Pamela Kibbons v. Anthony Peloso

Title VII, breach of contract, and intentional infliction of emotional distress. The district court granted the School District summary judgment. On appeal, Kibbons's arguments are waived because she failed to develop them, and her brief does not comply with Federal Rule of Appellate Procedure 28. Accordingly, we affirm the district court and we order Kibbons's attorney to show cause as to why he should not be sanctioned under Federal Rule of Appellate Procedure 38.

I. Background

In 2016, Taft School District 90 hired Dr. Pamela Kibbons on a two-year contract in a dual role as superintendent and principal. During her time with the School District, Kibbons felt that some of her interactions with Anthony Peloso, the School District's Board President, were unpleasant or harassing. On several occasions, Peloso asked Kibbons if she wanted to go across the street to a cemetery and drink. Peloso also would frequently enter Kibbons's office to work on his laptop and watch Kibbons work. Peloso twice instructed Kibbons to climb a ladder to the school rooftop to address concerns he had about the roof. On each occasion, Kibbons was wearing high-heeled shoes and a skirt, and she felt embarrassed to climb the ladder while Peloso watched. After declining an offer to renew her contract and resigning upon its expiration, Kibbons filed a charge with the U.S. Equal Employment Opportunity Commission for alleged harassment, retaliation, and constructive discharge. The EEOC issued a right to sue letter on November 30, 2018. In February 2019, Kibbons sued the defendants. In her First Amended Complaint, Kibbons alleged that Peloso subjected her to a hostile work environment and constructively discharged her from her job because of her sex, in violation of Title VII of the Civil Rights Act of 1964, 42 U.S.C. § 2000e et seq. (Counts 1 and 2); that the Board breached its employment contract with her (Count 3); and that Peloso subjected her to intentional infliction of emotional distress (IIED) (Count 4). Kibbons based her claims on Peloso's actions as described above. After the close of discovery, the defendants moved for summary judgment in December 2023. While that motion was pending, in April 2024, Kibbons moved for sanctions, claiming misconduct by defendants' counsel. In June 2024, the magistrate judge presiding over the case issued a report and recommendation denying Kibbons's sanctions motion because it was untimely and she had failed to identify a discovery violation warranting sanctions. In September 2024, the district court granted the defendants' motion for summary judgment, holding that Kibbons had abandoned her claims by failing to meaningfully respond to the defendants' arguments. The court also

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denied Kibbons's objections to the magistrate judge's order and found that the magistrate judge properly denied her sanctions motion as untimely. In response, Kibbons moved for reconsideration of the district court's opinion and order. In December 2024, the defendants moved for sanctions based on Kibbons's "vexatious motions and filings."²In March 2025, the court denied Kibbons's motion for reconsideration. The court also granted the defendants' sanctions motion under Rule 11 because Kibbons's counsel "did not possess a subjective good faith basis that the claims were well grounded in fact and warranted by existing law." It further found sanctions appropriate under 28 U.S.C. § 1927 because Kibbons's motions "showed a serious and studied disregard for the orderly process of justice." This appeal followed.

II. Discussion A. The District Court's Summary Judgment Decision

This court reviews a grant of summary judgment de novo, viewing the record in the light most favorable to the nonmoving party and drawing all reasonable inferences in that party's favor. Osborn v. JAB Mgmt. Servs., Inc., 126 F.4th 1250, 1258 (7th Cir. 2025). To obtain summary judgment, a party must demonstrate that "there is no genuine dispute as to any material fact and that the movant is entitled to judgment as a matter of law." Fed. R. Civ. P. 56(a); id.

The district court granted the defendants' motion for summary judgment on all four of Kibbons's claims because "she failed to substantively respond to any of Defendants' arguments in her responsive brief and because there is no material dispute of fact that would allow a reasonable jury to find in Kibbons's favor on any of her ²Kibbons previously had filed: (1) "Plaintiff's Motion for Sanctions for Defendants' Discovery Violations, their Failure to Preserve and Produce ESI Evidence, their Failure to Fulfill Discovery Requests, their Attorney's Inappropriate and Obstructive Behavior Before and During Depositions, their Attorney's Contumacious Conduct, His Dishonest Statements to the Court to Mislead the Court and Opposition Counsel, and their Attorney's Failure to Observe the Local Rules Requiring Meet and Confer Among Lawyers"; (2) "Plaintiff's Objections to the Magistrate Judge's Order and in Support of Imposing Sanctions Against Defendants and Their Attorneys For Discovery Violations and For Suborning Perjury And/or Perjurious Behavior Before the Court"; and (3) "Plaintiff's Motion to Reconsider the Court's Order Granting Summary Judgment to Defendants."

