Police Unions Won Power Using His Playbook. Now He’s Negotiating the Backlash.

The union voted to increase dues for a “war chest.” It also hired a new chief negotiator: Ron DeLord.

After the city sued over a contract provision it claimed was unconstitutional, the union’s longtime president, Michael Helle, arranged attack ads targeting Ms. Sculley. In an interview, Mr. Helle bragged about “how much I got underneath her skin.” He said the ads, which often had unflattering close-ups of her face, preyed on her vanity. They accused her of being an overpaid, wasteful power-monger who thought cops made too much money.

The union also scoured through her expenses and publicized payments that the union felt were questionable, he said.

Mr. DeLord’s book advises unions to comb through public records about any “enemy.” The New York Times found that unions nationwide deployed the tactic to intimidate city officials or overwhelm them with paperwork. In Denver, for instance, the union filed a public-records request in 2016 asking the city’s police monitor for voluminous records from its investigations.

“I’m sure they are sweating bullets now,” the union president wrote in an email to the union’s lawyer, obtained through a public-records request. “Let’s make them pay on this one.”

In San Antonio, after two years of fighting, a judge overseeing the lawsuit ordered the city and the union into mediation. The deal would limit the legal fund and make officers contribute to some health care premiums. Both sides claimed victory.

Yet Ms. Sculley, who later wrote a book about the city’s struggle, said in an interview she was disappointed that years of negotiations hadn’t achieved more.

While the updated contract has cut costs, it continues to give officers disciplinary protections that some city officials and residents feel impede good policing. In many instances, infractions more than a few years old can’t be considered during disciplinary proceedings — in effect, erasing them from review. And arbitrators, not city officials, ultimately decide whether an officer is fired.

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