Why Conservatives Keep Losing…And How They Can Win Again

Dan O’Donnell does a deep dive on the Supreme Court debacle, what keeps going wrong in Wisconsin, and how the Right can right its sinking ship


April 5, 2023
Perspective by Dan O’Donnell


There is no way to sugarcoat this: Conservatives are in a whole lot of trouble in Wisconsin.  It’s not just that they lost control of the Supreme Court for the first time in 15 years or that former Justice Dan Kelly suffered the worst shellacking since…the last time he lost a Court race, it’s that this is just the latest in a long, long line of statewide losses.

After nearly a decade of dominance that culminated in a Republican winning Wisconsin in a presidential race for the first time in 32 years in 2016, conservatives have won just four of 14 statewide races (and one was unopposed).  How did the right go so wrong?


The Campaign Finance Factor

Many of their problems are largely self-inflicted, chief among them a massive fundraising gap that has been exacerbated by what has become known in political circles as the “Scott Walker Loophole.”

In 2014, four years after the US Supreme Court’s landmark decision in Citizens United v. FEC, justices handed down perhaps an even more significant ruling in the far less noticed McCutcheon v. FEC.  The Court struck down “aggregate contribution limits” an individual can make to national political parties and federal candidate committees in a two-year election cycle.

The decision forced Wisconsin to drop its limit on donations to its two major state parties, but it also dropped limits on how much money those parties can give to individual candidates.  Through this loophole, individuals could give millions of dollars to, say, the Republican Party of Wisconsin, which could then turn around and give those millions to candidates.

For a few years, Republicans were the primary beneficiaries of this loophole, as Governor Walker built up a network of national donors following the battle over Act 10 and subsequent recall election.  Democrats tried desperately to get the State Legislature to close the loophole, but the Republicans who controlled it refused.

In 2020, though, everything changed.  When Wisconsin became the first state to hold a presidential primary following the COVID-19 lockdown, the state was thrust into the national spotlight—and so was its campaign finance loophole.

National Democrats realized that they could give unlimited amounts of money in perhaps the key presidential swing state and Wisconsin Democratic Party Chairman Ben Wikler courted out-of-state donors by hosting Zoom reunions of television shows as fundraisers.  Behind the scenes, he and other Wisconsin Democrats were making impassioned pleas to a new class of political whales—tech billionaires who were infinitely more likely to spend their money on politics than the titans of industry that came before them.


All Politics is National

At almost the exact same time, the George Floyd protests and riots gave rise to “woke capitalism” that went well beyond adorning corporate logos with rainbow colors during Pride Month.  Tech CEOS especially felt it to be their duty to make political spending a part of their professional and personal identities, and where better to spend than in a swing state with essentially no donation limits?

Emboldened by the fervor for social justice and resolute in their desire to oust President Donald Trump that November, they gave millions to the Democratic Party, dramatically out-giving the biggest Republican donors.  17 of the 20 biggest donors to Wisconsin’s political parties in 2020 gave to Democrats.  They gave a whopping $9.9 million to the Democratic Party of Wisconsin, compared with just $3.5 million donated by the top three Republican megadonors.  Notably, all three either live or have substantial business interests in Wisconsin.  The top 17 Democrat donors, were almost all from outside of the state and included J.B. Pritzker, the Governor of Illinois, New York-based financier George Soros, and LinkedIn cofounder Reid Garrett Hoffman.

The extreme advantage from national whales only intensified over the past three years, culminating in the Supreme Court election cycle, in which 18 of the top 20 donors to Wisconsin’s political parties (all but two of whom live out of state) in the first three months of 2023 gave a truly jaw-dropping $12.68 million to Wisconsin’s Democratic Party.  The remaining two Republican donors (both of whom either live or work in Wisconsin) gave a total of just $650,000 to the GOP.

