Court Opinion

ID: 9929460
Source: CourtListenerOpinion
Date Created: 2024-02-02 18:01:26.97125+00
Date Added: 2024-06-11T10:23:23.954925
License: Public Domain

FOR PUBLICATION

  UNITED STATES COURT OF APPEALS
       FOR THE NINTH CIRCUIT

DEREK TUCSON; ROBIN                       No. 23-35449
SNYDER; MONSIEREE DE
CASTRO; ERIK MOYA-DELGADO,               D.C. No. 2:23-cv-
                                           00017-MJP
             Plaintiffs-Appellees,
 v.
                                            OPINION
CITY OF SEATTLE,

             Defendant-Appellant,
and

ALEXANDER PATTON; TRAVIS
JORDAN; DYLAN NELSON; JOHN
DOES, 1-4; 1-2,

             Defendants.

      Appeal from the United States District Court
        for the Western District of Washington
      Marsha J. Pechman, District Judge, Presiding

         Argued and Submitted January 9, 2024
               San Francisco, California

                Filed February 2, 2024
2                    TUCSON V. CITY OF SEATTLE

     Before: EUGENE E. SILER, * RICHARD R. CLIFTON,
           and MILAN D. SMITH, JR., Circuit Judges.

             Opinion by Judge Milan D. Smith, Jr.

                          SUMMARY **

           Overbreadth and Vagueness Doctrines

    The panel reversed the district court’s order
preliminarily enjoining enforcement of a Seattle ordinance
that criminalizes the intentional writing, painting, or drawing
on property without the express permission of the property’s
owner or operator.
    Plaintiffs brought suit pursuant to 42 U.S.C. § 1983
alleging, in part, that the Seattle ordinance was substantially
overbroad under the First Amendment and facially vague
under the Fourteenth Amendment.
    The panel first determined that plaintiffs had Article III
standing because enjoining enforcement of the ordinance
was substantially likely to redress plaintiffs’ injury by
allowing them to chalk political messages on City sidewalks
and barriers erected on public walkways without fear of
arrest.

*
 The Honorable Eugene E. Siler, United States Circuit Judge for the U.S.
Court of Appeals for the Sixth Circuit, sitting by designation.
**
  This summary constitutes no part of the opinion of the court. It has
been prepared by court staff for the convenience of the reader.
                  TUCSON V. CITY OF SEATTLE                3

    The panel next held that the district court erred when it
enjoined the ordinance as facially overbroad. To justify
facial invalidation, a law’s unconstitutional applications
must be realistic, not fanciful, and their number must be
substantially disproportionate to the statute’s lawful
sweep. Here, the district court never acknowledged the
ordinance’s numerous applications that would not implicate
protected speech. By failing to inquire into the ordinance’s
numerous lawful applications, the district court was unable
to analyze whether the number of unconstitutional
applications was substantially disproportionate to the
statute’s lawful sweep. The panel therefore reversed the
district court’s order granting plaintiffs a preliminary
injunction on their First Amendment facial overbreadth
claim.
    The panel next held that the district court erred in
applying the facial vagueness doctrine. Instead of
examining whether the ordinance was not vague in the vast
majority of its intended applications, the district court
instead speculated about possible vagueness in hypothetical
and fanciful situations not before the court. The district
court’s failure to employ the requisite analysis to sustain a
facial vagueness claim was sufficient to warrant reversal.

                        COUNSEL

Kerala T. Cowart (argued) and Jessica L. Zornes Leiser,
Assistant City Attorneys; Ann Davison, Seattle City
Attorney; Seattle City Attorney’s Office, Seattle,
Washington; for Defendant-Appellant.
Nathaniel Flack (argued) and Braden Pence, MacDonald
Hoague & Bayless, Seattle, Washington; Neil Fox, The Law
4                 TUCSON V. CITY OF SEATTLE

Office of Neil Fox, Seattle, Washington; for Plaintiffs-
Appellees.
Charlene Koski, Van Ness Feldman LLP, Seattle,
Washington; Adam L. Rosenberg, Keller Rohrback LLP,
Seattle, Washington; for Amici Curiae Washington State
Association of Municipal Attorneys and the International
Municipal Lawyers Association.
Taryn Darling and Brent Low, American Civil Liberties
Union of Washington, Seattle, Washington; Brian Flaherty,
King County Department of Public Defense, Seattle,
Washington; for Amici Curiae American Civil Liberties
Union of Washington and King County Department of
Public Defense.

