In the

    United States Court of Appeals
                 For the Seventh Circuit
                     ____________________
No. 17-2582
LEONARD THOMAS,
                                                  Plaintiff-Appellant,
                                 v.

NICHOLAS P. WARDELL, et al.,
                                               Defendants-Appellees.
                     ____________________

         Appeal from the United States District Court for the
         Northern District of Indiana, South Bend Division.
          No. 15-cv-548 — Joseph S. Van Bokkelen, Judge.
                     ____________________

   ARGUED DECEMBER 13, 2019 — DECIDED MARCH 4, 2020
               ____________________

   Before MANION, KANNE, and BRENNAN, Circuit Judges.
    BRENNAN, Circuit Judge. Indiana inmate Leonard Thomas
sued state correctional officials, alleging deficient health care,
inadequate conditions of confinement, and that officers
treated him with excessive force. The district court found
Thomas’s pro se complaint deficient and gave him opportu-
nities to remedy its problems but ultimately dismissed his
case for failure to prosecute. The court also denied three re-
quests by Thomas for appointed counsel.
2                                                              No. 17-2582

   Because Thomas made reasonable attempts to obtain
counsel and the district court did not assess whether Thomas
appeared competent to litigate the case given its difficulty, we
conclude the district court abused its discretion by denying
Thomas’s requests to appoint counsel. This outcome preju-
diced Thomas, so we reverse and remand for an attorney to
be appointed for him.
    The district court also provided insufficient grounds on
which to dismiss Thomas’s case for failure to prosecute.
Therefore we also vacate the dismissal of Thomas’s case, rein-
state it, and remand the case to proceed.
                                        I.
    Thomas was convicted of the voluntary manslaughter of
his uncle and is serving a 40-year sentence at the Westville
Correctional Facility in LaPorte County, Indiana. 1 He has a
history of mental illness which began before his incarceration;
the symptoms of which include suicidal ideations, paranoia,
and hallucinations. Thomas has also been diagnosed with ep-
ilepsy, antisocial personality disorder, and anxiety, for which
he has received various medications while incarcerated.




    1 Since 2014 Thomas has been housed in isolation at this facility’s
Westville Control Unit. In June 2015 Thomas was transferred to the Wa-
bash Valley Correctional Facility, just south of Terre Haute, Indiana,
where he was assigned to the special needs unit for inmates diagnosed as
seriously mentally ill. In January 2016 Thomas was transferred back to
Westville and its control unit. We do not conclude these transfers im-
pacted Thomas’s litigation of this case. See, e.g., James v. Eli, 

,
327 (7th Cir. 2018) (noting transfer of facilities can affect difficulty of pro
se prisoner litigating a case).
No. 17-2582                                                    3

    In late 2015, proceeding pro se, Thomas sued numerous
correctional officers for a host of claims. He alleged his re-
quests for medical care—especially concerning his mental
health treatment—were improperly denied or ignored.
Thomas saw a psychiatrist and a psychologist but complained
about the effects of psychotropic medications which were
then discontinued. He also alleged correctional officials failed
to protect him from self-harm. Thomas described numerous
incidents which he believes support his claims, including
three suicide attempts over about one year and an incident in
which he was pepper sprayed.
    For about 20 months Thomas’s case traveled a lengthy
journey which included amendments to his complaint and
denials of his requests for counsel. Within the first month
Thomas twice asked the district court to appoint him a lawyer
(“2015 requests”). Before ruling on those motions, though, the
court struck his complaint for containing too many unrelated
issues and parties but granted him leave to amend. Within a
month Thomas amended his complaint, but the court quickly
struck that pleading for the same reason and again granted
him leave to amend.
    Shortly after striking the complaint a second time, the dis-
trict court denied Thomas’s two 2015 requests for counsel. In
its order the district court cited this court’s familiar decision
on appointment of counsel, Pruitt v. Mote, 

(7th
Cir. 2007) (en banc), and concluded that Thomas had not
made a reasonable effort to obtain counsel on his own. While
Thomas had written 14 attorneys seeking representation, the
court found those letters did not provide information about
the claims Thomas was pursuing and some pre-dated certain
events in his complaint. The court decided that even if
4                                                  No. 17-2582

