The case is Dorsett v. County of Nassau, decided on October 18. I co-wrote the brief on appeal. The theory was that Dorsett's association with a civil rights lawyer is protected under the First Amendment. There is case law to support that theory of liability, but the Second Circuit (Wesley, Walker and Winter) focuses on plaintiff's standing to sue and whether you even have a right to settle a case.
Here is the sequence of events: while the settlement was pending, Dorsett's lawyer filed a Voting Rights Act case against the County, angering the legislative chairman, Schmitt, who publicly said the Dorsett settlement was not finalized by the Legislature because “I did not feel comfortable voting on a settlement that would put a couple million dollars into [Brewington’s] . . . pocket while we were being sued [in the Boone case], so I requested an opinion of the County Board of Ethics to see that there was no conflict there.” The Court of Appeals notes that, "[i]n fact, Schmitt had received the ethics opinion in September – two months before this interview – and the settlement was still not approved until January. Plaintiffs allege that Schmitt actually requested the ethics opinion to hold up the settlement in retaliation for their political activities."
Plaintiff loses the case under Rule 12 because she had no right to a settlement in the first instance, even if the informal agreement had been reached.Of course, the case eventually did settle, but it was delayed, costing Dorsett money. On the way to affirming the dismissal of the complaint, the Court of Appeals clarifies that First Amendment retaliation cases do not always require proof that the government's response to the speech chilled further speech. You can also win if the plaintiff suffered a concrete loss of some kind from the retaliation. However, the Court says in dismissing the case:
Eight million dollars is certainly concrete, but this does not tell the whole tale. Plaintiffs had no right to have the settlement approved by a date certain. The settlement did not include a time‐is‐of‐the‐essence clause, nor have Plaintiffs pointed to anything that required the legislature to act. The legislature's agenda is subject to its absolute discretion. It was not required to vote on the settlement – ever. Much less was it required to approve it.