No. The City Standard Operating Procedure on Special Events, passed in 2009, distinguishes between “Special Events” — sports events, pageants, music festivals, etc., — and “demonstrations,” a term that refers to “non-commercial expression protected by the First Amendment of the United States Constitution (such as picketing, political marches, speechmaking, vigils, walks, etc.) conducted on public property, the conduct of which has the effect, intent or propensity to attract a crowd of onlookers.” Jason Kessler is holding a “demonstration,” not a “Special Event.”
If you read the Procedure closely, you will see that on page 6 — at section 3.5.4. — the document says that “sponsors of demonstrations and special events for which a permit is required shall be required to indemnify and hold harmless the City… from any personal injury, death and damages to property, and any other loss, cost and/or damage occurring as a result of the demonstration of [they probably mean “or”] the event.” In paragraph d., the document requires that “the sponsor of a special event shall furnish a general liability and property damage insurance contract insuring the Sponsor’s liability for personal injury and death and damages to property resulting from its use of public property.”
But remember that “special event” is a term that does not include “demonstration.” So while the procedures require that sponsors of both activities must “indemnify and hold harmless the City,” only sponsors of special events — and not sponsors of demonstrations — have to actually buy insurance to cover that liability. So the fact that Kessler had bought a one-day insurance policy that has since been cancelled (see NBC29’s coverage, here) has no real bearing on anything. Kessler was not required to have insurance anyway.
Likewise, the provisions of §3.5.15. that state that “No Special Event shall be permitted unless adequate security will be provided for the welfare and safety of those attending the event and of the general public” does not apply to Kessler’s “demonstration.”
One putting on a demonstration cannot be held liable for the actions of third parties. In NAACP v. Claiborne Hardware Co., the Supreme Court held that an organization exercising its First Amendment rights may not be held liable for the conduct of a third party “without a finding that [it] authorized—either actually or apparently—or ratified unlawful conduct.” 458 U.S. 886, 931, 102 S.Ct. 3409, 73 L.Ed.2d 1215 (1982). That is a decision that is worth reading simply for its history, and to get a sense of the tactics that nonviolent organizers were using in the South. In that case, the NAACP was conducting a boycott of certain businesses, including Claiborne Hardware Company. The boycott lasted for 7 years, and the white-owned businesses sued the NAACP, its local organizer Charles Evers, and about 100 other people, awarding about $1 million in damages. The Supreme Court made a couple of rulings that are worth noting in the context of this discussion:
1. You can only be held responsible civilly for what you actually do yourself, or what you specifically join with others to do. You cannot be responsible for what others do simply because you get them excited — liability has to be based on a specific incitement (“Go burn that building; go attack that white guy over there.”).
2. An organizing group like the NAACP cannot, in the ordinary case, be held financially responsible for what its members might do, at least in the absence of some action that is obviously the action of the corporate entity.
With this backdrop, let’s look at the caselaw that specifically discusses insurance requirements. A decision that is very thorough, and discusses the issue in perhaps mind-numbing detail, is the decision of the Tenth Circuit in iMatter Utah v. Njord, 774 F.3d 1258 (10th Cir. 2014), starting at about page 15 in the version that is hyperlinked.
If you look at the decision in iMatter Utah, ask yourself, “If I wanted to insist on an insurance policy, and I wanted it to be constitutional, what requirements would I be allowed to put in?” I, for one, have a hard time figuring out what such a requirement could do and still pass the constitutional test enunciated in iMatter Utah.
If a city wanted to be constitutionally adventurous, it could adopt an insurance requirement and try to tailor it as the Tenth Circuit suggested, but I am not sure that it is possible to do it under those constitutional standards. Of course, you could always try to take the case to the United States Supreme Court and try to convince that court that they are being too restrictive… and if you do, and you lose, you have to pay the other side’s attorney’s fees, which would probably end up well into 6 figures. And that is why Charlottesville has not insisted on a liability insurance policy in its Standard Operating Procedure.