Thomas had reasonably tried to find a lawyer, the claims
Thomas would pursue were unclear given the number of de-
fendants he had listed (26 initially, 9 after amendment). The
district court noted that Thomas “is seriously mentally ill,”
had engaged in previous suicide attempts, and had received
assistance from other inmates. But the court also cited
Thomas’s medical records that showed average intellect, in-
tact memory, and a logical thought process, as well as
Thomas’s numerous coherent requests for medical care. On
this record, the district court concluded that Thomas, even
without assistance from other inmates, could prepare an
amended complaint and move for appointment of counsel
again, if necessary.
    In March of 2016, Thomas filed a second amended com-
plaint which remained pending for some time until the dis-
trict court struck it, again for containing too many unrelated
claims and parties. That version of the complaint predomi-
nately alleged that Thomas was denied necessary medical
treatment for his mental illness by healthcare providers and
correctional officials. The district court granted Thomas time
to amend his complaint or face dismissal. The court also di-
rected the clerk of court to send Thomas a prisoner complaint
form and instructed Thomas how to proceed with his claims.
    Thomas followed later that year with his third motion for
appointment of counsel (“2016 request”). He pleaded his
mental illness and his epilepsy and asked the court to appoint
a particular attorney who represented him in a different case
in the U.S. District Court for the Southern District of Indiana,
No. 17-2582                                                                   5

even if she could only help him amend his complaint. 2 The
following day the district court denied the request concluding
that Thomas himself could ask the attorney who represented
him in the other case to represent him here. Even more, the
district court found that Thomas’s failure to approach that at-
torney showed Thomas had not reasonably attempted to ob-
tain counsel on his own, as Pruitt requires. The court also
ruled on a motion by Thomas to obtain more time to amend
his complaint. Rather than rule on serial requests for exten-
sions, the court granted his motion to amend his complaint
but stayed the case and statistically closed it. 3
    After not hearing from Thomas for nearly six months, the
court gave Thomas one month to show cause why this case
should not be dismissed as abandoned. The court stated:
“[Thomas] is CAUTIONED that if he does not respond by
that deadline, this case will be dismissed without further no-
tice.” After the deadline passed without word from Thomas,
the district court dismissed this case pursuant to Federal Rule
of Civil Procedure 41(b).
   Thomas timely appealed and challenges the district
court’s dismissal of his case for failure to prosecute, its failure

    2 Our review shows that Thomas filed seven cases in the U.S. District
Court for the Southern District of Indiana between April 2012 and March
2019, all of them now closed.
    Thomas has filed three cases in the U.S. District Court for the Northern
District of Indiana between November 2015 and now. In addition to this
case, one other remains open.
    3 Administratively closing a case moves it to a court’s inactive docket,

while the court retains jurisdiction for purposes of future activities on the
case. See, e.g., American Cas. Co. of Reading, PA v. Schilli Transp. Svcs., 

, *2 (N.D. Ind. 2011).
6                                                         No. 17-2582

to sever claims instead of dismissing his case for including
unrelated claims, its denials of his request to appoint counsel
under 28 U.S.C. §1915(e)(1), and its decision to not screen his
complaint under 28 U.S.C. § 1915A.
                                    II.
   We first consider the question of appointed counsel for
Thomas. Resolution of his other arguments proceeds from
there. 4
    We review a decision not to appoint counsel for abuse of
discretion. 

. The district court does not
abuse its discretion unless: (1) the record contains no evidence
upon which the court could have rationally based its decision;
(2) the decision is based on an erroneous conclusion of law;
(3) the decision is based on clearly erroneous factual findings;
or (4) the decision clearly appears arbitrary.” 

v. Gentiva Health Servs., 

, 755 (7th Cir. 2004)).
    A. Appointment of Counsel
    A plaintiff such as Thomas does not have a statutory right
to court-appointed counsel in federal civil litigation, although
an indigent litigant 5 may ask the court to request an attorney
to represent him. 28 U.S.C. § 1915(e)(1). Appointment is per-
missive under this statute, which provides a court “may” re-
quest an attorney represent a party. The decision whether to


    4 Because of our resolution of Thomas’s appeal on appointment of
counsel grounds, we do not reach Thomas’s argument that the district
court failed to screen his complaint under 28 U.S.C. § 1915A.
    5Early on the district court found Thomas indigent. In this appeal
Thomas paid the full filing fee, and he has been ably represented by ap-
pointed appellate counsel with our sincere thanks and appreciation.
No. 17-2582                                                   7

recruit pro bono counsel is left to the district court’s discre-
tion. 

