The writer and satirist who identifies himself as William Needham Finley IV presented an enthusiastic post in his ITB Insider blog on March 28, announcing the Raleigh City Council candidacy of lawyer Stacy Miller.

Calling Miller’s entry into the race “great news for a number of reasons,” Finley wrote, “We have the chance to add another Broughton [High] graduate to the council, and he’s got some great ideas for Raleigh. Plus, he let me announce this decision, which further legitimizes ITB Insider as a media empire and source for real news.”

The post is topped by an image of Miller riding a bright-green dinosaur splashed with the LaCroix logo, surrounded by schoolchildren and a cop and firefighter giving thumbs-up.

Using his real name, Seth Crossno, the blogger then submitted the post as a $500 in-kind donation to Miller’s campaign, as seen in documents filed July 28 with the Wake County Board of Elections.

ITB Insider adroitly pokes fun at everything that’s pompous and self-involved about old Raleigh society, while also reporting on development inside the Beltline. However, posting the article praising Miller, then claiming it as a campaign donation, raises questions about the sometimes murky line between traditional journalism and online speech.

Crossno says in an email that everything was right and proper about the donation to Miller, and another he made to candidate Bonner Gaylord.

“Considering the fact that I took extreme caution to fill out the appropriate paperwork and made sure I was following the rules, it’s insulting to insinuate that I’m intentionally trying to mislead readers of my satirical blog,” Crossno writes. “The in-kind donation form I filled out stated the donation came from me as an individual. This means that I personally reimbursed [his media company] XNO, LLC for these two blog posts.”

Blannie Cheng Miller, an attorney advising Miller’s campaign, says that Crossno sometimes sells blog posts to sponsors. Out of an abundance of caution, Cheng advised him to put a fair market value on the post, pay his company for it, and disclose the in-kind donation.

Election finance officials and experts, however, say that listing a blog post as a campaign donation is highly unusual. Sabra Faires, a Raleigh attorney whose specialties include elections and political law, asks whether the $500 value represents Crossno’s work in writing the post, or the act of putting it on the ITB Insider site.

“Is this really an individual donation as opposed to a donation from the site itself?” Faires says. “That would be illegal, because it would be a contribution from a business, since he is in effect advertising for that guy. If this is his personal view, you wonder why he counts that as a paid contribution.”

“It seems to me that’s confusing the line,” says Meredith University political science professor David McLennan. “That’d be like the N&O‘s endorsement being considered a contribution. It’s pushing the envelope of what we consider campaign finance reporting.”

Jonathan Jones, director of the N.C. Open Government Coalition, asks whether a positive article should be valued in the same manner as more typical in-kind contributions, such as food at a reception.

“You’d never see a disclosure saying INDY Week endorsed us,” Jones said. “My question is, Was this done out of a belief that that disclosure was necessary to cover everyone’s behind?”

The Miller Law Firm—Stacy Miller’s firm—is listed as an ITB Insider sponsor. Crossno says the law firm’s contribution had nothing to do with his in-kind donation.

An announcement of candidate Bonner’s candidacy was labeled as humor. Crossno says the in-kind donation for that story has been submitted and will be listed on a future disclosure form.

Crossno, who attended Broughton, gained international prominence by tweeting out details and photographs of the failed Fyre Festival in the Bahamas. In May, Crossno and another plaintiff sued the festival to reclaim damages allegedly incurred during their attendance at the April event.

The Miller Law Firm represents the plaintiffs, according to court records.