In the
United States Court of Appeals
For the Seventh Circuit
No. 09-1487
H. M ICHAEL S TANARD , individually and
d/b/a One Zero Charlie Productions and
Galt Festivals, et al.,
Plaintiffs-Appellants,
v.
K EITH N YGREN, individually and as Sheriff
of McHenry County, Illinois, et al.,
Defendants-Appellees.
Appeal from the United States District Court
for the Northern District of Illinois, Western Division.
No. 07 C 50132—Frederick J. Kapala, Judge.
A RGUED O CTOBER 28, 2010—D ECIDED S EPTEMBER 19, 2011
Before M ANION, R OVNER, and S YKES, Circuit Judges.
S YKES, Circuit Judge. 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
2 No. 09-1487
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 dis-
missed 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 discre-
tion 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 preju-
dice. Moreover, like his pleadings in the district court,
Maksym’s appellate briefing is woefully deficient, raising
serious concerns about his competence to practice before
this court. Accordingly, we order Maksym to show cause
why he should not be suspended from the bar of this
court or otherwise disciplined under Rule 46 of the
Federal Rules of Appellate Procedure. Finally, we direct
the clerk to send a copy of this opinion to the Illinois
Attorney Registration and Disciplinary Commission.
No. 09-1487 3
I. Background
We describe the facts only briefly and as best we can
decipher them from the second amended complaint and
Stanard’s appellate briefs. The procedural history of the
case is also important to the resolution of the issues on
appeal.
The plaintiffs are H. Michael Stanard, his wife Joeleen,
and their company One Zero Charlie Productions.1 They
constructed an open-air amphitheater on their property
in rural McHenry County and began staging public
events there. Stanard claims that Sheriff Nygren com-
pelled him to hire off-duty sheriff’s deputies at inflated
rates as private security for these events. To coerce
Stanard into accepting, Nygren threatened to close the
road leading to Stanard’s property. This went on for a
number of years; Stanard claims he was afraid to
disobey Nygren. He also claims that Nygren engaged in
this course of conduct against other residents of
McHenry County. Finally, Stanard alleges that Nygren’s
deputies menaced the spectators who attended the
events on Stanard’s property and otherwise created an
intimidating environment.
Stanard, by his counsel Walter Maksym, sued Nygren
in his individual and official capacities, along with
22 deputies, McHenry County, and unknown additional
1
We refer to them collectively as “Stanard.”
4 No. 09-1487
defendants.2 The original complaint was 52 pages long
and purported to assert 28 counts, including civil RICO
claims, §§ 1983 and 1985 claims, and various state-law
claims. Each claim targeted “the defendants” as a
group; the complaint did not specify which individual
defendants were alleged to be liable on each claim. The
complaint also included a number of obviously frivolous
claims; for example, a violation of the Hobbs Act (a crimi-
nal statute that does not provide a private right of ac-
tion), something called a “direct action under [the] U.S.
Constitution,” and a generic “federal class action.”
The defendants moved for a more definite statement
under Rule 12(e) of the Federal Rules of Civil Procedure.
Stanard was ordered to either respond or file a notice
saying that he declined to do so. Maksym ignored the
motion and order. Nevertheless, a magistrate judge
denied Rule 12(e) relief. Nygren then moved to dismiss
the official-capacity claims. Maksym continued to disre-
gard deadlines. Stanard’s response to Nygren’s motion
was due in October 2007, but Maksym failed to respond.
Three months later, the court, on its own motion, extended
this deadline to February 11, but again Maksym failed
to respond by that date. On February 19 he finally filed
a response to Nygren’s motion.
In the meantime, the defendants jointly moved to
dismiss the rest of the complaint pursuant to Rule 12(b)(6)
of the Federal Rules of Civil Procedure. The court set a
2
All the defendants are represented by counsel from the
McHenry County State’s Attorney’s office.
