Former State Senator Ray Holmberg's sentencing hearing on Wednesday has raised a looming question: will he appeal the ten year prison sentence handed down by Judge Hovland? Prairie Public's Director of Radio Ann Alquist talked to federal and state defense attorneys Dane Dekrey and Bruce Ringstrom for their analysis and perspective.
Listen or read the transcript.
Dane: My name is Dane Dekrey. I am a partner at the law firm Ringstrom Dekrey, and I've been a lawyer for 10 years.
Bruce: My name is Bruce Ringstrom Jr. I'm the founding partner of Ringstrom Dekrey. Grew up in Moorhead, and I have been a lawyer for about 16 years.
Ann: I know both of you had your eye on the sentencing hearing for former State Senator Ray Holmberg. You're both defense attorneys. This was pretty tough stuff for his defense attorney Mark Friese. Mr. Holmberg's defense attorney Mark Friese came out very strong, I would say. I mean, and as one would expect, he's got a client.
Ann: I went out with a public defender once, and I asked him what he did for a living, and he said, I defend the Constitution. So it feels like a very sacred job in that respect. He took a long time with his sentencing recommendation, actually longer speaking than his opponent, the US attorney Jennifer Poole.
Ann: It was over an hour. Is that unusual?
Dane: Well, there are sentencing arguments that can go a very long time. I think Dane is in a better position to speak to this particular sentencing because of his expertise in federal court.
Dane: I have had sentencing hearings in state court where the stakes, in fact, were higher than for Senator Holmberg that went an hour, hour and a half, just my part. But most of the time, when the issues are clear and we understand the proclivities of the judge, the sentencing hearings will often be shorter. I was not particularly surprised at the length. I think Dane's opinion matters more here.
Bruce: In federal court, that's an objectively long recommendation by defense counsel. But I think that we need to view everything related to Mr. Holmberg's case in a one-off prism.
Bruce: I think for the defense lawyer, for Mr. Friese, for the, I guess it's the acting US attorney right now, Jen Poole, Jennifer Poole, and even Judge Hovland, who's been on the bench for many years, this has got to be among the three biggest cases that they've probably ever had in their career. And so I think when you also know that the eyes of the state are upon you, I think you take it upon yourself to make sure that you don't leave any stone unturned. But I would say that, at least in my experience, sometimes what you're really looking for is the Goldilocks sentencing argument, which is not too hot, not too cold, just right.
Bruce: And I wasn't there in the courtroom, but in my experience, sometimes if you go a little bit too long, especially in federal court, because going into the hearing, both sides have already given forth their written arguments to the judge. And so if you give a long written argument, and then you go into court, and you give the same long oral argument, the question sort of becomes, did you not think the judge has read it before, or was listening? And so I wasn't there, but this is probably rare in terms of the length of a normal federal sentencing hearing.
Dane: There are optics involved, too, as Dane pointed out. The judge has read everything. Lots of sentencing in federal court, and in state court, are reviewing issues that judges see over and over again in cases. There's a set of cases, you know, in federal court, you have drug conspiracies, you have child sex abuse material cases, and the like. Everybody knows what the ranges are, and it requires a particularly odd set of facts for a judge to go beyond what is predicted. Here, this was a rare case. This was something that Judge Hovland probably hadn't seen ever in his career, or certainly nothing close to it. So that's a justification for a much longer comprehensive sentencing argument.
Ann: The hearing itself was almost seven hours. So, I mean, it sounds like that was unusual as well.
Dane: Yeah, that is among the longest that I've heard of in this district. And I do also want to credit Judge Hovland. My guess is Judge Hovland knew going in relatively where he was going to land. And if he knew going in that he was going to land above what's called the sentencing guidelines, he knows that there's a good chance that his decision will be appealed. And the best thing a judge can do when they think an appeal may happen is to make a very comprehensive record. And the most comprehensive record is a seven-hour hearing where everything's on the record.
Dane: So if you just refer to this nebulous sentencing argument or the earlier written papers, that makes it hard for the Court of Appeals to know exactly what you're talking about. And so I use this term a lot, and I'm going to get a smirk from Bruce, but this was a belt and suspenders moment. This was a, I'm going to make sure that I do everything in my power to let the Court of Appeals know what I did and why.
