Milwaukee County sheriff’s race: Robert Ostrowski challenges his boss for top job

MILWAUKEE -- Milwaukee County sheriff's deputy Robert Ostrowski admits he's the underdog in the race for his agency's top job.

"But just because I'm the underdog doesn't mean I still can't win this campaign," Ostrowski said during an interview at his campaign manager's home in South Milwaukee.

Ostrowski, a 16-year veteran of the sheriff's office and a past president of the deputies' union, said he wants to tell voters "what's really going on." The agency has been plagued by controversies in recent years under former Sheriff David Clarke, who resigned in August 2017.

Ostrowski said Acting Sheriff Richard Schmidt, who was Clarke's top administrator for seven years, shares blame for alienating the community and running multi-million dollar deficits.

Who was in charge?

When asked who was in charge of the sheriff's office while Clarke took frequent out-of-state trips, Ostrowski said it was Schmidt. He said Schmidt would send agency-wide emails and had "a lot of power."

Schmidt has countered that Clarke had ultimate decision-making authority.

"A leader, in my opinion, would stand up to his boss and tell him when his policies are wrong. I'm doing it in this campaign," Ostrowski said.

Nevertheless, Ostrowski praised Schmidt as a person, calling him "very personable" and said Schmidt "is easy to talk to."

Robert Ostrowski

$362 in the bank

By the numbers, Ostrowski is a long-shot to win. His last fundraising report showed he had $362 in his campaign bank account as of June 30 -- 1 percent or less of rivals Schmidt and Earnell Lucas, a former Milwaukee Police captain and current Major League Baseball executive.

Asked what he's say to people who don't view his campaign as legitimate, Ostrowski said, "I would disagree. I'm doing the best I can with what I've got."

In December, Ostrowski lost re-election as president of the Milwaukee County Deputy Sheriff's Association. He said he was already focused on the sheriff's campaign.

"I really did not try that hard to try to win that race, because I knew deep down the only way I could make change was to be the sheriff of the agency," Ostrowski said.

Ostrowski said he does not disagree with any of Schmidt's initiatives the acting sheriff has undertaken over the past 11 months. Schmidt has slashed spending and stepped up public messaging on operating while intoxicated laws. He has made numerous personnel changes inside the county jail, where seven inmates died over an 18-month period in 2016 and 2017.

But the deputy said the public wants more, a message he said has been clear throughout the campaign.

"They want to look at us like they're looking through a pane of glass and can see what's going on," Ostrowski said.

Robert Ostrowski

Ostrowski, Lucas and Schmidt all agreed that they would not seek to participate with federal agents in immigration enforcement through the controversial 287(g) program, which Clarke had applied for.

The Democratic primary is Aug. 14. No Republicans are on the ballot this fall.