.
   That discretion is governed by the legal standard an-
nounced in Pruitt:
       When confronted with a request under
       § 1915(e)(1) for pro bono counsel, the district
       court is to make the following inquiries: (1) has
       the indigent plaintiff made a reasonable attempt
       to obtain counsel …; and if so, (2) given the dif-
       ficulty of the case, does the plaintiff appear com-
       petent to litigate it 

–55 (citing Farmer v. Haas, 

, 321–22
(7th Cir. 1993)).
    Pruitt first requires the indigent litigant to reasonably at-
tempt to get a lawyer. When the district court denied
Thomas’s 2015 requests for counsel, it enumerated the law-
yers whom he contacted, when he did so, and what he said to
them. In its denial of Thomas’s 2016 request for counsel, the
district court addressed Thomas’s request that his counsel in
another case be appointed here. In its brief denial order (about
a single page of text) the court concluded that Thomas could
ask the lawyer himself and that his failure to do so proves he
did not reasonably attempt to obtain counsel on his own.
    On this first requirement, the district court satisfactorily
evaluated the 2015 requests, but the court’s brief order on
Thomas’s 2016 request for counsel was insufficient. The dis-
trict court cursorily dismissed Thomas’s 2016 request on the
grounds that Thomas did not personally reach out to that law-
yer. Thomas’s working relationship with that attorney and
8                                                             No. 17-2582

the district court’s failure to take that relationship into ac-
count calls into question the district court’s conclusion that
Thomas did not reasonably try to get a lawyer.
    The second requirement under Pruitt is whether the plain-
tiff appeared competent to litigate the case in light of its diffi-

. 6 As this court stated in Pruitt:
         [t]he inquiries are necessarily intertwined; the
        difficulty of the case is considered against the
        plaintiff’s litigation capabilities, and those capa-
        bilities are examined in light of the challenges
        specific to the case at hand. … [T]he question is
        whether the difficulty of the case—factually and
        legally—exceeds the particular plaintiff’s capac-
        ity as a layperson to coherently present it to the
        judge or jury himself.

“[B]ecause the decision belongs to the district court,
we have resisted laying down categorical rules regarding re-
cruitment of counsel in particular types of cases.” 

“[T]here are no hard and fast rules for evaluating the factual
and legal difficulty of the plaintiff’s claims,” nor are there
“fixed requirements for determining a plaintiff’s competence
to litigate his own case … .” 

Some of the circum-
stances that require judicial consideration are the phase of the


    6 Among its rulings, Pruitt clarified that the district court can only de-
cide based on the record when the motion was brought, and that appellate
review is limited to the record when the decision was 

. Pruitt also explained the district court, not this court, is to undertake
the analysis of the degree of case difficulty as against the plaintiff’s com-
petence to litigate it himself. 

No. 17-2582                                                     9

litigation, if the prisoner has been transferred between facili-
ties, if the claims involved the state of mind of the defendant
such as those involving deliberate indifference, and if the case
involves complex medical evidence, including expert testi-
mony. See James v. Eli, 

, 327–28 (7th Cir. 2018).
    The district court’s assessment of Thomas’s 2015 requests
for counsel did not expressly consider “competency,”
although it did note Thomas’s mental illness and cited to par-
ticular records on Thomas’s mental condition. The court also
ruminated on what types of motions and filings Thomas
might make due to his mental illness.
    Such consideration is absent, however, from the order
denying Thomas’s 2016 request for counsel. That order does
not consider, or even mention, Thomas’s competence to liti-
gate this case himself, as required by 

. In
the order on the 2015 requests the court at least cited
Thomas’s intellectual capacity and psychological history. But
both denial orders fail to cover relevant topics, such as
Thomas’s literacy, communication skills, and litigation expe-
rience. 

