VIP OF BERLIN, LLC, Plaintiff-Appellee, v. TOWN OF BERLIN and Denise McNair, in her official capacity as Town Manager, Town of Berlin, CT, Defendants-Appellants, Herman Middlebrooks, Jr., in his official capacity as Town Manager, Town of Berlin, CT, Defendant, 593 F.3d 179

STRAUB, Circuit Judge: Defendants-Appellants Town of Berlin (“Berlin”) and Denise McNair appeal from a July 2, 2009 opinion and order of the United States District Court for the District of Connecticut (Stefan R. Underhill, Judge) preliminarily enjoining them from enforcing

Section 14-242 of the Berlin Code of Ordinances against Plaintiff-Appellee VIP of Berlin, LLC (“VIP”). The District Court granted the injunction at issue here because it concluded that VIP had shown a clear likelihood of success on the merits of its claim that the ordinance’s definition of an “adult oriented store” was unconstitutionally vague as applied to a zoning application that VIP submitted on March 26, 2009.

Berlin’s ordinance defines any establishment having “a substantial or significant portion of its stock in trade in Adult Books, Adult Videos or Adult Novelties ” as an “adult oriented store.” Berlin Code of Ordinances § 14-242 (emphases in original). The District Court did not find the ordinance’s

definitions of “Adult Books, Adult Videos or Adult Novelties” unconstitutionally vague. Rather, the District Court held that VIP had shown a clear likelihood of success on the merits of its claim that the phrase “substantial or significant portion of its stock in trade” was unconstitutionally vague. In sum, the District Court concluded that the ordinance, as applied to VIP’s March 2009 zoning application, failed to provide clear enforcement standards and adequate notice that the amount of VIP’s proposed adult inventory would qualify VIP as an adult oriented store.

The issue before us, therefore, is whether, as applied to VIP’s March 2009 zoning application, the phrase “substantial or significant portion” of a business’s stock in trade is unconstitutionally vague. For the reasons set forth below, we hold that the District Court exceeded its allowable discretion by concluding that VIP has shown a clear likelihood of success on the merits of its claim that this phrase, as applied to VIP’s March 2009 zoning application, is unconstitutionally vague.

FACTUAL AND PROCEDURAL BACKGROUND VIP owns an approximately 15,000 square-foot commercial building located at 717 Berlin Turnpike in Berlin, Connecticut. The property is presently zoned for retail use. Because the property is located within 250 feet of a residentially zoned area, however, VIP may not operate a retail store at that location if it is classified as an “Adult Oriented Store” under Berlin’s sexually oriented business (“SOB”) ordinance. I.

Berlin’s Current Ordinance and VIP’s March 2009 Zoning Application Berlin’s current SOB ordinance defines an “Adult Oriented Store” as any establishment having “a substantial or significant portion of its stock in trade in Adult Books, Adult Videos or Adult Novelties or any combination thereof.” Berlin Code of Ordinances § 14-242 (emphases in original). An adult oriented store falls into the category of a “Sexually oriented business,” which requires an SOB license to operate in Berlin and which may not be located within 250 feet of any residentially zoned land. Id. §§ 14-242, 14-291(c).

The stated purpose of Berlin’s SOB ordinance is to: promote the health, safety and general welfare of the residents of the town and[,] reduce or eliminate the adverse secondary effects of such sexually oriented businesses, protect residents from increased crime, preserve the quality of life, preserve the property values and the character of surrounding neighborhoods and businesses, deter the spread of blight, and protect against the threat to public health from the spread of communicable and social diseases. Id. § 14-241(6).

On March 26, 2009, VIP submitted an application for a zoning permit, along with a proposed inventory list and proposed floor plan. According to this March 2009 application, twelve percent of the stock in trade at VIP’s Berlin store would consist of books, magazines, DVDs, and novelties or products that could be defined as “adult videos,” “adult books,” or “adult novelties” (collectively, “adult” products) under the Berlin SOB ordinance.

Of VIP’s total inventory of 67,237 products, VIP represented that 8,242 of those items could be classified as adult products such as DVDs for rent, DVDs for sale, magazines, “sex positive lubricants,” and “sex positive toys.” On May 11, 2009, Berlin’s Chief Zoning Enforcement Officer, Hellyn R. Riggins, denied VIP’s zoning application on the ground that the Berlin Town Manager, Denise M. McNair, had determined that VIP’s proposed use would require an SOB license, which VIP lacked. II.

VIP’s Prior Zoning Applications and Berlin’s Prior Ordinance Although the District Court determined only that Berlin’s current ordinance is unconstitutionally vague as applied to VIP’s March 2009 zoning application, the District Court considered the parties’ prior dealings in making that determination.

Before submitting the March 2009 zoning application that is at issue here, VIP previously had applied for a certificate of zoning compliance, in an application dated July 25, 2006, seeking to open an “Adult Bookstore!,] including books, magazines, videos, clothing, novelties—no on-site presentation of any materials sold.” In a letter accompanying this application, VIP stated that “less than a majority of its stock and trade” would consist of items of an “adult” nature.