In the most expensive judicial election in Wisconsin history, Kelly was blown away by the sheer volume of ads from his liberal opponent, Justice-elect Janet Protasieiwcz, and the Super PACs supporting her candidacy.  This serves to explain how she, a soft-on-crime Milwaukee County judge, was able to win so convincingly when Wisconsin’s voters amended the state’s Constitution to make it easier to keep criminals in jail on cash bail with more than two-thirds of the vote.

With her nearly limitless supply of out-of-state campaign cash, Protasiewicz was able to portray herself as a tough-as-nails former prosecutor while Kelly was weak on the crime issue.  One of her ads even gravely intoned that “Daniel Kelly has never sentenced anyone to prison.”  Anyone paying attention to the race would understand that this was because Kelly, a former Supreme Court Justice, was never a trial court judge, but casual voters likely didn’t know this and Kelly simply didn’t have the resources to inform them.


Vote Erosion in the WOW Counties

Kelly’s cash disadvantage also helped exacerbate nearly decade-long trend in the heavily Republican “WOW Counties” of the Milwaukee suburbs.  Taken together, Waukesha, Ozaukee, and Washington Counties delivered 229,966 votes for Scott Walker in his 2014 re-election bid against Democrat Mary Burke.  Walker won nearly 73% of the WOW County vote, which very nearly matched Burke’s 230,997 votes in Milwaukee County (by far the state’s largest county).

The longtime—and very successful—strategy for Republicans to win statewide was for their strength in the WOW Counties to neutralize Milwaukee and have their votes in the rest of the state nullify Democrats’ major edge in Dane County.

It worked amazingly well…until it didn’t.  2014 was the last election in which a statewide candidate received anywhere near 70% of the vote in the WOW Counties.  Eight years after Walker’s win, Republican gubernatorial candidate Tim Michels received just 61.3% support in the WOWs and roughly 18,000 fewer total votes than Walker did.

Kelly’s margin of victory was even worse—dipping all the way to 58.7%.  While his raw vote total was enough to easily surpass the 170,000 ballots cast for Protasiewicz in Milwaukee, the inroads she made in the WOWs made his path to victory statewide all but impossible.

A number of theories for the collapse of the “red wall” that the WOW Counties used to give conservatives; and all are at least plausible.  “Liberal flight” from the neighboring high-crime, high-tax Milwaukee County can at least partially explain why Democrat vote totals and percentages have been steadily rising, as can the national suburban female abandonment of Republicans following the rise of Trump and the US Supreme Court overturning Roe v. Wade last summer.


Vote Explosion in Dane County

This Republican vote erosion might be survivable in statewide elections if it didn’t coincide with an absolute explosion in Democrat turnout in Dane County.  In 2014, Burke won Dane with 69% support and 175,604 votes.  On Tuesday, Protasiewicz won Dane with 82% of the vote and 197,004 total votes. Even though Burke received more than 100,000 more total votes statewide than Protasiewicz did in a lower-turnout election, Protasiewicz got nearly 22,000 votes more than Burke did in Dane County.

The dramatic increase in the use of mail-in and absentee voting in the wake of the COVID-19 pandemic allowed for far greater numbers of college students to more easily cast their ballots, and with Democrats’ and liberal special interest groups’ huge cash haul, they were able to hire a veritable army of get-out-the-vote activists to canvass dorms and apartments scrounging up every last student they could find and bring them to early voting locations, which of course Madison’s Democratic city clerk conveniently placed in the dormitories.

In addition, the boom in telework opportunities during COVID has meant that years’ worth of UW-Madison graduates never had to leave the state (or even the city) to launch their careers.  They could work for Google or Microsoft right from the same apartment in which they had been studying for finals and doing keg stands months earlier.

Madison itself has been growing by leaps and bounds, buoyed by Evers’ ever-expanding state government and the near-constant importing of workers to staff Epic Systems, the medical software company that is fast becoming one of the state’s largest employers.


