It may be that Drake’s lawyer could have done a better job of looking into and advising him about the possibility his Huber privileges would be revoked, but that doesn’t mean counsel was ineffective. Thus, Drake doesn’t get to withdraw his pleas.
Drake agreed to plead to theft and DC charges if he would get Huber privileges. The judge did grant Huber privileges on his 8-month sentence, but they were revoked shortly thereafter at the jail’s request. The jail explained Drake had been in administrative confinement since his arrest due to his mental health and to his history of behavioral issues, and jail staff hadn’t been able to move him to a less-restrictive setting; in the event he was moved and his behavior remained “stable and appropriate” for 120 days, he would be eligible for Huber release. (¶¶2-3).
Drake claimed that trial counsel was deficient because she didn’t inform Drake that the judge has discretion to grant Huber privileges, that not all inmates get the privileges, and that they could be revoked. The evidence at the Machner hearing refuted these claims. (¶¶8-10).
He also argued counsel should have investigated the likelihood that Drake’s status in administrative confinement made it likely the jail would deem him ineligible and ask for the privileges to be revoked. (¶8). The court agrees that “[i]n retrospect, in light of the importance that Drake placed on his ability to work and attend school while serving his sentence, the prudent course of action might have been to advise Drake that his Huber privileges were subject to revocation.” (¶12). But even if counsel was deficient, Drake hasn’t shown prejudice—namely, that had his lawyer advised him of the likelihood of revocation of his privileges, he would not have pleaded guilty but insisted on going to trial, State v. Bentley, 201 Wis. 2d 303, 312, 548 N.W.2d 50 (1996):
¶15 Drake’s testimony [at the Machner hearing] was not that he would have insisted on going to trial, rather it was that he would have waited for a “better plea deal” before pleading. Furthermore, Drake did not provide the circuit court below with any evidence that a “better plea deal” from the State was likely to be forthcoming and he has not given this court any reason to believe that it was. Drake also testified that he “could have waited a week,” at which point he would have been eligible for Huber privileges. Drake’s testimony suggests that he would have waited a week to enter his plea, at which point he believed that he would have been eligible for Huber privileges, not that he would have insisted that his case be tried. Because Drake failed to show that he would have insisted on going to trial, I conclude that Drake has not shown that he was prejudiced. ….