Milwaukee Sheriff David Clarke is gunning for a showdown

Louis Weisberg, Staff writer

Milwaukee County Sheriff David Clarke was made for events like the Milwaukee Memorial Day Parade. Astride a large horse, he cuts quite a figure, his tall frame decked out in dress uniform and cowboy boots, his jaw hard-set in a Clint Eastwood spaghetti-western scowl.

The crowning touch of Clarke’s drag is the pair of aviator sunglasses perched on his nose beneath the trademark 10-gallon hat, half-shielding the lawman’s face in menace. It’s a fashion statement that says, “Don’t mess with me.”

He recently delivered that statement out of costume to Dan Black, a man he ordered detained and questioned at Milwaukee’s airport for shooting him a disapproving look when the two boarded a plane in Texas. Later Clarke took to Facebook and warned, “Next time he or anyone else pulls this stunt on a plane they may get knocked out,” adding that he “does not have to wait for some goof to assault him.”

Black filed a lawsuit, claiming damages for Clarke’s published “statements to incite violent verbal assaults against Black, which has happened,” according to the court filing. The suit also claims Clarke’s published statements “give a false impression of what occurred on the airplane and … damage Black’s reputation.

Black’s was not the first lawsuit filed against Clarke.

The mother of a newborn who died in the Milwaukee County jail filed a suit against the sheriff in November 2016. The suit holds Clarke and correction officers at the jail responsible for the death. She claims an officer not only failed to help when she was going into labor, but also laughed at her. The neglect, she says, resulted in the baby’s death shortly after birth.

Officers claim the baby was stillborn. The complainant is seeking $8.5 million in damages.

The infant was one of four people who’ve died in a Milwaukee County jail cell since April 2016 and one of 12 who’ve died there since Clarke took office. In September, a man died of dehydration in the jail after guards ignored his pleas for water.

But lawsuits go both ways and Clarke is often on the filing end of them. Like his friend Donald Trump, he relishes a feel-good legal battle. The many lawsuits he’s filed against his employer — Milwaukee County — have cost county taxpayers about $400,000 since 2012.

Faux Democrat finally at risk

Despite his poor record in office, Clarke has been continually re-elected since he was appointed sheriff on March 19, 2002, by then-Gov. Scott McCallum, a Republican.

Clarke’s victories can be attributed to a convergence of factors, the most significant of which is the “D” after his name. Although he’s Republican-appointed and his views are far right of center, Clarke runs as a Democrat in overwhelmingly Democratic Milwaukee County. All he has to do is win the Democratic primary.

Right-wing Republican suburbanites cross over to vote for the man who calls himself “the black Rush Limbaugh.”

Clarke has benefited greatly from his popularity on the Republican right. A frequent guest of former right-wing radio host Charlie Sykes, Clarke has spouted virulent racist views — even though he’s black — to an audience that craves to hear them. He also appears frequently on Fox News, where he slams liberals and minorities to a national audience of conservatives. He gave a racially provocative speech at the Republican National Convention in Cleveland in 2016.

Despite being instrumental in Clarke’s rise, Sykes has broken off the relationship over Clarke’s support for Trump. The two have exchanged heated tweets since Sykes joined the #NeverTrump campaign.

Sykes is now calling out Clarke for a number of things, including one that’s likely to stick in voters’ minds — the sheriff’s lengthy absences from his job to give paid speeches to right-wing political, religious and gun-rights groups.

In 2015, Clarke earned $150,000 in outside income, gifts and travel expenses. In 2016, he hauled in an additional $220,000.

Other leaders, including Clarke’s nemesis County Executive Chris Abele, have jumped on the issue. Abele released a statement to WISN 12 News saying, “The people of Milwaukee pay the sheriff’s salary for him to do his job here in Milwaukee, not to spend 60-plus days of the year collecting fees to speak at events out of state.”

Downward trajectory

Clarke won his first race in 2002 with 64 percent of the Democratic primary vote. He was re-elected in 2006 and 2010 with margins of 73 percent and 74 percent, respectively. Conservative pundits were astounded at his success, which likely was based in part on the lack of attention paid by voters to down-ticket races.

Sheriff Clarke Donald Trump
Then-Republican presidential candidate Donald Trump talks with Milwaukee County Sheriff David Clarke during a campaign stop at Milwaukee County War Memorial Center in Milwaukee. Despite his Republican connections and policies, Clarke runs in Milwaukee as a Democrat. (AP Photo/Gerald Herbert)

In previous races, he also has benefited from weak competition and strong support from Milwaukee County’s conservative wards, areas that receive their news via Fox and right-wing talk radio.

Ironically, for a candidate who promotes racist views, Clarke also benefited from the support of black voters in Milwaukee.

But his victory margin declined sharply in the 2014 election and a recent Public Policy Polling survey found him with sky-high disapproval ratings that are setting up a showdown for him at the polls if he seeks a fourth term next year — something he apparently hopes to avoid by getting a federal appointment from the Trump administration.