                        OPINION

M. SMITH, Circuit Judge:

    On January 1, 2021, Derek Tucson wrote the words
“peaceful protest” in charcoal on a temporary wall built over
the sidewalk outside the Seattle Police Department’s (SPD)
East Precinct. SPD officers arrested Tucson for doing so.
The same night Tucson was arrested, SPD officers arrested
three other individuals for writing political messages in
charcoal and sidewalk chalk at or near the same location.
The arresting officers documented their offense as having
violated Seattle Municipal Code (SMC) § 12A.08.020,
which criminalizes “[w]rit[ing], paint[ing], or draw[ing] any
inscription, figure, or mark of any type on any public or
private building or other structure or any real or personal
property owned by any other person,” without “express
                   TUCSON V. CITY OF SEATTLE                  5

permission.” They were released from jail the next day, and
prosecutors did not pursue charges.
    Tucson and the three other individuals (together,
Plaintiffs) eventually filed suit pursuant to 42 U.S.C. § 1983
against the City and several of its officers in federal district
court. Apart from challenging the constitutionality of their
prior arrests, Plaintiffs asserted that SMC § 12A.08.020.A.2
is substantially overbroad pursuant to the First Amendment
and facially vague pursuant to the Fourteenth Amendment
such that it can never be enforced. The district court held
that Plaintiffs were likely to succeed on the merits of their
overbreadth and facial vagueness challenges and
preliminarily enjoined the City from enforcing it. Because
the district court erred in applying the overbreadth and facial
vagueness doctrines, we reverse.
                      BACKGROUND
    When SPD officers arrested Tucson for writing the
words “peaceful protest” in charcoal on a temporary wall
built outside the SPD’s East Precinct, the officers
documented his offense as “SMC – 12A.08.020 |
PROPERTY DESTRUCTION.” At the time of Tucson’s
arrest, SMC § 12A.08.020 provided that:

       A. A person is guilty of property destruction
          if he or she:
           1. Intentionally damages the property of
              another; or
           2. Writes, paints, or draws any
              inscription, figure, or mark of any
              type on any public or private building
              or other structure or any real or
6                 TUCSON V. CITY OF SEATTLE

               personal property owned by any other
               person.
       B.
            1. It is an affirmative defense to
               property destruction under subsection
               12A.08.020.A.1 that the actor
               reasonably believed that he had a
               lawful right to damage such property.
            2. It is an affirmative defense to
               property destruction under subsection
               12A.08.020.A.2 that the actor had
               obtained express permission of the
               owner or operator of the building,
               structure, or property.
       C. Property destruction        is      a   gross
          misdemeanor.

SMC § 12A.08.020 (2021). A violation of § 12A.08.020 is
punishable by imprisonment of up to 364 days and a fine of
up to five thousand dollars. See id. § 12A.02.070.A.
    The same night Tucson was arrested, SPD officers
arrested the remaining Plaintiffs pursuant to § 12A.08.020
for writing political messages in charcoal and sidewalk chalk
at or near the same location. Other than § 12A.08.020, no
other provision of law was cited by the arresting officers as
a basis for the arrests. The following day, Plaintiffs were
released from jail. Prosecutors did not charge any of them
within the two-year statute of limitations for violating
§ 12A.08.020. Two months later, SPD Lieutenant John
Brooks allegedly cited “SMC Property Destruction” while
threatening “enforcement action” against members of the
                  TUCSON V. CITY OF SEATTLE                 7

public for chalking the public sidewalk outside of the SPD’s
West Precinct.
    On January 4, 2023, Plaintiffs filed suit against the City
and several of its officers in federal district court. Two
months later, in response to the litigation, the City amended
§ 12A.08.020 as follows:

