Amir Brandy v. City of St. Louis, Missouri ( 2023 )

United States Court of Appeals
For the Eighth Circuit
___________________________
No. 22-2329
___________________________
Amir Brandy
Plaintiff - Appellee
v.
City of St. Louis, Missouri
Defendant - Appellant
John Hayden, COL, in his individual and official capacities
Defendant
William Olsten, Officer, in his individual and official capacities
Defendant - Appellant
____________
Appeal from United States District Court
for the Eastern District of Missouri
____________
Submitted: January 10, 2023
Filed: July 28, 2023
____________
Before GRASZ, MELLOY, and KOBES, Circuit Judges.
____________
GRASZ, Circuit Judge.
Officer William Olsten deployed pepper spray on Amir Brandy and others
during a protest in downtown St. Louis. Brandy sued Officer Olsten, Chief of Police
John Hayden, and the City of St. Louis (collectively, “City Officials”) alleging
various federal and Missouri law claims, including First Amendment retaliation.
The defendants moved for summary judgment on all claims. The district court
granted summary judgment to the City Officials on some of the claims. As relevant
to this interlocutory appeal, however, the district court concluded that neither the
City nor Officer Olsten were entitled to summary judgment on Brandy’s First
Amendment retaliation claim and therefore denied the motion in part. The district
court also reserved ruling on the City Officials’ motion for summary judgment on
two state law claims. We affirm in part and remand for the district court to resolve
the motion on the state law claims.
I. Background
The district court found the following facts to be undisputed. On September
15, 2017, former St. Louis police officer Jason Stockley was acquitted of first-degree
murder charges. There were protests held around St. Louis for the next month with
some becoming violent at times. During a protest on September 29 in downtown St.
Louis, an altercation occurred between officers and protestors, which led to an
officer deploying his taser and arresting two protestors. Officer Olsten and other
officers led an arrested protestor away from the scene. Other protestors began
shouting at and following the officers. Officer Olsten gave the crowd at least two
orders to “get back.” Brandy, who was in the crowd of protestors following Officer
Olsten, saw a pepper spray fogger in Officer Olsten’s hand and yelled: “If you put
that s*** in my face, I’ll f*** you up.” Officer Olsten stepped toward Brandy and
responded: “Come f*** me up then.” Two other officers then placed their hands on
Officer Olsten in order to assist him in moving away.
Brandy and the crowd of protestors stopped following the officers and Officer
Olsten transferred the arrested protestor to other law enforcement. However, Officer
Olsten and Brandy were soon standing face-to-face only a few feet apart. Brandy
-2-
said: “Put that s*** in my face.” Officer Olsten retorted: “Dude, back up.” Brandy
then called Officer Olsten a “p**** a** white boy.” Another protestor, Rasheen
Aldridge, inquired about who tased the arrested protestor and Officer Olsten
responded: “I didn’t tase him.” After this interaction, an unidentified female
protestor in the crowd shouted something. The appellants argue the protestor
shouted, “Shoot this motherf***er” or “shoot this motherf***er back.” While the
appellee contends the protestor yelled: “Shut this motherf***er down.” Immediately
after this unidentified protestor shouted, Officer Olsten deployed his pepper spray,
hitting Brandy, who was directly in front of him, and others in the crowd. Officer
Olsten continued to spray for several seconds as he walked toward the crowd of
protestors. None of the protestors who were impacted by the pepper spray, including
Brandy, were arrested.
The district court determined Officer Olsten was not entitled to summary
judgment on the First Amendment retaliation claim based on qualified immunity or
the state law claims based on official immunity. The district court reserved ruling
on the City’s sovereign-immunity-based motion for summary judgment founded on
two state law claims. The City Officials appealed the summary judgment order.
II. Analysis
“Ordinarily, we lack jurisdiction ‘to hear an immediate appeal from a district
court’s order denying summary judgment, because such an order is not a final
decision.’” Langford v. Norris, 614 F.3d 445, 455 (8th Cir. 2010) (quoting Krout v.
