Armstrong v. City of Milwaukee, No. 24-CV-1389-JPS (May 11, 2026)

Case details
Full caption
William Louis Armstrong, III v. City of Milwaukee
Country
United States
Jurisdiction
Federal
Decided
May 11, 2026
Disposition
Dismissed
WILLIAM LOUIS ARMSTRONG, III Plaintiff, v. CITY OF..., Slip Copy (2026) © 2026 Thomson Reuters. No claim to original U.S. Government Works.12026 WL 1283883Only the Westlaw citation is currently available.United States District Court, E.D. Wisconsin.WILLIAM LOUISARMSTRONG, III Plaintiff,v.CITY OF MILWAUKEE, CHADCRIVELLO, MILWAUKEE COUNTY,and SALAH AL-ZALLOUM, Defendants.Case No. 24-CV-1389-JPS|Filed 05/11/2026ORDERJ.P. Stadtmueller U.S. District Judge1. INTRODUCTION*1 Plaintiff William Louis Armstrong, III (“Armstrong”),proceeding pro se, sues the City of Milwaukee (the“City”), Chad Crivello (“Crivello”), Salah Al-Zalloum(“Al-Zalloum”), and Milwaukee County (the “County”)(collectively, “Defendants”) for various civil rights violations.As relevant here, in the most recent screening order, the Courtallowed Armstrong to proceed against the County under atheory of municipal liability under Monell v. Dep't of Soc.Servs. of City of N.Y., 436 U.S. 658, (1978) (hereinafter“Monell”), including a failure to train claim. ECF No. 16at 14–15. The County answered the operative complaint inSeptember 2025. ECF No. 33.Now before the Court is the County's fully-briefed motionfor judgment on the pleadings, ECF Nos. 38, 39, 42, 45, andvarious other motions. For the reasons set forth below, theCourt will grant the County's motion for judgment on thepleadings, ECF No. 38, and its motion to file a correctedreply brief, ECF No. 44. The County will be dismissed withprejudice from this action accordingly.Separately, the Court will deny Armstrong's motion fordefault judgment, ECF No. 32. Armstrong's most recentmotion, construed as a motion to stay the proceedings, ECFNo. 49, will also be denied.2. LEGAL STANDARDOnce the pleadings are closed, a party may file a motionpursuant to Federal Rule of Civil Procedure 12(c) to challengethe sufficiency of the pleadings. “Judgment on the pleadingsis appropriate when there are no disputed issues of materialfact and it is clear that the moving party ... is entitled tojudgement as a matter of law.” Unite Here Local 1 v. HyattCorp., 862 F.3d 588, 595 (7th Cir. 2017) (citing Fidelity LifeIns. Co. v. Karaganis, 811 F.2d 357, 358 (7th Cir. 1987)).A motion for judgment on the pleadings is analyzed underthe same standard as motions to dismiss brought pursuant toRule 12(b)(6). Adams v. City of Indianapolis, 742 F.3d 720,727–28 (7th Cir. 2014) (citing Pisciotta v. Old Nat'l Bancorp,499 F.3d 629, 633 (7th Cir. 2007)). To state a claim sufficientto withstand a Rule 12(b)(6) motion, the complaint mustprovide “a short and plain statement of the claim showingthat the pleader is entitled to relief.” Fed R. Civ. P. 8(a)(2).The allegations must “plausibly suggest that the plaintiff hasa right to relief, raising that possibility above a speculativelevel.” Kubiak v. City of Chicago, 810 F.3d 476, 480 (7thCir. 2016) (quoting Equal Emp't Opportunity Comm'n v.Concentra Health Servs., Inc., 496 F.3d 773, 776 (7th Cir.2007) (modifications omitted)). Plausibility requires “morethan a sheer possibility that a defendant has acted unlawfully.”Olson v. Champaign County, 784 F.3d 1093, 1099 (7th Cir.2015) (quoting Ashcroft v. Iqbal, 556 U.S. 662, 678 (2009)). Aplausible claim is one with “enough fact to raise a reasonableexpectation that discovery will reveal evidence” supportingthe plaintiff's allegations. Twombly, 550 U.S. at 556.In evaluating a motion for judgment on the pleadings, theCourt considers both the complaint and the answer(s), andas with Rule 12(b)(6) motions to dismiss, may also considermaterial subject to judicial notice. Federated Mut. Ins. Co.v. Coyle Mech. Supply, Inc., 983 F.3d 307, 312–13 (7th Cir.2020) (citing N. Ind. Gun & Outdoor Shows, Inc. v. City ofSouth Bend, 163 F.3d 449, 452 (7th Cir. 1998); Vrana v. FedExFreight, Inc., 638 F. Supp. 3d 927, 929 (C.D. Ill. 2022) (citingMohamed v. WestCare Ill., Inc., 786 F. App'x 60, 61 (7th Cir.2019)). The Court is required to “accept as true all of thewell-pleaded facts in the complaint and draw all reasonableinferences in favor of the plaintiff.” Kubiak, 810 F.3d at 480–81 (citing Tamayo v. Blagojevich, 526 F.3d 1074, 1081 (7thCir. 2008)). But the Court “need not accept as true ‘legalconclusion[s, or t]hreadbare recitals of the elements of a causeof action, supported by mere conclusory statements.’ ” Brooksv. Ross, 578 F.3d 574, 581 (7th Cir. 2009) (quoting Iqbal, 556U.S. at 678). Ultimately, dismissal is only appropriate “if it