       A. A person is guilty of property destruction
          if ((he or she)) the person intentionally:
            1. ((Intentionally d)) Damages         the
               property of another; or
            2. Writes, paints, or draws any
               inscription, figure, or mark of any
               type on any public or private building
               or other structure or any real or
               personal property owned by any other
               person unless the person has obtained
               the express permission of the owner
               or operator of the property.
       B.
            1. It is an affirmative defense to
               property destruction under subsection
               12A.08.020.A.1 that the actor
               reasonably believed that he had a
               lawful right to damage such property.
            ((2. It is an affirmative defense to
                 property destruction under subsection
                 12A.08.020.A.2 that the actor had
                 obtained express permission of the
                 owner or operator of the building,
                 structure, or property.))
8                  TUCSON V. CITY OF SEATTLE

       C. Property destruction          is     a   gross
          misdemeanor.

By removing the affirmative defense of “express
permission” and importing it into the elements of the
offense, the amendment newly required the prosecution to
prove beyond a reasonable doubt that the defendant “ha[d]
[not] obtained express permission of the owner or operator
of the property[]” to sustain a conviction.
    After obtaining leave from the court, Plaintiffs filed an
amended complaint challenging the amended § 12A.08.020.
In the complaint, Plaintiffs assert that the amended
§ 12A.08.020 is overbroad pursuant to the First Amendment
and facially vague pursuant to the Fourteenth Amendment.
Plaintiffs moved for a preliminary injunction to enjoin the
City from enforcing subsection A.2 of the amended
§ 12A.08.020, which criminalizes “intentionally . . .
[w]rit[ing], paint[ing], or draw[ing] any inscription, figure,
or mark of any type on any public or private building or other
structure or any real or personal property owned by any other
person” without “express permission” from “the owner or
operator of the property” (hereinafter, the amended
§ 12A.08.020.A.2 is referred to as the Local Ordinance).
The City opposed the motion by arguing that Plaintiffs
lacked Article III standing to pursue their requested
injunctive relief and otherwise were unlikely to succeed on
the merits of their challenge to the Local Ordinance.
    The district court ultimately granted the motion and
preliminarily enjoined the City from enforcing the entirety
of the amended § 12A.08.020, including subsection A.1,
which prohibits intentional property damage. By stipulation
of the parties, the district court modified its order so that it
                   TUCSON V. CITY OF SEATTLE                  9

now enjoins only the Local Ordinance. The City timely
appealed.
   JURISDICTION AND STANDARD OF REVIEW
    We have jurisdiction pursuant to 28 U.S.C. § 1292(a)(1)
to review the district court’s grant of a preliminary
injunction. Daniels Sharpsmart, Inc. v. Smith, 889 F.3d 608,
613 (9th Cir. 2018). “We review de novo a district court’s
determination whether a party has [Article III] standing.”
Jones v. Ford Motor Co., 85 F.4th 570, 573 (9th Cir. 2023).
“We review the district court’s decision to grant a
preliminary injunction for abuse of discretion.” Daniels
Sharpsmart, Inc., 889 F.3d at 613. “A district court abuses
its discretion if it rests its decision ‘on an erroneous legal
standard or on clearly erroneous factual findings.’” Am.
Beverage Ass’n v. City & Cnty. of San Francisco, 916 F.3d
749, 754 (9th Cir. 2019) (en banc) (quoting United States v.
Schiff, 379 F.3d 621, 625 (9th Cir. 2004)). “A district court’s
decision is based on an erroneous legal standard if: (1) the
court did not employ the appropriate legal standards that
govern the issuance of a preliminary injunction; or (2) in
applying the appropriate standards, the court
misapprehended the law with respect to the underlying
issues in the litigation.” California Chamber of Com. v.
Council for Educ. & Rsch. on Toxics, 29 F.4th 468, 475 (9th
Cir. 2022) (internal quotation marks omitted), cert. denied,
143 S. Ct. 1749 (2023).
                         ANALYSIS
I. Plaintiffs Have Article III Standing to Challenge the
   Local Ordinance.
   We begin our analysis by addressing the City’s threshold
challenge to Plaintiffs’ Article III standing. Specifically, the
10                TUCSON V. CITY OF SEATTLE

