2023 WI APP 29

COURT OF APPEALS OF WISCONSIN

PUBLISHED OPINION

Case No.: 2021AP1339-CR

Complete Title of Case: 

†Petition for Review Filed

STATE OF WISCONSIN,

PLAINTIFF-RESPONDENT,

V.

TRACY LAVER HAILES,

DEFENDANT-APPELLANT.

Opinion Filed: May 9, 2023

Submitted on Briefs: April 13, 2022

Oral Argument: 

JUDGES: Brash, C.J., Dugan and White, JJ.

Concurred:

Dissented:

Appellant

ATTORNEYS: On behalf of the defendant-appellant, the cause was submitted on the 

briefs of Christopher P. August of the Office of the State Public 

Defender in Milwaukee. 

Respondent

ATTORNEYS: On behalf of the plaintiff-respondent, the cause was submitted on the 

brief of Joshua L. Kaul and Kara L. Janson of the Wisconsin 

Department of Justice in Madison. 
2

2023 WI App 29

COURT OF APPEALS

DECISION

DATED AND FILED

May 9, 2023

Sheila T. Reiff

Clerk of Court of Appeals

NOTICE

This opinion is subject to further editing. If 

published, the official version will appear in 

the bound volume of the Official Reports. 

A party may file with the Supreme Court a 

petition to review an adverse decision by the 

Court of Appeals. See WIS. STAT. § 808.10 and 

RULE 809.62. 

Appeal No. 2021AP1339-CR Cir. Ct. No. 2015CF4326

STATE OF WISCONSIN IN COURT OF APPEALS

STATE OF WISCONSIN,

PLAINTIFF-RESPONDENT,

V.

TRACY LAVER HAILES,

DEFENDANT-APPELLANT.

APPEAL from a judgment and orders of the circuit court for 

Milwaukee County: JANET C. PROTASIEWICZ and MICHAEL J. 

HANRAHAN, Judges. Affirmed. 

Before Brash, C.J., Dugan and White, JJ. 
No. 2021AP1339-CR

3

¶1 DUGAN, J. Tracy Laver Hailes appeals his judgment of conviction 

and two orders of the circuit court denying his motions for postconviction relief.1 

On appeal, Hailes argues that the circuit court erroneously denied his motion to 

suppress evidence of drug activity at two apartments located at 618 North 30th 

Street (30th Street). He also argues that two penalty enhancers—one for repeat 

offenders and the other for second or subsequent offenders, found in WIS. STAT.

§ 939.62 (2021-22),2and WIS. STAT. § 961.48—were erroneously applied to the 

drug offense charges in his case—he was charged with and pled guilty to the drug 

charges with both of the enhancers. Hailes further argues that he is entitled to plea 

withdrawal, sentence modification, or resentencing based on the fact that he was 

erroneously charged with and pled guilty to the drug charges with both of the penalty 

enhancers. 

¶2 We conclude that the circuit court properly denied Hailes’ motion to 

suppress because the affidavits attached to the search warrants established probable 

cause to search the two apartments located at 30th Street. We further conclude that 

the two penalty enhancers were erroneously applied to Hailes because the plain 

meaning of WIS. STAT. § 973.01(2)(c) states that either WIS. STAT. § 939.62 “or” 

WIS. STAT. § 961.48 can apply to his drug charges—but not both. However, we 

nevertheless reject Hailes’ argument that he is entitled to plea withdrawal, sentence 

modification, and resentencing on the basis that these two penalty enhancers were 

applied to him. Hailes fails to demonstrate that the penalty enhancers in any way 

 

1

 The Honorable Janet C. Protasiewicz presided over Hailes’ plea and sentencing and 

entered the judgment of conviction and order denying Hailes’ first motion for postconviction relief. 

The Honorable Michael J. Hanrahan entered the order denying Hailes’ supplemental motion for 

postconviction relief.

2

 All references to the Wisconsin Statutes are to the 2021-22 version unless otherwise 

noted.
No. 2021AP1339-CR

4

induced him to plead guilty, such that he is entitled to plea withdrawal, and he fails 

to demonstrate that the penalty enhancers played any role at the sentencing hearing, 

such that he is entitled to sentence modification or resentencing. Accordingly, we 

affirm.

BACKGROUND

¶3 In a criminal complaint filed on September 25, 2015, the State charged 

Hailes with nine counts related to drug operations that Hailes ran out of two 

apartments located at 30th Street. The charges arose from the execution of three 

search warrants issued for three apartments connected to Hailes. One of the 

apartments was located at 520 North 29th Street (29th Street) and the other two 

apartments were located at 30th Street. The nine charges issued by the State resulted 

from evidence recovered from the two apartments—apartment 102 and apartment 

208—located at 30th Street. As to apartment 102, Hailes was charged with 

(1) possession of a firearm by a felon, (2) possession with intent to deliver heroin, 

(3) possession with intent to deliver cocaine, (4) possession with intent to deliver 

THC, and (5) keeping a drug house. As to apartment 208, Hailes was charged with 

(1) possession of a firearm by a felon, (2) possession with intent to deliver THC, 

(3) possession with intent to deliver cocaine, and (4) keeping a drug house. All the 

charges carried the penalty enhancer for a repeat offender, see WIS. STAT.

§ 939.62(1), and all charges, with the exception of the two charges of possession of 

a firearm by a felon, carried the penalty enhancer for a second or subsequent offense, 

see WIS. STAT. § 961.48(1).

¶4 Hailes filed a motion to suppress the evidence recovered at the two 

apartments located at 30th Street on the basis that the search warrants failed to 

establish probable cause of illegal activity at either of the apartments. Rather, Hailes 
No. 2021AP1339-CR

5

contended that the affidavits attached to the search warrants only established 

probable cause of illegal activity at the apartment located at 29th Street, and there 

was no nexus with the activity at 29th Street such that the activity there constituted 

probable cause to search the apartments at 30th Street.