Dane: So likely or inevitably, when Mr. Holmberg appeals, they will not wonder why I did something. Because you'll sometimes read Court of Appeals opinions where they'll say, we really wish the district court would have explained themselves more. And because we can't read their minds, we're going to have to decide A or decide B. Whereas here, I don't think anybody's going to say we didn't know what everybody was thinking and saying at that hearing.
Ann: And I will say it felt like a trial. It felt like a trial in there. I thought I was an extra from Law and Order or something because of the length of it, but also the pugilism that's involved in a courtroom between prosecution and defense attorneys that happens. And I sort of assumed it was because to get things on public record. Because there wasn't a trial, because evidence wasn't submitted in a public court record or exhibits or documents, this was an opportunity for the prosecution, for the US Attorney's Office to put it in public court record.
Bruce: Absolutely. In federal court, sentencings often look more like trials. There is a strategic posture that federal criminal defense attorneys will take, which is treat the sentencing like a trial. Do everything you would as though it were a trial. Contest every fact that you can, build out a narrative that is most likely to move the court, move the judge to give you the best possible sentence.
Ann: So this was a sentencing hearing, felt like a trial. Mr. Holmberg was indicted in August of 2024. He signed the plea agreement in September that convicted him of one count of intent to traveling to engage in illicit sex acts. Jennifer Poole, the acting US Attorney, relied heavily on evidence from special agent Cassetta's testimony that basically revealed just very detailed accounts of Mr. Holmberg's sexual life. It certainly did prove the intent to travel.
Ann: He traveled 14 times between 2011 and 2021. There was a number, 9,000 pages, I have in my notes of PDFs of cyber chats, 35,000 pages of investigative documents, exhibits, the nine exhibits of pictures and emails, but very little evidence of that pertained to the intent to travel for sex with minors, with underage sex workers, which is where Mr. Fries came in very explicitly to point that out. And yet the result of 10 years, exceeding the sentencing recommendation by acting US Attorney Jennifer Poole, you're a federal defense attorney.
Ann: How important is it for the emotional factor? She brought forth impact testimony. I mean, look, it was poignant. I mean, you couldn't help. I mean, especially when special agent Cassetta, this is what happened in the courtroom as probably one of Mr. Holmberg's first alleged victims spoke when he was a high school student in Grand Forks in 1990s and broke down and the special agent brought him a box of tissues. I mean, I was tearing up. How do you address that as a defense attorney? And I can talk about what Mark Fries did.
Ann: I mean, he was very noble about it. He commended the alleged victims for being courageous. But when you're in a process like that where the prosecution frankly had weak, it was weak, how do you address that as a defense attorney?
Dane: One of the interesting things about the approach in this case is something you brought up, which is there was a victim problem as we call it in defense land.
Dane: And that is the fact that what you're getting at is there's evidence that Mr. Holmberg traveled. There's evidence that he at least spoke about doing the conduct alleged, but there's nobody victim on the stand up there saying, I'm the person in Prague that Mr. Holmberg had sex with. And instead what it was was other people who were talking about conduct that they engaged with Mr. Holmberg that he wasn't charged for here.
Dane: Nor convicted. And I don't even know if these individuals were under age at the time. And that is a very interesting strategy that is allowed in federal court, which is to be able to use other bad acts at sentencing to try to help bolster the underlying act that you're convicted of. And from what I heard about the sentencing, I think that's what Mr. Friese talked about. And I have to say as a defense lawyer, I find some sympathy in that complaint.
Ann: And I think he did that for a reason because he was advocating the sentencing recommendation for home confinement.
Dane: I think if he had any inclination that the judge was going to depart as far up as he would have, he probably would have done a joint recommendation with the government for the 37 months. I mean, it's very easy in hindsight to try to say what you should do when you see what the judge did. But I think I would have taken a similar approach and Bruce and I would have worked together on this case.
Dane: We worked together on every case, but we would have made clear that we can both be sympathetic to these men's horrific stories with Mr. Holmberg, but also point out that that is not what we are talking about here today. And it's very easy to be distracted by other conduct that in our opinion we would argue is not relevant to these charges.
