It took the Court of Appeals 77 pages to say this, but the long and the short of it is that if you want to be a law enforcement officer, you probably shouldn't join the Outlaws Motorcycle Club, an organization which the government regards as a criminal enterprise, comparable to the Hell's Angels. Since many innocents no doubt belong to the Outlaws Motorcycle Club, the question is can the State of Connecticut can fire corrections officers who belong to this organization. Rejecting the officers' Freedom of Association claims, the Second Circuit (Kearse, Sack and Stanceu) upheld their terminations.
The case is Piscottano v. Murphy, decided on December 21, 2007. As the Court of Appeals likes to do, it uses this case to flesh out the state of the law on the right of association under the First Amendment, outlining how the Supreme Court has made it easier over the years to allow the government to restrict certain First Amendment freedoms among public employees.
The Court of Appeals first reviewed the Supreme Court's latest pronouncements on the regulation of a public employee's outside activities. Citing San Diego v. Roe, 543 U.S. 77 (2004), the Court stated that the government has leeway to discipline an employee whose outside speech or associations are detrimental to that operation. It is true, the Second Circuit held, that the plaintiffs in this case engaged in a "protected" association with the Outlaws in that their involvement with the organization raised a matter of "public concern" under the First Amendment. This is because, while the Outlaws Motorcycle Club does not as an organization engage in "public concern" speech, that organization's questionable existance itself would raise concern among the public.
But while "public concern" speech is protected by the First Amendment, the analysis does not end there. The government can still win the case by showing that this associational relationship can hurt governmental operations. Since the plaintiffs are corrections officers associating with an organization with a mission at odds with law enforcement, they can be fired for that association, overriding the First Amendment claim. Moreover, since membership in a large and non-selective social club like the Outlaws does not represent the kind of intimate (family) relationship for which you cannot be punished at work, the right of "intimate association" under the First Amendment does not help the corrections officers, either.