Under Berlin’s SOB ordinance in place at the time of VIP’s first zoning application, the definition of an “Adult Bookstore” or “Adult Video Store” was an establishment having a “majority of its stock and trade” in adult books, magazines, videos, and the like. The ordinance additionally defined an “Adult Novelty Store” as “any establishment having a substantial or significant portion of its stock and trade” in adult novelty products. Berlin’s zoning officer denied VIP’s July 2006 application on the ground that VIP was an SOB and did not have the appropriate license.

VIP’s subsequent appeal to the Berlin Board of Zoning Appeals was denied. In the meantime, on October 5, 2006, the Berlin Town Council amended its SOB licensing ordinance to create a single category of business known as an “Adult Oriented Store,” which is defined as any establishment having “a 'substantial or significant portion of its stock in trade in Adult Books, Adult Videos or Adult Novelties or any combination thereof.” Berlin Code of Ordinances § 14-242 (emphases in original).

It is the language in this version of the ordinance that the District Court held unconstitutionally vague and that is before us on appeal. After Berlin rejected VIP’s July 2006 application and amended its ordinance, VIP filed a new application for a zoning permit on March 30, 2007, along with a proposed inventory list, representing that none of its proposed items for sale could be construed as “adult use,” including “adult novelty” or “adult video” as defined in the Berlin SOB ordinance. Berlin’s Chief Zoning Enforcement Officer, Hellyn R.

Riggins, apparently disagreed with VIP’s characterization of its inventory. In response to VIP’s March 2007 application, Riggins stated: “I have carefully reviewed the list of items that you propose to sell [and have] personally viewed these items at your other locations in the state.” Rig-gins concluded that “[a] significant or substantial portion of these items constitute adult novelties under the current

definitions found in our [SOB] Ordinance.” In June 2007, VIP resubmitted its zoning application with a revised inventory list that eliminated some of the items that were of concern to the town zoning officer. After submitting that application, the zoning officer indicated orally to VIP’s principal, Dominick DeMartino, that she intended to deny that application for the same reason that she denied the March 30 application. As a result, VIP withdrew its June 6 zoning application on June 8, 2007. III.

District Court Proceedings and Decision In November 2006, after its first zoning application was denied, VIP brought an action in the District Court pursuant to 42 U.S.C. § 1983, alleging that Berlin’s SOB zoning ordinance was unconstitutional. Subsequently, after its March 2009 zoning application was also denied, VIP sought a preliminary injunction to enjoin defendants from enforcing Berlin’s SOB ordinance against VIP.

In support of its motion for a preliminary injunction, VIP argued that the Berlin ordinance’s definition of an SOB—an establishment with “a substantial or significant portion of its stock in trade” in adult merchandise—is vague as applied to VIP’s March 2009 application because it does not provide sufficiently clear notice or guidance about what portion of merchandise would allow VIP to operate as a non-SOB. On June 23, 2009, the District Court heard oral argument, as well as testimony from DeMartino and McNair.

DeMartino, VIP’s principal, testified that he eventually wishes to open an adult store in Berlin pending the outcome of another segment of this litigation. However, he testified that currently he is attempting to comply with the SOB ordinance and does not understand what he needs to do to avoid being classified as an SOB under the ordinance. McNair, Berlin’s town manager, testified that she reviews zoning applications “on an individual basis” and that, in her view, the phrase “substantial or significant” means “meaningful to either the business or the Town of Berlin....

It would have import to the business.” When asked why she denied VIP’s March 2009 zoning application, McNair stated, “By the list that I saw, there were over 8,000 items that the applicant had said were adult products .... which to me is substantial.” McNair stated, “ ‘Portion’ to me means an amount.

A portion of something is an amount, a part of something.” McNair further stated that “[t]he ordinance, in the way I’m asked to apply it, is to assist in the goals of the town, the security of its people, the health, welfare, and I believe it’s necessary to look at the cases individually, not be arbitrary but to really understand and take a look at each application as applied.” On July 2, 2009, the District Court granted VIP’s motion for a preliminary injunction. See VIP of Berlin, LLC v. Town of Berlin, 644 F.Supp.2d 151 (D.Conn.2009).

Specifically, the District Court concluded that VIP showed (1) that it will suffer irreparable harm in the absence of an injunction because it is being prohibited from exercising its First Amendment rights and (2) a clear or substantial likelihood of success on its claim that the Berlin ordinance’s definition of an SOB is unconstitutionally vague as applied to VIP’s March 2009 zoning application.

With regard to the likelihood of success on the merits, the District Court reasoned that “the statute does not give the person of ordinary intelligence a reasonable opportunity to know what portion of stock in trade would not qualify as substantial or significant or provide explicit standards for those who apply it.” DISCUSSION We review a district court’s decision to grant or withhold a preliminary injunction for abuse of discretion. Vincenty v. Bloomberg, 476 F.3d 74, 83 (2d Cir.2007).