No. 09-1487 5
January 11, 2008 deadline for Stanard to respond. Maksym
missed this deadline, too. On January 23, nearly two
weeks after the deadline to respond had expired, Maksym
asked for an extension of time. The court granted
this request and extended the deadline to March 18. 3 On
June 18, three months after the extended deadline, the
district court extended the deadline again and ordered a
response by July 2. The court’s June 18 order warned
Maksym that if he failed to timely respond, Stanard’s
case would be dismissed for want of prosecution under
Rule 41(b) of the Federal Rules of Civil Procedure.
Maksym filed his response on July 2.
The district court granted the motions to dismiss. The
court dismissed the frivolous claims mentioned above (the
Hobbs Act claim, the “direct action under [the] U.S.
Constitution,” and the “federal class action”) with preju-
dice.4 The court held that the rest of the complaint
suffered from serious deficiencies under Rules 8(a)(2)
(requiring a “short and plain statement” of the claims),
8(d)(1) (requiring pleading to be “simple, concise, and
direct”), and 10(b) (requiring claims to be set forth in
separate paragraphs and limited to single sets of circum-
stances “as far as practicable”). The court dismissed
3
The district court indicated that Maksym sought this exten-
sion of time for “personal reasons.” In Stanard’s reply
brief in this court, Maksym asserts that he needed more
time because of hip-replacement surgery and a recent cancer
diagnosis.
4
Stanard does not challenge the dismissal of these claims.
6 No. 09-1487
the remaining 25 claims without prejudice and gave
Maksym until September 30, 2008, to cure the com-
plaint’s deficiencies. Helpfully, the court included a list
of errors that needed to be fixed.
At 10:34 p.m. on September 30, Maksym moved for
an extension of time to file his amended complaint. The
stated basis for this motion was that Maksym’s
computer was damaged in an earthquake while he was
in California sitting for that state’s bar exam in late July.5
Over the defendants’ objection, the court granted the
motion and set a new due date of October 22 at 5 p.m.
At 4:59 p.m. on October 22, Maksym filed a motion for
leave to file his amended complaint; the amended com-
plaint itself was not filed until 7:01 p.m. that day. His
attempt to cure the deficiencies in the original complaint
was haphazard at best. Some of the counts were com-
pletely unchanged, and many of the specific concerns
raised by the district court were not adequately ad-
dressed. The court denied leave to file the amended
complaint. Rather than dismissing the case with
prejudice, however, the court gave Maksym one more
opportunity to submit a proper complaint, setting a
deadline of October 31 at 5 p.m.
5
The motion recounted Maksym’s strenuous efforts to get the
computer fixed. He said he visited Apple “Genius” teams in
both Los Angeles and Chicago and took the computer to a
“Macspecialist.” Though these efforts eventually resolved the
immediate problem, he claimed that intermittent data losses
persisted. Maksym also alleged that he was suffering from
bilateral carpal tunnel syndrome, severe back and hip pain,
and a serious infection.
No. 09-1487 7
On October 31, at 4:41 p.m., Maksym filed another
motion for leave to amend, along with a second amended
complaint inexplicably titled “First Amended Complaint.”
Again, few of the many errors in the earlier complaints
were fixed. The district court rejected Maksym’s latest
effort, outlining at length the many pleading defects in
the second amended complaint. To illustrate its basic
incoherence, the court quoted verbatim from a number
of its paragraphs, including one that contained a stag-
gering and incomprehensible 345-word sentence. The
court also took note of the “grammatical and spelling
errors” throughout the complaint, which it said were
“too numerous to add ‘[sic]’ where required.” Noting that
the purpose of Rules 8 and 10 is to provide “ ‘fair no-
tice’ of the claims and the grounds upon which the
claims rest,” the court held that the second amended
complaint was “so poorly drafted and obviously not
in compliance with” the rules of pleading that the de-
fendants were left to “guess which actions apply to
each claim.” Rather than give Maksym yet another op-
portunity to replead, by this time the court had
had enough:
Based on the lack of diligence, including a pattern of
waiting until the last minute (sometimes literally) to
file their motions to amend with non-compl[ia]nt
proposed amended complaints attached, the failure
to comply with this court’s previous orders, and this
court’s explicit warning of the consequences for
doing so, plaintiffs will not be afforded another op-
portunity to replead.
