                           In the

United States Court of Appeals
              For the Seventh Circuit

No. 10-3391

D ARRIN G RUENBERG ,
                                            Plaintiff-Appellant,
                              v.

D EBRA G EMPELER, Captain, et al.,

                                         Defendants-Appellees.


          Appeal from the United States District Court
               for the Eastern District of Wisconsin.
         No. 09-CV-00455—William C. Griesbach, Judge.



     A RGUED A PRIL 4, 2012—D ECIDED S EPTEMBER 26, 2012




 Before E ASTERBROOK, Chief Judge, and F LAUM and
M ANION, Circuit Judges.
  M ANION, Circuit Judge.      While incarcerated for
burglary, Darrin Gruenberg seized a set of keys from a
prison security guard and swallowed them. He was
taken to a hospital, where an x-ray showed that the
keys were lodged in his abdomen. A physician told the
prison officials that Gruenberg would probably pass
the keys naturally within five days. They returned him
2                                               No. 10-3391

to the prison and kept Gruenberg naked and in
restraints for five days until he passed the keys. After
five days, Gruenberg had not yet passed them and
surgery was needed to remove them. Gruenberg sued
the officials, claiming they violated his Eighth Amend-
ment right to be free from cruel and unusual punishment
by keeping him restrained for five days. The district
court granted summary judgment in favor of the defen-
dants, and because the officials have qualified im-
munity, we affirm.


                             I.
  On April 19, 2006, a security officer at Waupun Cor-
rection Institution (“Waupun”) was administering med-
ication to a prisoner, Darrin Gruenberg, 1 when
Gruenberg pulled the officer’s arm inside his cell and
grabbed the officer’s key ring. The key ring held three
keys: a handcuff key, a key to activate cell doors, and a
key for the padlock on waist restraints. The officer
ordered Gruenberg to return the keys, but Gruenberg
exclaimed, “watch this,” and proceeded to place each
key into his mouth and then swallow each one.
 This set off a security alert in the prison, and the
warden was immediately notified. Gruenberg was



1
  Gruenberg began serving a sentence for burglary in 1999.
Since first entering the Wisconsin Department of Corrections,
he has accumulated more than 230 misconduct reports at
seven different facilities. See Gruenberg v. Schneiter, 474
Fed. Appx. 459 (7th Cir. 2012).
No. 10-3391                                              3

taken to the emergency room at Waupun Memorial
Hospital for x-rays to determine the location of the keys.
The x-ray confirmed that they were in his abdomen. The
physician who treated Gruenberg believed that the
keys would pass through his system within five days
if Gruenberg took medication to help them pass.
Gruenberg agreed to take the medication, and was re-
turned to Waupun.
  The warden, the prison’s medical staff, and the
prison’s security staff developed a protocol for Gruen-
berg until the keys passed through his system. Gruenberg
was placed in Waupun’s Health and Segregation
Complex (“HSC”), the unit that houses inmates with
pending disciplinary hearings for rule violations, who
have been found guilty of rules violations, or who are
in administrative confinement. During his confinement
in the HSC, which lasted five days, he was kept naked
and restrained for approximately 22 to 23 hours per
day. Specifically, Gruenberg was restrained in a chair
during the day for twelve hours, and restrained to a
bed for twelve hours during the evening.2 The prison
officials thought it was necessary to keep Gruenberg
restrained to prevent him from re-swallowing the keys




2
  Gruenberg was restrained with RIPP restraints, which are
polypropylene belts approximately two inches wide. They are
adjusted with Velcro closures. The restraints were placed
around Gruenberg’s upper chest, wrists, thighs, and legs.
4                                                  No. 10-3391

after he had passed them.3 Twice per shift, on the first
and second shifts, Gruenberg was released from the
chair or bed and allowed to walk for 30 minutes.
   During the five-day period, Gruenberg complained of
being cold and repeatedly asked for a blanket. 4 This
request was denied because, the prison officials asserted,
a blanket would restrict the view of security staff who
monitored Gruenberg to ensure he was breathing. The
prison staff also thought it was necessary to monitor
any possible expulsion of the keys from Gruenberg, as
one of the keys he swallowed was a master key that
would open any restraint used in the prison and
another key could open any cell door in the prison.
Gruenberg was fed “nutri-loaf” (a sort of nutritional
food loaf which does not require utensils to eat) while
restrained, and was denied permission to brush his
teeth or wash his hands (but was permitted to shower
once). Gruenberg also complained that he was forced to
lie in his own feces on two occasions, despite the offi-
cials’ assertion that Gruenberg was allowed to use
the bedpan and urinal whenever he asked to do so.
  The security staff checked on Gruenberg every
15 minutes while he was restrained, and nurses from the