¶5 The circuit court denied Hailes’ motion.3 At the hearing on the 

motion, the circuit court stated that the affidavits provided statements by a 

confidential informant describing that he saw Hailes at the apartment on 29th Street 

with “substantial amounts of cocaine and heroin and some marijuana and a couple 

guns” on two separate occasions. The circuit court further noted that the 

confidential informant observed Hailes moving furniture into the apartment 

building located on 30th Street. The circuit court also stated that the affidavits 

described an independent investigation done by the police in which the police 

observed Hailes’ vehicles parked at the 30th Street address and a statement by an 

officer that, based on his training and experience, he knows that drug dealers have 

the tools of their trade located at their homes. Thus, the circuit court found, “in 

tying all that together,” the warrants were sufficient. 

¶6 Hailes subsequently entered a plea to five of the original charges, with 

the remaining four charges dismissed and read in for sentencing purposes. In all, 

Hailes pled guilty to two counts of possession of a firearm by a felon, as a repeater;4

one count of possession with intent to deliver heroin, as a repeater and as a second 

 

3

 The Honorable Timothy Witkowiak denied Hailes’ motion to suppress.

4

 See WIS. STAT. §§ 941.29(2)(a), 939.50(3)(g), 939.62(1)(b).
No. 2021AP1339-CR

6

or subsequent offense;5and two counts of possession with intent to deliver cocaine, 

as a repeater and as a second or subsequent offense.6 He was then sentenced on all 

charges to twenty-three years of imprisonment, composed of fourteen years of initial 

confinement and nine years of extended supervision.

¶7 Hailes filed his first motion for postconviction relief, in which he 

argued that he was entitled to plea withdrawal on the grounds that the repeat 

offender and the second or subsequent offense penalty enhancers were erroneously 

applied to him. See WIS. STAT. §§ 939.62(1) (repeat offender), 961.48(1) (second 

or subsequent offense). He argued that pursuant to WIS. STAT. § 973.01(2)(c), either 

penalty enhancer could apply to his drug charges, but not both. He alternatively 

requested sentence modification or resentencing based on the erroneous application 

of both penalty enhancers to his case. Relying on State v. Maxey, 2003 WI App 94, 

264 Wis. 2d 878, 663 N.W.2d 811, the circuit court denied his motion and found 

that both penalty enhancers were properly applied to his case. As a result, the circuit 

court did not reach Hailes’ remaining arguments for plea withdrawal, sentence 

modification, or resentencing.

¶8 Hailes subsequently filed a supplemental postconviction motion. He 

again argued for plea withdrawal based on an erroneous application of both penalty 

enhancers to his case. However, in his supplemental postconviction motion, he 

raised the additional arguments that he was entitled to plea withdrawal based on the 

legal impossibility of both penalty enhancers applying to his drug charges and the 

illusory benefit provided by his plea deal. The circuit court again denied Hailes’ 

 

5

 See WIS. STAT. §§ 961.41(1m)(d)3., 939.50(3)(d), 939.62(1)(c), 961.48(1)(a).

6

 Count three involved more than ten grams but not more than fifty grams. See WIS. STAT.

§§ 961.41(1m)(cm)4., 939.50(3)(c), 939.62(1)(c), 961.48(1)(a). Count eight involved one gram or 

less. See WIS. STAT. §§ 961.41(1m)(cm)1g., 939.50(3)(g), 939.62(1)(b), 961.48(1)(b). 
No. 2021AP1339-CR

7

motion and found that both penalty enhancers were properly applied to his drug 

charges.

¶9 Hailes now appeals. Additional relevant facts will be set forth below 

as necessary.

DISCUSSION

¶10 On appeal, Hailes raises two main arguments. First, Hailes argues 

that the circuit court erroneously denied his motion to suppress the evidence 

recovered from the two apartments located at 30th Street. Second, Hailes argues 

that the two penalty enhancers found in WIS. STAT. § 939.62(1) and WIS. STAT.

§ 961.48(1) were erroneously applied to him, and as result, he is entitled to plea 

withdrawal. In the alternative, he argues that he is entitled to sentence modification 

or resentencing. We address each argument in turn.

I. Motion to Suppress

¶11 Hailes first argues that the circuit court erroneously denied his motion 

to suppress because there was no probable cause to search the apartments located at 

30th Street. In particular, Hailes argues that the affidavits attached to the search 

warrants did not establish probable cause of illegal activity at the two apartments at 

the 30th Street address. He contends that there was no nexus between his drugrelated activity observed by the confidential informant at the apartment at 29th 

Street and his conduct at the two apartments at 30th Street, and therefore, there was 
No. 2021AP1339-CR

8

no probable cause to believe that evidence of criminal activity would have been 

found at 30th Street.7

¶12 We review a circuit court’s denial of a motion to suppress evidence 

using a two-step standard. State v. Lonkoski, 2013 WI 30, ¶21, 346 Wis. 2d 523, 

828 N.W.2d 552. We will uphold the circuit court’s findings of fact unless they are 

clearly erroneous, and we review independently the application of the facts to the 

constitutional principles. Id. 

¶13 Hailes contends that the circuit court erroneously denied his motion 

to suppress because the affidavits attached to the search warrants failed to establish 

probable cause. “Search warrants may issue only upon ‘a finding of probable cause 

by a neutral and detached magistrate.’” State v. Ward, 2000 WI 3, ¶21, 231 Wis. 2d 

723, 604 N.W.2d 517 (citation omitted). “[W]e accord great deference to the 

determination made by the warrant-issuing magistrate,” and the defendant bears the 

burden to show “that the facts are clearly insufficient to support a probable cause 

finding.” Id.

¶14 Probable cause is “a practical, common-sense decision whether, given 

all the circumstances set forth in the affidavit” that “there is a fair probability that 

contraband or evidence of a crime will be found in a particular place.” State v. 

Higginbotham, 162 Wis. 2d 978, 990, 471 N.W.2d 24 (1991) (citation omitted). 