8 No. 09-1487
Accordingly, the court dismissed the federal claims with
prejudice and relinquished jurisdiction over the supple-
mental state-law claims.
Maksym’s inability to articulate a “short and plain
statement” of his clients’ claims for relief did not end in
the district court, nor did he improve his approach to
court-ordered deadlines and following simple directions
once the case reached this court. Maksym sought and
received no fewer than three extensions of time to file
his opening brief on appeal.6 Along the way we admon-
ished him for filing his extension motions late and
failing to comply with Circuit Rule 26, which requires
specificity in motions to extend time. Even with three
extensions, Maksym was unable to file his brief on time.
Instead, he filed his opening brief four days after the
third extended deadline came and went, including with
it an instanter motion seeking leave to file the brief
late. Maksym claimed in the motion that he had mailed
the brief to the defendants on the due date (he in-
cluded FedEx receipts), but said he encountered some
duplication problems that prevented him from timely
filing the brief with the court. Over the defendants’ ob-
jection, we accepted the late brief. We later ordered
it stricken for failure to contain a jurisdictional state-
ment that complies with Rule 28(a)(4)(C) of the Federal
Rules of Appellate Procedure. Maksym subsequently
submitted a corrected brief.
6
Each of these extensions was requested based on some
combination of health issues, computer troubles, and pressing
deadlines in other cases.
No. 09-1487 9
II. Discussion
Stanard argues that the district court should not
have rejected his second amended complaint, or at least
should have dismissed without prejudice and with leave
to replead. The parties initially disagree about the
standard of review. Stanard argues that because the
district court dismissed the proposed amended com-
plaint, our review is de novo. See Palka v. Shelton, 623
F.3d 447, 451 (7th Cir. 2010) (An order dismissing a com-
plaint is reviewed de novo.). The defendants maintain,
however, that the standard of review is abuse of discre-
tion because the district court denied leave to file the
second amended complaint because it failed to comply
with Rules 8 and 10. See Davis v. Ruby Foods, Inc.,
269 F.3d 818, 820 (7th Cir. 2001).
The defendants are correct. This case comes to us as
an appeal from the district court’s order denying leave
to file the second amended complaint because it failed
to comply with Rules 8 and 10. Stanard has not chal-
lenged the dismissal of the original complaint for failure
to state a claim under Rule 12(b)(6); he challenges only
the denial of his motion for leave to file the second
amended complaint, as well as the district court’s deci-
sion to dismiss with prejudice. Leave to amend in this
situation is discretionary, see F ED. R. C IV. P. 15(a)(2), and
the court may reject a proffered amended complaint if
it fails to comply with basic pleading rules. “[D]istrict
courts have broad discretion to deny leave to amend
where there is undue delay, bad faith, dilatory motive,
repeated failure to cure deficiencies, undue prejudice to
10 No. 09-1487
the defendants, or where the amendment would be
futile.” Arreola v. Godinez, 546 F.3d 788, 796 (7th Cir. 2008)
(citing Foman v. Davis, 371 U.S. 178, 182 (1962)); see also
5 C HARLES A LAN W RIGHT & A RTHUR R. M ILLER, F EDERAL
P RACTICE AND P ROCEDURE § 1217 (3d ed. 2004) (“In the
exercise of their discretion and in order to promote
judicial economy, courts often will use a motion directed
at the form of a pleading (or a motion to dismiss under
Rule 12(b)(6)) as a vehicle for considering” whether
Rule 8’s requirements are satisfied). We will not reverse
a decision denying leave to amend unless the court has
abused its discretion. Hukic v. Aurora Loan Servs., 588
F.3d 420, 432 (7th Cir. 2009) (decision denying leave to
replead reviewed for abuse of discretion); Davis, 269 F.3d
at 820 (Abuse of discretion is “the normal standard
applied to decisions relating to the management of litiga-
tion, and the one by which dismissals for violation of
Rule 8 are reviewed.”).
