Tom Kertscher, and John Diedrich

Milwaukee

Ruling doesn't mean immediate release from prison

Prosecutors have 90 days to decide whether to retry Dassey or to appeal

Legal observers expect case to be ultimately decided by Chicago-based federal appeals court

Brendan Dassey, who was convicted along with his uncle, Steven Avery, in the murder of Teresa Halbach, had that conviction overturned Friday by a federal magistrate judge in Milwaukee.

The shocking ruling, in a case made famous in the Netflix series “Making A Murderer,” could result in Dassey getting a new trial or being freed from prison. It gives prosecutors 90 days to decide whether to retry Dassey, although an appeal could extend the proceedings.

In his 91-page decision, U.S. Magistrate Judge William Duffin was highly critical of investigators, Dassey’s pretrial attorney and the state courts on how they handled the case, concluding that Dassey’s constitutional rights were violated. He found that the prosecutor’s investigators made false promises to Dassey during multiple interrogations.

“These repeated false promises, when considered in conjunction with all relevant factors, most especially Dassey’s age, intellectual deficits, and the absence of a supportive adult, rendered Dassey’s confession involuntary under the Fifth and Fourteenth amendments,” Duffin wrote.

Original coverage of 2007 Steven Avery trial

A review of transcripts and several hours of recordings of the interrogations of Dassey, as well as interviews with legal experts, shows this:

Dassey — who at the time was a learning-disabled 16-year-old with no police record — was repeatedly questioned without an attorney by the prosecution’s investigators, who allegedly “fed” him facts of the crime that he eventually confessed to.

Dassey’s first lawyer not only allowed Dassey to be questioned alone, but had his own investigator pressure Dassey to confess.

Moreover — unlike Avery, whose conviction was based largely on DNA evidence — no physical evidence linked Dassey to the slaying of Halbach. The 25-year-old photographer was last seen alive with Avery, outside his Manitowoc County trailer, on Halloween 2005. After separate trials in 2007, both Avery and Dassey were sentenced to life in prison.

Federal habeas corpus petitions typically stand a minimal chance of success. A book co-authored by professor Joseph Hoffmann at Indiana University’s Maurer School of Law puts the failure rate at 99%.

But Dassey’s case, Hoffmann said before Friday’s decision, “is far from typical.”

Here’s a look at why Duffin ruled that Dassey’s confession was not voluntary:

Initial questioning

As a student at Mishicot High School at the time of Halbach’s murder, Dassey was taking mostly general classes but some special education classes, too. Though a minor, he was alone each time he was interviewed by law enforcement investigators.

That isn’t illegal. But Hoffmann said that how the questioning was done, as well as Dassey’s age and mental capacity, were part of what Duffin had to consider.

The questioning was done by the two lead investigators for the prosecution for both trials: Mark Wiegert, then a detective and now a lieutenant with the Calumet County Sheriff’s Department, which led the murder investigation; and Tom Fassbender who was a special agent with the state Department of Justice.

The sessions were marked by the two investigators alternately telling Dassey they were on his side, and pressing him to provide more details of the crime that they insisted they already knew.

The first interview, a roughly 80-minute session at Dassey’s school, was done Feb. 27, 2006, and recorded on audio (portions of which are inaudible) in twoparts. The investigators begin by telling Dassey he is not under arrest, can leave at any time and doesn’t have to answer questions; they remind him of that again near the end of the interview.

Speaking in low tones, the pair tell Dassey that other investigators believe he was involved in the murder, but that they don’t.

Investigators for the prosecution assure Dassey during questioning they are on his side in this video clip.

Ten minutes into the interview, they declare they’ll stand behind him:

Fassbender: Mark and I — yeah, we’re cops, we’re investigators and stuff like that. But I’m not right now. I’m a father that has a kid your age, too. I want to be here for you. There’s nothing I’d like more than to come over and give you a hug because I know you’re hurting ….I promise I will not let you high and dry. I’ll stand behind you.

Wiegert: We both will, Brendan. We’re here to help ya’.