“[A] probable cause determination must be based upon what a reasonable magistrate 

can infer from the information presented by the police.” Ward, 231 Wis. 2d 723, 

 

7

 Hailes concedes that there was probable cause to search the apartment at 29th Street, and 

he only takes issue with the probable cause to search the two apartments located at 30th Street, 

which he contends was based solely on his activities witnessed at the 29th Street apartment. Thus, 

we accept his concession that there was probable cause to search the apartment at 29th Street.
No. 2021AP1339-CR

9

¶26. “The test is not whether the inference drawn is the only reasonable inference. 

The test is whether the inference drawn is a reasonable one.” Id., ¶30. 

¶15 In this case, we conclude that there was a reasonable inference that 

evidence of drug-related activity would be found at the two apartments located at 

30th Street, given all the circumstances set forth in the affidavits attached to the 

search warrants. Here, we turn first to the substance of the attached affidavits in 

more detail. As both parties recognize, the affidavits attached to the search warrants 

in this case are nearly identical, with each affidavit containing information provided 

by an officer, a confidential informant, and Hailes’ probation agent.

¶16 In those affidavits, the officer described his experience conducting 

drug trafficking investigations and his participation in the execution of search 

warrants related to those investigations. Based on this experience, he described that 

he has personally recovered controlled substances, drug paraphernalia, firearms, and 

ammunition “located in elaborately hidden compartments within homes” of drug 

traffickers and that drug traffickers “commonly” have firearms and ammunition 

“either in their residences and/or in other locations where they exercise control and 

domination.” The officer further described that, based on his experience, drug 

traffickers keep records and other evidence of their drug trafficking activities in their 

residences. 

¶17 The officer then provided that he received the following information 

from a confidential informant about Hailes’ activities: Hailes trafficked cocaine, 

heroin, and marijuana at an apartment located at 29th Street during the day, Hailes 

kept the drugs in a red shoebox on top of the refrigerator at that address, Hailes was 

on probation and had to wear a GPS monitoring bracelet, and that Hailes stayed at 

an apartment located at 30th Street during his monitoring hours. Hailes had two 
No. 2021AP1339-CR

10

vehicles—a black Infiniti and a white Chevrolet—which the informant had seen 

Hailes driving and had seen them at both the 29th Street and the 30th Street 

addresses. The informant additionally observed Hailes with a firearm when driving 

the black Infiniti. The officer further described the police investigation confirming 

Hailes’ connection to these two vehicles based on observation of the 30th Street 

location and records of traffic stops in which Hailes was driving one of the two 

vehicles. 

¶18 The officer also obtained the following information from Hailes’ 

probation agent and the confidential informant: Hailes was reportedly living in 

apartment 307 at 30th Street, but stated that he would be moving to apartment 102 

at 30th Street. However, Hailes was also seen moving furniture into apartment 208 

at 30th Street. Additionally, during an unscheduled visit by the probation agent, the 

agent saw various extension cords and telephone wires were running from apartment 

307 to apartment 208. The officer further stated that, in his training and experience, 

an individual on probation who is still involved in drug trafficking activities will 

maintain multiple residences in order to avoid detection, a subsequent investigation 

revealed that Hailes was paying the utilities at apartment 208, and the presence of 

cords running from apartment 307 to apartment 208 was an attempt to defeat the 

electronic monitoring equipment Hailes was required to wear as a condition of his 

probation. 

¶19 The probation agent also told the officer that, when the probation 

agent arrived for unscheduled visits, the agent was greeted at the locked front door 

of the apartment building by a resident, the resident then located the apartment 

manager, and then the apartment manager unlocked the door for the probation agent 

and accompanied the probation agent to Hailes’ location within the apartment 

building. The probation agent further stated that he had observed what he believed 
No. 2021AP1339-CR

11

to be lookouts at the apartment building and that these individuals appeared to be 

monitoring the premises by walking the perimeter of the property and sitting at the 

front door. 

¶20 Finally, the affidavit referenced Hailes’ criminal record, which dates 

back to 2004 and contains multiple felony convictions and arrests for drug-related 

activity. He had convictions for drug violations in 2011, 2012, and 2013, and eleven 

arrests for drug violations from 2004 to 2013.

¶21 Despite the information provided in the affidavits, Hailes nevertheless 

argues that the affidavits attached to the search warrants here were insufficient under 

State v. Sloan, 2007 WI App 146, 303 Wis. 2d 438, 736 N.W.2d 189, and fail to 

establish probable cause. We disagree.

¶22 In Sloan, we addressed the sufficiency of an affidavit for the search 

of a residence after the defendant there attempted to mail a package containing 

marijuana through UPS. Id., ¶¶2, 28. The residence that was searched was listed 

as the return address on the package containing the marijuana. Id., ¶¶2, 6. The 

defendant’s address in Wisconsin Department of Transportation records matched 

the return address, and according to WE Energies records, the defendant also paid 

the utilities at that same address. Id., ¶5. However, the residence was owned by a 

Leslee Ericksen (formerly Leslee Sloan), the defendant also had a Florida driver’s 

license with a different address, and the defendant further told the UPS employee 

that he was shipping the package to himself in Florida. Id., ¶¶2, 5.

¶23 Under the facts presented in Sloan, this court concluded that the 

affidavit failed to establish probable cause to search the residence at the return 

address on the package because the affiant “never tells the reader that he believes 

Sloan is, or has recently been, engaged in any criminal activity at the residence to 
No. 2021AP1339-CR

12

be searched, or why he believes that is the case.” Id., ¶31. Importantly, we noted 

several facts that were missing from the affidavit that could have supported a finding 

of probable cause, including surveillance of the residence that “suggests criminal 

activity might be afoot.” Id., ¶32. We emphasized that there was no report about 

drug-related or other suspicious activity at the residence, no claim of prior police 

reports of drug-related activity at the residence, and no claim that the defendant had 

prior involvement with drug activity. Id.