Bruce: The most important piece of proof that Jennifer Poole had at her disposal was Senator Holmberg's guilty plea. Think about it from that perspective. Like that's the linchpin piece of evidence. And it does feel, set aside my personal feelings about whether this human being should be incarcerated for his behavior, bringing in evidence that doesn't bear directly on the crime that's been charged and the crime that's been pleaded guilty to is basically character evidence.
Bruce: And character evidence says, well, if you did it before, you'll do it again. Or propensity evidence really is the better way to describe it. In Minnesota court, and actually to a large extent in North Dakota court, you can't bring in propensity evidence absent very, well, you can't ever bring it in, but you can bring in evidence similar to that with very specific reasons to do so.
Bruce: And here, essentially it was used to prejudice the judge into saying, I can't turn a blind eye to these things. And from my perspective, I think that's unfortunate.
Ann: I just have one, I do wanna follow up on that because I've got a list of quotes from defense attorney Mark Friese that I wrote down. These things aren't recorded. Of course, it's gonna be a public court record, but I wanted to make sure I took copious notes. In his sentencing recommendation, one of the things that he did say, the arguments are meant to inflame.
Ann: That's a direct quote. So it was obvious as he was delivering his sentencing recommendation that he wanted to address, you talked about optics. There was definitely a bit of kabuki theater going on here.
Ann: There was definitely a sense from defense attorney Mark Friese to come back and make sure that he painted a picture of how much of this case was coming out of the court of public opinion.
Dane: I definitely think that there is a large component there, but our job when we're here today is sort of to look in both sides of this case. You know, the devil's advocate perspective there is if the defense counsel felt that strongly about the weaknesses of the case, they could have taken the case to trial.
Ann: Why not take this to trial?
Dane: Well, and at trial, just when Bruce was talking about, it's much harder to get character evidence in at trial than it is at sentencing. And so had this case gone to trial, Jennifer Poole still could have tried to get these other victims in to testify, but the standard is higher and harder because at that point you're presumed innocent. And therefore the standard to allow character evidence in is more difficult.
Ann: And the burden of proof would have been on Jennifer Poole.
Dane: Correct. And once you're at sentencing, the standard to allow character evidence in is much lower. And so there was a calculated decision behind closed doors that we will never know about between Ray Holmberg and his defense team to say, do we think that they have a good enough case? Or what is the reason why we are not putting them to their evidence and possibly eliminating these two victims that you heard from? Because at a trial, I would argue, in my opinion, they probably wouldn't have been allowed to testify. Now, I'm not a judge. I didn't get confirmed by the Senate, but it's much easier to get evidence in at sentencing than it is at trial.
Dane: And so going out of this, hearing Mr. Friese's arguments, hearing everyone's opinion, it's a universal opinion I've heard from people talking about how these victims, they didn't understand the relevance related to the actual charge. And so I'm curious as to the decision-making process, and I'm not second guessing it. It's very easy to play Monday morning quarterback. I am not doing that. But this would have been a very different experience had this been at a trial versus sentencing.
Bruce: One thing to remember about what a trial would look like, again, as Dane noted, we don't have access to discovery, and we've never spoken to Senator Holmberg, but the federal government, when they prosecute a case, are very good at using overwhelming volumes of circumstantial evidence to build a narrative such that a jury says, well, no, there's no direct evidence, but there's so much circumstantial evidence, I feel like all the doubts were ruled out.
Bruce: No, there are attacks that can be made, but you talked about how long the sentencing hearing was. Imagine three or four weeks of evidence from the government. Imagine that. And so the attack from defense counsel to chip away at that, I mean, it can be done. We've won big cases with lots of circumstantial evidence, but the risk is huge, and that had to have been something they were thinking about.
Dane: And they likely, but not certainly, would have needed Mr. Holmberg to testify. If you heard in the sentencing, even Judge Hovland was very direct about, why would you write this stuff? Why would you say this? And there was a lot of walking back, like it was puffery, or it was locker room talk, or I'm, you know, I was just bragging to my friends, and it seemed like Judge Hovland didn't buy it. And Judge Hovland was essentially the jury in this situation. And so there is just a lot of risks, even though there's not that direct evidence victim.