WILLIAM LOUIS ARMSTRONG, III Plaintiff, v. CITY OF..., Slip Copy (2026) © 2026 Thomson Reuters. No claim to original U.S. Government Works.2appears beyond doubt that the plaintiff could prove no set offacts in support of his claim that would entitle him to the reliefrequested.” Enger v. Chi. Carriage Cab Corp., 812 F.3d 565,568 (7th Cir. 2016) (quoting R.J.R Servs., Inc. v. Aetna Cas.& Sur. Co., 895 F.2d 279, 281 (7th Cir. 1989)). Notably, theCourt construes pro se complaints liberally and holds them toa less stringent standard than pleadings drafted by lawyers.Cesal v. Moats, 851 F.3d 714, 720 (citing Perez v. Fenoglio,792 F.3d 768, 776 (7th Cir. 2015)).3. PLAINTIFF'S ALLEGATIONS3.1 Factual Allegations*2 In the months leading up to November 2021 when theallegedly unconstitutional government actions took place,Armstrong had been “doing outreach to members of thepublic, in a manner devised to reach a high densityof members of historically marginalized and underservedcommunities.” ECF No. 14 at 2. He sought to run for mayor,“in furtherance of a lifelong dream,” and at the same time,“to develop a public benefit company benefiting prostitutes.”Id. As part of this plan, Armstrong “intended to advertisea business with his political candidacy” centered around a“financial services application, similar to Robinhood,” whichwould “cater to commercial users.” Id. The remaining planwas to “help prostitutes establish lawful passive incomes, byoffering them opportunities to engage in lawful work withthis business, and also by having some portion of the revenuefrom this benefit them any [ ] way in a charitable capacity.” Id.Armstrong “actively intended to write such would-be formerprostitutes into the cost structure of this business, operating itas something of a public benefit corporation.” Id.On the night in question, November 10, 2021, Armstrongwas driving in the Milwaukee area when he was “flaggeddown by a woman” seeking “to be given a cigarette.” Id.at 3. Armstrong pulled over and gave her a cigarette. Id.That woman, “named Channel,1 asked to ride around with[Armstrong].” Id. In response, Armstrong stated “Now don'tdo that thinking ... you'll get no money from me,” intendingto “communicate[ ] to her that she should not expect tomake a prostitution sale.” Id. She “persisted in expressinga desire to join ... Armstrong for a drive, and ... Armstrongpermitted her to do so, and off they were.” Id. Armstrongdenies anything more than flirtation occurred during thedrive. Id. Armstrong and Channel went to Bryant's and hadone drink each, while she continued to “flirt.” Id. Theyleft Bryant's together. Id. Armstrong then went to a localgas station to “purchase condoms” because “it seemed to[Armstrong] like things might continue to progress sexuallywithout incrimination.” Id. While in the gas station, Channeldrove off with Armstrong's] car. Id.Subsequently, he walked “a mile or so” to the police station toreport the theft and spoke with Crivello, a Milwaukee PoliceDepartment officer. Id. at 4. By then, it was late evening.Id. According to Armstrong, Crivello wrongly drew theconclusion that the woman who stole his car was a prostitutebecause of his description of the circumstances, whichincluded Armstrong's description of her as a black woman.Id. During this first interaction with Crivello, Armstrong alsoclaims that, in the police report that was eventually produced,Crivello lied by saying that Armstrong and the woman “justtalked,” which, in his view, was overly “reductive” because“[Armstrong] openly skipped over the middle part” whiletalking to Crivello. Id. After the police report was submitted,Armstrong went home. Id. Once home, Armstrong wantedto ensure police investigated, so he called the police stationto make sure they had obtained camera footage. Id. Crivelloanswered. Id. Crivello reported that police had the videos, butthat they would not help. Id. Armstrong “pressed” Crivello onwhy the videos would not help, and at that point, Armstrongknew it was “sex and gender discrimination.” Id. Crivello,in response, told Armstrong “because she was a prostitute Icould arrest you.” Id. Armstrong denied that it was “a crime tomeet them.” Id. Crivello and Armstrong went back and forthdisagreeing on this point. Id. Armstrong then stated that hecould come down to the police station to “sort this out.” Id.Crivello told him, “if you come here[,] I'm going to arrestyou.” Id. Armstrong replied, “I'm on my way.” Id. He went tothe police station, having locked his phone in advance. Id.There, Crivello and Armstrong rehashed what happened, withCrivello “claiming that [Armstrong] said she was a prostitute,in such a manner where [Crivello] was representing that[Armstrong] had represented that the woman who stole hiscar was a prostitute,” even though Armstrong had not madethat representation. Id. at 5. Armstrong only said that it was“not a crime to meet them.” Id. Armstrong, in the nextparagraph, then seems to identify Channel as the prostitute inquestion, while indicating that he “had been generally doingprofessional outreach to prostitutes, but that [this] specificwoman flagged him down under express lawful pretense, anddespite initially fitting a superficial profile, seemed less likea prostitute as things progressed.” Id. at 5.*3 Armstrong, while trying to advance his narrative ofevents, wanted to clarify his prior statements, but before