City argues that Plaintiffs have failed to satisfy the
redressability prong of Article III standing because the
district court’s order enjoining the Local Ordinance failed to
enjoin a nearly identical provision found in the State of
Washington’s malicious mischief statute. That statute
similarly prohibits “[w]rit[ing], paint[ing], or draw[ing] any
inscription, figure, or mark of any type on any public or
private building or other structure or any real or personal
property owned by any other person unless the person has
obtained the express permission of the owner or operator of
the property.” Wash. Rev. Code Ann. § 9A.48.090(1)(b). In
the City’s view, “[b]ecause the state law remains in force in
Seattle, the court’s order enjoining the [Local] Ordinance
cannot redress Plaintiffs’ claimed injury.”
    For a plaintiff to have Article III standing, there must be
a likelihood that a plaintiff’s injury will be redressed by a
favorable court decision. Lujan v. Defs. of Wildlife, 504 U.S.
555, 561 (1992). “The question in deciding whether a
plaintiff’s injury is redressable is not whether a favorable
decision is likely but whether a favorable decision likely will
redress a plaintiff’s injury.” Bonnichsen v. United States,
367 F.3d 864, 873 (9th Cir. 2004). Therefore, “redressability
analyzes the connection between the alleged injury and
requested judicial relief.” Washington Env’t Council v.
Bellon, 732 F.3d 1131, 1146 (9th Cir. 2013). In other words,
redressability asks whether “the district court had the power
to prevent the injury at the time the complaint was filed.”
Am. C.L. Union of Nevada v. Lomax, 471 F.3d 1010, 1016
(9th Cir. 2006).
    A plaintiff’s burden to demonstrate redressability is
“relatively modest.” Bennett v. Spear, 520 U.S. 154, 171
(1997). A plaintiff “need not demonstrate that there is a
guarantee that her injuries will be redressed by a favorable
                       TUCSON V. CITY OF SEATTLE                           11

decision; rather, a plaintiff need only show a substantial
likelihood that the relief sought would redress the injury.”
M.S. v. Brown, 902 F.3d 1076, 1083 (9th Cir. 2018) (cleaned
up). In evaluating whether the redressability prong is met,
courts “must look at the facts ‘as they exist at the time the
complaint was filed.’” Lomax, 471 F.3d at 1015 (quoting
Lujan, 504 U.S. at 569 n.4).
    Here, when Plaintiffs filed their amended complaint on
April 19, 2023, they requested in their prayer for relief that
the district court enjoin enforcement of the Local Ordinance,
such that they would no longer risk arrest pursuant to the
Local Ordinance if they resumed chalking political messages
on City sidewalks and barriers erected on public walkways.
This request for injunctive relief is clearly connected to
Plaintiffs’ alleged injury—i.e., being chilled in their free
exercise of speech for fear of future enforcement of the Local
Ordinance. 1 See Bellon, 732 F.3d at 1146 (“[R]edressability

1
  In its briefing on appeal, the City also suggests in passing that Plaintiffs
lack Article III standing to enjoin the future enforcement of the Local
Ordinance because there is no genuine threat that the City will enforce it
against individuals who chalk on sidewalks. But that suggestion is
unpersuasive given the district court’s factual findings. Notably,
Plaintiffs were previously arrested for writing political messages in
charcoal and chalk on a temporary wall built over the sidewalk outside
the SPD’s East Precinct and on other nearby public property. Moreover,
Plaintiffs alleged in their complaint that SPD Lieutenant Brooks in 2021
cited “SMC Property Destruction” while threatening “enforcement
action” against members of the public for chalking the public sidewalk
outside of the SPD’s West Precinct. It was therefore not clearly
erroneous for the district court to find, as a factual matter, that Plaintiffs
were chilled from chalking political messages critical of the SPD on
public property near SPD buildings, including City sidewalks. See Hajro
v. U.S. Citizenship & Immigr. Servs., 811 F.3d 1086, 1098 (9th Cir.
2016) (“The district court’s factual findings on jurisdictional issues are
reviewed for clear error.”).
12                 TUCSON V. CITY OF SEATTLE