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claims." In its order, the court characterized Kibbons's response brief on summary judgment as "invit[ing] the [c]ourt to tie disjointed factual assertions with under- developed arguments to construct a clear version of her rebuttal argument: courts generally decline such invitations."

The district court's rulings on Kibbons's claims are material to our consideration of this appeal. First, the court found that Kibbons failed to address the defendants' arguments that the sexual harassment claims were time-barred, resulting in waiver. Next, the court found that Kibbons waived her constructive discharge claim by failing to respond to the defendants' arguments. Then, the court ruled that Kibbons's breach of contract claim was based on similar allegations as her constructive discharge claim, and thus similarly deficient. Because Kibbons failed to identify any breached contractual term or evidence that would support an allegation of breach, she waived her breach of contract claim. Finally, the court found that Kibbons abandoned her IIED claim because she did not respond to the defendants' argument. In fact, Kibbons's response brief did not even mention "intentional infliction of emotional distress."

The district court correctly observed that it was Kibbons's job, not the court's, to develop and to present her arguments. See, e.g., Williams v. Dieball, 724 F.3d 957, 961 (7th Cir. 2013) (appellant waived argument by failing to present it with any level of specificity in district court); Puffer v. Allstate Ins. Co., 675 F.3d 709, 718 (7th Cir. 2012) ("arguments not raised to the district court are waived on appeal"). The district court concluded that Kibbons abandoned all four of her claims by failing to respond to the arguments set forth in the defendants' summary judgment motion.

B. Waiver

"Waiver occurs when a party intentionally relinquishes a known right."

Lukaszczyk v. Cook County, 137 F.4th 671, 674 (7th Cir. 2025). An appellant can waive an argument by failing to (1) raise the issue or argument in the district court, either at all or in a timely fashion, (2) raise the issue or argument in the party's opening brief on appeal, (3) present a developed argument on appeal that engages with the district court's reasoning, or (4) respond in a reply brief to a new argument raised by appellee. Bradley v. Village of University Park, 59 F.4th 887, 897 (7th Cir. 2023). We review the legal question of waiver de novo and the factual determinations predicating a finding of waiver for clear error. Smith v. GC Servs. Ltd. P'ship, 907 F.3d 495, 499 (7th Cir. 2018). Ordinarily, an appellant is expected to assert any available grounds for reversal on penalty of waiver. Bradley, 59 F.4th at 897. Arguments raised to the district court

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"may still be waived on appeal if they are underdeveloped, conclusory, or unsupported by law." Puffer, 675 F.3d at 718. Likewise, "perfunctory and undeveloped arguments, and arguments that are unsupported by pertinent authority, are waived." United States

v. Berkowitz, 927 F.2d 1376, 1384 (7th Cir. 1991). And "a skeletal argument, really nothing more than an assertion, does not preserve a claim." United States v. Dunkel, 927 F.2d 955, 956 (7th Cir. 1991) (citation omitted). It is not enough to preserve an issue by presenting an argument in general terms. See Fednav Int'l Ltd. v. Cont'l Ins. Co., 624 F.3d 834, 841 (7th Cir. 2010). This court has recognized that "[i]t is the parties' responsibility to allege facts and indicate their relevance under the correct legal standard." Econ. Folding Box Corp. v. Anchor Frozen Foods Corp., 515 F.3d 718, 721 (7th Cir. 2008) (citation omitted). Because Kibbons does not come close to developing any arguments to challenge the district court's bases for granting summary judgment, her arguments are waived.

On appeal, Kibbons has waived each of her four claims by failing to present a developed argument. In her opening brief, she does not clearly identify which of the district court's rulings she challenges. Instead, Kibbons requests a special master to conduct an evidentiary hearing on allegations of perjury and fabrication of evidence, and reversal of sanctions awards against Kibbons and her counsel. And though she asks for reversal of summary judgment, Kibbons merely recites the standard of review governing a motion for summary judgment and quotes case law unsupported by any facts from the record. She does not engage with either the district court's decision or the defendants' arguments, instead devoting the majority of her brief to an attempt to rewrite the factual record or dispute settled discovery issues. The little attention dedicated to the arguments is spent on accusing opposing counsel of perjury, "bad behavior" throughout litigation, and fabrication of evidence.