WILLIAM LOUIS ARMSTRONG, III Plaintiff, v. CITY OF..., Slip Copy (2026) © 2026 Thomson Reuters. No claim to original U.S. Government Works.3he could “make that [narrative] abundantly clear,” “another[Milwaukee Police Department] officer ... Al-Zalloum buttedin and kept interrupting.” Id. 5–6. The officers reiteratedthat it was a “crime to meet” prostitutes despite Armstrong'sprotestations to the contrary. Id. at 6. Al-Zalloum asked ina “compound way” if Armstrong “knew if something wouldbe a crime,” and the officers construed his response as anacknowledgment that he had committed a crime, althoughthat was not what he intended to say. Id. In Armstrong'sview, “police framed [him] for felony crimes that [he] wasinnocent of,” causing him “substantial mental trauma andsignificant economic injuries.” Id. at 6–7. He says that thepolice report that followed falsely indicated that “he admittedfelony crimes” and, as a result, he alleges he was wronglyprosecuted thereafter. Id.3.2 Legal ClaimsWith that context, the Court turns to the specifics ofArmstrong's claims against the County. First, Armstrongalleges that the County has a policy of “failing to comply withthe due process requirements that potentially exculpatoryevidence be provided to criminal defendants.” Id. at 25.Specifically, the County “has a custom of inadequatelypreserving and providing Brady and [G]iglio materials tocriminal defendants.” Id. (citing Brady v. Maryland, 373 U.S.83 (1983) and Giglio v. United States, 405 U.S. 150 (1972)).Pursuant to this County policy, “Crivello ... issued a citation,in order to avoid obligations related to the providing ofexculpatory evidence to [Armstrong], and ... to avoid havingto preserve the related Brady and Giglio materials createdduring the incident.” Id. “Milwaukee [C]ounty [D]istrict[A]ttorney John T. Chisholm, assistant district attorneys, andothers, have been aware of Brady and Giglio evidence notbeing preserved by the Milwaukee [P]olice [D]epartmentin numerous cases, and therefore not provided to criminaldefendants who would be entitled to it.” Id. at 26.Armstrong cites to Milwaukee Police Department GeneralOrder 2021-18 (October 8, 2021) and General Order 2016-34(July 15, 2016) as possible policies that could form the basisof said violations.2 Id. at 26. Armstrong also points to certainchapters of the Milwaukee Code of Ordinances discussingunder which circumstances an officer is to conduct an arrest.Id. at 8.Finally, Armstrong alleges the County has a policy of racialand sex based “discrimination and segregation, which caused[his] injuries.” Id. at 17. He claims this is evidenced, inpart, “by sex and gender segregated bathrooms throughoutthe county, and the register of deeds practices related toracially restrictive covenants including the ratification ofthose racially restrictive covenants.” Id. It is also evidencedby, in his view, “a policy of sex and racial discriminationand segregation that they were aware of and deliberatelyindifferent to, including ... sex segregated public restroomsand racial segregation enforced through racially disparatecriminal law enforcement involving detention of primarilyblack people in ... [C]ounty facilities.” Id.Armstrong clarifies that “[d]espite the fact that the Milwaukee[P]olice [D]epartment is a city agency, under [a Monell]theory of liability being pleaded in the alterna[tive], thedriving force behind the acts injuring [him] was the [C]ountypolicy,” because Crivello and Al-Zalloum “carried out theirfunctions related to the investigation and prosecution of statecrimes in coordination with the [C]ounty.” Id. at 25.4. RULE 12 MOTION ANALYSIS*4 The County asserts that it is entitled to judgment onthe pleadings for three reasons: first, it is not a proper partyto this action; second, Armstrong fails to meet the pleadingrequirements for a Monell claim premised on a County policyor custom; and third, Armstrong's failure to train allegationfails under Monell. ECF No. 39 at 4–9. As explained below,the County's motion for judgment on the pleadings will begranted for failure to state a claim under Monell, a fatal defectwhich also plagues Armstrong's corresponding failure to trainclaim.As a preliminary matter, the County moved for leave to file acorrected reply brief. ECF No. 44. Although the Court agreeswith Armstrong's assessment that the motion was necessitatedby the inclusion of a fictitious case, ECF No. 47 at 2, the Courtdoes not have more information as to why that happened.Regardless, the County caught and corrected the error thesame day, meaning that there is no prejudice in allowing thecorrection. Further, the County's original reply brief includedreal case law in support of the proposition that the Countysought to make, meaning that the fictitious case would beredundant even if it were real. Thus, the Court will grant theCounty's motion to amend and correct the brief, ECF No. 44,and has considered the corrected brief, ECF No. 45, in theanalysis below.4.1 Armstrong Fails to Properly Plead a Monell Claim