3
  This has actually happened. See, e.g., Malone v. Oklahoma, 168
P.3d 185, 213 (Okla. Crim. App. 2007) (an inmate who secretly
brought a key into jail by swallowing it retrieved it from his
feces after passing it and then swallowed it again).
4
  The record shows that the indoor cell temperatures of the
area in which Gruenberg was restrained varied between
72 degrees and 77 degrees during the five-day period.
No. 10-3391                                                5

prison’s Health Services Unit checked his condition
every four hours. The HSC’s clinical staff also saw
him regularly. All told, during the five-day period
Gruenberg was restrained he was checked by nurses
31 times and assessed by the clinical staff nine times.
He was also visited by the Waupun Psychological
Services Staff each day, who noted in several reports
that Gruenberg was frustrated by the situation but re-
mained cooperative.
  By April 24 (the fifth day), Gruenberg was experi-
encing pain in his lower spine, tailbone, buttocks, and
joints. He developed cuts and raw skin on his wrists
and ankles from the restraints. He was taken to the
hospital for another x-ray, which revealed that the
keys had not moved from his abdomen. The prison
staff then determined that Gruenberg no longer needed
to be restrained because it was unlikely that he would
be able to pass the keys naturally. He was placed in a
“dry cell” in the prison’s Health Services Unit (a dry
cell being one in which the water has been turned off
so that the toilet does not flush). The health services
staff could monitor Gruenberg in this cell and, being
isolated, it was impossible for Gruenberg to pass the
keys to another inmate if he were to expel them natu-
rally. Additional security staff were assigned to sit outside
Gruenberg’s cell to monitor his bowel movements to
determine if the keys passed.
  The keys did not pass, and on April 26, Gruenberg
was again taken to the hospital where he underwent an
endoscopy and colonoscopy to remove the keys. The
6                                              No. 10-3391

endoscopy procedure successfully removed two of the
keys, but the third key (the padlock key) remained in
his body. Finally, on May 4, Gruenberg passed the re-
maining key naturally.
   Gruenberg filed a pro se suit against some 25 staff
members and officials at Waupun on May 5, 2009,
asserting that the defendants violated his Eighth and
Fourteenth Amendment rights under 42 U.S.C. § 1983.
Gruenberg also filed a motion requesting the appoint-
ment of counsel. On August 24, 2009, the district court
denied Gruenberg’s request for counsel, finding that
Gruenberg demonstrated his “ability to petition this
court for redress of his grievances.” On December 17,
2009, the defendants filed a motion for summary judg-
ment, and on September 30, 2010, the district court
granted summary judgment in favor of the defendants
on all claims. The district court ruled that a trier of
fact could find that Gruenberg’s Eighth Amendment
rights were violated, but held that the doctrine of
qualified immunity shielded the defendants from suit.
Gruenberg’s Fourteenth Amendment procedural due
process claim was dismissed on the grounds that it was
“better conceptualized under the Eighth Amendment,”
see Bowers v. Pollard, 345 Fed. Appx. 191, 196 (7th Cir.
2009), not the Fourteenth Amendment. Gruenberg ap-
pealed in February 2011, and in June 2011 we determined
that counsel should be appointed to represent Gruen-
berg on appeal. We issued an order striking the previously-
filed briefs, and Gruenberg, now represented by counsel,
filed his appeal in November 2011.
No. 10-3391                                               7

                            II.
   We review the district court’s grant of summary judg-
ment de novo. Int’l Union v. ZF Boge Elastmetall LLC, 649
F.3d 641, 646 (7th Cir. 2011). In considering the district
court’s grant of summary judgment, we construe all
facts and draw all inferences in favor of Gruenberg,
and will affirm if “the movant shows that there is no
genuine dispute as to any material fact and the movant
is entitled to judgment as a matter of law.” Id.
  Gruenberg argues that because he was kept
immobilized, naked, cold, and in pain for five days, the
defendants deprived him of basic human needs and
violated his clearly established rights under the Eighth
Amendment. The defendants counter that the novelty of
Gruenberg’s situation and his past history of being a
difficult prisoner necessitated restraining Gruenberg,
that the unique circumstances presented by Gruenberg’s
situation demonstrate that none of the defendants
could have been on notice that they were violating
a clearly established constitutional right, and that the
district court properly found that none of the defendants
acted with deliberate indifference to Gruenberg’s needs.
Thus, they argue, the district court correctly applied
qualified immunity.
   We review the validity of a qualified immunity defense
de novo. Elder v. Holloway, 510 U.S. 510, 516 (1994). Quali-
fied immunity shields government officials from
liability under Section 1983 “for actions taken while
performing discretionary functions, unless their conduct
violates clearly established statutory or constitutional
8                                               No. 10-3391