A district court exceeds its allowable discretion if its decision “rests on an error of law” or a “clearly erroneous factual finding,” or if its decision “cannot be located within the range of permissible decisions.” Id. (internal quotation marks omitted). “The ultimate question ... remains whether, in light of the applicable standard, the court has abused its discretion; and ‘[i]f the underlying constitutional question is close, therefore, we should uphold the injunction.’ ” Id. (quoting Ashcroft, 542 U.S. at 664, 124 S.Ct. 2783).

Where a party seeks a preliminary injunction that challenges “government action taken in the public interest pursuant to a statutory or regulatory scheme” and that would “alter, rather than maintain, the status quo,” the moving party must demonstrate irreparable harm and a “clear” or “substantial” likelihood of success on the merits. Jolly v. Coughlin, 76 F.3d 468, 473-74 (2d Cir.1996) (internal quotation marks omitted).

For the reasons set forth below, the District Court exceeded its allowable discretion when it held that VIP demonstrated a clear likelihood of success on the merits of its as applied vagueness challenge. I. Vagueness Doctrine “As one of the most fundamental protections of the Due Process Clause, the void-for-vagueness doctrine requires that laws be crafted with sufficient clarity to give the person of ordinary intelligence a reasonable opportunity to know what is prohibited and to provide explicit standards for those who apply them.” Thibodeau v.

Portuondo, 486 F.3d 61, 65 (2d Cir.2007) (internal citations and quotation marks omitted). “A statute can be impermissibly vague for either of two independent reasons. First, if it fails to provide people of ordinary intelligence a reasonable opportunity to understand what conduct it prohibits. Second, if it authorizes or even encourages arbitrary and discriminatory enforcement.” Hill v. Colorado, 530 U.S. 703, 732, 120 S.Ct. 2480, 147 L.Ed.2d 597 (2000). In reviewing a statute’s language for vagueness, “we are relegated ... to the words of the ordinance itself, to the

interpretations the court below has given to analogous statutes, and perhaps to some degree, to the

interpretation of the statute given by those charged with enforcing it.” Grayned v. City of Rockford, 408 U.S. 104, 110, 92 S.Ct. 2294, 33 L.Ed.2d 222 (1972) (internal quotation marks and footnotes omitted). “The degree of vagueness tolerated in a statute varies with its type: economic regulations are subject to a relaxed vagueness test, laws with criminal penalties to a stricter one, and laws that might infringe constitutional rights to the strictest of all.” Rubin v. Garvin, 544 F.3d 461, 467 (2d Cir.2008).

When a statute “is capable of reaching expression sheltered by the First Amendment, the [vagueness] doctrine demands a greater degree of specificity than in other contexts.” Farrell v. Burke, 449 F.3d 470, 485 (2d Cir.2006) (internal quotation marks omitted). A. Berlin’s SOB Ordinance Survives an “As Applied” Vagueness Challenge 1.

Notice The first way that a law may be unconstitutionally vague as applied to the conduct of certain individuals is “if it fails to provide people of ordinary intelligence a reasonable opportunity to understand what conduct it prohibits.” Hill, 530 U.S. at 732, 120 S.Ct. 2480. “Animating this first vagueness ground is the constitutional principle that individuals should receive fair notice or warning when the state has prohibited specific behavior or acts.” Thibodeau, 486 F.3d at 65.

The relevant inquiry is “whether the language conveys sufficiently definite warning as to the proscribed conduct when measured by common understanding and practices.” Rubin, 544 F.3d at 467 (internal quotation marks and citations omitted). “Condemned to the use of words, we can never expect mathematical certainty from our language.” Grayned, 408 U.S. at 110, 92 S.Ct. 2294; see also id. at 106, 109-10, 92 5.

Ct. 2294 (rejecting a facial vagueness challenge to an ordinance that implicated First Amendment rights and prohibited certain demonstrations “adjacent” to schools that “disturb[ ] or tend[ ] to disturb the peace or good order of such school session or class thereof ... ”). For this reason, we respectfully disagree with the dissent that it is constitutionally problematic that McNair testified that “she ‘was unable to supply a mathematical definition’ ” or a percentage to quantify the cutoff point for the amount of adult materials in a store’s stock in trade that would qualify it as an SOB.

See Dissent, infra, at 194-95. And, in any event, although the zoning officer’s understanding of the ordinance’s terms is relevant “perhaps to some degree,” Grayned, 408 U.S. at 110, 92 S.Ct. 2294, our inquiry begins with the text of the ordinance. In the present case, Berlin’s ordinance defines a sexually oriented business, or SOB, as an establishment that has a “substantial or significant portion” of its stock in trade in adult merchandise.

VIP asserts that this definition is so vague that it fails to provide VIP with notice that its proposed inventory of 8,242 adult items— approximately twelve percent of its total inventory of 67,237 items—would qualify it as an SOB. VIP further argues that, because the statute uses the words “substantial or significant portion,” it would be inappropriate to look at the absolute number of adult items being sold, as opposed to the proportion of the store that is adult-oriented, when determining whether a business is an SOB. Such a reading, however, ignores the common, ordinary meaning of the ordinance’s words.

