Retired judge Dennis Challeen was living in a boathouse on Latsch Island when he started something that would make him a nationally known pioneer in criminal justice reform. “I became an oddity,” he said.

Winona’s judicial trailblazer



In 1967 Dennis Challeen was a young lawyer just a few years into his career when a judge told him to back down. “Mr. Challeen, this court will not be badgered. You have interrupted the court twice now … I must warn you that are treading on very thin ground,” Judge John McGill told the young attorney. Challeen had been arguing aggressively with the judge that the bail set for his client, a defendant in a burglary case, was too high. “This is discrimination against the poor man,” Challeen stated, according to a Winona Daily News report from the hearing. “A rich man can make bail, but a poor man has to remain in jail.” It violates the right to equal protection, Challeen contended.

The prosecutor said that Challeen was arguing, not for a different interpretation of the law, but for entirely different laws, and McGill ruled that Challeen’s arguments had no place in the hearing, according to the report. A defiant Challeen told Judge McGill, “This is going to end up in the Supreme Court.”

Sixteen years later, the U.S. Supreme Court ruled in Bearden v. Georgia that if citizens are genuinely unable to pay a fine, their inability to pay is not a legal reason to jail them. It violates the right to equal protection, the justices determined.

Challeen would go on to serve as a judge in Winona County for decades, where he was an outspoken critic of the justice system’s failures and an early advocate for reforms that have gained traction over the past half century. “He was so far ahead of his time in terms of restorative justice and offender-based sentencing … which nowadays are accepted in criminal justice as common concepts that everyone knows, but back in the 1970s, they were completely unique,” Winona attorney Rich McCluer said of the former judge. McCluer practiced law in Challeen’s courtroom in the late ‘80s and ‘90s and described him as a great mentor. Now 83, Challeen spoke with the Post from the deck of his house overlooking the Mississippi River.

“I call this my boathouse up in the sky,” Challeen said of the lofty, blufftop view. It is a nod to his days residing in an actual boathouse on Latsch Island, canoeing to high ground during the spring floods and riding his motorcycle to court. He was living on the island in 1972 when he launched an alternative sentencing program that garnered national attention. “In those days, if you sped, a cop arrested you, and if you didn’t pay the fine, you went to jail. That’s it,” Challeen said. Instead, the young judge offered community service for those who could not afford to pay fines. He promoted restitution paid to victims instead of fines paid to the government, and he asked convicts to participate in deciding their own sentence — deciding how they would make things right. Challeen famously sentenced a teen who vandalized Winona’s Veterans Memorial Park to watch “Saving Private Ryan” and write an essay about how his actions affected local veterans of World War II. The late James Heinlen served as the director of court services at the time and played a crucial role in administering the Judge Challeen’s alternative sentences. It was controversial. “All the judges said, ‘You’re going to get yourself in trouble because you can’t create the law,’” Challeen recalled. “I was threatened with being sued and all this, but I thought, ‘Well, the most I have is my boathouse.’” It was bold. “Fortunately, I was on the right track,” he said.

Elsewhere in the U.S., few community service sentencing programs existed. A 1966 program in California is credited as the first in modern American history, and the practice was rare, if not unheard of in Minnesota. The Minnesota Department of Corrections did not begin its own Sentencing to Serve program until 1986. Network television crews came to profile Challeen. The Minneapolis Tribune extolled the approach. Not everyone loved it. “Back in those days, if you wanted to change the world you were a crazy hippie liberal,” Challeen recalled. “I got it from both sides. The conservatives said it was leniency, and the liberals claimed it was a chain gang,” he said.

During his time as a judge, Challeen became convinced that the status quo was not working. In most cases, incarcerating people did not help, he contended. Violent criminals should be locked up to protect society, but the vast majority of crimes are non-violent offenses committed by “losers,” who are more pathetic than dangerous, Challeen wrote in his 1986 book “Making it Right.” He argued that while jail sentences are supposed to act as a deterrent to committing crime, the deterrent does not work because many offenders have trouble making responsible decisions and thinking logically about consequences. They need to learn responsibility, and jail does not help much with that, he stated. It is a viewpoint epitomized by Challeen’s widely quoted poem, “Prisoners.” In it, he wrote, “We want them to take control of their lives … / So we make them totally dependent on us.” It was a view informed by the lives of people who frequented his courtroom, and cemented by his experience voluntarily spending three days in state prison as an inmate. “I saw people who were trying to make it, and the system was not helping them. It was actually harming them,” Challeen told the Post. “It was making learning responsibility more difficult.”

“What I think is a core concept of [Challeen’s] is that we tend to assume other people think exactly as we do or process things as we do,” McCluer said. Laws, law enforcement, and courts are run by normal, ordinary, responsible people — NORPs, in Challeen’s parlance — who expect offenders will react to punishment the same way they would. McCluer shared one example from Challeen’s courtroom of how offenders sometimes saw things differently. A defendant told Challeen, “I just want to plead guilty to this thing and get it over with, and then I’m going to leave this goddamn town. You know, everyone is picking on me,” McCluer recalled the defendant saying. The man said he was going far away from Winona, out to California, where things would be different. “You know, when you get out there you’re going to find that the guy who is always causing you these problems is right there with you,” Challeen told the man, as McCluer remembered. “Oh no,” the man replied, with complete confidence. “I’m going alone.”

Asking offenders to help decide their own sentence, in Challeen’s opinion, forced them to acknowledge that they did something wrong and they needed to do something about it. The judge saw restitution and community service as ways offenders could benefit victims and their community, learn some responsibility, and engage in the process of making up for their crimes, rather than sitting in jail, the resentful, passive recipients of a punitive sentence.

Challeen was criticized for being too soft, too idealistic and being “conned by the convicts.” However, as he looked out over the island city from the ridge last week, he seemed to have a sober view of human nature. The city looks beautiful from up here, Challeen said, adding that he knows better. “You’ve got some pretty ugly stuff going on down there every day and every night,” he stated.

Challeen had other ideas that did not catch on, including taking issue with the 0.08 percent blood-alcohol content limit for driving. “In practice, drunk driving laws in America have succeeded in scaring the living hell out of ordinary, responsible people who are not the problem, but have done little to thwart the habitual chronic, hard-core, irresponsible alcohol abuser who is the greatest threat to our highway safety,” he argued in the Winona Post in 1992.

The judge travelled the country, giving presentations and speeches on his criminal justice philosophy, and he became a prolific writer, penning numerous books and scores of columns. He taught other judges as a part-time faculty member at the National Judicial College for over 30 years and received multiple honors from the organization for his service. The courtroom was still his favorite place. “In college, you’re off in this theoretical land,” Challeen said. “In my courtroom, every day was the real world — real people going through real turmoil.”

While he helped pioneer reforms, Challeen admits there is no easy solution. “How do you teach responsibility to someone who doesn’t understand responsibility?” Challeen asked. “Maybe there never has been and never will be an answer, but I think we can make it a little easier,” he said.


Enter the code shown above in the box below
(Items marked * are required)

Search Archives

Our online forms will help you through the process. Just fill in the fields with your information.

Any troubles, give us a call.