rights of which a reasonable person would have
known.” Brokaw v. Mercer County, 235 F.3d 1000, 1022 (7th
Cir. 2000). It protects “all but the plainly incompetent
or those who knowingly violate the law. . . . If officers of
reasonable competence could disagree on the issue [of
whether or not an action was constitutional], immunity
should be recognized.” Malley v. Briggs, 475 U.S. 335, 341
(1986). To defeat a claim of qualified immunity, Gruenberg
must show that the defendants violated a constitutional
right and demonstrate that the right in question was
clearly established at the time of the alleged violation.
Saucier v. Katz, 533 U.S. 194, 201-02 (2001).
   Thus, when analyzing a qualified immunity defense,
courts consider whether the alleged facts demonstrate
a constitutional violation, and whether the constitu-
tional right was clearly established. Pearson v. Callahan,
555 U.S. 223, 232 (2009). A constitutional right is clearly
established when “it would be clear to a reasonable
officer that his conduct was unlawful in the situation
he confronted.” Saucier, 533 U.S. at 202; see also Estate
of Escobedo v. Bender, 600 F.3d 770, 779 (7th Cir. 2010)
(“For a constitutional right to be clearly established,
its contours must be sufficiently clear that a reasonable
official would understand that what he is doing
violates that right.”) (quotations omitted).
  Gruenberg claims that the defendants violated his
constitutional right to be free from cruel and unusual
punishment. Specifically, he argues that when the de-
fendants restrained him naked for five days, they
deprived him of basic human needs and thus violated
No. 10-3391                                                   9

his clearly established rights under the Eighth Amend-
ment. To defeat the defense of qualified immunity,
Gruenberg must present evidence from which the finder
of fact could conclude that the conditions of his confine-
ment resulted in “the denial of the minimal civilized
measure of life’s necessities,” and that the defendants
were “deliberately indifferent” to the conditions in
which he was held. Townsend v. Fuchs, 522 F.3d 765, 773
(7th Cir. 2008) (citations omitted); see also Estelle v. Gamble,
429 U.S. 97, 104 (1976) (“deliberate indifference” to a
prisoner’s serious medical needs is cruel and unusual
punishment). The Eighth Amendment proscribes condi-
tions that “involve the wanton and unnecessary inflic-
tion of pain.” Rhodes v. Chapman, 452 U.S. 337, 347 (1981).
The Supreme Court has held, however, that “[n]ot
every governmental action affecting the interests or well-
being of a prisoner is subject to Eighth Amendment
scrutiny . . . .” Whitley v. Albers, 475 U.S. 312, 319 (1986).
Indeed, “conduct that does not purport to be punish-
ment at all must involve more than ordinary lack of
due care for the prisoner’s interests or safety. . . . It is
obduracy and wantonness, not inadvertence or error
in good faith, that characterize the conduct prohibited
by the Cruel and Unusual Punishments Clause . . . .” Id.
  Even if we were to find, at least in some context, that
the conditions under which Gruenberg was confined for
five days could have amounted to cruel and unusual
punishment, the defendants here are entitled to
qualified immunity. As Judge Griesbach reasoned in his
opinion, “[t]his case presents a classic situation in which
the doctrine [of qualified immunity] is required to shield
10                                           No. 10-3391

officials acting in good faith in responding to a unique
situation that involved both inmate health and prison
security.” While the condition in which Gruenberg
was held was undoubtedly uncomfortable, there is no
evidence in the record that demonstrates that any
member of the prison staff showed “deliberate indif-
ference” to Gruenberg’s health or safety. In fact, the
record shows otherwise—Gruenberg was monitored
constantly to ensure that he was not in danger, and was
visited 31 times by nurses and nine times by the
prison’s clinical staff. The prison’s psychological staff
also visited Gruenberg several times to check on his
mental health. As Judge Griesbach rightly noted, such
frequent medical and mental health monitoring is incon-
sistent with claims that the defendants intentionally
or recklessly subjected Gruenberg to cruel and unusual
punishment.
  Furthermore, instead of forcing Gruenberg to undergo
immediate surgery to remove the keys (a decision
which could have raised more serious Eighth Amend-
ment concerns than presented here), the defendants
relied on the advice of a physician who thought that
Gruenberg would pass the keys within five days. And
while keeping Gruenberg in restraints for five days ulti-
mately proved ineffective in light of the fact that he
had two of the keys removed later via a colonoscopy
and the third passed naturally while he was held unre-
strained in a dry cell, qualified immunity protects deci-
sions made in the moment, when the benefit of hindsight
No. 10-3391                                                     11