Kibbons's "few bare assertions" that the district court erred in granting summary judgment and denying the sanctions motion are insufficient to preserve either issue for appeal. Puffer, 675 F.3d at 720. Her arguments are underdeveloped, conclusory, and unsupported by law. Id. at 718. And an appellant who does not engage with the reasons for which she lost "has no prospect of success." Klein v. O'Brien, 884 F.3d 754, 757 (7th Cir. 2018). Thus, Kibbons has waived her arguments for reversal of summary judgment for the defendants.

C. Kibbons's Motion for Sanctions

In an October 17, 2023 minute entry, the magistrate judge expressed concerns about Kibbons's anticipated sanctions motion because "it is unclear why plaintiff

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intends to seek discovery related sanctions now, more than two months after fact discovery cutoff and presumably even longer after the underlying misconduct that defendants allegedly engaged in." Six months after these concerns were raised, Kibbons moved for sanctions. In a June 3, 2024 recommendation to deny sanctions, the magistrate judge commented that, "[d]espite the breadth of its title and its length (41 pages and more than 300 pages of exhibits), the motion is nothing more than a laundry list of plaintiff's counsel's grievances with how defendants and their attorneys have comported themselves during the discovery process and a rehashing of multiple discovery disputes that plaintiff brought and lost—some on multiple occasions."

Ultimately, the magistrate judge found the motion untimely after properly considering the required factors, including "when the movant learned of the discovery violation, how long [Kibbons] waited before bringing it to the court's attention, and whether discovery has been completed."

Kibbons objected to the magistrate judge's order denying sanctions. In doing so, she made unsupported arguments, cited irrelevant cases, and then attempted to relitigate discovery disputes. For example, she began her objections by citing our decision in Pope v. Taylor, 100 F.4th 918 (7th Cir. 2024), which upheld a district court's decision to conditionally grant a habeas corpus petition. She then cited Novotny v. Plexus Corp., 777 F. App'x 164 (7th Cir. 2019), which affirmed the entry of summary judgment against the plaintiff-debtor based on judicial estoppel. Neither case is relevant to the magistrate judge's order. Kibbons continued by accusing defendants and their counsel of perjury because "[d]efendants' testimony under oath at depositions taken many months apart is so consistent among them that it must have been carefully crafted among them and their counsel." Further, she insisted Thompson v. Clark, 596 U.S. 36 (2022), a case reviewing a malicious prosecution claim under the Fourth Amendment, gives her the right to use evidence—which she fails to specify—before the trier of fact. The district court concluded that Kibbons waived her objections by failing to respond to the magistrate judge's order. She "submit[ed] an oversized brief that addresses irrelevant areas of law and throws block quotations from other cases at the Court, with no effort to show how the precedent is relevant to her objections to the magistrate judge's recommendation."

An appellant waives an issue or argument by failing to raise them in the district court, "either at all or in a timely fashion." Bradley, 59 F.4th at 897. We agree with the magistrate judge's conclusion that Kibbons's arguments were unsupported and with the district court's finding that Kibbons's failed to respond to the magistrate judge.

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Propositions were stated without any citation. The cases that were cited did not relate to the claims at issue but instead were used to ask the district court for extraordinary remedies, such as judicial estoppel to "prevent[] improper use of judicial machinery and protect[] the integrity of judicial proceedings." Thus, the district court correctly denied Kibbons's motion for sanctions.

D. Fed. R. App. P. 28 Noncompliance

As one might anticipate from the discussion above, Kibbons's written submissions to this court are deficient. Both her principal and reply briefs fail to comply with Federal Rule of Appellate Procedure 28 and Circuit Rule 28. Neither brief contains

"a concise statement of the case setting out the facts relevant to the issues submitted for review." Fed. R. App. P. 28(a)(6). Nor do they contain a summary of the argument with

"a succinct, clear, and accurate statement of the arguments made in the body of the brief." Fed. R. App. P. 28(a)(7). Finally, the briefs neglect to include citations to authorities and the record and fail to include reasons for Kibbons's contentions. Fed. R. App. P. 28(a)(8).

Representative examples from Kibbons's principal brief show her unsupported assertions and undeveloped arguments. That brief:

• makes sweeping and unsupported declarations that "[p]rinciples enunciated in important landmark decisions and holdings of the United States Supreme Court and the Seventh Circuit Court of Appeals are disregarded";

• charges opposing counsel with "find[ing] ways to ignore discovery obligations and later their obligations to tell the truth under oath in judicial proceedings";

• contends opposing counsel must "prepare a Supplemental Privilege Log clearly indicating who is present at each closed session board meeting"

because opposing counsel "are asserting privileges over all the recorded closed session board meetings"; and

• includes unsupported headings such as, "Litigation Over Attorneys' Fees Is a Waste of Judicial Resources."

