Two blog posts in one week! What’s the occasion, you ask? Recall that there were two criminal defense wins in the Court of Appeals out of Barron County. In yesterday’s post, I discussed State v. Sprague, in which the defendant finally won the right to actually hold the prosecutor to their agreement to recommend 5 years of initial confinement at his sentencing. Unfortunately, this victory was announced over five years after Mr. Sprague was sentenced. NOT IDEAL, GUYS.

Some may consider Mr. Sprague’s victory to be a Pyrrhic one even in the absence of the delay. After all, Mr. Sprague is still convicted, and after he’s resentenced his conviction will still be the same. The folks who think that are probably the same folks who ask defense attorneys about their win-loss records. Sometimes a favorable outcome at sentencing is a great victory, and can be even better than a trial win. Perhaps you’ll be surprised to hear me admit this, but some defendants are guilty, and sometimes the State actually has the evidence to prove it. But for the reader who thinks only a complete acquittal counts as a defense victory, I present to you State v. Kelsy Wooldridge (2022-AP-1927).

Officer Prinsen pulled over Ms. Wooldridge’s vehicle, and she consented to a search of her vehicle. (DON’T DO THIS.) Officer Prinsen found a syringe that “had a bloody substance inside the tube and on the point of the needle” inside her purse, at which point

Prinsen then walked over to Wooldridge, showed her the syringe, and told her that he found it in her purse, after which she nodded. At no point did Wooldridge suggest that the syringe belonged to someone else or that she had a medical reason to possess it. Prinsen then asked Wooldridge if she had used methamphetamine, and she “acknowledged that she did,” with the most recent time being “[a]pproximately one week prior.” Prinsen did not ask Wooldridge if she had recently used the syringe, if she knew what was inside of it, or if she had put the syringe in her purse. After speaking with Wooldridge, Prinsen seized the syringe as evidence.

Ms. Wooldridge was charged with possession of methamphetamine, and was convicted at trial. To understand what makes this case interesting requires an explanation of what the prosecution must actually prove at a jury trial for this type of offense, and the Court of Appeals provides as good an explanation as any:

The circuit court instructed the jury on the elements of possession of methamphetamine, including that the State was required to prove: (1) Wooldridge possessed and had actual physical control of the substance; (2) the substance was methamphetamine; and (3) Wooldridge knew or believed that the substance was methamphetamine. The court also instructed the jury that it “cannot look into a person’s mind to determine knowledge or belief. Knowledge or belief must be found, if found at all, from the defendant’s acts, words, and statements, if any, and from all the facts and circumstances in this case bearing upon knowledge or belief.” See WIS JI—CRIMINAL 6030 (2024). The court further instructed that, in weighing the evidence, jurors “may take into account matters of your common knowledge and your observations and experience in the affairs of life”; that the jury’s duty was “to scrutinize and to weigh the testimony of the witnesses and to determine the effect of the evidence as a whole”; and that the jury was “the sole judge[] of the credibility” or “believability of the witnesses and of the weight to be given to their testimony.” See WIS JI—CRIMINAL 195 (2000); WIS JI—CRIMINAL 300 (2023).

Read about enough cases and you’ll see all three of these elements challenged in different trials. Sometimes the issue at trial is whether the defendant actually possessed the thing. Sometimes the issue is whether the thing is actually the drug alleged, or even a drug at all. And sometimes the issue is whether the defendant knew that the thing they possessed was the drug.

The defense brief lays out rather well why the evidence at trial wasn’t enough to prove beyond a reasonable doubt that Ms. Wooldridge knew that she possessed methamphetamine. The plunger on the syringe was already pushed all the way down. All the officer could see inside it was a red residue, and no liquid. The analyst from the Wisconsin State Crime Lab testified that the residue could not be identified by sight, and that methamphetamine isn’t red. Instead, the analyst had to perform several chemical tests to identify the presence of methamphetamine, and couldn’t determine the actual amount present.

That is, how could Ms. Wooldridge possibly know that there was methamphetamine in the syringe? Ms. Wooldridge consented to the vehicle search, and she even answered questions after Officer Prinsen found the syringe, acknowledging her methamphetamine use. But she was very lucky that Officer Prinsen apparently never actually asked her whether she had used that syringe, let alone knew that it had ever contained methamphetamine. If Officer Prinsen had been more thorough in his on-scene questioning, or if Ms. Wooldridge had visible fresh track marks on her arm, the circumstantial evidence may have been sufficient.

Reversals of jury convictions are very rare. The entire criminal justice system is built on the idea that the jury is the best entity to make determinations of fact based on the evidence presented at trial, and so jury verdicts are given great deference. If a jury finds a defendant not guilty, the State cannot appeal that verdict. And if a jury finds a defendant guilty, a defendant challenging that verdict must convince the reviewing court that, even considering the evidence in the light most favorable to the State, “no trier of fact, acting reasonably, could have found guilty beyond a reasonable doubt.” In other words, the Court of Appeals doesn’t consider whether the jury got it wrong; the Court of Appeals considers whether the jury couldn’t possibly have gotten it right. And in most criminal cases, there will usually be enough evidence somewhere in the record for a court to determine that, if you look at this testimony from this angle, and if you believed this testimony and not this testimony, then that would be sufficient to find the defendant guilty.