Dane: You know, Mr. Holmberg, those 8,000 texts you mentioned, and that five-person group chat, I mean, it would be very hard, I think, day after day, having those be read into the record, providing all of the context, to then try to say with a straight face that this was all merely puffery, or this was all just boys being boys. It could be done, it is done, but it's always easy for people to second-guess decisions made in these types of cases. And we are doing our best knowing the tip of the iceberg.
Dane: What we saw at the hearing, and what we know about, is that little part that pokes out of the water. Underneath is a whole vast piece of ice that very good lawyers, and I think even at the hearing, Mr. Fries was complimented by the judge. He's a very good attorney.
Ann: They both were. The quote that I have from Judge Hovland was, and he said this directly to Mr. Holmberg, this has been excellent lawyering, and that he got the best defense, that he could possibly have wanted. And then the other quote that I have from the judge as well, that he directly said to Mr. Holmberg was, you didn't have the best hand of cards.
Ann: It was tough stuff. As Mark Fries spoke during his sentencing recommendation, I'm a student of history, legal history, he did have a bit of a Clarence Darrow moment, who of course was famous for defending the biology teacher in the Scopes Monkey trial, but specifically he defended Leopold and Loeb, the two young men who stalked and murdered a 14-year-old Bobby Franks, stuffed his body into a pipe. Terrible, brutal crime that just shocked the nation.
Ann: Guilty, 100%. But then went in front of the judge, pleading with him for 12 hours that they not be hanged. And there was a little bit of that. He wasn't pleading necessarily, but he did speak directly to the media. He said, it's hard to blame the media. They had no idea five men were being investigated and received immunity and cooperation agreements.
Ann: I'm presuming he said that because he wanted it on the record, and again, to the optics point. But the other piece that he talked about, and this was a political element to it, where he spoke to the tone nationally, events going on in Washington, D.C. He talked about how the Department of Justice is being weaponized. He talked about a mob mentality that pervades our environment that is scary to him.
Ann: These are direct quotes from the courtroom. Does that surprise you, that he made those larger contextual comments about the time that we're in? Is that something you would do? Again, I realize it is a very unusual, almost a once-in-a-lifetime case.
Bruce: It doesn't surprise me, but there's a little bit of a logical gap there because this was, the indictment was brought under a different Justice Department. It is carried through.
Ann: You're talking about the Department of Homeland Security?
Bruce: No, I'm talking about how there was a different presidential administration, there was a different attorney general when this indictment came down than the attorney general now. And so the argument that this case could be considered a product of the weaponization of the Justice Department doesn't make sense in the way that you might argue that about other things.
Bruce: You could make the case, this isn't about the Justice Department, but that the Biden pardons were impermissible or the Trump pardons were impermissible or what the Justice Department or the Biden administration did was unjust, the Trump, you know, so on. But here, this one ranged across two of them. So I sort of understand what he's saying.
Bruce: I do wonder whether, I mean, it obviously didn't have the right effect on the judge. Remember in the Leopold and Loeb case that Clarence Darrow successfully got life on, the default was death and he got life. Here, my understanding was it probably could have landed on 36 months and the judge gave him three times the amount. So ultimately the arguments were unavailing. Not only did they not work, the end result was something like triple what it could have been.
Ann: Well, but the end result could be that he dies in prison.
And if it were 36 months, it could be that he would not die in prison because he would only have to, I mean, I think I'm just- That's my point.
Bruce: That's my point, that the argument didn't achieve what the defense would have hoped.
Ann: And then that was the age argument and his heart issues, his medical issues just didn't play. What about the other, the media component of this? I did have a moment watching one of the local commercial TV news here where they talked about the crimes of Ray Holmberg. And I did have a moment. I was like, what crimes? It was one count.
Ann: I got into very sort of specific anal retentive accuracy mode. And I'm curious as you watch your cases get played out in the media, what do you wish the media would pay attention to? What do they get wrong? And where are they getting things right?