analyzes the connection between the alleged injury and
requested judicial relief.”). Given that Plaintiffs had been
arrested for violating the Local Ordinance prior to its
amendment, and the amendment did not alter the scope of
the conduct that the Local Ordinance criminalized, an order
from the district court enjoining enforcement of the Local
Ordinance was “substantial[ly] likel[y]” to redress
Plaintiffs’ injury by allowing them to chalk political
messages on City sidewalks and barriers erected on public
walkways without fear of enforcement. M.S., 902 F.3d at
1083. Thus, their injury was redressable by a favorable
decision from the district court.
    The City’s argument that Plaintiffs’ alleged injury is not
redressable because the district court ultimately failed to
enjoin a nearly identical provision found in the State of
Washington’s malicious mischief statute, is unpersuasive.
As a threshold matter, the City errs by suggesting that
redressability hinges on whether the relief the district court
ultimately fashioned actually redresses Plaintiffs’ injury. As
noted earlier, in evaluating whether the redressability prong
is met, courts “must look at the facts ‘as they exist at the time
the complaint was filed.’” Lomax, 471 F.3d at 1015 (quoting
Lujan, 504 U.S. at 569 n.4). Accordingly, courts must
examine whether “the relief sought” at the time the
complaint was filed was “substantial[ly] likel[y]” to redress
their injury. M.S., 902 F.3d at 1083. The City’s attack on
the adequacy of the preliminary injunction that the district
court ultimately issued nearly two months after the
complaint was filed is therefore misplaced. The appropriate
inquiry centers on whether Plaintiffs, at the time the
complaint was filed, sought relief from the district court that
was substantially likely to redress the injury they alleged in
their complaint.
                   TUCSON V. CITY OF SEATTLE                  13

    The fact that Plaintiffs did not challenge the State of
Washington’s malicious mischief statute, which
criminalizes the same conduct, does not jeopardize the
redressability of their injury, which is traceable to the City’s
credible threat to enforce the Local Ordinance. Plaintiffs
have never alleged that they are injured by a genuine risk of
future enforcement of the State of Washington’s malicious
mischief statute. That is because, as Plaintiffs point out in
their answering brief, that statute “has never been applied
against Plaintiffs” or cited as a basis for their arrests. In
addressing redressability, Plaintiffs are not required to
challenge all laws that plausibly criminalize their desired
course of conduct in a given jurisdiction, regardless of how
credible the threat to enforce those laws is. Such a
requirement would necessarily conflict with the injury-in-
fact doctrine, which requires “a credible threat” to enforce a
specific criminal provision before a plaintiff may have
standing to request that a district court enjoin that
provision’s future enforcement. See Susan B. Anthony List
v. Driehaus, 573 U.S. 149, 159 (2014).
    Based on the allegations outlined in Plaintiffs’ amended
complaint, there was no credible threat that the City would
begin enforcing the State of Washington’s malicious
mischief statute against Plaintiffs in the future. In its
opposition to Plaintiffs’ motion for a preliminary injunction,
the City never argued that it would start enforcing it against
Plaintiffs; nor did it provide any evidence in support of such
capability or intent. Accordingly, the district court was
correct to credit Plaintiffs’ allegations and evidence showing
that they faced a credible threat of future enforcement of the
Local Ordinance but not the State of Washington’s malicious
mischief statute. Significantly, Plaintiffs would have lacked
Article III standing to ask the district court to enjoin the City
14                TUCSON V. CITY OF SEATTLE

