Rakeem Harris v. City of Bloomington, Illinois

filed frivolous objections and motions to reconsider seeking that relief. The court advised Harris that his submissions violated Rule 11(b) of the Federal Rules of Civil Procedure and warned him that he risked dismissal of his lawsuit if he continued to submit frivolous papers. After Harris filed another frivolous and malicious motion for monetary sanctions against opposing counsel for overlooking a discovery deadline, the court dismissed Harris's case. We affirm the judgment.

Following his arrest, Harris filed a 37-count, 300-page complaint naming as defendants the City of Bloomington, the Bloomington Police Department, and five officers involved in his arrest and subsequent prosecution. The district court denied his motion to proceed in forma pauperis based on apparent false representations regarding his indigency. After the court denied reconsideration, he prepaid the filing fee in full and unsuccessfully moved for reconsideration again. Harris soon returned executed summons, and on the same day filed a motion for entry of default. A magistrate judge noted that the police department was not a suable entity and found that Harris had not properly served the other defendants, so the judge denied the motion for default and granted Harris an extension to effectuate proper service. Harris twice sought reconsideration of that decision, and the magistrate judge denied each motion. Meanwhile, Harris served the defendants, who moved for an extension of the deadline to file a responsive pleading on the day it was due. The magistrate judge granted the motion the next day. Soon after, Harris asked the court for the third time to enter default and objected to the magistrate judge's decision to give more time. The defendants then filed a combined answer and motion to dismiss, which the district court struck as defective, giving them additional time to file them as separate documents. Yet again, Harris objected to that additional time and renewed his request for entry of default. The court denied that request and highlighted a pattern: Harris had

"filed frivolous objections and motions to reconsider to almost every ruling … draining the Court's limited resources." It advised Harris that, under Rule 11, he was representing to the court that all his filings were not frivolous or filed for improper purposes. It further warned him that he could face possible dismissal of his case if he

"submit[ted] another frivolous or malicious filing."

The court soon granted, only in part, the motion to dismiss and gave Harris leave to amend. After the deadline passed without an amendment, Harris responded by resubmitting his complaint with the dismissed counts intact "under duress" and filing a petition for a writ of mandamus, which the court construed as a request for an

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interlocutory appeal of the order granting an extension of time to file an answer. The court denied that request and rejected the improper amendment. The case proceeded to discovery on the remaining claims in the original complaint, and at the parties' request, the court set a December 20, 2024, deadline for initial disclosures, which the defendants missed. In the afternoon on Friday, December 27, Harris sent one of the attorneys for the defendants an email requesting initial disclosures within the hour or he "may have to make a motion to compel it." Counsel requested clarification, asking Harris which of his three pending cases against the city and city employees Harris was referencing. See, e.g., Harris v. City of Bloomington, No. 25-1762, 2026 WL 281032 (7th Cir. Feb. 3, 2026) (nonprecedential decision) (affirming dismissal of similar suit). Harris responded promptly, and the attorney for the defendants apologized for the delay, assuring Harris that disclosures would be provided by the end of the next week. Harris did not wait that long. On Monday, December 30, he filed not a motion to compel as promised, but a motion seeking monetary sanctions against the defendants for missing the initial disclosure deadline. The defendants served the initial disclosures upon Harris and filed their response to Harris's motion for sanctions the very next day.

At this point, the court acted on its warning and dismissed the case based on Harris's pattern of frivolous filings. The court found that Harris had "completely disregarded Rule 37(a)'s certification requirement and instead brought a frivolous and malicious motion for sanctions against opposing counsel, who, it appears, was making a good faith effort to confer with Plaintiff and promptly obtain the discovery."

Harris filed a motion to amend the judgment, contending that his sanctions motion was a proper response to incomplete discovery, that he was still entitled to default judgment, and that the district judge was biased against him because the judge had worked as a prosecutor and as an attorney for a nearby city decades ago. The court denied this motion, too, and Harris appealed.