¶24 While the affidavits here may share some similarities to the affidavits 

in Sloan, a thorough reading of Sloan shows that it is inapplicable here. As clearly 

set forth in the affidavits to search the apartments at 30th Street, Hailes’ probation 

agent observed what he believed to be suspicious activity at the two apartments, 

including the presence of lookouts monitoring the premises and extension cords 

running between the two apartments in a potential attempt to defeat the monitoring 

equipment used for Hailes’ probation. Hailes also reported that he was moving to 

apartment 102, but he was instead seen moving furniture into apartment 208. Thus, 

many of the facts “suggest[ing] criminal activity might be afoot” and noted as 

missing in Sloan, 303 Wis. 2d 438, ¶32, are present in this case. Moreover, while 

there may be innocent explanations for some of these activities, as Hailes 

acknowledges, “[t]he test is not whether the inference drawn is the only reasonable 

inference,” but rather “whether the inference drawn is a reasonable one.” See Ward, 

231 Wis. 2d 723, ¶30. Further, unlike the facts in Sloan where we stated that there 

was no claim that the defendant had prior involvement with drug activity, here, the 

record shows that Hailes had a long history of drug convictions and arrests dating 

back to 2004. Accordingly, we conclude that Sloan does not support Hailes’ 

argument that the affidavits in this case are insufficient to sustain a finding of 

probable cause.
No. 2021AP1339-CR

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¶25 Additionally, while the confidential informant may have only seen 

Hailes with drugs at the 29th Street apartment, the apartments at 30th Street were 

nonetheless clearly linked to Hailes, given that he was seen driving from one address 

to the other and his probation agent regularly visited him at the 30th Street address. 

The probation agent also observed suspicious activity at the 30th Street address, and 

the officer clearly stated in the affidavit that, based on his experience, individuals 

involved in drug trafficking activities keep records or other items related to those 

activities at their residences. We conclude that taken together, the affidavits 

establish probable cause.

¶26 Consequently, we conclude that the affidavits attached to the search 

warrants establish probable cause to search the two apartments located at 30th 

Street, and the circuit court properly denied Hailes’ motion to suppress.8

II. Penalty Enhancers

¶27 Hailes next argues that the two penalty enhancers found in WIS. STAT.

§ 939.62(1) and WIS. STAT. § 961.48(1) were erroneously applied to him. 

Specifically, Hailes argues that the plain language of WIS. STAT. § 973.01(2)(c) 

provides that either the penalty enhancer found in § 939.62(1) “or” the penalty 

enhancer found in § 961.48(1) applies—but not both. He then argues that he is 

entitled to plea withdrawal because both of the penalty enhancers were applied to 

his drug charges in violation of § 973.01(2)(c). In the alternative, he argues that he 

is entitled to sentence modification or resentencing.

 

8

 Hailes additionally argues that the good faith exception does not save the unlawful search 

in this case. As a result of our conclusion, we do not address his argument. See State v. Blalock, 

150 Wis. 2d 688, 703, 442 N.W.2d 514 (Ct. App. 1989) (“[C]ases should be decided on the 

narrowest possible ground.”).
No. 2021AP1339-CR

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A. Interpretation of WIS. STAT. § 973.01(2)(c)

¶28 We first address Hailes’ argument that both penalty enhancers cannot 

be applied to him under WIS. STAT. § 973.01(2)(c), the statute that governs the order 

in which penalty enhancers are applied when more than one applies to a case. This 

presents an issue of statutory interpretation. “[S]tatutory interpretation ‘begins with 

the language of the statute. If the meaning of the statute is plain, we ordinarily stop 

the inquiry.’” State ex rel. Kalal v. Circuit Ct. for Dane Cnty., 2004 WI 58, ¶45, 

271 Wis. 2d 633, 681 N.W.2d 110 (citation omitted). We give statutory language 

“its common, ordinary, and accepted meaning, except that technical or speciallydefined words or phrases are given their technical or special definitional meaning.” 

Id. “[T]he purpose of statutory interpretation is to determine what the statute means 

so that it may be given its full, proper, and intended effect.” Id., ¶44. We review 

issues of statutory interpretation independently. See State v. Arberry, 2018 WI 7, 

¶14, 379 Wis. 2d 254, 905 N.W.2d 832.

¶29 Turning to the text of the statute, WIS. STAT. § 973.01(2)(c) provides:

1. Subject to the minimum period of extended supervision 

required under par. (d), the maximum term of confinement 

in prison specified in par. (b) may be increased by any 

applicable penalty enhancement statute. If the maximum 

term of confinement in prison specified in par. (b) is 

increased under this paragraph, the total length of the 

bifurcated sentence that may be imposed is increased by the 

same amount.

2. If more than one of the following penalty enhancement 

statutes apply to a crime, the court shall apply them in the 

order listed in calculating the maximum term of 

imprisonment for that crime:

a. Sections 939.621, 939.623, 939.632, 939.635, 

939.645, 946.42(4), 961.442, 961.46, and 961.49.

b. Section 939.63.
No. 2021AP1339-CR

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c. Section 939.62(1) or 961.48.

¶30 In his argument, Hailes highlights the use of the word “or” in 

subparagraph c. and contrasts the use of “or” in subparagraph c. with the use of the 

word “and” in subparagraph a. He argues that the use of the word “or” indicates 

that only one of the penalty enhancers found in WIS. STAT. § 939.62(1) and WIS.

STAT. § 961.48 can apply, but not both. 

¶31 We agree. “When the legislature chooses to use two different words, 

we generally consider each separately and presume that different words have 

different meanings.” See Pawlowski v. American Fam. Mut. Ins. Co., 2009 WI 

105, ¶22, 322 Wis. 2d 21, 777 N.W.2d 67. “The use of different words joined by 

the disjunctive connector ‘or’ normally broadens the coverage of the statute to reach 

distinct, although potentially overlapping sets.” See id. (emphasis added). Thus, 

we conclude that the plain language of the statute clearly indicates that either 

§ 939.62(1) “or” § 961.48 can apply to enhance a penalty, but not both. 

¶32 By contrast, the State argues that Maxey, 264 Wis. 2d 878, controls. 

In Maxey, we addressed whether the penalty enhancers found in WIS. STAT.

§ 939.62(1) and WIS. STAT. § 961.48 could both be applied to a defendant at the 

same time, and we concluded that both could apply. Maxey, 264 Wis. 2d 878, ¶23. 

