Dan Snyder is perhaps the only man in Washington less popular than Congress. The long-running owner of the Washington Redskins NFL team, Snyder is best known for alienating fans, sparring with local media and pricing the team’s diehards out of their tickets. He’s also the most visible face of a routinely disappointing franchise that hasn’t won a Super Bowl, to the locals’ deep chagrin, in 20 years.

Dave McKenna, a writer for the Washington City Paper alternative weekly, handily chronicled many of these blemishes last November, at the tail end of another losing season, in an A-to-Z cover spread titled “The Cranky Redskins Fan’s Guide to Dan Snyder.”

Then, as if to further illustrate McKenna’s point, Snyder sued the paper for libel.

The lawsuit, first filed in February in New York State, immediately reeked of the worst kind of defamation litigation: that of an obscenely wealthy plaintiff looking to bankrupt his critics in court, regardless of the merit or eventual outcome of the case. In fact, Snyder’s lawyers communicated exactly this intention when they sent a letter on Redskins letterhead last fall to the investment group that owns the City Paper, concluding with this warning shot:

“Mr. Snyder has more than sufficient means to protect his reputation and defend himself and his wife against your paper’s concerted attempt at character assassination. We presume that defending such litigation would not be a rational strategy for an investment fund such as yours. Indeed, the cost of litigation would presumably quickly outstrip the asset value of the Washington City Paper.”

States across the US have been passing laws to prevent deep-pocketed, litigation-happy bullies from filing exactly these types of suits to intimidate critics from making protected speech. There’s even a name for the strategy: Strategic Lawsuits Against Public Participation. The statutes pre-empting them are commonly known as anti-SLAPP laws, and, in fact, the District of Columbia put one on the books this spring.

Among other things, it requires that plaintiffs demonstrate early in the legal process that they’re likely to prevail on the merits of a complaint (as opposed to bankrupting a defendant in discovery before the question of merit ever comes before a judge).

Now Snyder is challenging that law, too, broadening his sights from the City Paper to a legal protection that’s enjoyed by citizens throughout the District. And the city has had to intervene in the lawsuit to defend its law, with an amicus brief filed by the ACLU, the American Society of Newspaper Editors, the Society of Professional Journalists and a whole slew of other media organizations.

Back in April, Snyder moved the suit from New York to Washington. The City Paper then requested the suit be dismissed in June under the new anti-SLAPP law. Snyder’s lawyers, in response, are arguing that the anti-SLAPP law itself is unconstitutional (according to a convoluted legal arrangement that restricts the District of Columbia from governing itself in the same way other states and municipalities in the U.S. can).

The case has since evolved well beyond the small-bore debate over the tongue-in-cheek tone of McKenna’s original story and into a much larger one over the right of media outlets — and others — to legitimately criticise wealthy people without fear of legal harassment.

This much at least is clear: When the case finally reaches its conclusion, Snyder will have provided enough material to supplant the Cranky Redskin’s Guide with an entire book.