Wisconsin’s Pain is Florida’s Gain

As younger, more liberal, and far more engaged voters flood into Dane County and stay there, the Scott Walker coalition has begun to reach retirement age and is in sizable numbers fleeing Wisconsin for (literally) greener pastures.

A recent student from Forward Analytics reveals that Wisconsin’s population has grown by just 3.6% over the past few years, making it one of the slowest growing states in the country.  It’s not just that the birthrate is slowing—it is, but somewhat uniformly across all states—but that older Wisconsinites are leaving the state.

Wisconsin has always had “snow birds” who head south for the winter, but increasing numbers of them have been becoming Florida residents so as to avoid Wisconsin’s state income tax (Florida has no state income tax) and comparatively poor governance under Evers.

Florida and Texas (which also has no individual state income tax) are easily the fastest-growing states in the country, and since they are also well known as two of the most conservative, they are also more likely to attract retiring Republicans than Democrats.

The Sunshine State in particular has been growing by more than 1,100 residents per day—many of them retirees or snow birds who have transformed Florida from the quintessential swing state into a shade of deep red.  Governor Ron DeSantis, who narrowly won election in 2018, dominated his re-election bid in November by 20 points.  Republicans won every statewide election by double digits and dominated congressional and state legislative races as well.

As Republicans from across the country are apparently heading for Florida in droves, Democrats from Illinois are seemingly moving into Wisconsin.  In 2021, more people left Illinois than any other state in America and many of them have headed north.

Milwaukee is currently the top destination for people fleeing high-crime, high-tax Chicago (someone should really tell them Milwaukee isn’t much better), and approximately 3,000 people each year are moving from Illinois to Wisconsin.  A 2019 Marquette Law School poll determined that approximately half of these transplants are from uber-liberal Cook County (home to Chicago), so it should come as no surprise that they are bringing their politics with them.

As a result, the counties nearest the Illinois border—Racine and Kenosha—have grown steadily bluer.  Scott Walker won 54% of the vote in those two counties in his successful 2014 re-election effort, while Michels won 51% in his loss last year.  On Tuesday, Kelly barely won Racine County and lost Kenosha County with just 46% of the vote.


Candidate Quality Matters                    

This, however, may well be less the result of broader population shifts than it is a reflection of Michels and Kelly being far weaker candidates than Walker ever was.  Rather remarkably, within the past year Wisconsin Republicans have nominated two candidates for statewide office that had both previously lost statewide elections by double digits.

When Kelly, who was appointed to the Supreme Court by Walker in 2016, ran for a full term in 2020, he lost to liberal Justice Jill Karofsky by 120,000 votes.  His campaign assured voters that he was merely the victim of circumstance—there was a contested Democratic presidential primary that day but not a Republican one—and that his loss was a fluke.  He lost on Tuesday by 203,000 votes.

In 2004, Michels ran for Senate against incumbent Democrat Russ Feingold and lost by 11% and 331,514 vote.  In the same election, incumbent President George W. Bush came within 0.4% and 11,384 votes of beating Democrat John Kerry.  While both Bush and Feingold enjoyed the power of the incumbency, Michels badly underperformed.

18 years later, he joined the Republican gubernatorial primary in its final stages and, boosted by a Trump endorsement, swept to victory in the primary before again underperforming another Republican on the same ballot.  While Michels lost to Evers by 3.4% and 90,239 votes, incumbent Republican Senator Ron Johnson won re-election by 1% and 26,718 votes.

It is almost unheard of for a candidate in Wisconsin who loses a statewide race to give it another go and win, but Republicans somehow thought they could do it twice in six months.  If that sounds utterly insane, it is.  General election voters said loudly and clearly that they did not like either Michels or Kelly, but Republican primary voters nonetheless chose them.

They might not have understood how stupid this was, but Democrats certainly did.  They spent millions in the primary relentlessly attacking Kelly’s conservative opponent, Waukesha County Judge Jennifer Dorow, who had earned unanimous national plaudits for her handling of the Waukesha Parade Massacre trial last fall.