There, however, we interpreted the two statutes without the benefit of WIS. STAT.

§ 973.01(2)(c). Since our decision in Maxey, § 973.01(2)(c) went into effect. See

2001 Wis. Act 109, § 1129 (creating § 973.01(2)(c)); Maxey, 264 Wis. 2d 878, ¶1 

(interpreting the 1999-2000 version of the Wisconsin Statutes). Consequently, we 

conclude that our prior conclusion in Maxey is inapplicable here, and our conclusion 

today is instead controlled by the plain language of § 973.01(2)(c), which plainly 
No. 2021AP1339-CR

16

instructs that § 939.62(1) “or” § 961.48 may be applied by the circuit court in 

calculating the maximum term of imprisonment, but not both.

¶33 Having concluded that both penalty enhancers cannot apply at the 

same time, we turn next to whether Hailes is entitled to any of the relief he seeks 

based on the application of both penalty enhancers to his drug charges in this case.

B. Plea Withdrawal

¶34 Hailes first argues that he is entitled to plea withdrawal on the basis 

of the erroneous application of both penalty enhancers to his drug charges. He 

makes this argument both on the grounds that his plea was not knowing, intelligent, 

and voluntary and that he received ineffective assistance of counsel. We address 

each argument for plea withdrawal in turn.

¶35 “A defendant is entitled to withdraw a guilty plea after sentencing 

only upon a showing of ‘manifest injustice’ by clear and convincing evidence.” 

State v. Bentley, 201 Wis. 2d 303, 311, 548 N.W.2d 50 (1996) (citation omitted). 

A defendant may demonstrate a manifest injustice in several ways. State v. Dillard, 

2014 WI 123, ¶37, 358 Wis. 2d 543, 859 N.W.2d 44. “One way is to show that the

defendant did not enter the plea knowingly, intelligently, and voluntarily.” Id. 

“When a guilty plea is not knowing, intelligent, and voluntary, a defendant is 

entitled to withdraw the plea as a matter of right because such a plea ‘violates 

fundamental due process.’” State v. Brown, 2006 WI 100, ¶19, 293 Wis. 2d 594, 

716 N.W.2d 906 (citation omitted). “Whether a defendant’s plea was entered 

knowingly, intelligently, and voluntarily is a question of constitutional fact.” 

Dillard, 358 Wis. 2d 543, ¶38. We uphold the circuit court’s findings of historical 

facts unless they are clearly erroneous, and we independently determine whether 
No. 2021AP1339-CR

17

those facts demonstrate that the defendant’s plea was knowing, intelligent, and 

voluntary. Id.

¶36 Hailes argues that his plea was “uninformed and its voluntariness 

compromised” because he was provided “affirmative misinformation” about the 

applicability of both penalty enhancers to his drug charges. The State argues that 

although Hailes claims that misinformation about the law “requires plea 

withdrawal,” that is not what our supreme court has held. Citing Dillard, 358 

Wis. 2d 543, ¶39, the State asserts that “affirmative misinformation about the law 

... can support a holding that” plea withdrawal is warranted, but not in all cases. In 

his reply brief, Hailes states that he does not dispute, and never claimed, that any 

inaccuracy, no matter its materiality, “torpedoes” any otherwise knowing, 

intelligent, and voluntary plea. We agree that not every misinformation about the 

law entitles a defendant to withdraw his or her plea. Thus, the issue here is whether 

the misinformation about the applicability of both of the enhancers entitles Hailes 

to withdraw his pleas in this case.

¶37 Although Hailes states that he does not dispute and never claimed that 

any inaccuracy, no matter its materiality, “torpedoes” any otherwise knowing, 

intelligent, and voluntary plea, he argues that the cases that he cites stand for that 

very proposition:

Numerous cases have held that affirmative misinformation 

about the law given to the defendant requires plea 

withdrawal because the plea is uninformed and its 

voluntariness compromised. See, e.g., State v. Riekkoff, 112 

Wis. 2d 119, 332 N.W.2d 744 (1983) (holding that when the 

defendant pled guilty, incorrectly believing that he could 

seek appellate review of an evidentiary order, he 

misunderstood the effects of his plea and the plea was 

therefore involuntary); [State v. Dawson, 2004 WI App 173, 

276 Wis. 2d 418, 688 N.W.2d 12] (holding that the legally 

unenforceable reopen-and-amend provision of the 

defendant’s plea deal rendered the plea involuntary); State v. 
No. 2021AP1339-CR

18

Woods, 173 Wis. 2d 129, 496 N.W.2d 144 (Ct. App. 1992) 

(holding that a guilty plea entered at least in part based on 

inaccurate legal information about sentencing was neither 

knowing or voluntary); State v. Brown, 2004 WI App 179, 

276 Wis. 2d 559, 687 N.W.2d 543 (holding that when the 

State promised to drop, but did not drop, all charges 

requiring the defendant to register as a sex offender or 

subjecting the defendant to a Chapter 980 civil confinement, 

the defendant’s plea was involuntary).

Hailes further argues that:

Significantly, case law does not require that the 

decision to plead be based exclusively on the misinformation 

the defendant received. [Dillard, 358 Wis. 2d 543, ¶60.] 

Rather, a guilty or no-contest plea is not voluntary unless the 

defendant is “fully aware of the direct consequences [of his 

plea], including the actual value of any commitments made 

to him by the court, prosecutor, or his own counsel...” Id.

¶38 However, as noted above, and acknowledged by Hailes, a defendant 

is not entitled to withdraw a guilty plea whenever he or she is provided 

misinformation about the law. Rather, courts address the issue under the totality of 

the circumstances. See Dillard, 358 Wis. 2d 543, ¶34 (“We first address whether, 

under the totality of the circumstances, the defendant has the right as a matter of law 

to withdraw his no-contest plea on the ground that it was not entered knowingly, 

intelligently, and voluntarily.”). We conclude that the cases discussed below 

demonstrate that the totality of the circumstances includes whether the 

misinformation provided to Hailes in part induced his decision to enter his plea.