What a wonderful win for Ms. Wooldridge, right? Nothing Pyrrhic here, right? HAHAHA, YOU FOOL! HAVE YOU LEARNED NOTHING?

This case was filed against Ms. Wooldridge on March 9, 2021. The trial took started on the morning of May 5, 2022, and the guilty verdict came early enough in the afternoon for the court to have enough time to sentence her to a year of probation before the courthouse closed at 5:00 PM. The final appeal brief was submitted on April 26, 2023, eleven months into her twelve months of probation. But at least she never had to go to jail, right? HAHAHA, YOU FOOL! HAVE YOU LEARNED NOTHING?

Ms. Wooldridge’s probation was revoked in March 2023, and on April 18, 2023, she was sentenced to four months jail with work release, with 103 days credit for the time she had already spent in custody, presumably during the probation revocation proceedings. This one is hard to blame on the Court of Appeals, since Ms. Wooldridge was almost certainly back out of custody. And it’s difficult to fault the attorneys working on the appeal, which progressed at a relatively quick pace. I’d be more inclined to blame the circuit court if it had sentenced her to jail on the day of her trial, but it placed her on probation instead. I suppose the circuit court could have stayed that probation, but then she still would have been out on bail during the conduct that resulted in her revocation.

Frustrating, eh? Welcome to my life. Let me know what you think in the comments!

My CaseLaw Express workflow hasn’t changed in probably fifteen years. When I get the weekly email, I save the criminal, mental health, parental rights, and any other interesting-looking cases to my Pocket account. (That workflow became less optimal when the links in the weekly email switched from web versions of the decisions to PDF versions. Obviously the links still saved, but the content became invisible to Pocket.) So the news that Mozilla is shutting down Pocket is very disappointing. I’m not sure what I’m going to do, although, just like my Instapaper account filled with news articles, it’s not as if I was going to actually cut into my backlog any time soon.

This post isn’t about any of that. It’s about two Court of Appeals decisions released on May 20, 2025, that I found surprisingly interesting and want to write about. As On Point noted, both are criminal defense wins out of Barron County. Every criminal defense win is notable, especially on appeal, and two out of the same small county in the same week would be notable by itself.

This post isn’t about that. It’s about the two cases. The first is State v. Donaven C. Sprague (2022-AP-876). In the case,

Pursuant to a plea agreement, Sprague agreed to plead guilty to the single charge. In exchange, the State agreed to cap its sentencing recommendation at 10-years’ imprisonment, consisting of 5 years of initial confinement followed by 5 years of extended supervision. Sprague’s trial counsel remained free to argue as to a sentencing recommendation.

But then at sentencing,

Placing emphasis on the seriousness of the offense and protection of the public factors, the State concluded its sentencing argument by noting the PSI’s recommended sentence and then stating that “given the aggravated nature of this case and the position of trust that Mr. Sprague was in, he falls on the upper end of that, of the 16 years confinement with four years extended supervision, and that’s the recommendation that I think is appropriate for him under the circumstances.”

This is what the criminal defense bar refers to as “such bullshit,” and observers may wonder how the fuck this could ever happen. I always tell my clients that my goal is to be the most prepared person in the courtroom and the most familiar with the case. Sometimes that goal is easier to achieve than it should be. The prosecutor in the courtroom for a given hearing isn’t always the main prosecutor handling the case, and even if it is that doesn’t guarantee that the prosecutor is actually familiar with their file, or even the content of their own plea agreement. Last month during a sentencing hearing I had a prosecutor who negotiated our plea agreement whisper to me asking what the agreement was while the case was being called.

When Mr. Sprague’s attorney corrected the prosecutor about the plea agreement, the prosecutor replied, “Yeah, that was. That is correct. I would stand with the recommendation of ten years, five years in, five years out,” and when the judge confirmed the terms of the agreement, the prosecutor replied, “Yes, it is. That was in my letter. My apologies.”

The judge called a recess to allow Mr. Sprague and his defense attorney to discuss

whether Sprague wanted to withdraw his plea “or some other option in between,” whether the State’s comments “were so out of bounds” that Sprague could not get a fair sentencing, and whether Sprague felt comfortable continuing with the sentencing in light of the State’s correction of its error.

Mr. Sprague decided to proceed with sentencing, asking for 3 years of initial confinement and 7 years of extended supervision. Instead the judge gave him 10 and 5. Note that in Wisconsin the judge always has the discretion to impose up to the maximum sentence for the offenses to which the defendant is convicted. The parties’ recommendations for the sentence are not binding. The upshot of this is that there are effectively two things that a defendant and the prosecutor can negotiate: the charges to which a defendant will plead guilty and the sentence that the prosecutor will recommend. While some counties in Wisconsin may have a strong tradition of negotiating joint recommendations that judges are expected to approve without much risk, under the law the only method the parties have of limiting the court’s sentencing discretion is in choosing the specific charges for which the defendant is being convicted, and the court even has some limited, though rarely exercised, discretion to reject plea agreements that the court believes to be contrary to public policy.