WILLIAM LOUIS ARMSTRONG, III Plaintiff, v. CITY OF..., Slip Copy (2026) © 2026 Thomson Reuters. No claim to original U.S. Government Works.4The Court addresses the County's arguments that it is nota proper party to this action and that Armstrong fails tosufficiently plead a Monell claim premised on a County policyor custom together in this Section.In general, to state a claim for relief under 42 U.S.C. § 1983,a plaintiff must allege that someone deprived him of a rightsecured by the Constitution or the laws of the United Statesand that whoever deprived him of this right was acting underthe color of state law. D.S. v. E. Porter Cnty. Sch. Corp.,799 F.3d 793, 798 (7th Cir. 2015) (citing Buchanan–Moorev. County of Milwaukee, 570 F.3d 824, 827 (7th Cir. 2009)).A plaintiff may proceed against a municipal government ona § 1983 claim under Monell if the constitutional violationwas caused by: (1) an express government policy; (2) awidespread and persistent practice that amounted to a customapproaching the force of law; or (3) an official with finalpolicymaking authority. Glisson v. Ind. Dep't of Corrs., 849F.3d 372, 379 (7th Cir. 2017) (en banc) (citing Monell, 436U.S. at 690–91). “For a defendant to be liable under § 1983,he or she must have participated directly in the constitutionalviolation.” Hildebrandt v. Ill. Dep't of Nat. Res., 347 F.3d1014, 1039 (7th Cir. 2003). In the Monell claim context, thismeans that a complaint that “fails to allege any actions” by,or which can be attributed to, a particular municipal entityis subject to dismissal against that entity. See Wilson v. CivilTown of Clayton, 839 F.2d 375, 383 (7th Cir. 1988). There is ahigher bar to proceed past a Rule 12 motion on Monell claimsthan other claims. Braun v. Abele, 15-CV-252-JPS, 2015 WL3904960, at *5 (E.D. Wis. June 25, 2015) (“Because a Monellclaim is complex, more factual specificity is required tosustain a Monell claim.” (citing McCauley v. City of Chicago,671 F.3d 611, 615 (7th Cir. 2011))).Here, the County correctly notes that the record reflectsCrivello and Al-Zalloum are City, not County, employees.See ECF No. 24 at 1 (City's Answer is on behalf ofitself, Al-Zalloum and Crivello). Armstrong's allegations ofwrongdoing against City employees, on their own, cannotsupport Monell liability against the County. See Burks v. Tate,Case No. 20-cv-782-pp, 2023 WL 7301853, at *9 (E.D. Wis.Mar. 30, 2023) (noting that the “police department is anagency of the [C]ity”) (citing Averhart v. City of Chicago, 114F. App'x 246, 247 (7th Cir. 2004)); see also Wilson, 839 F.2dat 383 (affirming the dismissal of a Monell claim against theCounty of Hendricks where the complaint failed to allege anyacts of wrongdoing by the County of Hendricks or any of itscommissioners).*5 Armstrong suggests that the County had a policy ofinadequately preserving and providing Brady and/or Gigliomaterials and/or that Crivello declined to seek criminalcharges against him to avoid having to comply with thisCounty policy. His only allegations in support of thattheory are the two General Orders by the Milwaukee PoliceDepartment and certain provisions relating to procedures ofarrest from the Milwaukee Code of Ordinances, neither ofwhich are promulgated by the County. Accordingly, thesepolicies cannot serve as a basis for Monell liability againstthe County. See, e.g., Boardroom Entm't MKE, LLC v. City ofMilwaukee, 158 F. Supp. 3d 743 (E.D. Wis. 2016) (the CityAttorney's office defended a claim that an ordinance in theMilwaukee Code of Ordinances violated the Constitution);Ott v. City of Milwaukee, 48 F. Supp. 3d 1197, 1205, 1208–09 (E.D. Wis. 2014) (evaluating the liability of the Citybased on a General Order issued by the Milwaukee PoliceDepartment); Milwaukee County v. City of Milwaukee, 49N.W.2d 902 (Wis. 1951) (the caption itself reveals they aretwo separate and distinct entities); see also Wilson, 839 F.2d375 at 383 (demonstrating that, to sustain a Monell claim,plaintiff must show that the specific entity is liable). And,for the reasons explained in the prior paragraph, Crivello'salleged skirting of this policy cannot serve as a basis forCounty liability.Armstrong provides no factual basis to conclude that thoseMilwaukee Police Department General Orders or Ordinanceswere