¶39 In the cases cited by Hailes in support of his argument, those courts 

concluded that the defendant, in part, entered his or her plea based on the 

misinformation. In State v. Woods, 173 Wis. 2d at 140, the court stated, “The record 

is clear that Woods, at least in part, made the decision to plead guilty based on 
No. 2021AP1339-CR

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inaccurate information provided to him by the lawyers and judge.”9 In State v. 

Riekkoff, 112 Wis. 2d at 120-21, Riekkoff pled guilty pursuant to a plea agreement 

that had preserved his right to appeal the circuit court’s denial of his motion to admit 

evidence that he sought to introduce at trial.10 Our supreme court stated, “One thing, 

however, clearly stands out from the record, and that is that Riekkoff pleaded guilty 

believing that he was entitled to an appellate review of the reserved issue.” Id. at 

128.

¶40 Hailes also cites to State v. Brown, 276 Wis. 2d 559, to support his 

argument. However, in Brown, this court concluded that “Brown’s plea agreement 

was purposefully crafted to only include pleas to charges that would not require him 

to register as a sex offender or be subject to post-incarceration commitment under 

WIS. STAT. ch. 980.” Id., ¶13. Clearly, Brown entered his plea primarily because 

the court, the prosecutor, and his counsel told him that he could plead no contest to 

the felony charges and not be subject to sex offender registration or postincarceration commitment, but as a matter of law, he could not. Hailes further cites 

to State v. Dawson, 276 Wis. 2d 418, to support his argument. However, in 

Dawson, this court allowed Dawson to withdraw his plea because he “relied on ... 

a possibility that did not, in fact, exist” when deciding to enter a plea. Id., ¶10.

 

9

 The inaccurate information in Woods was that an adult court could impose an adult 

sentence consecutive to a juvenile court disposition. State v. Woods, 173 Wis. 2d 129, 132-33, 496 

N.W.2d 144 (Ct. App. 1992).

10

 Riekkoff had sought to introduce the opinion testimony of a psychiatrist that, because 

of his intoxication, he lacked the mental capacity to form the requisite intent for the charge of 

burglary. State v. Riekkoff, 112 Wis. 2d 119, 121, 332 N.W.2d 744 (1983). When he appealed the 

circuit court’s denial of his motion, this court refused to review the circuit court’s exclusion of the 

psychiatric testimony. Id. at 122.
No. 2021AP1339-CR

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¶41 Lastly, Hailes argues that Dillard, 358 Wis. 2d 543, supports his 

argument.11 However, in Dillard, our supreme court concluded that “‘the 

fundamental error of law [about the applicability of the persistent repeater enhancer 

to the defendant] that pervaded the plea negotiations and sentencing’ rendered the 

defendant’s plea unknowing, unintelligent, and involuntary.” Id., ¶35 (emphasis 

added). The court further noted that “the State acknowledges that trial counsel also 

identified the dropped persistent repeater enhancer as ‘the most significant factor’ 

contributing to [Dillard’s] decision to enter a plea of no contest.” Id., ¶54. Thus, 

the court concluded that Dillard presented a persuasive account of “why, absent the 

misinformation he received about the persistent repeater enhancer, he would not 

have entered a no-contest plea, why he would have gone to trial, and why the nocontest plea was not knowing, intelligent, and voluntary.” Id., ¶52.

¶42 In contrast to the cases above that Hailes cited, we conclude that 

Hailes has failed to establish that the penalty enhancers in any way induced his plea, 

such that Hailes can now claim that his plea was not knowing, intelligent, and 

voluntary. Rather, the record here demonstrates that Hailes was induced to enter a 

plea as a result of the circuit court’s denial of his motion to suppress and the strength 

of the State’s case, instead of induced by any “affirmative misinformation” provided 

to him about the penalty enhancers. 

¶43 After the circuit court denied Hailes’ motion to suppress, the court 

asked, “[H]ow would you like the matter calendared?” After taking a moment to 

 

11

 The court phrased the issue as “whether, under the totality of the circumstances, the

defendant has the right as a matter of law to withdraw his no-contest plea on the ground that it was 

not entered knowingly, intelligently, and voluntarily.” State v. Dillard, 2014 WI 123, ¶3, 358 

Wis. 2d 543, 859 N.W.2d 44. The inaccurate information involved in the case was that the State, 

the circuit court, and Dillard’s trial counsel mistakenly advised him that he was facing a mandatory 

sentence of life in prison without the possibility of extended supervision for his charge. Id.
No. 2021AP1339-CR

21

talk with Hailes, trial counsel requested to have the matter set for plea and 

sentencing and indicated that he would like to obtain details of the State’s offer. 

¶44 Then, at a subsequent hearing, the circuit court confirmed the State’s 

final offer, and Hailes’ knowledge of that offer. At that time, Hailes stated that he 

was rejecting the State’s offer. The court then turned to setting the matter for trial, 

and asked the State how many days it would need. The State described its evidence 

as follows:

There are really two different scenes at issue here, two 

apartments that the defendant was alleged to be in control of. 

The defendant also made a very complete statement that the 

State will probably be playing in most of its entirety. There’s 

obviously the crime lab testimony. There’s fingerprint 

testimony. I think that it’s more than a three-day trial likely. 

Hailes then interrupted saying, “I’d like to address something to the court.” After 

Hailes spoke with trial counsel, trial counsel relayed, “I think what he’s saying is he 

does want to resolve it.” The State then agreed to reopen its offer and continue 

discussions, and the circuit court set the matter over for another hearing. Hailes 

then said, “I will appreciate if we can resolve this matter before a trial issue. ... I 

would love to take the—take a plea offer and plead guilty, but I’m just not willing 

to accept the offer that the State is offering at this point.” Hailes continued, “But I 

would—I would recommend that I would plead guilty, and I don’t know if—if I 

don’t accept the State’s offer, do I have to—am I forced to go to trial if I doesn’t—

if I don’t accept the State’s offer?” 

