From Standard v. Nygren, 2011 U.S. App. LEXIS 19213 (7th Cir. Sept. 19, 2011):

Michael Stanard built an outdoor stage on his property in rural McHenry County, Illinois, and began hosting events there. He claims that Keith Nygren, the Sheriff of McHenry County, forced him to hire off-duty deputies as a private security force for these events and threatened to close the road leading to his property if he did not comply. Stanard sued Nygren, 22 of his deputies, and McHenry County, alleging a conspiracy to violate his rights, but his attorney Walter Maksym proved unable to file an intelligible complaint. After giving Maksym three tries at producing a complaint that complied with Rules 8 and 10(b) of the Federal Rules of Civil Procedure, the district court dismissed the case with prejudice. On Stanard's behalf Maksym brought this appeal, insisting that the second amended complaint satisfied the rules, and even if it did not, the district court should have given him yet another chance to replead.

We affirm. The district court was well within its discretion to reject the second amended complaint and dismiss the case with prejudice. Each iteration of the complaint was generally incomprehensible and riddled with errors, making it impossible for the defendants to know what wrongs they were accused of committing. Maksym's persistent failure to comply with basic directions from the court and his open defiance of court orders amply justified the judge's decision to dismiss with prejudice. ***

Though length alone is generally insufficient to justify rejecting a complaint, unintelligibility is certainly a legitimate reason for doing so. Again, the issue is notice; where the lack of organization and basic coherence renders a complaint too confusing to determine the facts that constitute the alleged wrongful conduct, dismissal is an appropriate remedy. In Garst we affirmed the dismissal of a 155-page, 400-paragraph complaint that would have forced the defendants to spend countless hours "fishing" for the few relevant allegations:

[E]ven if it were possible to navigate through these papers to a few specific instances of fraud, why should the court be obliged to try? Rule 8(a) requires parties to make their pleadings straightforward, so that judges and adverse parties need not try to fish a gold coin from a bucket of mud. *** Garst's lawyer filed documents so long, so disorganized, so laden with cross-references and baffling acronyms, that they could not alert either the district judge or the defendants to the principal contested matters.

Id.; see also Davis, 269 F.3d at 820 ("The dismissal of a complaint on the ground that it is unintelligible is unexceptionable.").

Applying these principles here, the district court was well within its discretion in refusing to accept Stanard's proposed second amended complaint. We agree that it crossed the line from just "unnecessarily long" to "unintelligible." Though the complaint was far longer than it needed to be, prolixity was not its chief deficiency. Rather, its rampant grammatical, syntactical, and typographical errors contributed to an overall sense of unintelligibility. This was compounded by a vague, confusing, and conclusory articulation of the factual and legal basis for the claims and a general "kitchen sink" approach to pleading the case. This was Maksym's third attempt to draft a comprehensible pleading, yet his effort to comply with the court's earlier directions was half-hearted at best; the proffered second amended complaint was rife with errors. We include a sampling to provide an understanding of its shortcomings:

o Lack of punctuation. At least 23 sentences contained 100 or more words. This includes sentences of 385, 345, and 291 words but does not include sentences set off with multiple subsections.

Footnote 7. We acknowledge the unfortunate reality that poor writing occurs too often in our profession, but Maksym's complaint is far outside the bounds of acceptable legal writing. See, for example, this 345-word sentence. All errors are in the original:

That pursuant to the RICO Act, Defendants extortive activities constituted a Pattern of Racketeering activity and conspiracy involving violations of 1956(a)(1)(B)(ii), and 18 U.S.C. § 1341 (wire fraud--the use of interstate mail or wire facilities, here telephone and facsimile transmissions), or the causing of any of those things promoting unlawful activity), and 18 U.S.C. § 1951 (interference with commerce and extortion by using and threatening to use legitimate governmental powers to obtain an illegitimate objectives under color of official right by wrongful plan, extortion, intimidation and threat of force and/or other unlawful consequence and through fear and misuse of there office to obstruct, hinder, interfere with, and/or affect commerce and the use and enjoyment of Plaintiffs' property and obtaining, as uniformed public officials payment for unwanted services to which they were not entitled by law, attempting to conceal from the United States of America their true and correct income and the nature thereof so obtained from Plaintiffs in order to attempt to evade paying lawful taxes thereon in violation of 26 U.S.C. § 7201, et. seq., thereby using the governmental powers with which they have been entrusted to gain personal or illegitimate rewards and payments which they knew or should have known were made and/or obtained in return for the colorable official acts as aforesaid, and knowing that the property involved in a financial transaction represents the proceeds of some form of unlawful activity, conducts or attempts to conduct such a financial transaction which in fact involves the proceeds of specified unlawful activity with the intent to promote the carrying on of specified unlawful activity all in violation of RICO and the other laws set forth herein, inter alia, as well as acts chargeable under any of the following provisions of the laws of the State of Illinois 720 ILCS 5/33-3(d) (official misconduct); 720 ILCS 5/12-11 (criminal home invasion); 720 ILCS 5/19-4 (criminal trespass to a residence) 720 ILCS 5/19-4); (theft 720 ILCS 5/16 (a)(1)&(3) by knowingly obtaining or exerting unauthorized and/or through threat control over Plaintiff's property as aforesaid.

o Near incomprehensibility. Much of the writing is little more than gibberish. An example:

Stanard and attendees, were stunned on the day of the family-oriented event, when an even more menacing law enforcement presence was created when Nygren's armed deputies, without prior consent or permission, warrant or probable cause, arrived, not a part of any agreement and a surprise and upset when it arrive, uninvited, on and entered and trespassed on Plaintiff property with drug-sniffing 'K-9' dogs, obviously and unfortunate that Defendants were 'looking for trouble' where there was none as distinct from "looking to serve".

o Failure to follow basic directions. Given three attempts to file a proper complaint, Maksym could not even bring himself to correct the errors cataloged by the district court following the first two rejections. The district court directed Maksym to separate his facts into sections relevant to each claim rather than just one massive section of "facts common to all counts." Maksym failed to do so. When it came to identifying the claims, conclusory allegations abounded. A few examples: (1) the defendants used wire transmissions to facilitate the scheme; (2) the defendants engaged in a pattern or practice of wrongful behavior; (3) Nygren had decision-making authority for the county; and (4) the defendants' actions implicated interstate commerce because McHenry County is near the Wisconsin border.

o Failure to put defendants on notice. Despite the complaint's length — or perhaps in part because of it — it remains unclear what constitutes the core of the claims against Nygren and the other defendants. ***

o Grammatical and syntactical errors. The district court put it best: "The grammatical and spelling errors" are "too numerous to add '[sic]' where required."

Perhaps these defects, considered alone, might not justify the court's rejection of the second amended complaint. Collectively, however, they are easily egregious enough to warrant denial of the motion for leave to amend. The complaint's lack of clarity would have severely disadvantaged the defendants when it came time to responsively plead to, much less defend against, the claims. To form a defense, a defendant must know what he is defending against; that is, he must know the legal wrongs he is alleged to have committed and the factual allegations that form the core of the claims asserted against him. Deciphering even that much from the second amended complaint is next to impossible. To the extent that discerning the basic legal and factual basis of the claims is not impossible but merely unnecessarily difficult, we restate the primary teaching of Garst: A federal court is not obligated to sift through a complaint to extract some merit when the attorney who drafted it has failed to do so himself. See Garst, 328 F.3d at 378. "Rule 8(a) requires parties to make their pleadings straightforward, so that judges and adverse parties need not try to fish a gold coin from a bucket of mud." Id. Maksym failed so thoroughly in this regard that the district court was well within its discretion to deny the motion for leave to amend.