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Notes -
While FECA is best-known for its direct contribution limits on candidate-specific communications, much of the point of McCain-Feingold in 2002 was to expand the law's definition of 'electioneering communications' to cover matters that did not target or support a specific politician directly, but also matters like 'issue ads', which focused on topic areas, if usually to highlight a candidate on those matters. In addition to restrictions on when they could run them and how they could fund them, candidates running issues ads (or coordinating with those running issue ads) were required to disclose their participation, known as the "Stand By Your Ad" provision.
This was mostly used where the third-party issue ads explicitly named politicians (such as Citizens United involving a movie about Clinton's history), but the law held a candidate was clearly identified a "specific candidate" where a communication asked to call their representative, even if this resulted in many different 'specific' candidates being involved. And while the Federalist Papers genuinely were more focused on the theoretical foundations, their calls to action and some of the more subtle components would pass this requirement.
The larger length of time between the issuance of the Federalist Papers and the local elections for the convention might have put it outside of the FECA safe harbor timeline, but I'm honestly not sure, and the Stand By Your Ad requirement probably would have applied by its strict text. (In practice, the FEC tends to avoid cases with that clear a First Amendment component, lest they get slapped by SCOTUS again.) And most FECA provisions have a 50k audience requirement and only covered audio and video, which obviously would have been hard to hit in the Founding era.
And, of course, New York law can be much more aggressive than federal law : a New York organization opposing or supporting even specific ballot issues, separate from any specific candidate, must register with the state, report to the state any donations above a certain (low) threshold, and refuse any anonymous contributions. The Federalist Papers would clearly hit that requirement by strict read of the text, though there's both official and unofficial exceptions for organizations whose free speech the ACLU cares about. I think the Federalist Papers could also hit the PAC requirements by a strict read of the text, but I'd have to look through that in more detail to say for sure.
I'm still not really getting it. I was under the impression that the Federalist papers were a series of essays published in newspapers. As far as I know, they weren't ads. Why would they be governed by the rules that apply to modern ads and not the rules that apply to modern newspaper editorials?
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McCain-Feingold's (and I think NY law) definitions of electioneering communications are not limited to advertisements. Famously so, given that Citizens United revolved around a case where the FEC both prohibited ads for a movie and simply showing that movie.
There are exceptions for contributions (ie costs) by independent news media reporting bonafide news, but the "stand by your ad" rules, reporting provisions, and time provisions do not have such exceptions, and some of the Federalist newspapers probably would fail the modern independence test (if only because almost all newspapers at the Founding Era were tied heavily to local political parties, or were vanity press). In practice, the FEC almost never takes such charges, because at least some would fail Mills (though Mills was about uncoordinated expenditures, and Hamilton was clearly coordinating them), but the strict text would allow them.
Okay, so is the answer to the hypothetical then that yes the Federalist Papers would have been legal but they would have needed to include a "I'm James Madison and I approve this message" style notification?
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I'm asking you! I sincerely don't have a strong understanding of the operation of the law in this respect and am trying to get my head around it. Have I understood you correctly?
Definitely not legal as pseudonymous pieces; coordinated works are required to disclose, even in newspapers. I'm moderately confident the law would trigger certain reporting requirements in New York, and probably those would be mandated by federal law for Hamilton, possibly some other writers. Not sure on the journals themselves; we have mixed information on what extent they were bonafide publishers or party outfits.
... by the text of the statutes. The First Amendment raises an absolute ton of legal questions, here, and the question of whether these disclosure, reporting, and 'stand by' requirements are legal gets complicated (albeit generally expressive association, rather than free speech). Many rules have been invalidated by SCOTUS jurisprudence as overly broad, ill-defined, or improperly tailored for how large of a chilling effect on free speech they have. And there is specific precedence on reporting requirements having massive chilling effects.
Ok. So is it your position then that by the text of the statutes, when the NYT publishes an anonymous article saying "I am part of the resistance inside the Trump White House", that article would be illegal? But no one prosecutes it because it would so obviously infringe on free speech?
Possibly. The NYT specifically is a lot more likely to be a bonafide publisher by FEC regs compared to the various Federalist-era papers, and some of the electioneering requirements only apply to 'broadcast' communications, but the disclosure requirements in the statutes did not have such exceptions.
See Buckley v. Valeo. It's a bit of a dogs breakfast of a decision with a ton of balancing tests, or where the government conceded a much more restricted version of the statute on, but on the specific matter a section of the law which mandated disclosure of independent contributions :
Note that these restricted definitions, unlike many other components, were not conceded by the state at previous court hearings, but the result of SCOTUS trimming down the statute to avoid declaring the whole thing unconstitutional.
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It would have been "I'm 'Publius' and I approve this message", so probably illegal I suppose.
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