His weaknesses as a candidate were starting to show in the 2014 election. Although his opponent was Milwaukee police Lt. Chris Moews — a largely unknown man whom Democratic insiders regarded as weak, Clarke’s 2014 victory margin in the Democratic primary sank to 52 percent. Moews reportedly was aided by a strong influx of donations, including from the PAC of former New York Mayor Michael Bloomberg. Abele also was a major donor.

In that race, Clarke won in conservative wards in Oak Creek, Franklin, South Milwaukee, Greenfield, Cudahy and Brown Deer, where Republicans switched ballots to vote for him. But his margins were close in central city wards and there were large turnouts against him in liberal areas such as Shorewood, Milwaukee’s East Side and Glendale.

Seemingly, Clarke’s numbers have taken a hit from his increasingly bizarre, headline-grabbing statements and actions. His yearning for the spotlight — even when the attention is negative — is irresistible to his Trump-style ego.

In addition, Clarke’s early, enthusiastic support of Trump, who promotes racist and anti-immigrant views, has probably hurt him with identity voters who’ve supported him in the past. Channeling Trump in early February, Clarke planned to deputize his officers to assist the federal government in rounding up immigrants allegedly living in the country without legal permission. Although the Milwaukee County Board of Supervisors, Milwaukee Mayor Tom Barrett and Milwaukee Police Chief Ed Flynn want to maintain the area’s status as a “sanctuary” city for immigrants, Clarke’s status as a constitutional officeholder gives him the autonomy to pursue his own policies on the issue.

But his brazen actions and statements put him on a collision course with Latino and energized progressive voters who oppose Trump’s immigration and refugee ban.

Showdown coming

Trump’s victory has emboldened Clarke. Like Trump, he’s ramped up his Twitter rants and he’s also posting increasingly bizarre statements on his official Facebook page. Local observers on the political scene say he’s behaving like someone who doesn’t plan on staying around much longer.

In January, he was interviewed by the Trump administration for a high-ranking position in Homeland Security. But he came home empty-handed and more fiercely provocative than ever.

According to the Democratic rumor mill, Clarke and his wife are still scoping out the D.C. area for new digs. But as the weeks between his initial interview and Trump’s inaction piles up, it’s beginning to seem as if he’s too much of a loose cannon even for that administration.

Meanwhile, a super PAC is trying to draft Clarke to take on U.S. Sen. Tammy Baldwin in her re-election bid next year. Before the rise of Trump, it would have been impossible for a character like Clarke to consider such a prospect. But with Trump’s victory in Wisconsin, all bets are off.

Right out of the box, the super PAC attacked Baldwin as “a liberal lesbian extremist.”

Baldwin turned those words into an opportunity, sending out a fundraising email saying, “Of course, they didn’t challenge my policies or try to question my record of fighting for Wisconsinites. They went straight to the sort of stomach-turning name-calling we’ve grown so accustomed to in today’s post-Trump-campaign landscape.”

If he doesn’t find a new job by next year, Clarke faces the toughest election of his career. According to that recent Public Policy Polling survey, his approval rating in the county stands at 31 percent, while 62 percent disapprove of the job he’s doing.

The survey also found that voters consider Clarke’s bizarre behavior and outrageous statements to be a national embarrassment. Sixty-five percent said he’s had a negative impact on Milwaukee County’s image nationally, while only 29 percent said he’s had a positive impact.

And Clarke no longer benefits from identity politics. The survey found that only 22 percent of black Milwaukeeans currently approve of him, versus 72 percent who disapprove.

PPP concluded that Clarke has no path to re-election as a Democrat. Although he probably could be the Republican candidate for sheriff — he has a 72 percent approval rating in the GOP — he’d have virtually no chance of winning the general election either way, according to the Democratic-leaning polling organization.

Clarke has been hurt not only by his own incendiary shenanigans, but also by tying his political fortunes to Trump. The current president has a 30 percent approval rating in Milwaukee County and a 63 percent disapproval rating.

There’s no question that a showdown at the polls is coming for Milwaukee’s cowboy sheriff.

Clarke controversies

Among his encyclopedia of controversial statements and actions, Sheriff David Clarke has:

  • blasted CNN contributor Marc Lamont Hill as a “jigaboo” in a tweet.
  • speaking of African-Americans, said, “They’re uneducated, they’re lazy and they’re morally bankrupt.”
  • denied the nation has a police-brutality problem.
  • called members of Black Lives Matter “subhuman creeps.”
  • branded the Black Lives Matter movement as “Black Lies Matter.”
  • told people to rise up with “pitchforks and torches” against government institutions and the media.
  • urged county citizens to arm themselves to provide vigilante justice to help his office deal with budget cuts;
  • refused to provide his department’s share of security for a visit by President Barack Obama to Milwaukee in 2012.
  • opposed government-funded drug rehabilitation programs in favor of Bible study.
  • proposed sending up to 1 million people to Guantanamo Bay.

On the cover: Maureen Kane created the cover illustration, using photos taken by John Klein for the Milwaukee Journal Sentinel (via AP) and Travis Heying for The Wichita Eagle (via AP).