is not available.5 As we have previously held, qualified
immunity depends “upon all the circumstances as they
reasonably appeared to the official at the time the chal-
lenged conduct took place.” Crowder v. Lash, 687 F.2d
996, 1006-07 (7th Cir. 1982).
  Thus, the defendants here faced what Judge Griesbach
called an “unprecedented breach of security”: an excep-
tionally disruptive prisoner with over 230 documented
citations for misconduct who stole and then swallowed
three critical security keys.6 The potential security prob-
lems this could cause are numerous, and the defendants
had to ensure that Gruenberg would not pass the keys
only to re-swallow them. While a less disruptive
prisoner may not have merited such measures, Judge
Griesbach rightly pointed out that the defendants here
were in “uncharted waters” and that the Eighth Amend-
ment “does not provide a clear roadmap as to how


5
  While our analysis here focuses on qualified immunity, we
note that the Supreme Court rejected a post-hoc reasonableness
approach that would deem acts as cruel and unusual punish-
ment due to the fact that they appear to have been unneces-
sary in hindsight. See Whitley, 475 U.S. at 319 (“The infliction of
pain in the course of a prison security measure, therefore,
does not amount to cruel and unusual punishment simply
because it may appear in retrospect that the degree of force
authorized or applied for security purposes was unreasonable,
and hence unnecessary . . . .”).
6
  This is not the first time Gruenberg has attempted to steal a
guard’s keys. See Gruenberg v. Schneiter, 474 Fed. Appx. 459,
460 (7th Cir. 2012)
12                                                   No. 10-3391

prison staff must treat an inmate who has swallowed a
set of keys.” 7 Furthermore, there is no evidence that
the defendants acted with deliberate indifference or
recklessness towards Gruenberg’s health.8 Qualified
immunity is intended to shield officials from liability
when they exercise judgment, and here they exercised
that judgment when dealing with a difficult prisoner in
a unique situation. For those reasons, we affirm the
district court’s grant of qualified immunity.
 Gruenberg also raises a procedural due process claim
under the Fourteenth Amendment, arguing that he has


7
   The district court also raises an interesting point: Gruenberg’s
situation involved more than 25 members of the prison staff,
none of whom evidently thought the protocol developed for
handling Gruenberg was unreasonable. While not dispositive,
the fact that so many individuals found Gruenberg’s treat-
ment to be reasonable seriously undercuts Gruenberg’s claim
that a reasonable person would have been aware that this
conduct violated Gruenberg’s clearly established consti-
tutional rights.
8
  While the defendants have qualified immunity, we hasten to
note that the confinement and treatment of Gruenberg was not
“punishment,” let alone cruel and unusual punishment. The
only thing unusual here was Gruenberg’s extreme behavior:
he grabbed a guard’s arm, pulled it through the bars of his cell,
seized the guard’s key ring, said “watch this,” and then swal-
lowed the keys. This was obviously a serious security problem,
and was exacerbated by Gruenberg’s extensive history of
misbehavior. However, in a different setting, with a less
troublesome prisoner, keeping a prisoner in near-constant
restraints, naked, in a cell under continual observation might
constitute cruel and unusual punishment.
No. 10-3391                                            13

a liberty interest in avoiding being held in restraints
for five days and that the defendants unconstitutionally
deprived him of that interest when he was restrained
without notice or an opportunity to be heard. In essence,
Gruenberg argues that his restraint was punishment
for swallowing the keys, and that he was deprived of
the right to have a hearing before he was placed in re-
straints. The record is devoid of any evidence to
support this claim, and in fact the record entirely
supports the defendants’ contention that placing
Gruenberg in restraints was solely out of a concern
for security.
  Furthermore, we have found only two instances in
which the Fourteenth Amendment’s due process clause
created a liberty interest in the context of a prison
sentence: a transfer to a mental hospital, see Vitek v.
Jones, 445 U.S. 480, 493 (1980), and the involuntary ad-
ministration of psychotropic drugs, see Washington v.
Harper, 494 U.S. 210, 221-22 (1990). Neither is implicated
here, and we have previously held that claims
such as those raised by Gruenberg here “are better con-
ceptualized under the Eighth Amendment.” Bowers, 345
Fed. Appx. at 196. Thus, we affirm the district court’s
grant of summary judgment in favor of the defendants
on Gruenberg’s procedural due process claim.
  Gruenberg also argues that he should be allowed to
advance claims against the defendants under the Fourth
Amendment and under the Fourteenth Amendment
substantive due process clause. However, Gruenberg
mentions these arguments for the first time on appeal. He
14                                              No. 10-3391