otherwise caused by a County official. His threadbareallegations here mirror those in Wilson, 839 F.2d 375, whichwere not well taken by the Seventh Circuit. In that case,the court noted that the plaintiff's allegations suggested “the[town] Marshals had the authority to make law enforcementpolicy for the town, [and, thus] could create official policyand the [allegedly unconstitutional] eviction could havebeen undertaken pursuant to this official policy.” Id. at 382(citation omitted). Here, Armstrong has similarly suggestedthat the County had the authority to make the allegedlyunconstitutional ordinances and orders, which Crivello andAl-Zalloum allegedly acted in accordance with in arrestinghim. However, as in Wilson, to reach the conclusion that theCounty was “in a position to establish final police policywould require wild speculation, totally unsupported by evena liberal reading of the complaint.” Id. at 382–83.Armstrong's theory that the County District AttorneyChisholm and assistant district attorneys are policy makersfor the City would require even “wild[er] speculation.” Id.Such individuals are not employed by the County. Ass'n of
WILLIAM LOUIS ARMSTRONG, III Plaintiff, v. CITY OF..., Slip Copy (2026) © 2026 Thomson Reuters. No claim to original U.S. Government Works.5State Prosecutors v. Milwaukee County, 544 N.W.2d 888, 889(Wis. 1996) (“As of January 1, 1990, all district attorneysbecame state employees.”). Even if these individuals wereCounty employees, Armstrong's allegations that Chisholmor an assistant district attorney caused or permitted Cityemployees such as Crivello or Al-Zalloum to commit Bradyor Giglio violations, see ECF No. 14 at 26, are entirelyspeculative and therefore insufficient to state a Monell claimagainst the County.As such, Armstrong's claim that the County had a custom,practice, or policy of inadequately preserving and providingBrady and Giglio materials to criminal defendants, whichsomehow caused the alleged wrongdoing by City employeesCrivello and Al-Zalloum, fails as a matter of law. See Elkinsv. Schrubbe, No. 04 C 85, 2006 WL 1663779, at *3 (E.D.Wis. June 15, 2008) (“To establish liability under § 1983,[the plaintiff] must show that a county policy, practice,or custom ... caused his constitutional deprivation” (citingCalusinksi v. Kruger, 24 F.3d 931, 936 (7th Cir. 1994))(emphasis added)).Armstrong's other attempted connection between the policeand the County is also unpersuasive. He suggests that theCity of Milwaukee Code of Ordinances also allows for theimprisonment of individuals for nonpayment of fines andthat County officials are responsible for this unconstitutionalpolicy because they run the House of Corrections and CountyJail. ECF No. 42 at 17–18. However, he has no standing toproceed against the County on this theory of Monell liability.*6 To have standing to advance any constitutional claimin federal court, a plaintiff must demonstrate “(1) that hehas suffered ‘injury in fact’; (2) that the injury is ‘fairlytraceable’ to the actions of the defendant; and (3) that theinjury will likely be redressed by a favorable decision.” MDK,Inc. v. Village of Grafton, 277 F. Supp. 2d 943, 946–47(E.D. Wis. 2003) (citing Bennett v. Spear, 520 U.S. 154, 162(1997)). Armstrong has not alleged that he was imprisonedbecause of a failure to pay a fine under the local code hecites. See generally ECF No. 14. To the extent Armstrongalleges he was “subjected to a threat of imprisonment incounty facilities” due to this ordinance, ECF No. 42 at 18,Armstrong cannot proceed because such allegations are onlyhypothetical. Spokeo, Inc. v. Robins, 578 U.S. 330, 339 (2016)(citing Lujan v. Defenders of Wildlife, 504 U.S. 555, 560(1992)). For these reasons, the Court's analysis as to thisargument is at an end.Armstrong's last argument is that Monell liability does notrequire “employment or agency by policy executors.” ECFNo. 42 at 2 (citing Monell, 436 U.S. at 694). In support, heturns to a City of Birmingham's provision, ostensibly duringthe Jim Crow era, requiring the segregation of bathrooms,even in private restaurants. Id. at 4. He also observes thatcertain Federal Rules of Civil Procedure similarly direct theparties on how to effectuate service of certain filings, eventhough the parties executing service are not employees of thefederal government. Id. at 4 (citing Fed. R. Civ. P. 5). He thenreturns to a discussion of the legislative history of § 1983,citing the following language in Monell in support: “Indeed,the fact that Congress did specifically provide that A's tortbecame B's liability if B ‘caused’ A to subject another to atort suggests that Congress did not intend § 1983 liability toattach where such causation was absent.” Id. at 3 (citing 436U.S. at 692).First, Armstrong cannot construe Monell's holding requiringcausation as suggesting that any