A Fair Shake

Ray Dall’Osto began thinking about how he could make a difference while attending Marquette in the early 1970s. Inspired by the Civil Rights Movement and other social reforms of the previous decade, Dall’Osto set his sights on service. He invokes the classic John F. Kennedy quote: “Ask not what your country can do for you—ask what you can do for your country.”

“I think that is emblematic of what it means to do pro bono work, and also what has sort of been the guiding light in my career choices,” he says.

Dall’Osto started as a public defender with the Legal Aid Society of Milwaukee and later for the state-run public defender system. From 1978 to 1980, he served as legal director of the American Civil Liberties Union of Wisconsin. Dall’Osto taught the criminal defense clinic program at Marquette University Law School, his alma mater, for five years before entering private practice at Gimbel, Reilly, Guerin & Brown in 1990.

To Dall’Osto, pro bono work is not something to squeeze into a schedule—it’s what energizes him.

“I view it as broader than simply representing or handling a case for a client for free or at a lower cost than is typical,” he says. “I view it as more of a giving back to the American public and affirming our legal principles—and that means equal access to justice and a fair shake for everyone.”

His highest profile pro bono win came in the case of Daryl Holloway, a Milwaukee man convicted of sexual assault in 1993. Dall’Osto was initially retained by Holloway’s wife and her family to conduct a post-conviction investigation. He hired forensic expert Alan Friedman to do DNA testing, which hadn’t been done during the trial.

Friedman’s results did not definitively include or exclude Holloway, so he recommended further testing. By that time, the funds from Holloway’s family had run out. But Dall’Osto was resolute.

“What kept me going is that I knew the science was changing,” Dall’Osto says.

He took the case to the Wisconsin Innocence Project, hoping funding for additional DNA testing might become available. He also pressed the district attorney’s office about the need for testing, along with what he saw as alibi evidence and inconsistencies in Holloway’s case.

After long meetings with assistant DA and the Innocence Project, Dall’Osto persuaded them to do additional testing. The results definitively excluded Holloway, proving that he had been wrongfully convicted. By the time he was released in October 2016, Dall’Osto says, Holloway had been wrongfully incarcerated for 24 years.

“You feel, number one, elated; two, you wish it had happened earlier,” Dall’Osto says. 

He says revisiting convictions and sentences is like “trying to dig up a coffin in January in Wisconsin with a spoon.”

“It just takes time,” he adds. “You have to be patient and persistent.”

As a member of the Wisconsin Legislature’s Wrongful Conviction Task Force in the early 2000s, Dall’Osto helped draft reforms to interrogation and fair identification procedures.

He also helped clear the path for a women’s and children’s domestic violence shelter in Elkhorn. After the city’s common council rejected a conditional use permit for the shelter, he represented New Beginnings Association for Prevention of Family Violence to appeal the decision.

In April 2020, a circuit court judge sided with Dall’Osto and New Beginnings’ arguments that the denial by the common council was “arbitrary and unreasonable,” according to Janesville’s Gazette. The domestic violence shelter was ultimately opened and is currently in operation—the first of its kind in Walworth County.

Dall’Osto says he believes all attorneys should take to heart the ABA’s recommended 50 hours of pro bono work each year.

“Bottom line, we all need to do the right thing to be a strong profession and to be good human beings,” he says. “Pro bono work for me has got to come from the heart. If you’re walking down the street and you see someone just collapse, do you just stand there and look? Or do you do something to help?”

A Different Kind of Discovery

In 2022, at age 70, Dall’Osto undertook a new hobby: scuba diving.

“I dove at numerous sites in and around Negril, Jamaica, with a good friend of mine, and out on the Great Barrier Reef last November, north of Port Douglas, with my son,” he says. “Truly a vivid, new world to explore.”