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That Microsoft is using this silly word in TV and online ads nevertheless remains a conundrum. I’d thought the company had stopped nastily smearing competitors right after its painful antitrust experience. Now I’m wondering if this inexplicable little word is just a simple faux pas, or a sign that the company is returning to its innately competitive, if not exactly pleasant, roots.

I broke my own rules and turned to Google’s search engine to dig deeper. I was surprised to find a richer and more revealing trove of information than Bing had offered me.

I learned that Microsoft’s ad campaign is designed to lure Gmail customers into the realm of Microsoft’s recently launched and updated Outlook e-mail system. (This is a replacement for its old Hotmail product, which I’ve  used for eons.)

Mark Penn, Idea Man

The person behind the ad campaign is Mark Penn, who made his mark as a political operative and is best known for his involvement in Hillary Clinton’s unsuccessful 2008 presidential campaign.

He joined Microsoft last year because its CEO, Steve Ballmer, was reportedly impressed by Penn’s novel ideas of how to present Microsoft’s products to the public. I’m surprised the company hired him, knowing from a most trusted source that he was one of the most useless consultants Microsoft hired during its antitrust trial. He apparently believes that where search engines are concerned, “people these days are making a choice, just like they’re making a political choice.”

So here we have it. What works well in politics should, according to him, work as well for Microsoft in the 21st century. The notion of this software-driven company resorting to politics is nothing novel. The only surprise for me is that its latest target is now its current and former customer base.