entity or person can serve asthe casual link. Monell explained how and why municipalityliability was limited to particular circumstances. See Smithv. Milwaukee County, Case No. 22-CV-1555-PP, 2023 WL4595701, at *4 (E.D. Wis. July 18, 2023) (explainingthat, under Monell, “[§] 1983 limits liability to publicemployees who are personally responsible for a constitutionalviolation” (citing Burks v. Raemisch, 555 F.3d 592, 595–96(7th Cir. 2009))). The law on this point is clear and there is noreason to dive into the history behind the statute's enactment,as Armstrong attempts to do. See Tenn. Valley Auth. v. Hill,437 U.S. 153, 184 n.29 (1978) (“When confronted witha statute which is plain and unambiguous on its face, weordinarily do not look to legislative history as a guide to itsmeaning.” (citing Ex parte Collett, 337 U.S. 55, 61 (1949))).To the extent Armstrong invokes Jim Crow laws and theFederal Rules of Civil Procedure to provide an exampleof policies that do not require employment or agency tocause constitutional violations, the Court is not persuadedeither. Neither of these establish the standard for causation orotherwise bear on this case in any way.Ultimately, there is no County policy, custom, or practicesufficiently pled here, so Armstrong does not meet thepleading standard for a Monell claim premised on a Countypolicy or custom. Abele, 2015 WL 3904960, at *5. The Courtwill, therefore, dismiss that claim with prejudice.4.2 Armstrong Fails to Properly Plead a Failure to TrainClaim
WILLIAM LOUIS ARMSTRONG, III Plaintiff, v. CITY OF..., Slip Copy (2026) © 2026 Thomson Reuters. No claim to original U.S. Government Works.6“In limited circumstances, a local government's decisionnot to train certain employees about their legal duty toavoid violating citizens’ rights may rise to the level of anofficial government policy for purposes of § 1983.” Connickv. Thompson, 563 U.S. 51, 61 (2011). “A municipality'sculpability for a deprivation of rights is at its most tenuouswhere a claim turns on a failure to train.” Id. (citing Okla.City v. Tuttle, 471 U.S. 808, 822-23 (1985)). A claim can onlyexist where the failure “amounts to deliberate indifference tothe rights of a persons with whom [the untrained officials]come into contact.” Id. (citing City of Canton v. Harris,489 U.S. 378, 388 (1989)). As the County notes, andas explained above, Armstrong “identifies no ... Countyemployee, policymaker, or policy.” ECF No. 43 at 6. Indeed,there are no allegations to shore up this claim, nor factsevidencing a “pattern of similar constitutional violations byuntrained employees” which is “ ‘ordinarily necessary’ ” fora Monell claim under that theory. Connick, 563 U.S. at 62(quoting Bd. of Comm'rs of Bryan Cnty. v. Brown, 520 U.S.397, 410 (1997)).*7 With no allegations that would show of any violationof Armstrong's constitutional rights by the County, there canbe no liability under Monell for failure to train. Jenkins v.Bartlett, 487 F.3d 482, 492 (7th Cir. 2007) (citing Alexanderv. City of South Bend, 433 F.3d 550, 557 (7th Cir. 2006)). Assuch, Armstrong's Monell claim premised on a failure to trainmust also be dismissed with prejudice.4.3 The County's Alleged Improper DenialsIn paragraph 88 of the operative complaint, Armstrong allegesthat Defendants:did subject [him] to or caused [him] to be subjected to thedeprivation of rights secured the United States Constitutionand laws of the United States, under color of law, andin such manner as to be unlawful for both individuals aswell as municipality defendants, and by doing so did causeredressable damages to [him].ECF No. 14 at 21. In its answer, the County responds that“[t]his is a legal conclusion to which no answer is required.”ECF No. 33 at 37. Armstrong argues that this was an improperresponse because the County must either admit or deny orstate a lack of knowledge to admit or deny. ECF No. 42 at 11(citing Fed. R. Civ. P. 8(b)). Based on the Court's review of thecase law, Armstrong may have a point. Valley Forge Ins. Co. v.Hartford Iron & Metal, Inc., Case No. 1:14-cv-00006-RLM-SLC, 2017 WL 1101096, at *3 (N.D. Ind. Mar. 21, 2017)(collecting cases by district courts in the Seventh Circuit thatsuggest that such an answer is insufficient and improper);contra U.S. v. 45.43 Acres of Land Situate in Ada Cnty., CaseNo. CV 08–463–S–CWD, 2009 WL 1605127 at *7 (D. IdahoJune 4, 2009) (noting that “whether a particular statute or lawapplies to the [facts] is a question for judicial review” (citingUnited States v..95 Acres of Land, 994 F.2d 696, 699 (9th Cir.1993))).The County's use of the phrase “to the extent that” at otherpoints in its answer may also be, as Armstrong notes, ECF No.42 at 9,3 an improper qualified response under the law. See,e.g. ECF No. 33 at 46 (“This paragraph contains no factualallegation directed at Defendant requiring a response. To theextent [that] a response is required, Defendant denies theallegations.”); Keller v. Enhanced Recovery Co., LLC, CaseNo. 