Tony Portra’s predictable schedule of court hearings and meetings with attorneys will soon transition into retirement with no known daily routine.
He’s fine with that.
After 25 years as a judge for the Brown County-based 5th Judicial Circuit, Portra is retiring at the end of November. He and his wife Jamie plan to settle near their daughter and granddaughter in the southern part of the country where a warmer climate prevails.
Jamie will continue teaching, so Tony Porta said one of the few things known about his soon abundance of free time is that they will escape the heat of summer by camping in northern states.

Portra tapped as magistrate after three years as an attorney
Now 55, Tony Portra started his career as a judge in 1999 when he was appointed a magistrate. He was relatively fresh out of law school and had been a lawyer for just three years at what is now the Richardson, Wyly, Sauck and Hieb law firm.
At the time, Judge Jon Flemmer, who had been serving as magistrate, moved up to circuit judge after winning a contested race against sitting 5th Circuit Judge Myles DeVine.
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The idea of being a judge was sparked when Portra was a law clerk under Judge Larry Lovrien, who asked Portra if he had ever considered being a judge.
Portra was 25 at the time. Little did he know he’d be asked to serve as and encouraged by colleagues to take the local magistrate post five years later.
“I was the youngest on the bench,” he said.
Portra said it’s surreal that he’s on the cusp of retirement. He said he still feels the same as he did when he started as a judge, but knows time has marched on as his son just turned 30.
Portra served nearly eight years as magistrate before seeking a circuit judge position when Lovrien retired in 2006.
Today, Portra serves with Larry Lovrien’s son, Marshall, who is now also a 5th Circuit judge.
“It is odd,” Portra said about serving with Marshall Lovrien.
That’s because when Portra hears the name Judge Lovrien, he still thinks of Larry.
But, Portra said, when he first started as a magistrate judge, his dad was sometimes asked if he was the new judge.
Memorable cases include when teen was accused of murder
Portra said one of his more memorable cases came shortly after he became a judge, and it’s partly because of the national media attention the scenario garnered.
It was a case Portra wouldn’t have normally handled, but he was covering court appearances in Selby for Judge Jack Von Wald, who was on vacation.
The first hint that the day wasn’t going to be routine was when he heard a news broadcast on the radio as he was pulling into the Walworth County Courthouse parking lot. That’s when he learned four teenagers were going to appear that morning on murder-related charges.
Race became a touchy subject in the 1999 death of Robert “Boo” Many Horses, who was just 22 at the time. Many Horses was Native American.
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Portra said all five young people had been out drinking the previous night. When Many Horses passed out, he said, the other four, who were white, loaded him into a car to drive him home.
Then, Portra said, “Two thought it would be funny to put him in a garbage can.”
The teens were thinking about the reaction Many Horses would have when he woke up, but that never happened. Instead, Many Horses was found dead in the garbage bin.
One of the teens was accused of murder and the other three faced charges of aiding and abetting.
Because Von Wald was absent, Portra covered a hearing in June 1999 during which he set bond and made sure all of the defendants had legal representation. He also wound up handling the preliminary hearing that September.
Hearing in death of 22-year-old was a test for Portra

“It was a test to see if I would do what was called for,” Portra said.
During the preliminary hearing, Portra heard testimony from a medical examiner that Many Horses had a blood alcohol level of 0.446. For comparison, 0.08 is the legal limit to drive.
The medical examiner concluded that the level of alcohol caused Many Horses to die, not where he was found, Portra said.
After hearing that testimony, Portra decided there wasn’t enough evidence for the charges against the defendants.
“They didn’t do anything to kill him,” he said.
Portra said he remembers hearing from legal colleagues who told him they were proud of him for making the difficult decision. However, the decision angered some in the Native American community.
In dismissing the charges, Portra didn’t absolve the teens completely.
Portra said their placing Many Horses in a garbage receptacle was “stupid and extremely dangerous,” according to media reports at the time.
’20/20′, other national outlets report on charges being dismissed
The case caught the attention of “20/20” and other national media, some of which found medical examiners who came to a different conclusion about the death.