The conversation focuses on a fire outside Avery’s trailer on the night Halbach disappeared and whether Dassey saw body parts in it. The investigators say they know something must be bothering Dassey, based on what he saw. But at one point when they ask Dassey what else is bothering him, he says: “Trying to find a girlfriend.”

Dassey eventually says he saw parts of an intact body in the fire and that Avery had told him he stabbed Halbach. Toward the end of the interview, the investigators ask about a gun and raise the possibility that Halbach was raped — details that would become important in their later sessions with Dassey.

At the end of that first interview, the investigators ask Dassey if he wants to go home, saying he must be tired. He says he’d rather go to his eighth-hour class, Earth Science. And that’s what he does.

In an appeal filed in state court, Dassey’s previous lawyers argued that Wiegert and Fassbender used fact feeding and suggestions of leniency that, as the appeals court put it, “overbore his will and exceeded his personal ability to resist due to his age, intellectual limitations and high suggestibility.”

But the state appeals panel agreed with Dassey’s trial judge, who concluded that Dassey did not appear agitated or intimidated during the interviews, and that his confession was voluntary.

Other testimony

Avery was arrested about a week after Halbach’s disappearance. The involvement of Dassey, who lived in a different home on the same Avery family property, didn’t surface until more than two months later.

In January 2006, Kayla Avery, a cousin and classmate of Dassey’s, sought out a school counselor because she was scared about something her uncle, Steven Avery, had done.

Kayla later told Wiegert and Fassbender that Dassey had told her he saw Halbach’s body parts in a fire outside Avery’s trailer. She also provided a written statement in which she said she hated Avery.

At Dassey’s trial, things changed. Kayla testified that she had made up the conversations she had with Dassey.

But by then, Dassey had already confessed.

The confession

After the first interview at Dassey’s high school, Wiegert and Fassbender called Dassey’s mother, Barb Janda, who came to the school. According to the investigators’ report, Dassey and Janda agreed to a second, videotaped interview, later on the afternoon of Feb. 27, 2006, at the Two Rivers Police Department. They wrote that they asked Janda if she wanted to be in the interview room and that she said it wasn’t necessary; and, according to the report, Dassey said he didn’t care.

Dassey was given his Miranda warning before the second interview, and waived his right to a lawyer. The interview covered much of the same ground regarding the fire. Asked if he stabbed Halbach or helped put her body in the fire, Dassey says no; and asked if Avery said he sexually assaulted Halbach, Dassey says no.

The confession came two days later, during Dassey’s third interview, which was videotaped in twoparts. The session began with the Miranda rights, and Fassbender telling Dassey that he and Wiegert are “in your corner” -- but it “it’s real obvious” that Dassey had left out some things in the previous interviews.

Investigators for the prosecution tell Dassey during questioning that he shouldn't worry in this video clip.

Even then, the investigators seem to suggest he is not in serious jeopardy.

Fassbender: From what I’m seeing, even if I filled those in, I’m thinking, you’re all right. OK, you don’t have to worry about things.

Wiegert: Honesty, here, Brendan is the thing that’s going to help you, OK, no matter what you did. We can work through that. OK? We can’t make you any promises, but we’ll stand behind you no matter what you did. OK? ...

And by you talking with us, it’s helping you, OK? Because the honest person is the one who’s going to get the better deal out of everything. You know how that works. (Dassey appears to agree, saying: Mmm-hmmm.) You know? Honesty is the only thing that will set you free. Right?

Wiegert and Fassbender then repeatedly tell Dassey they already know what happened, but that he needs to be honest and tell them. They also tell Dassey not to guess or make anything up.

That’s when Dassey spills more details — for example, saying he had seen Halbach naked and handcuffed to Avery’s bed, screaming for help.

“Now I can start believing you, OK?” is Fassbender’s response.

Dassey then reveals more. He says Avery told him he raped Halbach. He says he himself then raped her. He says Avery stabbed and choked Halbach until she went unconscious.

But a final, crucial detail emerges only after the investigators repeatedly ask Dassey what happened to Halbach’s head.