Goemmer, 583 F.3d 557, 563–64 (8th Cir. 2009)). However, we do have limited
jurisdiction under the collateral order doctrine to hear an interlocutory appeal of a
denial of qualified immunity. Ehlers v. City of Rapid City, 846 F.3d 1002, 1008 (8th
Cir. 2017). Our jurisdiction “extends only to abstract issues of law, not to
determinations that the evidence is sufficient to permit a particular finding of fact
after trial.” Shannon v. Koehler, 616 F.3d 855, 861 (8th Cir. 2010) (cleaned up)
(quoting Krout, 583 F.3d at 564). “Although this court cannot find facts, it may
determine whether the undisputed facts support the district court’s legal
-3-
conclusions.” Kong ex rel. Map Kong v. City of Burnsville, 960 F.3d 985, 991 (8th
Cir. 2020). “This court views disputed facts most favorably to the plaintiff,
including all reasonable inferences.” Id. Therefore, we can review “whether the
uncontested evidence demonstrates that the defendants violated a clearly established
constitutional right” because this is “a legal issue falling squarely within our limited
interlocutory appellate jurisdiction.” Solomon v. Petray, 795 F.3d 777, 785 (8th Cir.
2015) (quoting Brown v. Fortner, 518 F.3d 552, 557 (8th Cir. 2008)).
A. Qualified Immunity
We review de novo a district court’s denial of a motion for summary judgment
on the basis of qualified immunity. Shannon, 616 F.3d at 861–62. “To defeat
qualified immunity, [Brandy] must prove that: ‘(1) the facts, viewed in the light most
favorable to [him], demonstrate the deprivation of a constitutional or statutory right;
and (2) the right was clearly established at the time of the deprivation.’” Pollreis v.
Marzolf, 9 F.4th 737, 743 (8th Cir. 2021) (quoting Howard v. Kansas City Police
Dep’t, 570 F.3d 984, 988 (8th Cir. 2009)). “For a right to be clearly established, ‘the
contours of the right must be sufficiently clear that a reasonable official would
understand that what he is doing violates that right.’” Kelsay v. Ernst, 933 F.3d 975,
979 (8th Cir. 2019) (en banc) (cleaned up) (quoting Anderson v. Creighton, 483 U.S.
635, 640 (1987)). A “case directly on point” is not required, “but existing precedent
must have placed the statutory or constitutional question beyond debate.” Ashcroft
v. al-Kidd, 563 U.S. 731, 741 (2011).
The appellants argue the district court made three errors in denying Officer
Olsten qualified immunity. They maintain the district court should have concluded:
(1) Brandy’s purported First Amendment right was not clearly established at the time
of the alleged violation; (2) there was no First Amendment violation because Brandy
was not engaged in First Amendment protected expression; and (3) there was no
First Amendment violation because Officer Olsten’s use of pepper spray was not
motivated, even in part, by Brandy’s protected expression.
-4-
The district court reasoned that “[a]n individual’s right to exercise First
Amendment rights without facing retaliation from government officials was clearly
established . . . ” at the time of the protest in 2017. But the appellants contend the
district court failed to “address the crucial question of whether it was clearly
established that deploying pepper spray at a crowd of hostile, belligerent, combative
protestors who threatened officers with violence and refused their lawful commands
was a violation of a person’s First Amendment rights.”
While the appellants are correct that “‘clearly established law’ should not be
defined at a high level of generality[,]” White v. Pauly, 580 U.S. 73, 79 (2017), “[a]n
exact match . . . is not required if the constitutional issue is ‘beyond debate.’”
Quraishi v. St. Charles Cnty., 986 F.3d 831, 838 (8th Cir. 2021) (quoting Ashcroft,
563 U.S. at 741). “A general constitutional rule already identified in the decisional
law may apply with obvious clarity to the specific conduct in question, even though
the very action in question has not previously been held unlawful.” Winslow v.
Smith, 696 F.3d 716, 738 (8th Cir. 2012) (quoting Shekleton v. Eichenberger, 677
F.3d 361, 367 (8th Cir. 2012)). In other words, “officials can still be on notice that
their conduct violates established law even in novel factual circumstances.” Hope
v. Pelzer, 536 U.S. 730, 741 (2002).
