Microsoft's (NASDAQ:MSFT) relentless Scroogled campaign that takes jabs at Google (NASDAQ:GOOGL) has an unlikely new target: Chromebook.

The latest spot features the stars of The History Channel's Pawn Stars as someone tries to pawn a Chromebook at the Gold & Silver Pawn Shop.

"When you're not connected, it's pretty much a brick," she's told. "That's a major drawback. A traditional PC utilizes built-in applications like Office and iTunes that work even when you're offline."

Wait. Did Microsoft just throw Apple a bone by pushing iTunes as a reason to get a Windows laptop? It doesn't end there. The Scroogled site offers up a few media quotes detailing Chromebook's shortcomings, and it kicks things off with a quote that casts Apple's Mac in a favorable light. 

"I gave up my Mac for a Google Chromebook Pixel and loved it -- until it became a brick at Starbucks," begins the first Julie Bort quote from a Business Insider article

It makes sense for Microsoft lend a positive spin to Apple's iTunes and Mac. Apple is no longer the enemy. That is so 2003. Google is the enemy. The point is clear if you actually click through to the Business Insider article where Julie Bort reveals her reasons for considering a Chromebook in the first place. 

"That was fine for my job because at Business Insider, we rely almost entirely on cloud apps," she explains. "We use Gmail and Google Apps. Our main application, the content management system where we write stories, is accessed through a browser. Editors chat to each other through an online chat program called Campfire, or through Google Chat."

Yes, that's a problem. The same tastemakers Microsoft is relying on to get folks to go back to the stodgy laptop aren't computing the way Microsoft would like. They no longer need to pay a premium for Office when Google has a free cloud-based solution. They have become operating-system agnostic, and that's a bad thing when you're trying to get folks to pay a premium for your computing solution.

To be fair, Microsoft knows its target audience with this campaign. It offers a link to a handful of Windows-fueled laptops that start at $250. It knows that it's dealing with customers flocking to Chromebooks because they can be had for as little as $200. 

It's true. Chromebooks aren't very useful when an Internet connection isn't around. However, can't the same be said about most computing experiences these days? Google gets it. It may have seemed strange to see Microsoft take a shot at a lowly rival when it comes to its operating system stronghold, but maybe Microsoft has a stronger grasp on its fading relevance than it's letting on.

Longtime Fool contributor Rick Munarriz has no position in any stocks mentioned. The Motley Fool recommends and owns shares of Apple and Google. It owns shares of Microsoft. Try any of our Foolish newsletter services free for 30 days. We Fools may not all hold the same opinions, but we all believe that considering a diverse range of insights makes us better investors. The Motley Fool has a disclosure policy.