Rule 8 requires that a complaint contain “a short and
plain statement of the claim showing that the pleader is
entitled to relief.” FED. R. C IV. P. 8(a)(2). Moreover, “[e]ach
allegation must be simple, concise, and direct.” Id. 8(d)(1).
Rule 10 requires the pleader to state his claims in
separate numbered paragraphs, “each limited as far as
practicable to a single set of circumstances,” and also
requires that “each claim founded on a separate trans-
action or occurrence” be “stated in a separate count” if
“doing so would promote clarity.” Id. 10(b). The primary
purpose of these rules is to give defendants fair notice
of the claims against them and the grounds supporting
the claims. Killingsworth v. HSBC Bank Nev., N.A., 507 F.3d
No. 09-1487 11
614, 618 (7th Cir. 2007) (Rule 8(a)) (citing Bell Atl. Corp. v.
Twombly, 550 U.S. 544, 555 (2007)). The pleading require-
ments also “frame[ ] the issue[s] and provide the basis
for informed pretrial proceedings.” Bautista v. Los Angeles
Cnty., 216 F.3d 837, 841 (9th Cir. 2000) (discussing
Rule 10(b)); see also Anderson v. Dist. Bd. of Trs., 77 F.3d 364,
367 (11th Cir. 1996) (same).
Two themes emerge from our cases applying Rules 8
and 10. First, undue length alone ordinarily does not
justify the dismissal of an otherwise valid complaint.
Where a complaint does not comply with Rule 8’s
mandate of “a short and plain statement of the claim”
but nevertheless puts the defendant on notice of the
plaintiff’s claims, dismissal is inappropriate “merely
because of the presence of superfluous matter.” Davis,
269 F.3d at 820. Davis held that “[i]f the [trial] court under-
stood the allegations sufficiently to determine that
they could state a claim for relief, the complaint has
satisfied Rule 8,” and dismissal based on the inclusion
of superfluous material is inappropriate. Id. at 820-21
(quotation marks omitted); see also Bennett v. Schmidt,
153 F.3d 516, 518 (7th Cir. 1998) (“Prolixity is a bane
of the legal profession but a poor ground for rejecting
potentially meritorious claims. Fat in a complaint can be
ignored, confusion or ambiguity dealt with by means
other than dismissal.”); cf. Hrubec v. Nat’l R.R. Passenger
Corp., 981 F.2d 962, 963 (7th Cir. 1992) (complaints con-
strued in favor of drafters in order to do substantial
justice). But see United States ex rel. Garst v. Lockheed-
Martin Corp., 328 F.3d 374, 378 (7th Cir. 2003) (“Length
may make a complaint unintelligible[] by scattering
12 No. 09-1487
and concealing in a morass of irrelevancies the few al-
legations that matter.”).
Though length alone is generally insufficient to justify
rejecting a complaint, unintelligibility is certainly a legiti-
mate 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, dis-
missal 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. Federal judges
have better things to do, and the substantial subsidy
of litigation (court costs do not begin to cover the
expense of the judiciary) should be targeted on those
litigants who take the preliminary steps to assemble
a comprehensible claim. Garst’s lawyer filed docu-
ments so long, so disorganized, so laden with
cross-references and baffling acronyms, that they
could not alert either the district judge or the defen-
dants 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 unex-
ceptionable.”).
No. 09-1487 13
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 “unintel-
ligible.” Though the complaint was far longer than it
needed to be, prolixity was not its chief deficiency.
Rather, its rampant grammatical, syntactical, and typo-
graphical 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:
• 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.7
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
(continued...)
14 No. 09-1487
7
(...continued)
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 com-
merce 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. § 7201,
et. seq., thereby using the governmental powers with
which they have been entrusted to gain personal or illegiti-
mate 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);
(continued...)
No. 09-1487 15
• 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 De-
fendants were ‘looking for trouble’ where there
was none as distinct from “looking to serve”.
