Best Misguided Show-and-Tell
Bill Gates

Microsoft’s former geek-in-chief has given us plenty to snicker at (his clothes, his mug shot…the Zune), but it’s hard to ridicule his foundation’s antimalaria crusade. Okay, it was hard, but then, to make a point at an elite tech-related conference in January, he went all “lord of the flies” by releasing a jar of mosquitoes and proclaiming that “there is no reason only poor people should be infected.” The bugs were disease-free, and Gates gets theatricality points, but when did DEET become a required accessory for PowerPoint viewing?

Best Media Misdirection
Terry Drayton

In January, the Bellevue founder of Count Me In—a software company that manages sports league membership fees—snagged the cover of Seattle Business Monthly and some starry-eyed praise as a guy who “knows how to keep a start-up alive during a recession.” What a model of ethical economic survival! But before the issue rolled off the press, news hit that Count Me In allegedly owed $5 million to its Little League clients. The profile did not include Drayton’s tips for avoiding lawsuits in a recession.

Best Brand-Expansion Fail
Pet Holdings Inc.

The Queen Anne start-up’s Internet-meme empire built on ICanHasCheezburger.com and its collection of LOL-worthy cat pictures with absurdist, misspelled captions was the online phenom of the year—in 2007. So with its cultural relevance in the litter box this February, the company decided to monetize its fleeting fame by hawking plush versions of its celebrity kitties. And what was once a quirky time-killer for depressed office drones became a corporate, cotton-stuffed totem of misguided diversification.

Best Ruthless Attempt to Cut Costs
Microsoft

Maybe you’ve heard about this apocalyptic recession we’re in. The ’Softies have, and they pink-slipped 1,400 employees in January to curb future fiscal bloodshed. But then they turned the dime-a-dozen unemployment bummer into a PR firestorm by informing 25 of the former employees that they got more severance than they deserved and, oh, by the way, could they return it? The company eventually backed off the request, but the damage was done. Note to Microsoft accountants: Acquire Quicken before the next round of layoffs.

Best Lawless eBay Bidder
James Garrett

What the Fall City man—and compulsive Star Wars memorabilia collector—said when a state trooper nailed him for driving 110 miles per hour in the I-90 express lane in March: I was rushing home to bid on an about-to-expire eBay auction. What he should have said: No, officer, these aren’t the action figures you’re looking for. Move along.