Bruce: Well, I think Dane and I can both opine on that in different ways. Whenever you work in a field, in a specialty, you often find yourself bristling at the way the media report it, whatever it may be. There are other fields and avocations that I know a great deal about. And when I see the media report them, I think those are the wrong words. They don't know what they're talking about.
Bruce: And it certainly is true with criminal work. I will read an article about one of my clients. Trial begins next Tuesday. It's not trial. It's a pretrial or it's an omnibus or it's a dispositional conference. And so it sort of frames it as though the jury is gonna come on that day. Yes, when members of the media say Senator Ray Holmberg's crimes, they are assuming that he is guilty. And that's really problematic. Dane and I have a deep concern for due process. And part of due process is helping people understand, helping the media understand how the process actually works.
Dane: And I think the question that when it bothers judges with sloppy lawyers and lawyers with sloppy journalists is number one, how frequent does it happen? And number two, maybe more with the media is, is there something more at play than just we were in a rush to try to get the story out? I think news is becoming a bit shaded in whatever direction that the company or the organization is pushing. And that goes on both sides of the political spectrum.
Dane: And I think if I had to guess, I'm sure Mr. Friese was talking about that more than the media getting a small detail wrong. I sympathize with the issue related to the secrecy of the other individuals. Because without knowing that, it does really make it seem like it was Mr. Holmberg and Mr. Holmberg alone.
Dane: And it was all of these things that it was much more complicated than that. And I don't know if that was because it was under seal, or there was not an ability to talk about that because I've talked about this case as it's gone on because of my time in federal court. And I was left opining, thinking, there must be more to this.
Dane: There must be more to this story that we're not being told because the trajectory was just being, it was going in a different path than I'd ever seen. And the problem with people, humans in general, is when you're left in the dark, you draw your own conclusions, or you go to these bad places where it might not be a nefarious reason, but when you don't know, you begin to assume the worst. And I think that happened a couple of times in this case where people jumped to that conclusion. And I think that's what Mr. Friese was talking about in his argument.
Bruce: I agree completely. It's hard when the government is allowed to give consideration to other witnesses.
Bruce: And then depending on the situation, defense counsel can't even really bring that out in a way that helps the fact finder, the judge, the jury, whatever, to understand that really influences what's going on here. So from a simplistic perspective, someone might say, well, it really doesn't matter whether they were cooperators or not. If he did it, he did it, and he deserves this.
Bruce: The problem is if the process is so lopsided, then even an innocent person can be forced to plead guilty. And I have seen that happen because the weight of the government can be so oppressive. Somebody who's factually innocent or innocent of the most serious charges will plead because they know even with the best defense counsel, they're not gonna win a trial.
Ann: There was an undercurrent of politics. Attorney General Drew Wrigley was there the whole day. There was that undercurrent.
Ann: I'm not gonna say it felt like a witch hunt, but it definitely had that. And I think this is probably a rare example, actually, of where politics and criminal justice intersect, which is probably why it's so fascinating to us as well, because he was such a powerful man and a charming man. He was well-liked, is still well-liked by many of his constituents. And I'm curious to hear, was justice served on Wednesday?
Bruce: A number of years ago, I represented someone who was charged with what used to be called child pornography. We now call it child sex abuse material, CSAM. My client had never touched a child.
Bruce: He had never taken a photograph of a child. He had used his computer to download a very large number of images and videos of child sex abuse material. He didn't have so much as a speeding ticket on his record.
Bruce: And after a year and a half of litigation, my client was sentenced to 13 years in prison. Now, I abhor the very existence of child sex abuse material, and I condemn as a private citizen the possession, the transmission, and so on. But is it just that that person who never touched a child got 12 and a half years in federal prison, whereas someone who, based on what the guilty plea is, based on the evidence that was put forth, almost certainly did have sexual contact with underage children, get 10 years? That's a difficult question to answer.
Dane: And Bruce's example is exactly what Judge Hovland was talking about. He packaged it in a different way, but Judge Hovland has been on the bench for at least 20 years, I would guess more. He's a senior judge.
Dane: He's the dean of the North Dakota Federal Bench. He's widely respected on both sides of the aisle. He's methodical, he's thoughtful, he speaks very slowly and deliberately.