According to the Supreme Court, “the law is settled that as a general matter
the First Amendment prohibits government officials from subjecting an individual
to retaliatory actions . . . for speaking out.” Hartman v. Moore, 547 U.S. 250, 256
(2006). We have similarly confirmed that this right is clearly established in
Thurairajah v. City of Fort Smith, 925 F.3d 979, 985 (8th Cir. 2019) and Baribeau
v. City of Minneapolis, 596 F.3d 465, 481 (8th Cir. 2010). This “general
constitutional rule” would apply with “obvious clarity to the specific conduct in
question.” See Winslow, 696 F.3d at 738 (quoting Shekleton, 677 F.3d at 367).
Because an officer in Officer Olsten’s position would have been on notice that he
could not use his pepper spray as a means to retaliate against a citizen for his or her
protected expression, we agree with the district court that Brandy’s right to exercise
-5-
his First Amendment rights without facing retaliation from government officials is
clearly established.
But just because the law is clearly established does not mean there was a
constitutional violation. Brandy must also show that the facts, viewed in the most
favorable light, demonstrate the three elements of his First Amendment retaliation
claim: (1) he engaged in protected expression; (2) Officer Olsten took an adverse
action that would chill a person of ordinary firmness from continuing the activity;
and (3) there was a but-for causal connection between Officer Olsten’s retaliatory
animus and Brandy’s injury. See Quraishi, 986 F.3d at 837 (setting forth the
elements generally); Laney v. City of St. Louis, 56 F.4th 1153, 1157 (8th Cir. 2023)
(holding but-for causation is required to satisfy the third element). Officer Olsten
argues Brandy cannot meet the first element of having engaged in protected
expression. While “[c]riticism of public officials and the administration of
governmental policies ‘lies at the heart of speech protected by the First
Amendment,’” Rinne v. Camden Cnty., 65 F.4th 378, 383 (8th Cir. 2023) (quoting
Williams v. City of Carl Junction, 480 F.3d 871, 874 (8th Cir. 2007)), the appellants
argue Brandy’s speech was unprotected because his speech constituted a “true
threat.” “True threats of violence . . . lie outside the bounds of the First
Amendment’s protection.” Counterman v. Colorado, ___ S. Ct. ___, No. 22-138, at
*3 (U.S. June 27, 2023).
“[A] true threat is a statement that a reasonable recipient would have
interpreted as a serious expression of an intent to harm or cause injury to another.”
Doe v. Pulaski Cnty. Special Sch. Dist., 306 F.3d 616, 624 (8th Cir. 2002) (en banc).
A non-exhaustive list of factors to consider includes: (1) “the reaction of those who
heard the alleged threat”; (2) “whether the threat was conditional”; (3) “whether the
person who made the alleged threat communicated it directly to the object of the
threat”; (4) “whether the speaker had a history of making threats against the person
purportedly threatened”; and (5) “whether the recipient had a reason to believe that
the speaker had a propensity to engage in violence.” Id. at 623.
-6-
Therefore, the first critical question is this: viewing the evidence in the light
most favorable to Brandy, was his speech at the protest protected expression or did
it constitute a true threat? If his speech was a true threat and consequently
unprotected, there was no constitutional violation, and Officer Olsten is entitled to
qualified immunity and thus summary judgment. In the absence of unusual facts
though, the question whether a statement amounts to a true threat is a question
generally left to a jury. Nielander v. Bd. of Cnty. Comm’rs of Cnty. of Republic, 582
F.3d 1155, 1166 (10th Cir. 2009) (First Amendment retaliation case); see also
United States v. Dillard, 795 F.3d 1191, 1199 (10th Cir. 2015) (criminal case);
Melugin v. Hames, 38 F.3d 1478, 1485 (9th Cir. 1994) (criminal case). The district
court held there was a genuine factual dispute about whether Brandy’s taunts
“crossed into unprotected territory,” which prevented it from entering summary
judgment on this issue.