Liberals clearly felt as though Dorow was the stronger of the two candidates and, as they had in various Republican primaries in 2022, interfered to ensure that the weaker conservative emerged to face Protasiewicz.


Mutually Assured Destruction

Kelly did, but he was so politically bloodied and financially tapped out following his bruising battle with Dorow that he couldn’t possibly match the ad blitz that Protasiewicz had waiting for him the day after the primary was decided.  With just a six-week sprint to the general election, Kelly stood almost no chance after having to expend so many resources to fend off a challenge from his right.

Like Michels, Dorow entered the race late in the primary season and forced Kelly’s team into a battle after they had spent more than a year attempting to clear the field for him.  Dorow was the stronger candidate, and much of the conservative movement knew it.  Mark Belling, the most influential talk radio host in the state, openly called for Kelly to drop out of the race so that Dorow would not have to expend resources in a primary, but Kelly steadfastly refused to bow out.

Instead, he fired at Dorow with both barrels, enlisting the help of Wisconsin Court of Appeals Judge Shelley Grogan, who attacked Dorow’s credentials and character any chance she got.  Kelly himself pointedly and repeatedly refused to promise to endorse Dorow should she have won the nomination—a clear bit of foreshadowing of his angry, bitter concession speech to Protasiewicz Tuesday night.

Kelly just wasn’t ever a particularly likeable candidate, and the primary revealed it.  He and Grogan angered untold thousands of conservatives with their behavior, and though these voters likely understood the stakes of a Kelly loss in the general election, they never had the enthusiasm for him that they otherwise might have.

The bad blood and deep divisions were eerily reminiscent of last summer’s all-out brawl between Michels and former Lieutenant Governor Rebecca Kleefisch, who, like Kelly, had spent years trying to clear the Republican field so as to avoid the same primary bloodbaths that doomed both Tommy Thompson and Leah Vukmir in their 2012 and 2018 Senate runs against Tammy Baldwin.

At the urging of a handful of very influential behind-the-scenes Republican power players, Michels jumped in the race in April and, after getting Trump’s endorsement in June, started to run away with the race.  Kleefisch, like Kelly, went extremely negative in her ads and Michels responded in kind.  Michels won the battle last August, but lost the war in November.  Like Thompson and Vukmir before him, he was too broke and beaten up to withstand the onslaught of ads against him.


A Pro-Choice Problem

A substantial percentage of these focused on Michels’ opposition to any exception to Wisconsin’s abortion ban, even in cases of rape or incest.  Michels responding with “Uh, that’s correct” to a question about whether the total ban on abortions was a mirror of his position was a ubiquitous presence on TV, computer,  and phone screens for months.

So damaging were these three words (technically two words and a sound) that Michels was forced to very publicly change his position with just weeks to go in the general election campaign, sheepishly admitting on “The Dan O’Donnell Show” that yes, he did back rape and incest exceptions.

It didn’t matter.  Pro-abortion groups bombarded the state with broadcast, digital and print ads and direct mail literature claiming that Michels wanted to lock up as many pregnant women as he could find and Michels simply didn’t have the resources to fight back.

Kelly fared even worse.  The national political left made the race explicitly about abortion and openly court donors with the idea that Kelly would put the final nail in Roe v. Wade’s coffin if given the chance.  A full one-third of the Protasiewicz campaign’s ads focused on the issue, and as much as Kelly tried, he simply couldn’t shift the public debate back to crime and the Rule of Law.

Abortion is now a primary driver of young voters, who fear that an unplanned pregnancy could derail their life’s plans.  Fear is quite possibly the single greatest motivator, and the fear that “women’s rights” could be trampled (by a man, no less) motivated a voter base already whipped into a frenzy following the repeal of Roe.

