There's a huge irony here. Winston was ethically bound to file an Answer that best positioned their client without regard to a settlement because that settlement might never happen.
At the same time, a counterclaim may well have been construed as unnecessarily aggressive given Friday's announcement about the suit going away.
In her interview on the pro-Axanar Fan Film Factor blog, attorney Erin Ranahan explained that with the deadline for the Answer already having been set, combined with Judge Klausner's well known dislike of delays, she felt bound to file the Answer instead of asking for an extension.
That may have been a strategic error. Since the announcement happened on a Friday and the Answer was due on Monday, there was no time to digest what had actually happened. Hell, most of the news media thought the suit was being dropped when it actually hadn't, and the Axanar camp was already touting their victory.
By moving ahead with the Answer as scheduled instead of asking the judge for an extension given that it might've been possible to resolve the case, Ranahan felt she simply had file an Answer with a counterclaim in it because that was in the best interests of her clients. Unfortunately, that appears to have sent the wrong public message, given the inaccurate but widely held media narrative that the case was being dropped.