See generally Perrin v. United States, 444 U.S. 37, 42, 100 S.Ct. 311, 62 L.Ed.2d 199 (1979) (“A fundamental canon of statutory construction is that, unless otherwise defined, words will be interpreted as taking their ordinary, contemporary, common meaning.”). One of the common

definitions of the term “substantial” is “of ample or considerable amount [or] quantity.” 15 Oxford English Dictionary 67 (2d ed.1989); see also Webster’s Third New Int’l Dictionary 2280 (1993) (defining substantial as “considerable in amount”). Similarly, one common definition of the term “significant” is “of a noticeably or measurably large amount.” Merriam-Webster Online Dictionary, http://www.merriam-webster.com/ dictionary/significant (last visited Jan. 22, 2010); see also Webster’s Third New Int’l Dictionary 2116 (1993) (defining significant as “important, weighty, notable”). “Portion” simply means a “part” of something. Webster’s Third New Int’l Dictionary 1768 (1993). Applying these

definitions to the present case, VIP’s proposed 8,242-item adult

section clearly falls under the ordinance because the “part” of its stock in trade devoted to adult merchandise is of “considerable quantity” and “of a noticeably or measurably large amount.” Congress has used similar phrasing in many other statutory contexts, including various portions of the patent laws, securities laws, environmental laws, and civil rights laws. The 1964 Civil Rights Act, for example, applies to a business if, inter alia, “a substantial portion of the food which it serves ... has moved in commerce.” 42 U.S.C. § 2000a(c) (emphasis added).

Despite repeated attacks on the Civil Rights Act’s validity under the Commerce Clause, it appears that no litigant ever thought to challenge the phrase “substantial portion of the food which it serves” as unconstitutionally vague. Although these statutes do not regulate First Amendment activity, and are thus subject to a lower required level of specificity in the face of a vagueness challenge, it is nonetheless worth noting that the legislature has used the phrase “substantial portion” to organize our society in a wide variety of contexts.

In addition to the plain meaning of the ordinance’s wording, which has been used in a wide variety of statutory contexts, the ordinance’s stated purpose^—preventing the adverse secondary effects associated with the presence of SOB’s—provides additional clarity and guidance. See Grayned, 408 U.S. at 112, 92 S.Ct. 2294 (noting that “[a]lthough the prohibited quantum of disturbance is not specified in the ordinance, it is apparent from the statute’s announced purpose that the measure is whether normal school activity has been or is about to be disrupted” (emphases added)).

Given the ordinance’s stated purpose, as well as the plain meaning of the ordinance’s words, the phrase “substantial or significant portion” clearly encompasses not only the percentage of adult items sold, but also the absolute number of adult items sold. It would make little sense to allow this store with an 8,242-item adult

section to operate as a non-SOB when a similarly located 8,242-item store devoted solely to adult merchandise would be required to obtain an SOB license and locate itself elsewhere. The neighborhood is no less likely to experience detrimental effects if the 8,242 adult items were sold through a small stand-alone business rather than through a large store’s “adult” department equally substantial in size. Despite the ordinance’s plain meaning and stated purpose, the District Court agreed with VIP that the ordinance was impermissibly vague.

Specifically, the District Court noted that the “language ‘substantial or significant portion of its stock in trade’ suggests that a retail establishment could have something more than zero percent adult media and adult products without being classified as an ‘adult oriented store.’ ” VIP of Berlin, LLC v. Town of Berlin, 644 F.Supp.2d 151, 162 (D.Conn.2009). The District Court concluded that “it is not readily apparent from the face of the ordinance what amount of stock in trade would qualify as a substantial or significant portion.” Id.

We have previously noted that, “[t]he evaluation of whether [a statute] ... is vague as applied to [a litigant] must be- made with respect to [the litigant’s] actual conduct and not with respect to hypothetical situations at the periphery of the [statute’s] scope.” Perez v. Hoblock, 368 F.3d 166, 175 (2d Cir.2004); see also Rubin v. Garvin, 544 F.3d 461, 468 (2d Cir.2008) (“Because we must examine the complainant’s conduct before analyzing other hypothetical applications of the law, we turn first to his as-applied challenge.” (internal quotation marks and citation omitted)).

To be clear, a court may analyze whether a reasonable person would understand that the litigant’s conduct was prohibited. See Hill, 530 U.S. at 732, 120 S.Ct. 2480. However, in the context of an as-applied vagueness challenge, a court’s analysis should be confined to the litigant’s actual conduct, and a court should not analyze whether a reasonable person would understand that certain hypothetical conduct or situations violate the statute. See Perez, 368 F.3d at 175; see also Farrell, 449 F.3d at 494.

Here, although its decision related only to VIP’s as-applied vagueness challenge, the language and logic of the District Court at times slipped into hypothetical analysis, questioning where in general the line between adult and non-adult businesses is drawn. The pertinent issue, however, is not whether a reasonable person would know what amount of adult merchandise, in general, would qualify a business as adult oriented. Rather, the issue in this particular as-applied challenge is whether a reasonable person would know that a proposed inventory of 8,242 adult items would qualify VIP as an adult oriented store.