Most pro-life Republicans are understandably nauseated by the idea that so many voters are so hellbent (no pun intended) on killing the unborn, but it is the political reality.  For nearly 50 years, Americans were accustomed to the idea of legal abortions even if the thought of ever personally having a child aborted was something they could never abide.

As difficult as this may be to come to grips with, Republicans are on the wrong side politically of an issue that they are clearly on the right side of morally.


The Trump Effect       

Abortion may have been a motivator since Roe was overturned, but over the past seven-plus years nothing has unified the left or polarized America quite like Donald Trump.  Even now, more than two years after leaving office, he is dominating every news cycle as Democrats have proven themselves unable to shake their obsession with exacting revenge on him for the unforgivable sin of beating them in the 2016 election.

No President and perhaps no human being has ever been subjected to as much negative coverage as Trump, and both it and Trump’s own behavior have succeeded in turning off huge swaths of the American electorate.  Liberals despise him and moderates are just tired of him and wish he would go away.

Either way, he is (whether conservatives want to admit it to themselves or not) the anchor to which every other Republican is tied. Consider recent polling showing that 76% percent of Americans believe his indictment is politically motivated but 60% support it anyway.  Does that sound like a man who could win the presidency again?

Americans implicitly understand that Trump is being persecuted by a rogue Manhattan District Attorney, but seemingly either believe actually did commit actionable crimes (he didn’t) or are just sick of the circus that perpetually surrounds him.

And just as Democrats interfered in Republican primaries—almost always to boost the Trump-endorsed candidate—they are openly giddy about the opportunity to use Trump’s indictment to improve his standing amongst Republican diehards just enough to vanquish DeSantis in next year’s primary only to be slaughtered in the general election.

“The political arithmetic here is that Donald Trump cannot get elected without getting people who didn’t vote for him in 2020 to vote for him in 2024,” Democratic pollster Geoff Garin told The Washington Post Tuesday. “The fact that he is being indicted on one crime and is facing multiple other criminal investigations will make it much harder for him to find new voters.”

Not only that, any tie to him is immediately used against candidates like Kelly—who helped him bring his 2020 lawsuit in Wisconsin—as a way of turning off independent voters.  Conservative primary voters may love Trump, but more independent general election voters do not.  They made that abundantly clear in 2020 and, despite the clear irregularities and blatant illegality that marred that election, Trump lost rather decisively.  What makes anyone believe that 2024 will be any different for him or any other Republican closely tied to him?


Mass Media Censorship

In fairness to Trump, the hair-on-fire media coverage of is downright laughable, but the deadly serious reality is that a significant number of swing voters still rely on it to be informed about candidates and issues.

This was bad enough when the media was simply biased; now it appears to exist solely to suppress any story that could in any way harm a liberal.  Hunter Biden’s laptop in 2020 served as the template for the Wisconsin’s legacy media outlets to bury any mention of serious allegations of elder abuse and racist language against Protasiewicz, potentially disqualifying revelations that never reached beyond either Wisconsin Right Now, the publication that broke them, or conservative talk radio.

Nearly as rare was any mention of Protasiewicz’s disturbing record of extreme leniency as a judge, which included giving 14 months in jail to a man who raped his unconscious cousin and gave no prison time at all to a child rapist because she was worried he might get COVID-19 behind bars.  In another era, either of these stories might dominate news cycles, but the Wisconsin media learned its lesson from Scott Walker.

In 2014, allegations of plagiarism helped bring down Burke’s campaign as multiple media outlets ran stories questioning her fundamental honesty.  Four years later, when it became apparent that Evers—then Wisconsin’s Superintendent of Schools—plagiarized pretty much every education plan he ever put forward, the media totally ignored it.


How the Right Can Get Right Again

Walker tried his best to highlight the story and force the media to cover it, but Kelly never did.  Even when asked directly why he declined to bring up the abuse and racism allegations against Protasiewicz during their lone debate, he said that he just couldn’t bring himself to accuse his opponent of something that he wasn’t able to prove.

