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For Evanstonian Ben Wolf, becoming an ACLU lawyer was the realization of a long-held dream.

“I grew up in a family that had very progressive values,” said Mr. Wolf. “My father was a rabbi and an advocate for civil-rights and an opponent of the Vietnam war. He marched with Martin Luther King and others in Selma, Cicero and Marquette Park. So I was brought up in a family that always believed in the rights of powerless people.”

Mr. Wolf, who has been with ACLU of Illinois for 35 years, and became the agency’s legal director at the beginning of 2016, will be retiring once his replacement is lined up.

Mr. Wolf explained that his agency “looks at the broad perspectives of life and liberties.”

He said, “The ACLU is the one organization that’s trying to defend everybody’s rights. That is a great strength when we deal with all the intersectional issues nowadays. I’ve represented all the foster kids in Illinois in a federal-class action for several years. We had an issue one time involving a couple of private agencies that didn’t want to license gay and lesbian foster parents—even after civil unions and then marriage became legal in Illinois.”

While working on that litigation, Mr. Wolf recalled that he was able to “bring together the leading LGBT legal advocates for the State, the leading child welfare experts in the State and the leading First Amendment experts in the State. … So we were able to take a nuanced and effective view of why—the important thing in the foster care system is the best interests of the child—if the best interest of the child is a gay couple, there’s no reason in the world the child shouldn’t be there.”

But sometimes that means taking up legal positions that are unpopular with the political Left, where much of ACLU’s support lies.

“We are the leading legal advocate in Illinois and perhaps in the country for reproductive-rights for women,” Mr. Wolf added. “But we also advocate the rights of protestors when they behave lawfully and appropriately, even if they’re against abortion, or against freedom of speech, or if they’re bigots in other ways. It’s a great strength for our legal work and our advocacy. But it also makes it hard to raise money for the ACLU, because somebody’s always mad at us about something. My relatives on the North Shore and Chicago are mad about the [Skokie] Nazi case that we did in the ’70s, before I was even here.”

Closest to his heart has been litigation on behalf of prisoners, children and people with disabilities.

“That is partly because I was a bit of a juvenile delinquent,” Mr. Wolf said. “Although I never got in serious enough trouble to disrupt my future, I was always skeptical of authority. That was one reason I was drawn to the ACLU.”

The scope of ACLU’s work shifted significantly following the 2016 presidential elections. Mr. Wolf explained that many clients whose interests would have been argued by lawyers on behalf of federal agencies under the previous administration have now turned to the state affiliates of the ACLU for representation.

“The Chicago Police Department was under investigation by the Obama administration Justice Department and was found to have seriously violated the rights of people of color and people with disabilities, and to have used force inappropriately,” he added. “We would have expected the Justice Department to follow up with litigation leading to an injunction [and] possibly a consent decree. But Jeff Sessions, when he became attorney general, completely dropped that and, if anything, wanted to use his voice on behalf of the people defending police abuse. … We ended up working with the State Attorney General’s office, which also filed a case, helping to craft a consent decree which we hope helps form the dynamic for reform. None of that would be necessary if the Justice Department had done its job.”

Mr. Wolf has lived in Evanston for most of his life and said he is “not sure yet” what to expect from his imminent retirement, but that he “looks forward to not working 60 hours a week.”

Nevertheless, the agency’s executive director has floated the possibility of his staying on as a senior lawyer. Though the upcoming transition has left Mr. Wolf grappling with some life- and work-related choices, he is pleased with the work the agency he has devoted so much of his life to has accomplished.

“We’re proud of the fights we’ve won—and even the fights we’ve lost,” said Mr. Wolf.