Whether or not the ordinance provides a bright line rule about the specific amount of adult media that would qualify a store as “adult oriented” in hypothetical applications, there is no doubt that, as applied to VIP, the language of the SOB ordinance covers VIP’s March 2009 zoning application. As noted earlier, the portion of VIP’s proposed retail establishment that would be devoted to adult merchandise—8,242 items—is so substantial that it potentially eclipses the size of a free-standing store whose sole purpose is to provide adult merchandise.

One could analogize VIP to a department store, such as Macy’s, whose individual shoe department is so large that it exceeds the size of many stand-alone shoe stores. Even if Macy’s shoe department constituted only twelve percent of Macy’s total stock in trade, one would hardly call it an insubstantial or insignificant portion of the Macy’s store. Accordingly, even if there were a hypothetical situation that would fall under the ordinance’s “gray” area, the ordinance is sufficiently clear to provide VIP with notice that the proposed inventory in its March 2009 zoning application qualifies it as an SOB.

In addition to slipping into hypothetical analysis in the midst of determining whether the ordinance was vague as applied to VIP’s March 2009 zoning application, the District Court relied on several inapposite cases in reaching its conclusion. In particular, of the three state supreme court cases relied upon by the District Court, two involved language different from the language at issue here. In 105 Floyd Road, Inc. v. Crisp County, 279 Ga. 345, 613 S.E.2d 632, 634 (2005), the issue was whether the phrase “substantial business purpose ” was unconstitutionally vague.

The court noted that “[n]umerous courts have upheld statutory language against vagueness challenges where ‘substantial’ has modified matters such as stock in trade or interior business.” Id. at 634-35 (emphasis added). Specifically distinguishing those decisions, the court then found the phrase “substantial business purpose ” unconstitutionally vague because it “does not look to stock in trade, gross sales, floor space or some other readily quantifiable standard.” Id. at 635 (emphases added). Similarly, the issue in City of Columbia v.

Pic-A-Flick Video, Inc., 340 S.C. 278, 531 S.E.2d 518, 522-23 (2000) was whether the phrase “principal business purpose ” was unconstitutionally vague. Because the language at issue here is “substantial or significant portion of its stock in trade,” these two state supreme court cases are of limited applicability. Furthermore, one of the primary federal cases relied upon by the District Court, Wisconsin Vendors, Inc. v. Lake County, 152 F.Supp.2d 1087, 1094-95 (N.D.Ill.2001) (‘Wisconsin Vendors I ”), is also of limited persuasive value.

See id. (finding that plaintiff had shown a likelihood of success on the merits of its as-applied and facial vagueness challenge to the phrase “substantial or significant portion of its business”). Shortly after Wisconsin Vendors I was issued, the Seventh Circuit held in Pleasureland Museum, Inc. v. Beutter, 288 F.3d 988, 996-97 (7th Cir.2002), that the language “significant or substantial portion of its stock-in-trade” was not unconstitutionally overbroad on its face.

After the Seventh Circuit decided Pleasureland, the same District Court that decided Wisconsin Vendors I issued a new decision that rejected plaintiffs facial and as-applied vagueness challenges “[i]n light of Pleasureland.” Wisconsin Vendors, Inc. v. Lake County, No. 99 C 8340, 2003 WL 366580, at *4 (N.D.Ill. Feb.19, 2003). In sum, the plain meaning and stated purpose of Berlin’s ordinance, as applied to VIP’s March 2009 zoning application, provide adequate notice that the size of VIP’s proposed inventory would qualify it as an “adult-oriented” store under the ordinance.

In concluding to the contrary, the District Court’s decision at times slipped into hypothetical analysis ill suited for analyzing an as-applied vagueness challenge and failed to consider that the plain meaning of the ordinance encompasses not only the percentage of adult inventory items, but also the absolute number of adult inventory items. 2. Sufficiently Clear Enforcement Standards The second way in which a statute can be found unconstitutionally vague is if the statute does not “provide explicit standards for those who apply [it].” Thibodeau v.

Portuondo, 486 F.3d 61, 65 (2d Cir.2007) (internal quotation marks omitted).

When analyzing this issue, a court may determine that a statute provides adequate guidance if either: (1) the “statute as a general matter provides sufficiently clear standards to eliminate the risk of arbitrary enforcement;” or (2) “even in the absence of such standards, the conduct at issue falls within the core of the statute’s prohibition, so that the enforcement before the court was not the result of the unfettered latitude that law enforcement officers and factfinders might have in other, hypothetical applications of the statute.” Farrell v. Burke, 449 F.3d 470, 494 (2d Cir.2006).

For the same reasons that it gave VIP adequate notice regarding its March 2009 application, the language here, which defines an SOB as an establishment that has a “substantial or significant portion” of its stock in trade in adult merchandise, does not encourage or authorize arbitrary enforcement. The plain meaning of the ordinance, as discussed earlier, is not vague and clearly applies to VIP because the adult merchandise portion of VIP’s proposed retail establishment is so substantial that it potentially exceeds the size of some stand-alone stores.