Kibbons's reply brief is similarly deficient. The reply brief:

• makes several arguments, unrelated to the district court's reasoning, touting

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Kibbons's performance as superintendent and principal by accomplishing tasks such as procuring funding for textbooks and soliciting donations "to beautify[] the school";

• includes 14 pages of images displaying examples of such improvements to the school grounds—none of which are relevant to the claims underlying summary judgment;

• refuses to engage with either the district court's opinion or the defendants' brief, relying on claims without citations to the record, such as "[a] reasonable jury can easily conclude" why Kibbons was subject to constructive discharge and sexual harassment;

• continues to allege the defendants committed perjury, spoliation of evidence, and falsely drafted discovery certifications, without support from the record. Although the bar for a Rule 28-compliant brief is low, "briefs containing only minimal legal support do not pass muster." Sullers v. Int'l Union Elevator Constructors, Loc. 2, 141 F.4th 890, 896 (7th Cir. 2025). For instance, in another Title VII discrimination suit, we concluded that a brief "laden with assertions that ha[d] no basis in the record and arguments that ha[d] no basis in the law" was frivolous and violated Rule 28. McCurry v. Kenco Logistics Servs., LLC, 942 F.3d 783, 791 (7th Cir. 2019). Likewise, in Shipley v. Chicago Board of Election Commissioners (7th Cir. 2020), we decided that several claims were waived and a brief was noncompliant under Rule 28 when the appellants

"offer[ed] only a few cursory sentences in support of their … claims, buried in the middle of other arguments, and without any adequate explanation at all that would aid our review." 947 F.3d 1056, 1062-63. Meanwhile, in Sullers, we held the appellant avoided waiver despite a sparse brief of less than three pages containing minimal legal authority, "given our preference for a merits disposition and our ability to discern, from the briefs and the record, the basic facts … and general contentions." 141 F.4th at 897. The purpose of appellate review "is to evaluate the reasoning and result reached by the district court." Jaworski v. Master Hand Contractors, 882 F.3d 686, 690 (7th Cir. 2018); U NITED STATES COURT OF APPEALS FOR THE SEVENTH CIRCUIT, PRACTITIONER'S HANDBOOK FOR APPEALS 154 (2020 ed.). Thus, we "insist on meticulous compliance with rules sensibly designed to make appellate briefs as valuable an aid to the decisional process as they can be." Avitia v. Metro. Club of Chi., Inc., 49 F.3d 1219, 1224 (7th Cir.

1995).

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Kibbons's briefs do not identify which of the district court's rulings she is seeking to have this court review. Instead, her conclusory statements attempt to relitigate factual disputes or request evidentiary hearings based on allegations of misconduct that the district court already found baseless. Kibbons's briefs therefore substantially fail to comply with Federal Rule of Appellate Procedure 28.

E. Fed. R. App. P. 38 Sanctions

This court normally dismisses an appeal "if the appellant fails to supply a minimally adequate brief," P RACTITIONER'S HANDBOOK 161 (citing Anderson v. Hardman,

241 F.3d 544, 545-46 (7th Cir. 2001)). But under Rule 38, this court can impose sanctions when an appeal is (1) frivolous and (2) an appropriate case for sanctions. Id. at 125 (citing Harris N.A. v. Hershey, 711 F.3d 794, 802 (7th Cir. 2013); Lorentzen v. Anderson Pest Control, 64 F.3d 327, 331 (7th Cir. 1995)). An appeal is frivolous when the "result is foreordained by a lack of substance of appellant's arguments." Id. (citing Ashkin v. Time Warner Cable Corp., 52 F.3d 140, 146 (7th Cir. 1995); see also East St. Louis v. Circuit Court,

986 F.2d 1142, 1145 (7th Cir. 1993); Girard v. Girard, No. 25-1854, 2025 WL 3281313, at *3 (7th Cir. Nov. 25, 2025)). Further, "[n]oncompliance with appellate rules wastes time and resources and frustrates the review process." McCurry, 942 F.3d at 790. When these rules are violated, sanctions are appropriate. See Sambrano v. Mabus, 663 F.3d 879, 881- 82 (7th Cir. 2011).³

We have previously warned parties of the possibility of sanctions for submitting briefs with "lengthy explications of marginally relevant and irrelevant case law, and

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minimal analysis of th[e] case." Lukaszczyk, 137 F.4th at 675. Like her previous filings in the district court, Kibbons's briefs submit a series of unsupported arguments and assertions, many of which are unrelated to the district court's rulings. This is not a case

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