Even as the Supreme Court seemed poised to reject the view that the hundreds of flags the city had allowed were all government speech, some justices worried about the consequences of a broad ruling, asking, for instance, whether the city would have to fly a flag bearing a swastika.
Mathew Staver, a lawyer for Camp Constitution, said yes. He added that “an informed observer” familiar with the city’s flag program and its history would know that the flags flown on the third flagpole represented private speech.
That assertion met a skeptical response.
Such an observer must be “very informed,” Justice Kagan said. As for the more typical ones, she said, “all they know is: ‘I’ve seen the City of Boston flag here a thousand times, and now I see another flag. It must be the City of Boston decided to do something else today.’”
Douglas Hallward-Driemeier, a lawyer for Boston, said there were limits to what the city must be made to allow. “Private parties are free to wave their flags on City Hall Plaza or even raise a temporary flagpole there,” he said, “but they cannot commandeer the city’s flagpole to send a message the city does not endorse.”
The solution, some justices suggested, was for the city to exercise more control over the process, so that it would be plain that it was endorsing the messages the flags conveyed.
Justice Amy Coney Barrett sketched out what such an approach might include.
“The City of Boston sits down, asks what’s going to be expressed and says, ‘Yes, this is an idea that Boston can get behind,’” she said. “And a government official participates in the flag raising, participates in the ceremony, communicating that, ‘Yes, Boston is happy to celebrate and communicate pride in Juneteenth, but, no, Boston is not going to participate in a flag raising for the Proud Boys.’”