¶45 Accordingly, the record shows that Hailes was not in any way 

motivated by the application of the penalty enhancers when he decided to plead 

guilty. Rather, Hailes was motivated to plead guilty first, by the denial of his motion 

to suppress and second, by the evidence the State described it would present at his 
No. 2021AP1339-CR

22

trial. Thus, we conclude that Hailes is not entitled to plea withdrawal on the grounds 

that his plea was not knowing, intelligent, and voluntary as a result of any 

“affirmative misinformation” about the application of the two penalty enhancers to 

his drug charges. See Dawson, 276 Wis. 2d 418, ¶10 (allowing plea withdrawal 

when the defendant “relied on ... a possibility that did not, in fact, exist” when 

deciding to enter a plea (emphasis added)). We conclude that Hailes has not 

presented a persuasive account of why, absent the misinformation he received about 

the two penalty enhancers, he would not have entered guilty pleas, and why he 

would have gone to trial.

¶46 As previously stated, Hailes also seeks plea withdrawal on the 

grounds that he received ineffective assistance of counsel. Another way “to 

demonstrate manifest injustice [for plea withdrawal] is to establish that the 

defendant received ineffective assistance of counsel.” Dillard, 358 Wis. 2d 543, 

¶84. A defendant must show two elements to establish that his or her counsel’s 

assistance was constitutionally ineffective: (1) counsel’s performance was 

deficient; and (2) the deficient performance resulted in prejudice to the defense. 

State v. Balliette, 2011 WI 79, ¶21, 336 Wis. 2d 358, 805 N.W.2d 334. In the 

context of an argument for plea withdrawal, the prejudice prong “focuses on 

whether counsel’s constitutionally ineffective performance affected the outcome of 

the plea process.” Hill v. Lockhart, 474 U.S. 52, 59 (1985). “[T]o satisfy the 

‘prejudice’ requirement, the defendant must show that there is a reasonable 

probability that, but for counsel’s errors, he would not have pleaded guilty and 

would have insisted on going to trial.” Id.

¶47 “An ineffective assistance of counsel claim presents a mixed question 

of fact and law.” State v. Pico, 2018 WI 66, ¶13, 382 Wis. 2d 273, 914 N.W.2d 95. 

“We will not reverse the circuit court’s findings of fact unless they are clearly 
No. 2021AP1339-CR

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erroneous.” Id. “We independently review, as a matter of law, whether those facts 

demonstrate ineffective assistance of counsel.” Id.

¶48 In addressing Hailes’ claim of plea withdrawal based on ineffective 

assistance of counsel, we conclude that trial counsel’s performance was not 

deficient, nor was Hailes prejudiced by any presumed deficient performance. 

¶49 As to trial counsel’s performance, we do not consider trial counsel’s 

performance deficient for any failure to raise a novel legal issue. See State v. 

Lemberger, 2017 WI 39, ¶18, 374 Wis. 2d 617, 893 N.W.2d 232. At the time of 

the proceedings in this case, under the holding in Maxey, which had not been 

reversed, both penalty enhancers could apply to Hailes’ case, and there was no case 

law interpreting WIS. STAT. § 973.01(2)(c), as we have done in this decision.12 The 

application of both penalty enhancers to Hailes was, therefore, a novel issue, and 

we do not consider trial counsel’s performance deficient for failing to raise this 

issue. 

¶50 As to prejudice, the record clearly demonstrates, as discussed 

previously, that Hailes was motivated to plead guilty, not by anything related to the 

penalty enhancers, but by the circuit court’s denial of his motion to suppress and the 

strength of the State’s case. Moreover, in his postconviction motion and on appeal 

Hailes does not allege, let alone show, why, absent the misinformation he received 

about the two penalty enhancers, he would not have entered guilty pleas, and why 

he would have gone to trial. 

 

12

 We also note the fact that the circuit court relied on the holding in State v. Maxey, 2003 

WI App 94, 264 Wis. 2d 878, 663 N.W.2d 811, when it denied Hailes’ motion and found that both 

penalty enhancers were properly charged in this case, supports our conclusion that the issue was 

novel at the time Hailes entered his pleas.
No. 2021AP1339-CR

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¶51 Under the original charges and assuming the application of only one 

penalty enhancer, Hailes faced a maximum period of imprisonment of 151 years 

and 6 months for the nine original charges. See WIS. STAT. §§ 939.50(3)(c), (d), 

(g), (h), (i), 939.62(1)(b)-(c) (2013-14). Under the plea agreement, four charges 

were dismissed outright, and the maximum period of imprisonment, still assuming 

the application of only one penalty enhancer, was reduced by a period of 32 years 

and 6 months to a total of 119 years for the charges to which Hailes pled guilty. See

WIS. STAT. §§ 939.50(3)(c), (d), (g), 939.62(1)(b)-(c) (2013-14). Applying both 

penalty enhancers to the charges to which Hailes pled guilty, Hailes faced a 

maximum term of imprisonment of 135 years, which amounts to a difference of 16 

years. See WIS. STAT. §§ 939.50(3)(c), (d), (g), 939.62(1)(b)-(c), 961.48(1)(a), (b) 

(2013-14). Given the possible maximum terms of imprisonment Hailes faced, 

Hailes fails to explain why he would not have accepted the State’s offer and instead 

proceeded to trial, if he knew that both penalty enhancers could not apply to his 

case.

¶52 Hailes has, therefore, also failed to demonstrate “that there is a 

reasonable probability that, but for counsel’s errors, he would not have pleaded 

guilty and would have insisted on going to trial.” See Lockhart, 474 U.S. at 59. 

¶53 Consequently, we reject Hailes’ argument for plea withdrawal based 

on his argument that he received ineffective assistance of counsel, and we conclude 

that Hailes is not entitled to plea withdrawal for this reason. 

C. Sentence Modification

¶54 Hailes alternatively argues that he is entitled to sentence modification 

based on the existence of a new factor. However, we conclude that Hailes fails to 

state a claim for sentence modification.
No. 2021AP1339-CR

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¶55 “Whether a fact or set of facts presented by the defendant constitutes 

a ‘new factor’ is a question of law,” which we review independently. State v. 