Dane: And I'm sure, going into the case, he had his law clerks pull every case involving CSAM or having sex with underage individuals across North Dakota that he probably had in his whole career and I can't guarantee it, but I would stake quite a bit of my reputation on this case was markedly lower than any of those. And so that has to do with the federal sentencing guidelines, which I'm sure Jennifer Poole brought up, but I think he thought justice is not done if I stand here and give this individual, Ray Holmberg, a three-year sentence, even if the guidelines tell me to, when every criminal lawyer who practices in federal court has a client, Bruce talked about, who we call it passive and active. Both are wrong, both are horrible, but passive means there are not identifiable victims in the sense of new individuals.
Dane: All of CSAM, every person is victimized each time you view it. But I think he had trouble saying that I can't be the one that say justice is done and give this man a three-year sentence when normally people are lucky to get anything close to 10 years. And on top of it, and that this is probably an unfortunate coincidence, it certainly can't be a powerful state senator, which then allows the media and other people to say, there's two systems of justice, one for the Ray Holmbergs of the world and one for the Bruce's clients of the world.
Dane: And so to judge Hovland's credit, and it's his decision, I can't say I would act the same way. And that's again, why being a judge is a very terrifying prospect for me. But I think he said to himself, I'm going to put my thumb on the scale here and I'm going to find the justice that I think bears in this case.
Dane: And to him, it was seven years more. So to many people, it seems like an enormous increase, but to those who practice, that's still a low sentence. You would tell your client at the beginning of a case if they had this kind of a crime, if we get 120 months, because we talk about months in the federal court, we don't call it 10 years. If you get 120 months, we're going to be happy, which is a whole different discussion.
Ann: Do you anticipate an appeal? And I will say it was interesting to watch the judge address Mr. Holmberg directly and spend not an insignificant amount of time telling him about the appeal process. I mean, he didn't literally encourage him to appeal, but you know, it takes five minutes, Mr. Friese can get it done really quickly. I mean, it was...
Dane: It was belt and suspenders, because there will be an appeal. Mr. Holmberg has nothing to lose to do it. He has it by right, because they went over the guidelines. And Judge Hovland is very well known to be the most active individual judge who speaks to clients at sentencing. That is a rarity.
Dane: You saw it in people who don't go to court very often, maybe think that's normal. Usually judges just listen to what everybody has to say, and then make their decision. Judge Hovland here was very interested in this case and was very hearing from Mr. Holmberg before he sentenced him. And I think that too was an indication to me that this was going to be a different outcome than what was expected.
Bruce: And I want to talk about the appeal a little bit, because a conscientious judge will do whatever they believe will protect their rulings so that they don't get overturned on appeal. And so asking those questions, getting that evidence to support the sentence that was pronounced, I think is probably part of what Judge Hovland did.
Bruce: I also think, quite frankly, the fact that he told Senator Holmberg, you had an excellent defense, you had excellent defense counsel, is his way of saying, don't you dare claim ineffective assistance of counsel because you had great lawyers.
Dane: Because there's two things that Mr. Holmberg can appeal. Under a plea agreement in federal court, normally you don't get to appeal if it stays within the guidelines. The only thing you get to appeal is that you claim that you had an ineffective lawyer. If the sentence is above the guidelines, you can appeal and say that that sentence is unfairly too long or too harsh. So there will be two avenues that Mr. Holmberg can appeal.
Dane: One, I had really crappy lawyers, which Judge Hovland sort of fixed. And two is, you gave me way more time than you should have and way more time than the guidelines say you should. That's what the appeal will be about. But it's important to know, even if he wins, it doesn't start the case over. He's not guilty anymore. It's only a resentencing.
Dane: So they've accepted their fate as to there's no way to go back and have a new trial. All that happens is he's resentenced, likely in front of a new judge, because the idea would be it would be hard for Judge Hovland to make a different decision. But this appeal will be on one thing and one thing only.
Dane: Was this too harsh?
Ann: Gentlemen, this has been fantastic. Thank you so much for helping us understand our justice process in this extraordinary sentencing hearing of former Senator Ray Holmberg.