In addition to a statute’s plain meaning and stated purpose, courts should determine whether a statute provides sufficiently clear enforcement standards by analyzing “perhaps to some degree ... the

interpretation of the statute given by those charged with enforcing it.” Grayned v. City of Rockford, 408 U.S. 104, 110, 92 S.Ct. 2294, 33 L.Ed.2d 222 (1972). In the present case, McNair, Berlin’s town manager, testified that she reviews zoning applications “on an individual basis” and that, in her view, the phrase “substantial or significant” means “meaningful to either the business or the Town of Berlin....

It would have import to the business.” When asked why she denied VIP’s March 2009 zoning application, McNair stated, “By the list that I saw, there were over 8,000 items that the applicant had said were adult products .... which to me is substantial.” McNair stated, “ ‘Portion’ to me means an amount.

A portion of something is an amount, a part of something.” McNair further stated that “[t]he ordinance, in the way I’m asked to apply it, is to assist in the goals of the town, the security of its people, the health, welfare, and I believe it’s necessary to look at the cases individually, not be arbitrary but to really understand and take a look at each application as applied.” McNair’s testimony is consistent with the stated purpose and plain meaning of the ordinance as described earlier in this opinion.

McNair’s statement that she reviews zoning applications “on an individual basis” and that the ordinance’s terms do not necessarily trigger a specific percentage of stock in trade or a specific absolute number of trade items does not alter that conclusion. See Grayned, 408 U.S. at 114, 92 S.Ct. 2294 (noting that “enforcement requires the exercise of some degree of ... judgment”). Furthermore, even if, as the dissent asserts, Berlin’s ordinance did not provide sufficiently clear enforcement standards, VIP’s as-applied vagueness challenge still fails.

As noted earlier, even if a statute does not include clear enforcement standards, it may still survive a void-for-vagueness challenge if the “conduct at issue falls within the core of the statute’s prohibition.” Farrell, 449 F.3d at 494. In Farrell, a convicted sex offender challenged a condition of his supervised release that prohibited him from possessing “pornography,” arguing that the term pornography was unconstitutionally vague on its face and as applied to him.

Although we did “not disagree with Farrell’s argument that the term ‘pornography’ is inherently vague,” and “[although the actors in Farrell’s case had divergent views on what constituted ‘pornography’ and why,” id. at 490, we nevertheless rejected Farrell’s vagueness challenge, id. at 492. We reasoned that “[w]hether or not the term ‘pornography’ is inherently vague,” the items possessed by Farrell fit “within any reasonable understanding of the term,” id. at 490, and “[n]o reasonable officer could have doubted that Farrell’s possession ... violated the terms of his parole agreement,” id. at 494.

Here, because the portion of VIP’s business devoted to adult merchandise is so substantial, VIP’s proposed retail establishment falls under the “core” of the ordinance’s prohibition. For the reasons discussed above, VIP’s proposed 8,242-item adult inventory, which constitutes twelve percent of its stock in trade, falls “within any reasonable understanding of the [ordinance’s language].” Id. at 490.

Accordingly, even if the ordinance did not provide clear enforcement standards, the decision to classify VIP as an SOB was not the result of “unfettered latitude that law enforcement officers and factfinders might have in other, hypothetical applications of the statute.” Id. at 494. CONCLUSION For the reasons stated above, the preliminary injunction order of the District Court is VACATED and the case is REMANDED for further proceedings consistent with this opinion. . As noted earlier, whether the

definitions of these “adult” items are unconstitutionally vague is not before us because the District Court's decision to enjoin enforcement of the ordinance was not grounded on such a basis and no party in this appeal has presented arguments relating to these

definitions. However, for ease of reference and completeness, these

definitions are included here. Berlin's SOB ordinance defines "Adult Videos” as "films, motion pictures, videocassettes, DVDs, software, slides or other pornographic reproductions that depict, display or describe specified anatomical areas or specified sexual activities” as those areas and activities are defined by the Berlin Code. Berlin Code of Ordinances § 14-242.

Berlin's SOB ordinance defines "Adult Books” as "any books, magazines, periodicals, pamphlets, or other printed materials that depict, display or describe specified anatomical areas or specified sexual activities” as those areas and activities are defined by the Berlin Code. Id. Berlin's definition of “Adult Novelties” includes "oils, lotions, gels or creams that are designed for or marketed primarily for use upon specified anatomical areas and intended for stimulating human genital organs, sexual arousal or as an aid to enhace or promote specified sexual activities.” Id.

Furthermore, the term “Adult Novelties” includes "instruments, devices, toys, or paraphernalia that are designed for or marketed primarily for stimulating human genital organs, sexual arousal or sadomasochistic use” and "instruments, devices, gag gifts, toys or paraphernalia that depict, display or are shaped in the form of specified anatomical areas.” Id. . On July 30, 2009, a three-judge panel of our court stayed the District Court’s order pending appeal. See Dkt. No. 09-2950-cv, Order of July 30, 2009. .