We previously “emphasized the fact intensive nature of the true threat inquiry
and held that a court must view the relevant facts to determine ‘whether the recipient
of the alleged threat could reasonably conclude that it expresses a determination or
intent to injure presently or in the future.’” Doe, 306 F.3d at 622 (quotation marks
omitted) (quoting United States v. Dinwiddie, 76 F.3d 913, 925 (8th Cir. 1996)).
“[W]e do not have jurisdiction to decide whether or not we disagree with the district
court as to whether there was sufficient evidence to find a genuine issue of material
fact for resolution at trial.” Thompson v. Dill, 930 F.3d 1008, 1014 (8th Cir. 2019).
Because Officer Olsten cannot demonstrate that “the record plainly forecloses the
district court’s finding of a material factual dispute,” Mallak v. City of Baxter, 823
F.3d 441, 446 (8th Cir. 2016), we have no jurisdiction to disturb the district court’s
conclusion that this is a genuine dispute of material fact.
Finally, Officer Olsten argues there was no First Amendment violation
because his use of pepper spray was not motivated, even in part, by Brandy’s
purportedly protected expression. See Mitchell v. Kirchmeier, 28 F.4th 888, 896 (8th
Cir. 2022) (explaining that in order to prevail the plaintiff must show “the defendant
would not have taken the adverse action but for harboring ‘retaliatory animus’
-7-
against the plaintiff because of his exercise of his First Amendment rights”) (quoting
Nieves v. Bartlett, 139 S. Ct. 1715, 1722 (2019)). “The causal connection is
generally a jury question . . . [unless] the question is so free from doubt as to justify
taking it from the jury.” Peterson v. Kopp, 754 F.3d 594, 603 (8th Cir. 2014)
(ellipses and brackets in original) (quoting Revels v. Vincenz, 382 F.3d 870, 876 (8th
Cir. 2004)), abrogated on other grounds by Laney, 56 F.4th at 1157 n.2. “Generally,
‘more than a temporal connection is required to present a genuine factual issue on
retaliation.’” Tyler v. Univ. of Ark. Bd. of Trs., 628 F.3d 980, 986 (8th Cir. 2011)
(quoting Peterson v. Scott Cnty., 406 F.3d 515, 524 (8th Cir. 2005)). Here, the
district court again held that “a fact question remains as to whether Officer Olsten’s
deployment of pepper spray was motivated, even in part, by Plaintiff’s engagement
in a protected activity, or instead was prompted by Plaintiff’s potentially unprotected
activity or another cause altogether.”
The appellants argue this case is analogous to the consolidated cases in
Aldridge v. City of St. Louis, which arose out of the same incident. Aldridge, Franks,
and Brown were three other protestors in the same crowd as Brandy, and we affirmed
the grant of summary judgment to Officer Olsten based on qualified immunity.
Officer Olsten argued that the unidentified woman in the crowd screaming, what he
thought was, “shoot these motherf***ers,” precipitated his decision to deploy the
pepper spray. But there was nothing in the record that would have caused Officer
Olsten to single Aldridge, Franks, or Brown out of the crowd of protestors for an
adverse action. Conversely, Brandy was openly verbally antagonistic to Officer
Olsten by saying: “If you put that s*** in my face, I’ll f*** you up” and referring to
him as a “p**** a** white boy.” Brandy also elicited a hostile response from Officer
Olsten, who turned back to Brandy and responded: “Come f*** me up then.” In
fact, two officers even placed their hands on Officer Olsten to keep him moving
away from Brandy and the other protestors.
This interaction indicates Officer Olsten might have singled out Brandy for
the adverse action. Alternatively, Officer Olsten could have deployed his pepper
spray due to the increasingly aggressive crowd. In other words, Officer Olsten’s
-8-
motive was not “so free from doubt as to justify taking [the issue of causation] from
the jury.” Quraishi, 986 F.3d at 838 (quoting Revels, 382 F.3d at 876). Because the
record does not plainly foreclose the district court’s finding of a factual dispute as to
causation, “resolution of whether the evidence is sufficient to make that dispute
‘genuine’ is beyond our limited jurisdiction.” Thompson, 930 F.3d at 1015.