Harbor, 2011 WI 28, ¶33, 333 Wis. 2d 53, 797 N.W.2d 828. However, “whether 

that new factor justifies sentence modification is committed to the discretion of the 

circuit court, and we review such decisions for erroneous exercise of discretion.” 

Id.

¶56 A new factor is defined as: 

a fact or set of facts highly relevant to the imposition of 

sentence, but not known to the trial judge at the time of 

original sentencing, either because it was not then in 

existence or because, even though it was then in existence, it 

was unknowingly overlooked by all of the parties.

Id., ¶40 (citation omitted). “The defendant has the burden to demonstrate by clear 

and convincing evidence the existence of a new factor.” Id., ¶36.

¶57 In short, we conclude that Hailes fails to demonstrate that the fact that 

he pled guilty to the drug charges with both penalty enhancers was “highly relevant 

to the imposition of sentence.” See id., ¶40. Hailes points to nothing in the 

sentencing transcript to indicate that dismissal of one of the two penalty enhancers 

would have been highly relevant to the circuit court’s sentence, despite bearing the 

burden of demonstrating “by clear and convincing evidence” that a new factor 

exists. See id., ¶36 (emphasis added). Indeed, as evident from the sentencing 

hearing, the circuit court’s primary concern was the protection of the public from 

Hailes’ “very high-end dealing.” At the sentencing hearing, the circuit court stated, 

“So when we talk about the seriousness of the offense, sir, it doesn’t get more 

serious than the type of behavior that you were engaging in and the need to protect 

the community.” Moreover, the circuit court never mentioned the application of 

either penalty enhancer at the time of sentencing, and importantly, the sentence 
No. 2021AP1339-CR

26

imposed did not even include an enhanced term of imprisonment.13 Consequently, 

we conclude that Hailes is not entitled to sentence modification. 

D. Resentencing

¶58 Hailes additionally makes the alternative argument that he is entitled 

to resentencing. In this regard, Hailes argues that he was sentenced using inaccurate 

information when the circuit court sentenced him using both penalty enhancers. We 

conclude that Hailes has failed to present a claim for resentencing based on 

inaccurate information.

¶59 “A defendant has a constitutionally protected due process right to be 

sentenced upon accurate information.” State v. Tiepelman, 2006 WI 66, ¶9, 291 

Wis. 2d 179, 717 N.W.2d 1. We independently review a defendant’s claim that he 

has been sentenced on inaccurate information. Id.

¶60 “A defendant who requests resentencing due to the circuit court’s use 

of inaccurate information at the sentencing hearing ‘must show both that the 

information was inaccurate and that the court actually relied on the inaccurate 

information at sentencing.’” Id., ¶26 (citation omitted). Actual reliance generally 

requires that the sentencing court give “explicit attention” or “specific 

consideration” to the inaccurate information and that the inaccurate information 

 

13

 As previously noted, Hailes was sentenced to twenty-three years of imprisonment, 

composed of fourteen years of initial confinement and nine years of extended supervision. Hailes 

faced a maximum term of imprisonment of ninety-five years on the charges to which he pled guilty, 

without the penalty enhancers. See WIS. STAT. §§ 941.29(2)(a), 961.41(1m)(d)3., 

961.41(1m)(cm)4., 961.41(1m)(cm)1g., 939.50(3)(c), (d), (g) (2013-14). As it applies to initial 

confinement alone, Hailes faced a maximum term of initial confinement of fifty-five years, without 

the penalty enhancers. See WIS. STAT. § 973.01(2)(b)3., 4., 7. (2013-14).
No. 2021AP1339-CR

27

“formed part of the basis for the sentence.” State v. Travis, 2013 WI 38, ¶28, 347 

Wis. 2d 142, 832 N.W.2d 491 (citation omitted).

¶61 As noted, in this case, Hailes fails to point to anything in the record 

indicating that the circuit court actually relied on the penalty enhancers at the time 

of sentencing. See id., ¶32 (discussing actual reliance and describing at least four 

references by the circuit court to the inaccurate penalty at the time of sentencing). 

As stated above, the circuit court never mentioned the penalty enhancers at the time 

of sentencing, and a review of the sentencing hearing indicates that the circuit court 

was focused on protecting the community at the time of sentencing. Moreover, the 

sentence that the circuit court imposed did not include an enhanced term of 

imprisonment. As previously noted, Hailes was sentenced to twenty-three years of 

imprisonment, composed of fourteen years of initial confinement and nine years of 

extended supervision. At sentencing, he faced a maximum term of imprisonment 

of ninety-five years on the charges to which he pled guilty, without any of the 

penalty enhancers. As it applies to initial confinement alone, Hailes faced a 

maximum term of initial confinement of fifty-five years, without any of the penalty 

enhancers. The fact that the circuit court sentenced him to only fourteen years of 

initial confinement shows that the court did not actually rely on the penalty 

enhancers at the time of sentencing and further shows that the court would have 

imposed the same sentence absent the error regarding the penalty enhancers. 

Accordingly, we conclude that Hailes’ claim for resentencing fails.14

 

14

 As a result of our conclusion, we do not address Hailes’ argument that his trial counsel 

was ineffective for failing to object the penalty enhancers at the time of sentencing or the State’s 

argument regarding forfeiture. See Blalock, 150 Wis. 2d at 703 (“[C]ases should be decided on the 

narrowest possible ground.”).
No. 2021AP1339-CR

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CONCLUSION

¶62 Overall, we conclude that Hailes is not entitled to the relief he seeks, 

and we affirm. We conclude that the circuit court properly denied Hailes’ motion 

to suppress. In this regard, we conclude that the affidavits attached to the search 

warrants established probable cause to search the two apartments located at 30th 

Street. We also conclude that, under the plain language of WIS. STAT.

§ 973.01(2)(c), only one of the penalty enhancers found in WIS. STAT. § 939.62(1) 

and WIS. STAT. § 961.48 can be applied to a defendant at a time. However, we 

nevertheless conclude that Hailes is not entitled to plea withdrawal, sentence 

modification, or resentencing in his case. Accordingly, we affirm.

By the Court.—Judgment and orders affirmed.