At least one of our prior cases has suggested that, in reviewing a district court's grant of a preliminary injunction, "the constitutionality of a statute is a legal question subject to de novo review.” Field Day, LLC v. County of Suffolk, 463 F.3d 167, 176 (2d Cir.2006) (internal quotation marks omitted). This standard of review, however, is inconsistent with the Supreme Court's instruction in Ashcroft v.

American Civil Liberties Union, 542 U.S. 656, 664, 124 S.Ct. 2783, 159 L.Ed.2d 690 (2004) that "we should uphold the injunction” where "the underlying constitutional question is close.” In any event, we vacate the preliminary injunction here because the constitutional question at issue is not close and because the District Court's decision cannot be located within the range of permissible decisions. .

Where "the only vagueness in the ordinances relates to the amount of sexually explicit activity that may be portrayed before the material can be said to” fall within the scope of the ordinances, the Supreme Court has expressed skepticism about whether such ordinances have a "significant deterrent effect on ... First Amendment” rights. Young v. Am.

Mini Theatres, Inc., 427 U.S. 50, 60-61, 96 S.Ct. 2440, 49 L.Ed.2d 310 (1976) (rejecting a facial vagueness challenge to a zoning ordinance's regulation of adult theaters); see also id. at 70, 96 S.Ct. 2440 ("[TJhough we recognize that the First Amendment will not tolerate the total suppression of erotic materials that have some arguably artistic value, it is manifest that society’s interest in protecting this type of expression is of a wholly different, and lesser, magnitude than the interest in untrammeled political debate....”).

Accordingly, because the only vagueness challenge here relates to the ordinance’s definition of how much "adult” merchandise makes a store "adult oriented,” the degree of vagueness tolerated in this situation, although slightly unclear from existing case law, may be somewhat greater than if the ordinance regulated other types of more protected speech. Nevertheless, even if the expression at issue here were entitled to full First Amendment protection, the present ordinance's language is sufficiently specific to withstand VIP’s as-applied vagueness challenge. .

In addition to the plain meaning of the phrase, upon analyzing the phrase's application in other legislative contexts, it is clear that “substantial or significant portion of its stock in trade” should be considered in light of the absolute number of items offered for sale, not just the percentage of items offered for sale. In enacting 47 U.S.C. § 941, for example, Congress found that "a significant portion of all material available on the Internet is related to pornography,” Pub.L.

No. 107-317, 116 Stat. 2766, 2766 (2002) (emphasis added), even though it has been said that only "[a] little more than 1 percent of all [searchable] Web pages (amounting to approximately 275 million to 700 million Web pages) are sexually explicit,” Am. Civil Liberties Union v. Gonzales, 478 F.Supp.2d 775, 788 (E.D.Pa.2007) (finding the phrase "harmful to minors” in 47 U.S.C. § 231 unconstitutionally vague).

Because only one percent of web pages are sexually explicit, but the absolute number of sexually explicit web pages reaches into the millions, Congress's finding that a “significant portion” of the internet is sexually explicit likely contemplated the absolute amount, not just the percentage, of sexually explicit material available on the internet. .

The phrase “substantial portion” appears in the following categories of federal statutes: Banks and Banking, 12 U.S.C. § 1749aaa-5(3); Civil Rights Act of 1964, 42 U.S.C. § 2000a(c); Crimes and Criminal Procedure, Federally Protected Activities, 18 U.S.C. § 245(b)(3); Employee Retirement Income Security Act of 1974, 29 U.S.C. §§ 1107(e)(1)(B), (

C) and 1403(b)(2); Endangered Species Act Amendments of 1982, 16 U.S.C. § 1539(b)(2)(B); Farm Housing, 42 U.S.C. § 1484(f)(3); Foreign Relations and Intercourse, 22 U.S.C. §§ 3651(2) and 3984(a); Housing of Persons Engaged in National Defense, 42 U.S.C. § 1581(d)(4); Internal Revenue Code, 26 U.S.C. §§ 280G(b)(2)(A)(ii)(II), 4252(b)(2), 7507(a), 7701(a)(36)(A); Investment Companies, 15 U.S.C. §§ 80a-2(a)(5) and 80b-2(a)(2); Judiciary and Judicial Procedure, 28 U.S.C. §§ 456(d), (

e) and 460(b); Navigation and Navigable Waters, 33 U.S.C. § 1286(f)(1); Newspaper Preservation Act, 15 U.S.C. § 1802(4); Petroleum Marketing Practices, 15 U.S.C. § 2821(11); Public Health Service, 42 U.S.C. § 300e-l(4)(C); Public Works Acceleration Program, 42 U.S.C. § 2642(f)(3); Securities Exchanges, 15 U.S.C. § 78c(a)(6); Student Assistance, 20 U.S.C. § 1087-2(q)(2)(A); Water Resources, 42 U.S.C. § 1962d-14a(g)(l), (h). See also United. States v.