4:18-cv-15, 2018 WL 5650036, at *2 (N.D. Ind. Oct. 31,2018) (noting that this phrasing “is akin to an impermissiblequalified denial” (citing Valley Forge Ins. Co., 2017 WL1101096, at *2 and Trs. of Auto. Mechs. Local No. 71 Pension& Welfare Funds v. Union Bank of Cal., N.A., Case No. No. 08C 7217, 2009 WL 4668580, at *1 (N.D. Ill. Dec. 2, 2009))).However, none of these district court cases are bindingauthority on the Court. See Day v. Wooten, 947 F.3d 453,463 (7th Cir. 2020) (noting that district court opinions are“not binding precedential authority” (citing Mason-Funk v.City of Neenah, 895 F.3d 504, 509 (7th Cir. 2018))). Moreimportantly, the Court retains discretion to grant or denyArmstrong the relief he effectively seeks, be it in the formof striking the pleadings or deeming the allegations admitted.See Mulligan v. Bd. of Tr. of Ind. Univ., Case No. 1:24-cv-00096-TWP-MJD, 2024 WL 1972751, at *3 (S.D. Ind.May 3, 2024) (noting that the Court has discretion to grantor deny a motion to strike (citing McLeod v. Arrow Me.Transp., Inc., 258 F.3d 608, 617 (7th Cir. 2001))); Donnellyv. Frank Shirey Cadillac, Inc., Case No. 05 C 3520, 2005WL 2445902, at 1 (N.D. Ill. Sept. 29, 2005) (noting that “itis within the Court's discretion to find that the defendant hasnot denied the plaintiff's allegation and deem that allegationadmitted” (citing Fed. R. Civ. P. 8(d)). Even if Armstronghad brought either a motion to strike or a motion to deem theallegations admitted, the Court would not grant such a motion.*8 In this case, such relief would only serve to delay, and notexpedite these proceedings, which is entirely antithetical towhat these procedural rules seek to accomplish. See Mulligan,2024 WL 1972751, at *3 (suggesting that motions to strike aregenerally disfavored unless they “remove unnecessary clutterfrom the case” and “expedite” the proceedings (quoting
WILLIAM LOUIS ARMSTRONG, III Plaintiff, v. CITY OF..., Slip Copy (2026) © 2026 Thomson Reuters. No claim to original U.S. Government Works.7Heller Fin., Inc. v. Midwhey Powder Co., Inc., 883 F.2d1286, 1294 (7th Cir. 1989)); Fed. R. Civ. Pro. 8(e) (advisingcourts to construe as pleadings “so as to do justice”). Morepointedly, the imprecise or otherwise improper answer hereis completely resolved by the fact that the parties havealready briefed out this motion for judgment on the pleading,thereby correcting any imprecision or other defect. See N.Ind. Metals v. Iowa Exp., Inc., No. 2:07-CV-414-PRC, 2008WL 2756330, at *3 (N.D. Ind. July 10, 2008) (noting thatimprecise answers “may be made clear if contained withinthe context of an enlarged, clear, coherent response” (citingMcGrath v. Godshalk, Case No. 07 CV 34, 2007 WL2746865, at *12 (N.D. Ind. Sept. 18, 2007))). As such,the Court will not consider these allegations admitted orotherwise strike any part of the County's answer. Indeed,any allegedly improper answer would not have affected theCourt's decision here on this motion for judgment on thepleadings or otherwise changed the fact that the Court mustdismiss the County from this action based on the allegationsherein.5. OTHER MOTIONS5.1 Armstrong's Motion for Default JudgmentIn September 2025, Armstrong brought a motion for defaultjudgment. ECF No. 32. However, Armstrong failed tocomplete the first step, obtaining entry of default from theClerk of Court, rendering the motion premature. See Fed. R.Civ. P. 55(b)(1). More importantly, even if he had correctlymoved the Clerk of Court for entry of default, there wouldhave been no grounds to grant it. As the County notes,pursuant to the Memorandum of Understanding between theCourt and the County, the County has sixty days to file aresponsive pleading and, in this case, Milwaukee County fileda motion to dismiss on day fifty-eight of sixty. ECF No. 35at 1. When that motion was denied, the Court provided atimeframe for a further responsive pleading, and the Countythen filed an answer within that timeframe. Id. at 2 (citingECF No. 33). Accordingly, the County is not in default. Assuch the motion for default judgment must be denied.5.2 Armstrong's Motion to StayMore recently, Armstrong filed a motion for an extension oftime in connection with the deadlines set forth by the UnitedStates Supreme Court in another one of Armstrong's casesover which this Court presided and which is currently onappeal. ECF No. 49 (citing Armstrong v. Boyland Auto BGMCLLC, Case No. 24-CV-765 (E.D. Wis. 2024) (“BoylandDistrict Court Case”), Appeal No. 24-3182 (7th Cir. 2024)(“Boyland Appeal”). The Court dismissed that case, in part,due to Armstrong's failure to comply with the Court's orders, adecision which the Seventh Circuit affirmed. Boyland DistrictCourt Case, ECF Nos. 