• Failure to follow basic directions. Given three at-
tempts to file a proper complaint, Maksym could
not even bring himself to correct the errors cataloged
by the district court following the first two rejec-
tions. 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
7
(...continued)
720 ILCS 5/1211 (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)&(2) by knowingly obtaining or ex-
erting unauthorized and/or through threat control over
Plaintiff’s property as aforesaid.
16 No. 09-1487
defendants engaged in a pattern or practice of wrong-
ful behavior; (3) Nygren had decision-making author-
ity for the county; and (4) the defendants’ actions
implicated interstate commerce because McHenry
County is near the Wisconsin border.
• 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.
For example, the § 1983 claim does not allege
anything more concrete than that the defendants
violated Stanard’s First, Fourth, Fifth, and Fourteenth
Amendment rights.
• Grammatical and syntactical errors. The district
court put it best: “The grammatical and spelling
errors” are “too numerous to add ‘[sic]’ where re-
quired.”
Perhaps these defects, considered alone, might not
justify the court’s rejection of the second amended com-
plaint. 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
No. 09-1487 17
the extent that discerning the basic legal and factual
basis of the claims is not impossible but merely unneces-
sarily difficult, we restate the primary teaching of Garst:
A federal court is not obligated to sift through a com-
plaint 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.
The court’s decision to dismiss the case with prejudice
was also eminently reasonable. Again, this was Maksym’s
third attempt to plead properly, and he was still far
from doing so. Moreover, Maksym repeatedly failed to
follow explicit directions from the district court about
how to correct specific problems in the first two com-
plaints. The failures are too numerous to list here, but
take as an example Maksym’s approach to the § 1983
claim. As we have noted, the first complaint alleged in
a wholly conclusory fashion that the defendants had
violated Stanard’s First, Fourth, Fifth, Eighth, and Four-
teenth Amendment rights. Reviewing that complaint, the
district court noted that “the allegations in Count III [the
§ 1983 count] do not permit the court to determine
which of the allegations in paragraphs 1-41 . . . support
the alleged violations of the five constitutional amend-
ments referred to in Count III.” The court admonished
Maksym “to be mindful of his obligation . . . to ensure
18 No. 09-1487
that any claims asserted are warranted by existing law
or by a nonfrivolous argument for extending, modifying,
or reversing existing law or for establishing new law.”
The court issued this reminder “in light of the fact that
the current complaint contain[s] several questionable
claims,” noting in particular that it purported to assert
a violation of the Eighth Amendment, which protects
only those who have been convicted of a crime. See Lewis
v. Downey, 581 F.3d 467, 474 (7th Cir. 2009).
Rather than fix these and other errors identified by
the court, Maksym submitted a proposed amended com-
plaint that in most respects used exactly the same lan-
guage, even reasserting the frivolous Eighth Amendment
claim. As the district court noted,
plaintiffs have made no attempt to cure the problems
with the § 1983 based claims . . . . In fact, but for the
adjustment of paragraph numbers, these claims are
unchanged and remain deficient for the reasons
stated in [the court’s previous order]. . . . More-
over, plaintiffs’ counsel has failed to heed the
court’s warning to remain mindful of his obliga-
tions under Rule 11 by continuing to allege a viola-
tion of the Eighth Amendment without any facts
demonstrating the plausibility of such a claim. Failure
to comply with Rule 11 may result in sanctions.
Maksym was then given a third opportunity to plead
correctly despite his flagrant disregard for the court’s
first order. He continued to demonstrate either an inabil-
ity or unwillingness to comply with basic directions.
Although Maksym removed the reference to the Eighth
No. 09-1487 19
Amendment in the § 1983 claim, he made no other legiti-
mate effort to comply with the court’s directives. In
the district court’s words, Maksym’s latest amend-
ment did “nothing to correct the deficiencies previously
identified. The court and defense counsel remain in
the dark as to which acts . . . by which defendants
violated which of the four constitutional provisions
that plaintiffs allege were transgressed.”