Clark, 912 F.2d 1087 (9th Cir.1990) (finding that "substantial portion” as used in the Marine Mammal Protection Act, 16 U.S.C. § 1361, et seq., was not unconstitutionally vague). . The District Court expressly considered VIP's vagueness challenge "as applied to VIP’s present business plan, which was submitted to Berlin’s zoning enforcement officer on March 26, 2009” and did not hold that the ordinance was vague as applied to VIP’s previous zoning applications.

Given that the District Court’s decision addressed VIP’s vagueness challenge as applied to VIP’s March 2009 zoning application, VIP’s prior zoning applications are of limited relevance. VIP’s first zoning application was denied in 2006 pursuant to an ordinance whose wording differs from the present ordinance's language. Furthermore, VIP explicitly stated in that 2006 application that it intended to operate as an "Adult Bookstore." In addition, the denial of VIP’s March 2007 zoning application appeared to center, in part, around a dispute about whether certain items were adult or not.

See supra 184 The District Court's decision was not based on a finding that the ordinance's

definitions of "adult” merchandise were vague or overbroad and, therefore, those issues are not before us. . In addition, even if the District Court had been correct to engage in some facial analysis, it is not clear that its conclusion from that analysis is correct, as the majority of courts that have considered a facial challenge to similar language have reached the opposite conclusion. See, e.g., Ill. One News, Inc. v.

City of Marshall, 477 F.3d 461, 465 (7th Cir.2007) (finding that the definition of "adult bookstore” as "[a]n establishment having a substantial or significant portion of its stock in trade” in adult merchandise was not facially vague and noting that "[i]t is all but impossible to write a law or regulation without some qualitative words such as 'substantial' ”); Doctor John’s, Inc. v.

City of Roy, 465 F.3d 1150, 1157, 1160 (10th Cir.2006) (noting that to prevail on a facial vagueness challenge, a party "must show, at a minimum, that the challenged law would be vague in the vast majority of its applications” and that the phrase " 'significant or substantial’ portion of its wares devoted to adult material survives Dr. John’s facial vagueness challenge”); ILQ Invs., Inc. v. City of Rochester, 25 F.3d 1413, 1419 (8th Cir.1994); 511 Detroit St., Inc. v. Kelley, 807 F.2d 1293, 1295-97 (6th Cir.1986); Mom N Pops, Inc. v.

City of Charlotte, 979 F.Supp. 372, 393-94 (W.D.N.C.1997); 15192 Thirteen Mile Rd., Inc., v. City of Warren, 626 F.Supp. 803, 819-21 (E.D.Mich.1985); City of Chi. v. Scandia Books, Inc., 102 Ill.App.3d 292, 58 Ill.Dec. 72, 430 N.E.2d 14, 18 (1981) ("The word 'substantial' as used in the definition of adult bookstores is not so indefinite as to render the Ordinance void and unenforceable.”); Dandy Co., v.

Civil City of South Bend, County-City Complex, 401 N.E.2d 1380, 1386 (Ind.Ct.App.1980) ("The definition[s] of [substantial or significant] must necessarily be determined on a case-by-case basis and are therefore not capable of precise mathematical calculation.”); Golden Triangle News, Inc. v. Corbett, 689 A.2d 974, 984-85 (1997) (rejecting the argument that the phrase "substantial or significant portion” is impermissibly vague under Pennsylvania’s state constitution). But see City of Knoxville v.

Entm’t Res., LLC, 166 S.W.3d 650, 652, 656 (2005) (holding the phrase "substantial or significant portion of its stock and trade” unconstitutionally vague and relying heavily on the fact that "the officers charged with enforcing the ordinance [are unable] to define its key terms”). . One might argue that VIP's March 2007 application does not fall under the “core” of Berlin’s ordinance because VIP represented in that application that zero percent of its inventory would be adult merchandise. However, from the record it seems to be an open question whether or not the inventory was actually zero percent adult.

Riggins, one of Berlin's officials, certainly disagreed with the way that VIP had characterized its inventory. Furthermore, and more importantly, it is VIP's March 2009 zoning application that is at issue here, and VIP represents in that application that more than 8,000 items of VIP’s proposed inventory would constitute adult items.

In this regard, we note that, when looking to whether Berlin's ordinance provided sufficiently clear enforcement standards, the testimony of VIP's principal that he did not “know what substantial or significant portion of stock in trade means in an actual number” is of only marginal value. See Dissent, infra at 196. First, the First Amendment does not require that ordinances provide “mathematical certainty” when describing the conduct they prohibit. See Groyned, 408 U.S. at 110, 92 S.Ct. 2294.

Second, the more relevant question for DeMartino in this as-applied challenge is whether he knew that the proposed inventory in VIP’s March 2009 application would cause the store to fall within the purview of Berlin's SOB ordinance. Objectively speaking, the inquiry could yield only one reasonable answer: yes. Put another way, VIP's March 2009 application fit comfortably within the core of the ordinance’s prohibition.