On appeal, Harris first asserts that the district court abused its discretion in denying his initial request for entry of default and granting the defendants an extension of time to answer. But the court was correct that Harris had initially failed to serve the defendants personally or through an authorized agent, F ED. R. CIV. P. 4(e)(2), (j)(2), instead serving an "Assistant Hub Operation Manager" at the police department. The later decision to grant a short, three-week extension of time to respond to Harris's sprawling complaint was comfortably within the district court's "considerable

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discretion" to manage its docket and set deadlines. Keeton v. Morningstar, Inc., 667 F.3d 877, 884 (7th Cir. 2012). Even if the initial service had been proper, such an extension would have been entirely appropriate. Harris treats the deadline to answer as inviolable, but we even instruct district courts to vacate default liberally after it is entered, consistent with federal policy in favor of deciding cases on their merits. See Cracco v. Vitran Exp., Inc., 559 F.3d 625, 631 (7th Cir. 2009). A court certainly does not abuse its discretion granting an extension requested before the deadline has passed. See Simstad v. Scheub, 816 F.3d 893, 899 (7th Cir. 2016).

Harris next argues that the court abused its discretion when it dismissed his case. But Harris's abusive litigation strategy gave the court ample grounds to dismiss even despite the policy favoring a decision on the merits. Courts have "the inherent authority to manage judicial proceedings and to regulate the conduct of those appearing before it, and pursuant to that authority may impose appropriate sanctions to penalize and discourage misconduct." Ramirez v. T&H Lemont, Inc., 845 F.3d 772, 776 (7th Cir. 2016). In particular, district courts may dismiss a suit as a sanction for "willful," "malicious,"

and "flagrant" violations of Rule 11. Jimenez v. Madison Area Tech. Coll., 321 F.3d 652, 657 (7th Cir. 2003). One of the basic purposes of Rule 11 is to "deter baseless filings in the district court." Id. at 656 (quoting Cooter & Gell v. Hartmax Corp., 496 U.S. 384, 393 (1990)). Dismissal is a severe sanction, but one that a court has discretion to consider when it finds a party willfully abused the judicial process or otherwise conducted the litigation in bad faith. See Ramirez, 845 F.3d at 776.

This is one of those rare cases that justified the harsh sanction of dismissal. From the beginning of the case, Harris filed frivolous objections and motions to reconsider almost every ruling the court made, big and small. The court warned him to stop these baseless filings or face sanctions, including dismissal. When Harris "crossed the line yet again, he could not have been surprised at the ensuing consequences." Santoyo v. City of Chicago, 141 F.4th 1328, 1330 (7th Cir. 2025), cert. denied, 146 S. Ct. 907 (2025). Even to the extent an ultimatum on a Friday afternoon can generously be considered a good-faith attempt to confer under Rule 37(a)(1), Harris's request for monetary sanctions was frivolous. The default sanction for a party's failure to disclose is automatic and does not require a motion: that party is not permitted to use the information in the litigation, except on a showing that the failure was substantially justified or harmless—a showing that would likely have been simple here. See F ED. R. CIV. P. 37(c); Karum Holdings LLC v. Lowe's Cos., Inc., 895 F.3d 944, 951 (7th Cir. 2018). Although Rule 37(c)(1)(A) also authorizes "reasonable expenses, including attorney's

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fees, caused by the failure," Harris was representing himself and so could not obtain any attorney's fees. See Krecioch v. United States, 316 F.3d 684, 688 (7th Cir. 2003). And he made no effort to identify how the short delay imposed any other expense on him, beyond invoking the cliché that time is money.

Like his repeated demands for a default judgment, Harris's motion for sanctions was not a good-faith effort to remedy a wrong, but an attempt to win his lawsuit on any miniscule technicality instead of the merits. Because of his continued insistence that everyone but him was bound by the rules, and to deter further abuse of the court system, the court was justified in imposing on Harris the kind of severe sanction he wrongly sought to impose on others. See Jimenez, 321 F.3d at 657. Harris finally argues that the district judge should have recused himself. Harris asserts that the judge was biased against him and that this bias is reflected in adverse procedural rulings—though the judge also regularly denied the defendants' motions and offered Harris flexibility. Regardless, adverse "judicial rulings alone almost never constitute a valid basis" for questioning a judge's impartiality. Liteky v. United States,

510 U.S. 540, 555 (1994). And we have said it is "preposterous" to argue the judge's prior career casts any doubt on his impartiality even with respect to the city for which he worked decades ago, see Nicholson v. City of Peoria, 860 F.3d 520, 525 (7th Cir. 2017), let alone another nearby municipality.

AFFIRMED

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