Anyway,

On appeal, Sprague argues that his trial counsel was ineffective by failing to advise Sprague that the State had inadequately cured its material and substantial breach of the parties’ plea agreement and by failing to advise Sprague that he was entitled to resentencing before a different judge.

And the Court of Appeals agreed! The State first tried to argue that the prosecutor’s eventual acknowledgement of the correct recommendation and apology were sufficient to cure the breach of the plea agreement. The case law on how robust a prosecutor’s advocacy for a negotiated sentence recommendation must be is not great, but the Court of Appeals decided that this discrepancy was too great and the prosecutor’s “cure” too little.

The State’s correction of its initial confinement recommendation from 16 years to 5 years and its subsequent apology as to the mistake were insufficient to remedy the “taint” on the sentencing hearing created by the State’s sentencing argument implying that Sprague deserved 16 years of initial confinement rather than 5 years—a raw reduction of 11 years, equating to a near 70 percent reduction. This change was significant, and it required explanation and argument by the State to clarify the basis for the 9 difference between the two recommendations.

Mr. Sprague testified at a post-conviction hearing (we call them Machner hearings in Wisconsin) that his attorney didn’t tell him during the mid-sentencing recess that he had the option of requesting a new sentencing hearing in front of a judge who hadn’t just heard the prosecutor make a pitch for 16 years of initial confinement. And his attorney from the sentencing hearing didn’t testify that he did. I often disagree with the State’s appellate arguments, obviously, but I’m affirmatively disappointed with one of the State’s arguments in this one:

The State argues that Sprague was not prejudiced by counsel’s failure to advise him that he was entitled to resentencing before a different judge because Sprague “had already considered switching judges and declined. Had he been asked again, he would have provided the same answer.” Among counsel’s errors alleged by Sprague in his postconviction motion, one related to counsel’s advice on judicial substitution at the beginning of Sprague’s case. Relying on the circuit court’s conclusion that Sprague chose to forgo substitution at the beginning of his case, the State appears to contend that Sprague’s decision on that issue means he would not have chosen to seek resentencing before a different judge as a remedy for the State’s material and substantial breach of the plea agreement.

When I was reading the State’s brief to the Court of Appeals, I was initially confused about why the State was arguing that Mr. Sprague did, in fact, discuss whether to ask for a different judge, since the defense’s brief was very clear that he did not. It turns out that the State was trying to argue that because Mr. Sprague and his attorney had decided at the very beginning of the case not to ask for a different judge, this meant that he would not have done so if his attorney had told him he had the option during his sentencing hearing. Shame on the State.

That Sprague chose to forgo substitution at the start of his criminal case is irrelevant to determining whether Sprague would have taken advantage of his entitlement to resentencing before a different judge. Sprague made his decision on judicial substitution long before the State materially and substantially breached the plea agreement and long before the circuit court judge heard the State’s tainted sentencing argument. Therefore, Sprague’s original decision on judicial substitution has no effect on the prejudice inquiry.

I wish the Court of Appeals had been a bit more forceful with its rejection of this argument, but beggers can’t be choosers. Unless the Wisconsin Attorney General asks the State Supreme Court to review the decision, Mr. Sprague will receive a new sentencing hearing in front of a judge who will only hear the negotiated sentence recommendation from the prosecutor this time.

This post isn’t actually about any of that, though. It’s about the fact that Mr. Sprague’s sentencing hearing took place on December 12, 2019. Ignoring any sentence credit he may have already accumulated before that date, Mr. Sprague has been serving a prison sentence in prison for the last five and a half years. Remember that the prosecutor had agreed to recommend five years of initial confinement. Mr. Sprague has already served more prison time than that, and it’s not as if he’s being resentenced next week.

This isn’t entirely the Court of Appeals’ fault. It turns out Mr. Sprague’s first appellate attorney filed a no-merit report; in other words, they couldn’t find any issue to raise and wanted permission from the court to withdraw from the appeal. Luckily, that attorney ended up going on parental leave and Mr. Sprague’s next attorney withdrew that report. Appeals take time, of course, especially when there needs to be testimony taken on these issues, and COVID happened during all of that in this case, but the briefs and transcripts and everything else in the record was submitted to the Court of Appeals on December 19, 2023. A decision from the Court of Appeals shortly thereafter would have preserved an opportunity for Mr. Sprague to be receive the sentence that the prosecutor had agreed to recommend. Instead, the seventeen-month wait for the decision means that Mr. Sprague has lost that opportunity. Come on, judges!

This post is much longer than I’d anticipated, so I’ll save my discussion of the second Barron County case for another day, but hopefully quicker than seventeen months.