Rupert Murdoch Doubles Up, Throws Two Hail Mary Passes at Once

News Corp. (s nws) founder and CEO Rupert Murdoch is doubling down on his bets that paid content will eventually win the day online — in particular, on portable digital devices — by investing an undisclosed sum in Journalism Online, the venture from Steve Brill and former Wall Street Journal publisher Gordon Crovitz, and buying the Skiff e-reader business developed by competing media empire Hearst Corp. Hopefully Murdoch didn’t put too many markers down for either one of his latest gambles, however, because they look like sucker bets — or rather, the latest in a succession of loosely connected Hail Mary passes designed to make it look like News Corp. has a winning digital content strategy.

Although the Skiff e-reader has gotten some good reviews for its size and flexibility, the media giant is apparently not interested in the device itself, but more in the Skiff project as a platform for distributing content to multiple e-reader and portable devices. While focusing on the software and service rather than the hardware is smart — the Skiff reader doesn’t appear to stand much chance in what has become an increasingly crowded e-reader market — News Corp. is going to face some significant hurdles on the software and service side. For example, why would a content owner want to do a deal with a distribution platform controlled by a competing media giant like Rupert Murdoch? At least Amazon (s amzn) and Apple (s aapl) don’t publish newspapers and magazines.

It seems likely that Murdoch wants to put the Skiff and his investment in Journalism Online together in an attempt to create an Amazon-style, content-plus-platform strategy for News Corp., in which consumers would sign up for the Skiff service and then subscribe to content from the Journal and other media entities using the platform that Brill and Crovitz have been trying to construct. The big problem with the latter half of that strategy, however, is that it’s not clear what Journalism Online has actually managed to build after more than a year of work on the idea, apart from some trials with small chains, and trademarking some terms that appear related to charging users based on activity via a so-called “metered model.”

News Corp. has already launched metered paywalls at two of its European publications, the Times and the Sunday Times, an approach similar to that used by the Financial Times and the paywall that the New York Times (s nyt) is expected to launch later this year. And News Corp.’s flagship product, the Wall Street Journal, is one of the few examples (along with The Economist) that media outlets routinely point to as a sign that paywalls can work. So Murdoch certainly gets points for consistency — and if there is a contest to choose a poster boy for paywalls and paid content in general, the News Corp. billionaire would definitely win the title in a landslide.

Charging for access to WSJ articles, however, is a far cry from metering access to all kinds of content, let alone doing so through a service that hasn’t even been tested in the market yet, and hasn’t signed up a single high-profile partner or investor until Murdoch came along (or at least none it’s willing to name). It’s a good thing the News Corp. founder likes a fight; hopefully he likes really long bets against overwhelming odds, too.

Related content from GigaOM Pro (sub req’d): What We Can Learn From the Guardian’s Open Platform

Post and thumbnail post courtesy of Flickr user Ed Yourdon