Thomas’s lack of a high school educa-
tion should have been considered but was not. See Navejar v.
Iyiola, 

, 696 (7th Cir. 2013).
    Thomas’s claims also involve complex medical evidence.
His suit includes claims against a psychologist for denial of
necessary medical treatment, which raises questions about
the standard of care. See 

(acknowledging
that cases involving complex medical evidence are typically
more difficult for pro se litigants). Thomas also alleges he re-
ceived prescription medications inconsistently and he was not
properly treated for his conditions. Further, Thomas has been
10                                                   No. 17-2582

diagnosed with serious psychological and medical condi-
tions, including schizophrenia, antisocial personality disor-
der, anxiety, and epilepsy. His psychological and medical
diagnoses are relevant to determinations of whether prison
officials satisfied their standard of care.
   But neither of the district court’s orders denying counsel
contend with the complexities of this medical evidence, or
grapple with Thomas’s allegations that certain defendants de-
viated from the standard of care. 

thereat).
The district court did not show awareness of this complex
medical evidence or the standard of care, as required. 

the district court was required to weigh the
difficulty of Thomas’s claims against his competency to liti-
gate those 

. That did not happen here.
The district court did not consider the factual and legal com-
plexity of this case given Thomas’s capabilities as required by
Pruitt and this court’s case law since. See, e.g., 

–30. Thomas’s history of mental illness, in particular,
should have been relevant to the district court’s evaluation of
his competency. See Santiago v. Wells, 

, 762 (7th
Cir. 2010) (“[P]sychological history, to the extent that [it] [is]
known, [is] relevant.”); Walker v. Price, 

, 940 (7th
Cir. 2018) (“Not every cognitive limitation will require the
district court to recruit a lawyer, but the court should have
considered how [the plaintiff]’s mental health history would
affect his ability to think on his feet.”). On this point, we ask
“not whether [the judge] was right, but whether [the judge]
was reasonable.” 

. The absence of such
reasoning in the district court’s orders means that the reason-
ableness standard was not satisfied here.
No. 17-2582                                                     11

    As noted above, the decision whether to appoint counsel
is a discretionary call. Exercise of discretion requires a court
to consider those factors described in Pruitt. The district court
here fell short of that mark. We conclude that the district
court’s rulings on the two requirements from Pruitt are arbi-
trary, and that on some requirements the record contains no
evidence upon which the court could have rationally based its
decisions. So the district court abused its discretion in deny-
ing Thomas’s request for appointed counsel.
     “Even if a district court’s denial of counsel amounts to an
abuse of its discretion, we will reverse only upon a showing
of prejudice.” 

. “[A]n erroneous denial
of pro bono counsel will be prejudicial if there is a reasonable
likelihood that the presence of counsel would have made a dif-
ference in the outcome of the litigation.” 

counsel here would have significantly
changed the outcome of this case. The advice and counsel of
an attorney—which the record reveals Thomas wanted very
much—most likely would have resulted in Thomas respond-
ing to the court’s order to show cause why this case should
not be dismissed. This would have allowed Thomas’s claims
to proceed, so necessarily the lack of an attorney had a sub-
stantial impact.
   Further, a plaintiff’s deficient pretrial performance can es-
tablish prejudice. 

. This court can con-
sider a plaintiff’s inability to state a claim at the pleading stage
when ruling on a motion to appoint counsel. Armstrong v.
Krupiczowicz, 

, 1008 (7th Cir. 2017). On three oc-
casions Thomas was unable to comply with the district court’s
pleading requirements. The district court did not include this
12                                                   No. 17-2582

factor in its decisions, even as it ruled repeatedly that Thomas
had failed to meet the pleading requirements.
    We are aware that appointment of counsel is a difficult de-
cision, 

–31, and that district courts de-
serve substantial leeway in such a fact-bound decision. 

-59. But the governing legal stand-
ard from Pruitt is not met here because the district court failed
to weigh the difficulty of Thomas’s claims against his compe-
tency to litigate his allegations. Thus, the district court abused
its discretion in denying Thomas’s motions for counsel, and
this erroneous denial prejudiced Thomas because it most
likely resulted in his case being dismissed. So we reverse and
remand for counsel to be appointed for Thomas.
     B. Dismissal of Thomas’s Case
    Thomas has also appealed the district court’s dismissal of
this case for failure to prosecute and the district court’s han-
dling of the misjoinder issues in his complaint. We begin with
the district court’s dismissal for failure to prosecute, which we
review for an abuse of discretion. See Johnson v. Chicago Bd. of
Educ., 

