When I saw the headline, “Former Microsoft executive named to oversee ObamaCare website,” I was sure I’d fallen into some kind of time warp and popped out on April Fool’s Day. It had to be some kind of sick joke or the launch of a new reality show about insane ironies.

Need I remind you that …

- Microsoft (MSFT) is the company that produced Windows Vista – the most delayed and botched software launch in high-tech history.

- Microsoft is the company from which the term “vaporware” originated.

- Microsoft’s code is so full of bugs and holes that PCs need round the clock security software and daily updates just to keep them from crashing all the time.

- Microsoft fought a brutal battle with the U.S. Department of Justice over the monopolistic bundling of Internet Explorer with its ubiquitous Windows operating system.

- The executive in question, Kurt DelBene, may have overseen the development of Office 365, but let’s face it – Microsoft only embraced Cloud Computing when it knew it had no choice.  

You just can’t make this stuff up.

Still, after the laugh fit subsided and I climbed back into the chair I’d fallen out of, it all began to make sense. Not that I think DelBene can fix HealhCare.gov or the nightmare that is ObamaCare, for that matter, but I can see why he was the perfect choice to try.   

- He lasted 21 years at Microsoft, so he must like big-organization bureaucracy and politics. In other words, he is probably an empire builder and a glutton for punishment.

- Having led Microsoft into online services – kicking and screaming all the way – DelBene is certainly comfortable taking on impossible missions with huge obstacles.

- He is used to taking orders from women democrats (his new boss is U.S. Secretary of Health and Human Services Kathleen Sebelius and his wife is U.S. House of Representatives democrat Suzan DelBene). 

- DelBene just retired, so he’s ready to work about as hard as everyone else in Washington.

- Microsoft has a history of helping its archenemies – to its own detriment – having given Apple the $150 million cash infusion it needed to avoid bankruptcy in 1997. How much you want to bet this also comes back to haunt Bill Gates and company?

There are two things that continue to bug me, though. According to White House officials, DelBene is volunteering his time. But reports say he will return his entire compensation to the Treasury.

I don’t get it. DelBene made over $7 million at Microsoft last year. He’s a rich man. He’s getting paid but then he’s going to give it back. Then why pay him in the first place? I’m just asking …

Also, why did Barack Obama invite Zynga (ZNGA) founder Mark Pincus to his pow-wow with technology executives at the White House the other day? Pincus? Zynga? Really? What, is the President of the United States a fan of FarmVille? Mafia Wars? Maybe he just likes to play Words with Friends with Alec Baldwin?

In any case, I wish DelBene luck trying to fix the most botched launch since Vista – and with all the politicians in his life. Glutton for punishment indeed. He’s going to need a "glutton-free" diet after this gig.

Steve Tobak is a Silicon Valley-based strategy consultant and former senior executive of the technology industry.

Contact Tobak; follow him on Facebook, Twitter, or LinkedIn.