14, 26. Armstrong now states that theBoyland case is “currently pending in SCOTUS.” ECF No.49 at 4.Armstrong indeed filed a petition for a writ of certiorari,which is currently pending before the Supreme Court.Boyland Appeal, ECF No. 25. The Supreme Court has notmade a decision on whether to hear his case at this juncture.See generally Boyland District Court Case and Appeal.However, other than suggesting that Boyland is “pertinent”to this case and that the Court “may be familiar with the[S]eventh [C]ircuit mandate from Boyland,” Armstrong hasmade no showing that the Boyland bears in any way on thiscase, or that he will likely prevail on the merits before theSupreme Court. ECF No. 49 at 4. Such a showing must bemade to justify imposing a stay. Woods v. Dimensions LivingCudahy, LLC, Case No. 25-CV-378-JPS, 2026 WL 194680,at *1–2 (citing Grice Eng'g, Inc. v. JG Innovations, Inc.,691 F. Supp. 2d 915, 920 (W.D. Wis. 2010)). Accordingly,the argument is waived. Schaefer v. Universal Scaffolding& Equip., LLC, 839 F.3d 599, 607 (7th Cir. 2016) (notingthat perfunctory arguments are waived (citing United States v.Hook, 471 F.3d 766, 775 (7th Cir. 2006))). Plaintiff's motionfor a stay, ECF No. 49, will be denied.*9 In addition to the fact the motion has no merit, it alsodid not comply with the Court's Comprehensive Protocolsand Procedures Order, ECF No. 26 at 11, despite Armstrong'sassertion to the contrary. ECF No. 50 (citing ECF No. 26).It is apparent from Armstrong's own words that he did nothear back from counsel prior to filing the submission. Id.at 2. Although perhaps a few business days passed withouta response, the motion itself does not have the urgencyArmstrong claims, as no deadlines are forthcoming in thiscase, so Armstrong could and should have waited untilhearing back from opposing counsel before filing his motion.The Court admonishes Armstrong that further filings ofmotions that do not comply with the Court's orders may resultin dismissal of his case without further warning.6. CONCLUSIONArmstrong fails to state any claim under Monell againstthe County, and the County is entitled to judgment on thepleadings and will be dismissed with prejudice from thisaction. His motion for default judgment will be denied.
WILLIAM LOUIS ARMSTRONG, III Plaintiff, v. CITY OF..., Slip Copy (2026) © 2026 Thomson Reuters. No claim to original U.S. Government Works.8Similarly, the motion to stay the proceedings is likewisewithout merit and will be denied. As for the remainingDefendants, namely the City, Crivello, and Al-Zalloum, theCourt will order them to file a joint Rule 26(f) report withintwo weeks from the date of this Order. At that time, theCourt will enter a scheduling order so that this litigation maycontinue its course.Accordingly,IT IS ORDERED that Plaintiff William Louis Armstrong,III's motion for default judgment, ECF No. 32, be and thesame is hereby DENIED;IT IS FURTHER ORDERED that Defendant MilwaukeeCounty's motion for judgment on the pleadings, ECF No. 38,be and the same is hereby GRANTED;IT IS FURTHER ORDERED that Defendant MilwaukeeCounty's motion to amend or correct the reply brief, ECF No.44, be and the same is hereby GRANTED;IT IS FURTHER ORDERED that Defendant MilwaukeeCounty be and the same is hereby DISMISSED withprejudice from this action;IT IS FURTHER ORDERED that Plaintiff William LouisArmstrong, III's motion to extend time in connection with thedeadlines set by the Supreme Court of the United States, ECFNo. 49, be and the same is hereby DENIED; andIT IS FURTHER ORDERED that Plaintiff William LouisArmstrong, III and Defendants City of Milwaukee, ChadCrivello, and Salah Al-Zalloum file a joint Rule 26(f) reportwithin two weeks from the date of this Order.Dated at Milwaukee, Wisconsin, this 11th day of May, 2026.All CitationsSlip Copy, 2026 WL 1283883Footnotes1At later points, he also refers to her as Chanel and Chanelle. For consistency, the Court will simply use Channel.2Armstrong does not clarify what those orders allegedly involved or provide a copy. No judicially noticeable copy appearedonline during the Court's research. Ultimately, it does not matter what they contained for purposes of this decisionbecause, as described in more detail below, these orders were not promulgated by the County, and therefore, have norelevance here.3Armstrong also suggests that the County's answer to the first paragraph—“Defendant denies that Plaintiff is entitled tothe relief he seeks”—is improper. ECF No. 42 at 13 (citing ECF No. 33 at 2). But the Court can find no case law insupport of that proposition. To the contrary, the Court finds this language to constitute an unequivocal denial consistentwith Federal Rule of Civil Procedure 8(b).End of Document© 2026 Thomson Reuters. No claim to original U.S.Government Works.
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