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What's the real story behind Sheriff Clarke and the Homeland Security post?

From the start, Sheriff David Clarke seemed an odd choice for an assistant secretary position at the Department of Homeland Security, a Trump administration job requiring the skills of a diplomat. Diplomacy is not something the self-described “bare-knuckle fighter” is known for.

Clarke has never shied away from controversy. And his announcement that he was taking the role was met with substantial opposition.

A month later, in mid-June, Clarke abruptly announced he had rescinded his acceptance, claiming through a spokesman that his “skills could be better utilized to promote the president’s agenda in a more aggressive role.”

And then the normally mouthy Clarke went strangely silent, fueling speculation that the medal-wearing law enforcement chief was “too toxic” even for the Trump administration.

Milwaukee County Executive Chris Abele, who’s called Clarke an “unhinged and unpredictable” sheriff answering to no one, believes Clarke and Trump are too similar to get along in the long-term.

“The sheriff and the president are probably not a great mix. It’s the old joke about two sheriffs, one town,” says Abele, whom Clarke previously labeled a “little mouse” with “penis envy.”

“I imagine people with his track record here, certainly Reince Priebus, knew enough to know if you have a president who likes to occupy the spotlight but may distrust other people taking the spotlight, it won’t work.

“What was it the president said about [fired FBI director James] Comey grandstanding?”

Abele admits he had conflicting feelings when Clarke announced he was joining the Trump administration. “I loved the idea of a new sheriff that would work well, because Milwaukee deserves better. But so does Homeland Security. He is the last person the government needs,” he says.

Conservative talk radio veteran Charlie Sykes, a Trump critic who quit his long-running show in December after becoming disillusioned with the alt-right, points to the four deaths in Milwaukee County Jail last year, Clarke’s bizarre “standoff” with plane passenger Dan Black and a feud with a CNN commentator over allegations he plagiarized chunks of his master’s thesis as reasons the Homeland Security job never materialized.

Sykes, once considered Wisconsin’s conservative kingmaker, helped catapult Clarke into the national spotlight, then watched as the attention went to the sheriff’s head.

“You could do a coin flip that word came from Washington that he was too toxic, or he became impatient. The moment he announced it, Washington didn’t have to announce it. Maybe they let him twist in the wind,” says Sykes, who now refers to Clarke as his “Frankenstein’s monster.”

“He would have been, arguably, one of the most controversial appointments given his rhetoric and track record. It got to the point where he is relishing himself as bully-in-chief, a law enforcement officer spoiling for a fight.”

Like many in Milwaukee, Sykes believes Clarke isn’t interested in running for a fifth term as sheriff. But that would effectively end his second career as a “bomb-throwing” Fox News commentator.

“He wants to be a national figure, but that rests with the uniform and the props of sheriff to give him credibility, the uniform and all the medals,” says Sykes, who says Clarke has vanished from the TV studios in Milwaukee where he once broadcast regularly for Fox.

Clarke, 61, declined to be interviewed for this story. But GOP operative Craig Peterson, who acts as his spokesman on political matters, says the sheriff is normally called upon to commentate on TV only when there are law enforcement issues, such as police shootings.

He insisted the sheriff was “very much upbeat,” going into his office throughout the work week and exploring future opportunities.

Milwaukee County Supervisor Peggy West disagrees that Clarke is at his desk. “Personally I haven’t seen him for a year,” she says. “I am on the finance and judiciary committees and you would think he would show up at some of those.”

West, who recently called for Clarke to be held accountable for the dehydration death of an inmate and has described the county jail as a “medieval dungeon,” believes the sheriff will run for a fifth term or take a long shot at winning Democrat Tammy Baldwin’s U.S. Senate seat.

“He doesn’t concede he has made mistakes,” she says. “In his mind, he is right and if you don’t agree with him, there is something wrong with you, not him. He thinks he is smarter than anyone else.”

Wisconsin Congresswoman Gwen Moore spearheaded the campaign to block Clarke’s Homeland Security appointment, collecting 50 signatures from Democrats in the House of Representatives. But she wasn’t the only one to act.

Juliette Kayyem, who held the job offered to Clarke during the Obama administration, wrote an open letter to Homeland Security Secretary John Kelly saying Clarke’s “divisive rhetoric and action” would make him an “impossible figure for communities to engage with.”

Kayyem juggled numerous unexpected problems during her tenure, including the 2009 flu pandemic, an attempted al-Qaeda plane bombing over Detroit, the Haiti earthquake and the BP oil spill, along with regular issues like border control, intelligence sharing, military affairs, tribal needs and overseas territories.

“It’s a complicated job trying to manage a whole diverse homeland. There are different needs, priorities and risks. People in Mexico are different from New York,” says Kayyem, who had an extensive background in counterterrorism and national security affairs before she joined Homeland Security.

“The fact Clarke was even on the radar screen [for the job] was objectionable on so many levels, like his hatred and his divisiveness.

“There is nothing in his history to suggest it would have been a suitable role. At best, he would have been ineffectual in his job. Someone like that, in my opinion, has no role in federal government.”

And while Washington has possibly “dodged a bullet,” as Kayyem puts it, Clarke is now reconsidering his future options, including another run for sheriff in 2018. (He’s ruled out a run for U.S. Senate.)

But as Abele warns: “The climate has changed. He has spent the last two years telling the public he is too big for Milwaukee. I don’t know if his ego would allow him to come back, to accept things went wrong.” ◆


‘Reversal of Fortune’ appears in the September 2017 issue of Milwaukee Magazine.

Find it on newsstands beginning August 28, or buy a copy at milwaukeemag.com/shop.

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