concedes that he did not argue these issues because the
district court refused to appoint counsel (see below).
Nevertheless, “(i)t is a well-settled rule that a party op-
posing a summary judgment motion must inform the
trial judge of the reasons, legal or factual, why summary
judgment should not be entered. If it does not do so, and
loses the motion, it cannot raise such reasons on ap-
peal.” Domka v. Portage County, Wis., 523 F.3d 776, 783
(7th Cir. 2008) (quotations omitted); see also Arendt v.
Vetta Sports, Inc., 99 F.3d 231, 237 (7th Cir. 1996) (issues
that are not raised in the district court in response to a
motion for summary judgment are waived on appeal).
Furthermore, as we noted above, Gruenberg’s claims
are better addressed under the Eighth Amendment.
Thus, Gruenberg’s Fourth Amendment and Fourteenth
Amendment substantive due process claims are barred.
   Finally, Gruenberg argues that the district court abused
its discretion when it denied Gruenberg’s request for
counsel. We review a district court’s decision to deny
the appointment of counsel under 28 U.S.C. § 1915(e)(1)
for an abuse of discretion, but will reverse only “upon a
showing of prejudice.” Pruitt v. Mote, 503 F.3d 647, 659
(7th Cir. 2009). Gruenberg repeatedly requested counsel
to advance his claims here, and the district court denied
those requests, finding that, in light of the numerous
pro se lawsuits Gruenberg had filed in the past, Gruenberg
was competent to litigate his case. “An indigent civil
litigant may ask the district court to request an attorney
to represent him pro bono publico.” Id. at 649. When a
litigant requests counsel, the district court must ask
No. 10-3391                                                    15

(1) “has the indigent plaintiff made a reasonable attempt
to retain counsel or been effectively precluded from
making such efforts . . .”; and if so, (2) “given the difficulty
of the case, did the plaintiff appear competent to try it
himself?” Id. at 654.
  Gruenberg did attempt to seek counsel, apparently
contacting eight different attorneys to represent him.
When he was unable to find counsel, he petitioned the
district court to appoint counsel, arguing that his mental
health issues and lack of education precluded him from
conducting discovery and from briefing a response to a
summary judgment motion. The district court disagreed,
holding that, despite Gruenberg’s mental health issues,
he was competent enough to represent himself effec-
tively and to argue his case.
  The district court noted that the facts here were not
so complicated that a reasonable pro se litigant could
not advance them, and that Gruenberg had filed
numerous motions and declarations detailing what
had happened to him and the relief he sought, belying
his incompetence claim. In fact, the district court
pointed out that Gruenberg’s presentation of the case
was significantly above the capabilities of the average
pro se litigant.9 In light of this, the district court did not


9
  This is far from the only case Gruenberg has litigated pro se.
He has filed at least six cases pro se in state and federal court
alleging various violations during his incarceration. See, e.g.,
Gruenberg v. Schneiter, 474 Fed. Appx. 459 (7th Cir.); Gruenberg
                                                    (continued...)
16                                                No. 10-3391

abuse its discretion by ruling that Gruenberg
was competent to advance his case and was not entitled
to appointed counsel.


                             III.
  For the foregoing reasons, we affirm the judgment of
the district court. The defendants are entitled to qualified
immunity on Gruenberg’s Eighth Amendment claims.
Gruenberg’s procedural due process claim fails, and he is
barred from raising Fourteenth Amendment substantive
due process or Fourth Amendment claims on appeal.
Finally, the district court did not abuse its discretion
when it denied Gruenberg’s request for counsel.
                                                   A FFIRMED.




9
   (...continued)
v. Lundquist, 318 Fed. Appx. 424 (7th Cir. 2008); and Gruenberg
v. Pollard, No. 08-cv-0524-slc, 2008 U.S. Dist. WL 4722531
(W.D. Wis. Oct. 22, 2008).


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