by Shane O'Neill

Is It Cool to Root for Microsoft?

Mar 01, 2010
Data Center

It may sound crazy but a more modest Microsoft is out there taking risks. Does Microsoft the underdog deserve our sympathy?

Microsoft: the company you love to hate. Or is it?

A recent column by Fortune writer Jon Fortt casts Microsoft in quite a sympathetic light. It argues that the last decade has humbled the mighty Redmond, which had become fat and complacent after squashing the competition in the ’90s.

What followed for most of the 2000s was an era of mediocrity, where Microsoft relied too much on cash cows Windows and Office (it still does by the way) and mostly watched as Google, Apple and others redefined mobile, search and Web-based apps and grew more profitable and powerful.

But over the past year or so, Fortt writes, a more self-effacing Microsoft has emerged. He cites the launch of the Bing search engine as a jumping off point. Here, for the first time in awhile, Microsoft is a true underdog, standing up to the lord of all search, Google.

[ For complete coverage on Microsoft’s new Windows 7 operating system — including hands-on reviews, video tutorials and advice on enterprise rollouts — see’s Windows 7 Bible. ]

Bing has not been the disaster some predicted. It has made incremental market share gains each month since its launch with innovative mapping and social media features. Bing will soon become one with Yahoo and form an alliance against Google now that the Microsoft-Yahoo search partnership has been approved by the U.S. Department of Justice and the European Commission.

Another black mark against Microsoft has been the technical problems and negative perceptions that plagued Windows Vista. For all intents and purposes, Vista has been chucked in the recycling bin with the rave reviews and gangbuster sales of Windows 7, which shipped in October.

Regarding mobile, the reaction to Windows Phone 7 Series (the convoluted new name for the Windows 7 Mobile OS) at Mobile World Congress in Barcelona was surprisingly positive. After months and months of speculation over what the heck Microsoft was doing with its mobile strategy, it was almost surreal to hear reviewers gush over the development and design of the new mobile OS.

Slideshow: Seven Features in Windows 7 You Probably Don’t Know About

Slideshow: Windows 7 in Pictures: The Coolest New Hardware

Microsoft is way late to the mobile game. Nevertheless, it is boldly getting in the ring with the iPhone, BlackBerry and Google’s Android mobile OS, and boy is it an underdog here. You could even call it a suicide mission. Kind of makes you respect Microsoft. A little. C’mon, admit it.

Does Fortt go too far with his sympathy vote? Maybe. Microsoft is merely doing what a company of its size and talent should have been doing all along: taking risks and being innovative. As for winning back Microsoft haters, don’t count it. The angry mobs are not going to drop their pitchforks just because ole Redmond has its tail between its legs.

However, Microsoft’s new role as a determined underdog is an interesting plot twist and should earn the company some of the respect that’s been long lacking.

Is it cool to root for Microsoft? No. But lately there’s less to hate.

What do you think? Are attitudes toward Microsoft more positive recently? Should they be?

Shane O’Neill is a senior writer at Follow him on Twitter at Follow everything from on Twitter at