B. Official Immunity
The appellants next argue that Brandy’s state law claims should be barred by
official immunity. We have “limited jurisdiction to review issues of law related to
the district court’s denial of summary judgment based on [Officer Olsten’s] official
immunity defense.” Thompson, 930 F.3d at 1013. “We review the district court’s
denial of summary judgment based on official immunity de novo.” Torres v. City of
St. Louis, 39 F.4th 494, 507 (8th Cir. 2022).
“Under Missouri law, the official immunity doctrine protects public officials
from liability for injuries arising out of their discretionary acts or omissions, but not
from liability in claims arising from their performance of ministerial acts.”
Reasonover v. St. Louis Cnty., 447 F.3d 569, 585 (8th Cir. 2006). “However, official
immunity is a qualified immunity and does not apply to those discretionary acts done
in bad faith or with malice.” Id. (quoting Davis v. Bd. of Educ. of City of St. Louis,
963 S.W.2d 679, 688 (Mo. Ct. App. 1998)). “The use of force is a discretionary
duty.” Wealot v. Brooks, 865 F.3d 1119, 1129 (8th Cir. 2017). A finding of bad
faith “embraces more than bad judgment or negligence. It imports a dishonest
purpose, moral obliquity, conscious wrongdoing, [or] breach of a known duty
through some ulterior motive.” Id. (quoting State ex rel. Twiehaus v. Adolf, 706
S.W.2d 443, 447 (Mo. 1986) (en banc)). “[T]o act with malice the officer must do
that which a man of reasonable intelligence would know to be contrary to his duty
and intend such action to be injurious to another.” Thompson, 930 F.3d at 1015
(cleaned up) (quoting Conway v. St. Louis Cnty., 254 S.W.3d 159, 165 (Mo. Ct. App.
2008)).
-9-
The appellants argue the district court committed reversible error when it
denied summary judgment based on official immunity after holding Brandy stated
“facts from which it could be found that Officer Olsten acted in bad faith or with
malice when he applied pepper spray against” Brandy. According to Officer Olsten,
no reasonable jury could find Officer Olsten’s actions were motivated by bad faith.
“Under our limited review, we do not have jurisdiction to reverse the district court’s
determination that there were open fact questions as to whether [Officer Olsten]
acted maliciously.” Thompson, 930 F.3d at 1015. Based on Brandy’s interaction
with Officer Olsten and taking the facts in the light most favorable to Brandy, “a
jury could find that [Officer Olsten] acted with the prohibited . . . malice” if he
deployed the pepper spray with the ulterior motive of retaliation. Div. of Emp. Sec.,
Mo. v. Bd. of Police Comm’rs, 864 F.3d 974, 980 (8th Cir. 2017). Or a jury may
determine that Officer Olsten’s actions upheld his duty, but we have no basis to
decide that factual question on an interlocutory appeal.
C. Sovereign Immunity
Finally, the City maintains that the district court’s order denying summary
judgment on the state claims against the City should be reversed as it is entitled to
sovereign immunity. However, the district court did not rule on the City’s motion
for summary judgment and instead “reserved ruling . . . until after the trial
concludes.” “Missouri’s sovereign immunity statute . . . ‘specifically refers to the
immunity of a public entity from liability and suit.’” Torres, 39 F.4th at 502 (cleaned
up) (quoting Argonaut Great Cent. Ins. Co. v. Audrain Cnty. Joint Commc’ns, 781
F.3d 925, 930 (8th Cir. 2015)). Just as government officials “are entitled to a
thorough determination of their claims of qualified immunity if that immunity is to
mean anything at all[,]” Payne v. Britten, 749 F.3d 697, 701 (8th Cir. 2014) (cleaned
up) (quoting O’Neil v. City of Iowa City, Iowa, 496 F.3d 915, 918 (8th Cir. 2007)),
the City is entitled to a thorough determination of its claims of sovereign immunity.
Thus, we remand with instructions for the district court to reach the merits of the
sovereign immunity issue as to the state law claims.
-10-
III. Conclusion
The district court’s denials of summary judgment based on qualified
immunity and official immunity are affirmed. We remand with instructions for the
district court to reach the merits of the sovereign immunity issue on the state law
claims.
______________________________
-11-