It is true that the pleading rules favor decisions on the
merits rather than technicalities, see Foman, 371 U.S. at 182,
and also that leave to amend pleadings should be
freely given, FED. R. C IV. P. 15(a)(2) (“The court should
freely give leave [to amend] when justice so requires.”).
But these general principles have some limits. Leave to
replead need not be allowed in cases of “repeated failure
to cure deficiencies by amendments previously allowed.”
Foman, 371 U.S. at 182. We have shown considerable
deference to the informed judgments of district judges
who must decide whether to dismiss a case with preju-
dice when counsel repeatedly fails to plead prop-
erly. For example, we affirmed a district court’s decision
to dismiss with prejudice after giving counsel four op-
portunities over four years to file a proper complaint.
Airborne Beepers & Video, Inc. v. AT&T Mobility LLC, 499
F.3d 663, 668 (7th Cir. 2007). In Airborne Beepers the
district court had provided concrete instructions
about how to fix the defects in each successive ver-
sion of the complaint, and still counsel failed to do so.
Id. at 665-66.
The same is true here. Maksym had three oppor-
tunities to file a complaint that complied with the rules,
20 No. 09-1487
yet he failed to follow basic instructions from the court.
In many ways Maksym’s conduct was much more egre-
gious than that of the attorneys in Airborne Beepers.
There, plaintiff’s counsel at least had made concrete
changes to the complaint at each stage in an effort to
comply with the court’s directions. Here, in contrast,
Maksym made almost no changes in each new version
of his complaint. As such, he flagrantly disobeyed
the court’s patient instructions. Moreover, he missed
multiple deadlines and barely made others that had
been repeatedly extended. The record as a whole attests
to the district court’s diligence in attempting to move
the case past the pleadings stage; yet despite the court’s
earnest efforts, Maksym did not take advantage
of the repeated opportunities he was given. Under the
circumstances, the judge was fully justified in not
giving him another chance. See Frederiksen v. City of
Lockport, 384 F.3d 437, 439 (7th Cir. 2004) (dismissal with
prejudice was appropriate where plaintiff failed to
comply with Rule 10(b) over multiple attempts and years
and where district court reasonably viewed failure to
comply as defiance of court orders). The principle that
leave to amend should be freely granted does not
require district judges to repeatedly indulge attorneys
who show little ability or inclination to comply with
the rules. Cf. Atkins v. City of Chicago, 631 F.3d 823, 832
(7th Cir. 2011) (“The plaintiff’s lawyer has had four bites
at the apple. Enough is enough.”).
One final note: Compounding the problems he ex-
hibited in the district court, Maksym failed to file a rea-
sonably coherent brief on appeal. All the deficiencies
No. 09-1487 21
that plagued the various versions of the complaint
also infected his briefs here. Maksym never directly
addressed the issues before this court, relying instead
on cases of marginal or no relevance. In the table of
authorities in his opening brief, he cites 81 cases, but
almost all of them are completely irrelevant to the
issues presented here. In his reply brief, after the defen-
dants had crystallized the issues, Maksym again failed
to meaningfully—or even comprehensibly—articulate
an argument. His appellate briefing was characterized
by a reliance on irrelevant, conclusory, and often inco-
herent arguments of which the following is a representa-
tive example: “Plaintiffs claims were not ‘intelligible’—
no ‘needle in a haystack’ as Appellees’ claim.”
In short, Maksym’s entire approach to this case was
alarmingly deficient. For all the foregoing reasons, we
hold that the district court was well within its discre-
tion to deny leave to file the second amended com-
plaint and to dismiss the case with prejudice. We also
order Maksym to show cause within 21 days why
he should not be removed or suspended from the bar
of this court or otherwise disciplined under Rule 46(b) or
(c) of the Federal Rules of Appellate Procedure. We
also direct the clerk of this court to send a copy of
this opinion to the Attorney Registration and Dis-
ciplinary Commission of Illinois for any action it deems
appropriate.
A FFIRMED.
9-19-11