Portra and the local prosecutor responded at the time that it’s dangerous to pick and choose evidence in a case.
The case was one of several involving Native American victims about the same time that “touched off a statewide discussion of race relations, including a visit by the U.S. Commission on Civil Rights,” according to a Black Hills Pioneer story.
While the defendants ultimately weren’t charged, they faced a wrongful death civil lawsuit that was settled in 2003.
The case was a tragedy, but not a murder, Portra said.
Struggles by those in drug, DUI courts a ‘gut punch’
Since serving as magistrate, Portra has presided over drug court and drunken driving court cases. The programs give people who face felony charges the chance to stay out of prison as they learn the tools and find the support they need to stay sober.
Defendants in the program are under the intense supervision of a team that includes law officers, attorneys, a probation officer and a judge.
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“I understand when they aren’t doing well at first,” Portra said. “But, it’s when you work with someone for a year and a half. They’re doing well and they stumble. It’s a gut punch.”
He said that through the programs, the team gets to know the people involved and wants them to succeed. But that doesn’t always happen. If they violate too many rules, they are kicked out and sentenced to prison.
That, Portra said, is something he finds no pleasure in.
Magistrate Judge Cullen McNeece now handles the drug and DUI court programs.
Juvenile cases are the toughest
Portra has also been the primary judge on juvenile and abuse and neglect cases for the past seven years. They’re the toughest cases, he said, as they often involve instances in which there’s a “complete breakdown of the family unit.”
In many cases, he said, teenagers aren’t getting any direction from their parents.
“So often I’m trying to help the kid in spite of the parents,” Portra said.
The goal is always to get the juveniles to see the path down which their choices will lead them, he said. Even when Portra can see it’s a bad path, it can be hard to get teens to understand that, he said.
“I’ve seen this movie before. I know how it ends,” Portra said.
There are success stories, but they can sometimes be hard for people in the judicial system to follow.
“The ones who do (succeed), you never see them again,” Portra explained.
‘Nothing I can’t handle’
Portra said when his wife asks how his day went, his standard response is, “Nothing I can’t handle.”
While he feels he deals with the day-to-day stress of being a judge well, Jamie can tell when he’s had a trying day.
“The Tony I sent to work isn’t the Tony they sent back,” she sometimes tells him, he said.
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Exercise, sometimes to the point of exhaustion, helps with the stress, Portra said. Another option is escaping into a comedy or sports broadcast.
How his days go can vary from one ruling to the next.
“You make a decision and have to go on because life doesn’t stop and you have more the next day,” Portra said.
Ultimately, he said, he has to be confident he’s making the best decision possible based on the evidence available.
Important work gets done in judge’s chambers
Not all legal wrangling is done in the courtroom. There’s a lot that happens in a judge’s chambers.
Attorneys often visit the judge’s chambers prior to a court hearing. Sometimes the meetings mean a hearing doesn’t start on time, but that doesn’t mean work isn’t getting done, Portra said.
The conversations in chambers provide a time for attorneys on both sides to work through potential sticking points, he said.
“A lot of work gets done in this office so it doesn’t have to happen tenfold in the courtroom. The courtroom will always be there,” Portra said.
The meetings give litigators a chance to have their say in how proceedings will unfold.
“I feel like I try to foster more of a team approach,” Portra said.
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Figuring things out is better than fighting them out.
“Surprises in court are not fun,” he said.
Portra said his career as a judge fits his personality.
“I’m not a good sideline sitter,” he said.
Portra said he heard one judge describe retirement as a great weight being lifted. He’s looking forward to that feeling.
“It’s an honor you were put in this position,” he said. “It’s also a burden. The responsibility of doing the right thing.”
As for what specifically will happen when the burden is eased, well, there’s not yet enough evidence for the judge to rule on what he’ll do aside from potentially volunteering as a local track coach.
“I’m really looking forward to just finding my way,” Portra said. “I’m enjoying the prospect of not knowing.”