Dassey provides a series of answers: Avery cut off some of her hair; Avery punched her in the head; Dassey slit her throat. But the investigators continue to press for one particular fact.

Wiegert: What else happens to her in the head?

Fassbender: It's extremely, extremely important you tell us this, for us to believe you.

Wiegert: C’mon, Brendan, what else?

Fassbender: We know, we just need you to tell us.

Dassey: That’s all I can remember.

Wiegert: All right, I'm just gonna come out and ask you — who shot her in the head?

Dassey: He (Avery) did.

Fassbender: Then why didn't you tell us that?

Dassey: ’ Cuz I couldn't think of it.

It’s a dramatic admission.

Yet Dassey then offers more details that seem to contradict each other.

He says Avery shot Halbach three times — in the head, heart and stomach — next to Avery’s garage, and that Halbach was never in the garage. But moments later, he says Halbach was inside her car in the garage when Avery shot her — about 10 times. Then Dassey says Halbach was on the garage floor when she was shot.

After that last detail, Wiegert responds by saying: “That makes sense. Now we believe you.”

Dassey has just confessed to rape and murder, but appears not to understand when he asks the investigators: “Am I going to be (back) at school before school ends?”

Instead, he is arrested. He tells the investigators he understands, but then asks: “Is it only for one day, or — .”

Duffin's ruling

“The investigators’ use of leading questions and disclosure of non-public facts makes it difficult to evaluate whether Dassey really knew the facts or was simply agreeing with the investigators,” Duffin wrote in his decision.

“Based on its review of the record, the court acknowledges significant doubts as to the reliability of Dassey’s confession. Crucial details evolved through repeated leading and suggestive questioning and generally stopped changing only after the investigators, in some manner, indicated to Dassey that he finally gave the answer they were looking for.”

Duffin added:

“Most significantly, however, the (state) court of appeals erred when it focused on the statements of the investigators in isolation to conclude that they did not make any promises of leniency. True, no single statement by the investigators, if viewed in isolation, rendered Dassey’s statement involuntary. But when assessed collectively and cumulatively, as voluntariness must be assessed, it is clear how the investigators’

actions amounted to deceptive interrogation tactics that overbore Dassey’s free will.”

Dassey’s lead attorney, Laura Nirider of the Center on Wrongful Convictions of Youth at the Northwestern University Law School, argued in the habeas petition that Dassey’s constitutional rights were violated not only because of the way he was questioned but because Dassey’s pretrial lawyer, Len Kachinsky (who is now a municipal court judge in the Town of Menasha), actually helped the prosecution obtain his confession.

In an interview, attorney Steven Drizin, who handled the appeal with Nirider, said that if prosecutors decide to retry Dassey “they will have to do so without the confession.

“There is no case without the confession,” he said. “There is no other evidence besides the confession that could lead a jury to convict Brendan. I would not speculate what the state’s next move is likely to be.”

A judge removed Kachinsky from the case before Dassey’s trial after learning that Kachinsky had allowed Wiegert and Fassbender to question Dassey a final time, to confirm the confession, without Kachinsky being present. Kachinsky has said he was trying to minimize the time Dassey would face in prison. Had Dassey made a plea deal, rather than recanting his confession and going to trial, it’s possible he could be completing his sentence within the next several years.

Duffin wrote that although Kachinsky’s misconduct was indefensible, “the U.S. Supreme Court has never accepted arguments such as those Dassey makes here as a basis for relief.”

Duffin, a former business attorney at a Milwaukee firm who has been a magistrate since March 2014, received the case when it was filed in October 2014. The necessary filings from both sides had been with him since June 2015.

As the case stands, Dassey, now 26, is eligible for parole in 2048.

The attorney who handled the Dassey appeal for the state declined to comment Friday. A spokesman with the Wisconsin Department of Justice Johnny Koremenos wrote in an email, “As we are currently reviewing Magistrate Judge Duffin’s order, we have no comment to offer at this time.”

Mary Spicuzza, Ashley Luthern and Bruce Vielmetti of the Journal Sentinel staff and John Ferak of the USA TODAY NETWORK - Wisconsin contributed to this report.