Barry Diller's effort to pawn off Very Short List, his failed shopping newsletter for the rich, is turning into a classic New York media folly — a big drama over a puny digital property.

Very Short List was, from the beginning, an act of hubris. In 2007, Diller failed to buy Daily Candy, losing out to former AOL executive Bob Pittman. So the IAC chairman decided to round up some buddies and start and shopping list of his own. If Dany Levy could make a mint, why couldn't they?

Besides, VSL would be highbrow where Daily Candy was mass market, targeting a "smart set" of billionaires looking for a shortcut to cultural literacy. Diller is said to have seeded the list with own rich friends, but the early results were unimpressive, at least from a media standpoint: The list reportedly had collected just 20,000 subscribers.

By last year it was up to 100,000 subscribers; now it's 200,000. No matter: It's widely believed a dud, with no real revenues to speak of. Diller needs to dispense with VSL. Which means he needs, as P.T. Barnum would put it, a sucker. Luckily, he may have found one.

A quick sketch of the characters in this shakedown:

Barry Diller - The wily old ringleader. A consummate dealmaker who got the better of his evil master John "Darth Vader" Malone in a court fight over IAC. VSL was once his favorite toy; he once told a reporter, ""Without Very Short List, I would be much diminished." But he's moved on. He's putting $18 million into the Daily Beast, his new favorite toy.

Michael Jackson, the legman. A highflying television executive in Britain, Jackson has been vexed by the failure of VSL.A sale would help Jackson save face. After all, he co-founded VSL and has overseen it at IAC.

Yes, VSL has 200,000 email addresses. But one source tells us only 40,000 of readers open a typical mailing. And Jackson would appear to have fallen out with Diller, losing his title as IAC's president of programming right around the time Tine Brown came on board for the Beast. We hear his remaining portfolio at IAC consists entirely of VSL.

Kurt Andersen, the pretty girl (a.k.a. the bait). Like Diller and Jackson, Andersen was also a founder and also wants to save face. But he has a unique asset: His experience as a founder and writer at places like Spy, New York, the New Yorker and help make VSL — or at least a meeting with VSL — attractive to prospective rubesinvestors or buyers.

Jared Kushner, The Mark. The 28-year-old media mogul came into possession of the New York Observer just as the newspaper industry entered its death throes. He's rumored to be in talks with Diller about a joint venture.

While Kushner is likely impressed with VSL's 200,000 subscribers, he should ask IAC for specifics about the list's "open rate" — the number of subscribers who actually read it. Then, if he still wants to buy after learning only a fifth of readers do so, he should ask about those frequent ads from the blog Design Observer. Run, we hear, by Andersen's friends, the site is unlikely paying much, if anything, for the spots.

It might just be too late: Observer scuttlebutt has it that the "joint partnership" would amount to the newspapers' remaining staff writing the VSL. In that case, chalk another one up for Diller, an operator no more ruthless than his New York peers would expect him to be.

(Michael R. Jackson pic via Cityfile; top Diller pick by Esther Dyson on Flickr.)