, 732 (7th Cir. 2013).
    District courts generally have broad authority to dismiss a
case for failure to prosecute, and this includes failure to com-
ply with valid orders. See Wilson v. Bruce, 400 Fed. App’x 106,
108 (7th Cir. 2010). In its dismissal order the district court
listed one reason for terminating the case: Thomas had missed
the court-imposed deadline to contact his attorney in the
other case and to amend his complaint.
    When dismissal is based on a failure to prosecute, a court
is required to show a record of delay, contumacious conduct,
No. 17-2582                                                     13

or that lesser sanctions proved unavailable, as well as the prej-
udice that the delay caused the defendant. Kasalo v. Harris &
Harris, Ltd., 

, 561 (7th Cir. 2011). The district court
did not make any such findings, and we do not see the record
supporting such findings. The record does not reveal delay by
Thomas or obstinately disobedient conduct. While Thomas
failed to comply with the May 2017 order to show cause,
Thomas otherwise showed diligence in advancing his case.
He requested counsel when he first filed the case as well as a
month later. He amended his complaint about a month after
its initial dismissal; the same with a second amended com-
plaint. He updated the court numerous times on his change
of address. When review of his second amended complaint
took some time, he twice requested a status hearing. And
when his second amended complaint was struck, Thomas
filed his third request for counsel. Against this backdrop—a
history of compliance with other deadlines—dismissal with
prejudice for one missed deadline is harsh. See Sroga v. Huber-
man, 

, 983 (7th Cir. 2013).
    This dismissal was with prejudice under Federal Rule of
Civil Procedure 41(b), and dismissal for failure to prosecute is
a tough sanction. Dunphy v. McKee, 

, 1299 (7th
Cir. 1998). Lesser sanctions than dismissal were available. For
example, the district court could have issued Thomas a sec-
ond warning or dismissed allegedly nonviable claims. Those
steps did not happen here.
    Prejudice is another factor when considering whether dis-
missal for failure to prosecute is appropriate. 

. Courts have found dismissal for failure to prosecute
more fitting if the delay caused prejudice to the defendant. See

. The correctional officials have not cited
14                                                  No. 17-2582

any prejudice to themselves that would warrant dismissal.
Thomas’s case was dismissed before any defendants were
served, so they could have not suffered any prejudice. 

    In dismissing this case the district court cited to a single
missed deadline. No doubt, the district court here was patient
with Thomas, granting him numerous opportunities to
amend his complaint, as well as time to approach his counsel
in his other case and to amend his complaint yet again. But
viewing this case in its entirety, dismissal with prejudice due
to one missed deadline “clearly appears arbitrary,” 

, and an abuse of discretion. Moreover, while
Thomas failed to comply with the district court’s order to
show cause why the case should not be dismissed, we can
reasonably conclude this failure followed from Thomas pro-
ceeding without counsel. Reversal of the dismissal and rein-
statement of Thomas’s case follows from our decision that
counsel should have been appointed.
    On appeal Thomas also objects on the ground that the dis-
trict court erred by dismissing his complaint for misjoinder.
He argues the court should have severed or dismissed unre-
lated claims and then screened his complaint. But as the
correctional officials point out, the orders memorializing the
district court’s two-step dismissal process did not list misjoin-
der as a ground for case termination. So we find no reversible
error here. To the extent joinder issues exist in this case,
Thomas’s appointed counsel can address these difficulties on
remand.
No. 17-2582                                                    15

                                 III.
   Thomas was indigent and made reasonable attempts to
obtain counsel. The district court did not evaluate whether
Thomas appeared competent to litigate his claims in light of
the case’s difficulty. The district court abused its discretion to
Thomas’s prejudice in denying his request for counsel. So we
REVERSE the decision not to appoint counsel and ORDER that
counsel be appointed in the district court.
   At oral argument we asked Thomas’s appellate counsel if
she had interest in representing Thomas on remand, which
she did. On remand the district court can consider appointing
Thomas’s appellate counsel as his counsel in the district court.
    On this case’s facts and its procedural history, dismissal
for failure to prosecute as a result of one missed deadline is
arbitrary and an abuse of discretion. So we also VACATE the
district court’s dismissal of this case, reinstate this case, and
REMAND the case to the district court for further proceedings.