if its release date was timed to happen 30 days before the election
Well, what's interesting about the timing is that at the time HRC was involved in a primary battle with then-Senator Obama. So now, let's see, David Bossie can't be critical of Hillary Clinton because the Democrats are having a private election?
If it was and the film was designed to harm Mrs. Clinton's public image then it was also designed to improve the chances of her rival candidates winning and thus was an effective endorsement
Well, I'm not sure Citizens United could be said to be endorsing Obama of course, but generally I would say you are correct of course.
But now let's take it back one election cycle to Bush/Kerry when Michael Moore released Fahrenheit 9/11.
Well, Michael Moore is Michael Moore and David Bossie and David Bossie and unlike David Bossie, Michael Moore actually knows how to make movies and that's a corporation too, Dog Eat Dog, Inc. and his purpose was to defeat George W Bush. Now, of course he did release the movie and naturally Bush II was not subject to a primary challenge, but what if he had been? And of course the FEC's rules made sure that Fahrenheit 9/11 came out I think beyond the 60 day window, or 30 window?
Let's just look at this as a free press case for a second. The right criticizing, not just a candidate for public office, but in the case of Bush II and HRC, seated members of the government, falls within the very CORE of the freedom of the press. Would it be constitutional to prohibit a media corporation doing such things? Of course not. No one disputes that corporations like Fox, CNN, MSNBC, NY Times can editorialize. Other groups performing that same function have the same immunity from government even if they are not part of what we would call the main stream media. Who's to say who's in the media or not in the media? The FEC?
David Bossie actually was making a point by making the movie Hillary beyond simply criticizing Hillary Clinton.
Bossie had essentially argued in 2004 that Michael Moore's Fahrenheit 9/11 movie was a campaign ad.
https://www.npr.org/templates/story/story.php?storyId=3023147
And then the FEC dismissed the complaint:
https://www.rcfp.org/fec-dismisses-fahrenheit-911-complaint/
Well, that means Bossie should be able to do the same thing, right?
Well, yes, it does actually!