while Walker has not. Wisconsin handed two wafer-thin victories to Democratic presidential candidates in 2000 and 2004, but Obama won a clear majority in 2008. According to a poll released this month by St. Norbert College, 41% of Wisconsin residents think the country is on the right track. That may not seem like a lot, until you compare it with the number of “right track” folks in fall 2008 during Bush’s final days: a dismal 8%.

While Walker’s opponent may be conservative businessman Mark Neumann in the Republican primaries, he’ll likely face Gov. Jim Doyle, a strong Obama supporter, if he makes it to the general election. Despite the fact that President Obama will not be on the ballot next year, the November 2010 elections, including that of Wisconsin governor, will be, in part, a referendum on Obama as well as Doyle. Will the divisive Walker, who is about as un-Obama as you can get, be able to convince anyone other than conservative Republicans to vote for him in November 2010?

Will Walker even be able to win those conservatives away from Neumann in the Republican primary? The former congressman is about as right-wing as you can get, but in his last election, in 1998 against Sen. Russ Feingold, his campaign team did an excellent job of making him appear mainstream. Neumann runs a successful home-building business and supports a handful of Christian voucher schools. Neumann has sewn up the important endorsement of Jim Klauser, former Gov. Tommy Thompson’s top official and campaign strategist, who’s still influential in Republican circles. Which candidate will get the support of moderate Republicans? You know, the ones constantly disparaged as “RINOs” or even “socialists” by Walker supporter Charlie Sykes. Walker’s hoping that a hop on his Hog for a trip around the state will blind them to his record as Milwaukee County executive.

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