from enforcing the State of Washington’s malicious
mischief statute because Plaintiffs were not presently injured
by such a threat. Their failure to ask the district court to
enjoin a statute by which they were not injured for the
purposes of Article III could not deprive them of the
redressability of their injury arising from the City’s credible
threat to continue enforcing the Local Ordinance against
them. Accordingly, we hold that Plaintiffs had Article III
standing to sue and we proceed to the merits of the City’s
appeal of the preliminary injunction.
II. The District Court Erred in Its Application of the
    Overbreadth Doctrine.
    On appeal, the City argues that the district court abused
its discretion when it enjoined the Local Ordinance as
facially overbroad because the district court failed to
evaluate whether Plaintiffs demonstrated a substantial and
realistic danger that the protected speech of third parties
would be chilled. Plaintiffs have not moved for a
preliminary injunction on an as-applied basis. The City
emphasizes that apart from Plaintiffs’ “conduct of chalking
on walls and sidewalks without permission,” they only
provided “far-fetched” hypotheticals to demonstrate danger
to the rights of third parties without any “actual facts to
ground their claim of overbreadth.” Plaintiffs respond that
“an examination of the scope of speech which the [Local]
Ordinance’s plain language criminalizes,” which includes
the hypotheticals the City has criticized as far-fetched, “is
the necessary starting point in determining whether [the
Local Ordinance] is overbroad.” Plaintiffs add that they
need not produce “evidence of each and every application of
the statute” where those applications are clearly covered by
the plain language of the statute.
                   TUCSON V. CITY OF SEATTLE                   15

     As the Supreme Court recently observed, “litigants
mounting a facial challenge to a statute normally ‘must
establish that no set of circumstances exists under which the
[statute] would be valid.’” United States v. Hansen, 599
U.S. 762, 769 (2023) (quoting United States v. Salerno, 481
U.S. 739, 745 (1987)). However, “[b]reaking from [this]
rule, the [First Amendment] overbreadth doctrine instructs a
court to hold a statute facially unconstitutional even though
it has lawful applications.” Id. The Supreme Court has
justified this departure from the normal rule of facial
invalidation “on the ground that it provides breathing room
for free expression.” Id. “Overbroad laws ‘may deter or
“chill” constitutionally protected speech,’ and if would-be
speakers remain silent, society will lose their contributions
to the ‘marketplace of ideas.’” Id. at 769–70 (quoting
Virginia v. Hicks, 539 U.S. 113, 119 (2003)). “To guard
against those harms, the overbreadth doctrine allows a
litigant . . . to vindicate the rights of the silenced, as well as
society’s broader interest in hearing them speak.” Id. at 770.
“If the challenger demonstrates that the statute ‘prohibits a
substantial amount of protected speech,’ relative to its
‘plainly legitimate sweep,’ then society’s interest in free
expression outweighs its interest in the statute’s lawful
applications, and a court will hold the law facially invalid.”
Id. (quoting United States v. Williams, 553 U.S. 285, 292
(2008)).
    Explaining how the doctrine applies, the Court stated
that “[t]o justify facial invalidation, a law’s unconstitutional
applications must be realistic, not fanciful, and their number
must be substantially disproportionate to the statute’s lawful
sweep.” Id. “In the absence of a lopsided ratio, courts must
handle unconstitutional applications as they usually do—
case-by-case.” Id. The “mere fact that one can conceive of
16                 TUCSON V. CITY OF SEATTLE

some impermissible applications of a statute is not sufficient
to render it susceptible to an overbreadth challenge.”
Members of City Council of Los Angeles v. Taxpayers for
Vincent, 466 U.S. 789, 800 (1984). In determining whether
an unconstitutional application is realistic, courts may
consider whether that application has occurred in the past.
See Williams, 553 U.S. at 302 (“[W]e are aware of no
prosecution for giving child pornography to the police. We
can hardly say, therefore, that there is a ‘realistic danger’ that
§ 2252A(a)(3)(B) will deter such activity.”). Courts may
also consider whether an unconstitutional application is
“implausible.” Id. at 301–02 (“We think it implausible that
a reputable distributor of Hollywood movies, such as
Amazon.com, believes that one of these films contains
actual children engaging in actual or simulated sex on
camera; and even more implausible that Amazon.com would
intend to make its customers believe such a thing. The
average person understands that sex scenes in mainstream
movies use nonchild actors, depict sexual activity in a way
that would not rise to the explicit level necessary under the
statute, or, in most cases, both.”).
     In the district court’s order granting Plaintiffs’ request
for a preliminary injunction, the district court correctly
recognized that pursuant to the overbreadth doctrine, “a law
may be invalidated as overbroad if a substantial number of
its applications are unconstitutional, judged in relation to the
statute’s plainly legitimate sweep.” However, the district
court then proceeded to ignore that legal standard in its
analysis by erroneously conflating the overbreadth question
of whether a substantial number of the law’s applications are
unconstitutional with the merits question of whether the
law’s application to a particular set of facts is not narrowly
tailored to serve a significant governmental interest.
                  TUCSON V. CITY OF SEATTLE                 17