Ummm, that’s kind of how politics works.  If Kelly didn’t have the stomach for it, then why did he work so hard to clear the field of other conservatives with sharper elbows? Why did he attack his fellow conservative Dorow harder than he ever attacked Protasiewicz?

This may well be the single easiest thing for conservatives to fix as they look to stem the tide of statewide losses: Brutal primaries and weak-kneed candidates who only attack fellow conservatives have got to go.  That isn’t to say that candidates should be selected in smoky backrooms, but Republican candidates for all offices must be made to understand that primary attacks are unacceptable.

Think that’s impossible?  Johnson’s opponent in last year’s Senate race, former Lieutenant Governor Mandela Barnes, might well have been the only one of the half dozen Democrats running who could have lost.  He had unpaid taxes and so many unpaid parking tickets that he couldn’t register his car and had the State Patrol shuttle him around like his own personal Uber service.  He said radical and overtly racist things regularly.

Still, not a single one of his opponents ever once badmouthed him. Even as it became clear that doing so would be their only path to the nomination, they stayed silent and even dropped out of the race just a week before the primary so he wouldn’t even have to break a sweat before taking on Johnson.

Think there is any chance Republicans would behave that way? There needs to be, because the circular firing squad every primary season is only serving to fracture the party when it desperately needs to hang together and force candidates to spend ever-more valuable campaign cash that they can ill afford to waste.

To ensure that Republicans have as much cash as Democrats or are at least playing on a level field, the Legislature needs to adopt at least some of its most liberal members’ proposals to close the campaign finance loophole and end the practice of allowing unlimited donations from state parties to individual candidates.

Once they have it, Republican candidates and their consultants had better darn well do a better job of doing it.  Their ads need to hit harder, their get-out-the-vote efforts need to be better organized, and their direct voter contacts need to be constant.  Candidate vetting is as important as election strategy, and Republicans can no longer shrug their shoulders and ask whose turn it is to run for what.

Longer-term trends of outward migration from Wisconsin of more reliable conservative retirees may prove more difficult to overcome, but the Republican Legislature must continue to make Wisconsin’s tax climate as attractive as possible so that snow birds at least will maintain residency here.  Florida has enough Republicans; we need them here.

On the abortion problem, finding a compromise is the only path forward.  Johnson successfully deflected the issue by calling for a statewide referendum.  Even if that is ultimately unworkable, it shows that Republicans want to give the ultimate say on the issue to the people themselves.  This won’t betray any deeply held beliefs and it will allow the GOP to diffuse the issue—which will likely become moot anyways when Protasiewicz joins the Court this summer and overturns the state’s abortion ban.

Moving past Trump, however, will likely be more difficult. His supporters within the conservative movement see him as a martyr for them, a belief strengthened a hundredfold with his indictment.  Here too Republicans must use their heads and not their hearts.  Trump was a consequential president whose legacy is sacrosanct, but he is patently unelectable and the longer he is the face of the GOP and the conservative movement, the longer the party will suffer losses in ostensibly swing states like Wisconsin.

It is almost certainly not a coincidence that Republicans started consistently losing statewide races after Trump won Wisconsin in 2016.  He is and has long been the most polarizing figure in American politics and while he was an exciting outsider seven years ago, he is today a known commodity ultimately rejected by the American people.

Conservatives must stand with him but ultimately be pragmatic enough to know that too many Americans can’t stand him for him to be a viable presidential candidate.  Like Dan Kelly and Tim Michels, he had his chance and lost it.  There is little reason to believe anything will change next year.

For Wisconsin’s conservative movement more generally, things won’t change overnight and might not by the 2024 election.  Some of the trends working against it might be irreversible.  But there are relatively easy policy and political fixes that can go a long way in reversing the disturbing trends of the past seven years.

Politics, one must always remember, is cyclical.  Sometimes one just has to fight a little harder and a little longer to set things right again.