     The district court never acknowledged the numerous
applications of the Local Ordinance that would not implicate
any protected speech, such as spray-painting an individual’s
private home, vehicle, or other private property, or chalking
messages on an individual’s private driveway. See generally
Manhattan Cmty. Access Corp. v. Halleck, 139 S. Ct. 1921,
1931 (2019) (“The Constitution does not disable private
property owners and private lessees from exercising editorial
discretion over speech and speakers on their property.”). By
failing to inquire into the Local Ordinance’s numerous
lawful applications, the district court was unable to analyze
whether the number of unconstitutional applications was
“substantially disproportionate to the statute’s lawful
sweep,” such that a facial attack on the Local Ordinance was
warranted. Hansen, 599 U.S. at 770.
    The district court’s statement that “[t]he purported need
to prevent property destruction could be accomplished
without a provision criminalizing speech in public areas
without permission,” perfectly captures its error with respect
to the overbreadth doctrine. In the district court’s view,
because it found that the Local Ordinance as applied to
individuals chalking messages on public sidewalks was
likely to violate the First Amendment, the whole law had to
be invalidated. But the overbreadth doctrine may not be
employed so casually. See id. (“Because it destroys some
good along with the bad, invalidation for overbreadth is
strong medicine that is not to be casually employed.”
(cleaned up)). Contrary to what the district court suggested
in its order granting the preliminary injunction, the
overbreadth doctrine does not license the federal courts to
strike down laws in their entirety just because the legislature
could have more carefully crafted the statutory language to
18                TUCSON V. CITY OF SEATTLE

avoid some unconstitutional applications. See Members of
City Council, 466 U.S. at 800; Williams, 553 U.S. at 292.
    The district court’s failure to correctly apply the law of
the overbreadth doctrine is sufficient to reverse the
preliminary injunction as to Plaintiffs’ facial overbreadth
claim. See Sports Form, Inc. v. United Press Int’l, Inc., 686
F.2d 750, 752 (9th Cir. 1982) (“A district court’s order
[granting or denying a preliminary injunction] is reversible
for legal error if the court . . . misapprehends the law with
respect to the underlying issues in litigation.”). We therefore
reverse the district court’s order granting Plaintiffs a
preliminary injunction on their First Amendment facial
overbreadth claim.
III. The District Court Erred in Its Application of the
     Facial Vagueness Doctrine.
    On appeal, the City also argues that Plaintiffs are
unlikely to succeed on their facial vagueness claim because
the Local “Ordinance is not vague in all—or even a
substantial number—of its applications.” Plaintiffs do not
respond to that argument directly and instead emphasize that
when an individual undertakes to chalk in a public forum,
“there is no way for . . . a[] member of the public[] to know
how [to] obtain ‘express permission’” and that the very
requirement of obtaining express permission allows for the
City to enforce the ban in a viewpoint-discriminatory way.
    A law is unconstitutionally vague if it does not give “a
person of ordinary intelligence fair notice of what is
prohibited” or if it is “so standardless that it authorizes or
encourages seriously discriminatory enforcement.”
Williams, 553 U.S. at 304. “The operative question under
the fair notice theory is whether a reasonable person would
know what is prohibited by the law.” Tingley v. Ferguson,
                   TUCSON V. CITY OF SEATTLE                  19

47 F.4th 1055, 1089 (9th Cir. 2022), cert. denied, 144 S. Ct.
33 (2023). “The terms of a law cannot require ‘wholly
subjective judgments without statutory definitions,
narrowing context, or settled legal meanings.’” Id. (quoting
Holder v. Humanitarian L. Project, 561 U.S. 1, 20 (2010)).
As for the arbitrary enforcement theory of unconstitutional
vagueness, a law is void for vagueness if it “lack[s] any
ascertainable standard for inclusion and exclusion,” thereby
authorizing or encouraging “the authorities [to] arbitrarily
prosecute one class of persons instead of another.” Kashem
v. Barr, 941 F.3d 358, 374 (9th Cir. 2019) (cleaned up).
     While it is generally true that a vagueness challenge to a
statute must be examined as applied to the challenger, see
id., “facial vagueness challenges are appropriate if the statute
clearly implicates free speech rights.” Cal. Teachers Ass’n
v. State Bd. of Educ., 271 F.3d 1141, 1149 (9th Cir. 2001).
“When First Amendment freedoms are at stake, courts apply
the vagueness analysis more strictly, requiring statutes to
provide a greater degree of specificity and clarity than would
be necessary under ordinary due process principles.” Id. at
1150. “Nevertheless, perfect clarity is not required even
when a law regulates protected speech.” Id. “Condemned
to the use of words, [courts] can never expect mathematical
certainty from our language.” Grayned v. City of Rockford,
408 U.S. 104, 110 (1972). “Therefore, even when a law
implicates First Amendment rights, the constitution must
tolerate a certain amount of vagueness.” Cal. Teachers, 271
F.3d at 1151.
    For the purposes of a facial attack on a statute or
ordinance, a statute’s vagueness exceeds constitutional
limits if its “deterrent effect on legitimate expression is . . .
both real and substantial, and if the statute is [not] readily
subject to a narrowing construction by the state courts.”
20                TUCSON V. CITY OF SEATTLE

Young v. Am. Mini Theatres, Inc., 427 U.S. 50, 60 (1976)
(internal quotation marks omitted). “[S]peculation about
possible vagueness in hypothetical situations not before the
Court will not support a facial attack on a statute when it is
surely valid ‘in the vast majority of its intended
applications.’” Hill v. Colorado, 530 U.S. 703, 733 (2000)
(quoting United States v. Raines, 362 U.S. 17, 23 (1960)).
    In its order granting Plaintiffs’ request for a preliminary
injunction, the district court failed to employ the analysis
required by the facial vagueness doctrine. Instead of
examining whether the Local Ordinance is not vague “in the
vast majority of its intended applications,” Raines, 362 U.S.
at 23, the district court instead speculated about possible
vagueness in hypothetical and fanciful situations not before
the Court, such as whether the Local Ordinance criminalizes
“signing a guest book,” “drawing in the sand on a beach,”
and “marking public utilities on the street.” The district
court’s failure to employ the requisite analysis to sustain a
facial vagueness claim is sufficient to warrant reversal. See
Sports Form, 686 F.2d at 752.
    The City’s additional criticisms of the district court’s
vagueness analysis further support reversal. First, the
district court devoted much of its vagueness analysis to the
Local Ordinance’s failure to define the term “damage,” but
as the City correctly points out, “the word ‘damage’ appears
nowhere in the text of the [Local] Ordinance[]” that
Plaintiffs have challenged. And even if that word did appear
in the challenged portion of the statute, its meaning is
sufficiently clear.     See SMC § 12A.08.010 (defining
“damage” as “injury or harm to property sufficient to lower
its value or involving significant inconvenience or loss of
efficiency”).    Second, the fact the Local Ordinance
“delegates enforcement of [it] to the SPD without any
                  TUCSON V. CITY OF SEATTLE                 21

guidance or boundaries,” does not render it facially vague,
contrary to what the district court found. As the City
correctly observes, “executive branch discretion ‘to decide
how to prioritize and how aggressively to pursue legal
actions against defendants who violate the law’ is a
fundamental requirement of the separation of powers.” The
mere fact that the City and its officers have discretion to
enforce the Local Ordinance in some circumstances and not
others is not a sufficient basis for concluding that the Local
Ordinance is wholly vague such that it can never be
enforced. Accordingly, we reverse the district court’s order
granting Plaintiffs a preliminary injunction on their
Fourteenth Amendment facial vagueness claim.
                      CONCLUSION
     For the foregoing reasons, we REVERSE the district
court’s order preliminarily enjoining the City and its officers
from enforcing the Local Ordinance. We REMAND this
case to the district court so that Plaintiffs may continue to
litigate their challenge to the Local Ordinance as it applies
to them.