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In Pictures: CEOs Microsoft missed

In Satya Nadella, Microsoft played it sensible. Here are the Ballmer successors we tech wags wanted to make our Redmond-flogging jobs a little easier

  • Cringely’s top 10 finalists for Microsoft CEO Discussion, speculation, uncaring frivolity -- it's all fair game when it comes to assessing Microsoft’s choice of Satya Nadella to replace Steve Ballmer as CEO. How might Nadella right the Windows wrongs? What kind of voodoo will Redmond haters perform to hex the new head honcho? What should the street name of the new emperor of the evil empire be? But the real question on everyone’s lips is: Who would Cringely have hired? After all, years of being head public Microsoft scourge has given me unique insights into how Microsoft should be run for our best whipping-post amusement. Here’s the short list of who should have been chosen, organized in descending order of “Cringely viability.”

  • 10. Satya “The Needle” Nadella Yes, news broke that Satya Nadella has taken over for Ballmer. He’s done excellent work advancing the initiatives and direction of the previous president of the Windows Server division with just the right amount of surface input and no-boat-rocking activity. He says all the right buzzwords like “cloud,” “private cloud,” “public cloud,” “cloud services,” “death to AWS,” and “Hey, let’s find some teenage cheerleaders.” He should do great if the goal is to drive Microsoft into the 30th or 40th slot of somewhat important technology companies. But as far as tickling my rapier wit repeatedly in my column, he’s a bit of a boring choice, Microsoft. Thanks for nothing.

  • 9. Stephen “The Flop” Elop Stephen Elop’s nickname stems not from the mess he would have made of Microsoft as CEO (though he would’ve definitely sent MS into the toilet), but from his sizable man-boobs. Elop left Microsoft once to head up Nokia because he couldn’t handle the corporate pressure or the Seattle climate, and both were practically nonexistent at Nokia because everyone knows Finland has great weather and, at the time, Nokia had nowhere to go but up. Before that, he helped run Boston Market into bankruptcy as its questionably technology-savvy CIO. He’s got just the right amount of unreasoning Apple/Google-phobia to have rerouted Microsoft’s primary resources at Surface and Windows Phone so the company could have finally chucked its enterprise baggage and concentrated on the real money makers.

  • 8. Tony “I Wish I Was Gates” Bates This college dropout has attempted to mirror Bill Gates’ climb to filthy richness with limited success. He oversaw Skype’s transition from an important independent communication channel to a tertiary Microsoft property that will be absorbed by Lync, causing Skype’s employees to lose their jobs -- great experience for a future Microsoft CEO since the company started a regular cadence of layoffs, er, “reductions in force” whenever senior executives need to prove a stock increase during the week their bonuses are calculated. He’s famous for having made a list of three companies he’d like to lead as CEO before turning 45, though few know that’s because he was drunk and passed out before he could get to four. Think of how fun this guy would’ve been.

  • 7. Alan “Jaws” Mullaly So named for the big white teeth he shows with his oft-displayed politician’s grin, Alan Mullaly is credited with bringing Ford back from the brink, though he couldn’t save Detroit. He would have been perfect for Microsoft CEO (and Microsoft CEO critics) because he knows very little about technology, which would have continued the underlying flavor of confusion and incompetence we’ve come to associate with the job. He supposedly helped Ballmer organize last year’s teamwork-oriented reorganization of Microsoft, which, according to my sources, didn’t work at all. That probably had him a close finalist to Nadella. Rumor has it his longtime friendship with Ballmer and their frequent visits to Seattle’s opium dens knocked him out of contention in the end.

  • 6. Paul “Blitz” Maritz Paul Maritz has hopped furiously around head-honcho gigs for the past decade, flitting from one C-level exec role to another. He’s got tech chops, which helped his rise at Microsoft to govern both its server and client platform development. He resigned in 2000 just in time to dodge the Windows ME bullet. Since then, he co-founded Pi Corp. (which got munched up by EMC), jumped to CEO of rabidly anti-Microsoft VMware in 2008, and then to a CEO position with startup Pivotal in early 2013. This kind of corporate ADHD would have made Maritz a perfect match for Microsoft’s flailing product development initiatives, plus his hair seems to be going the way of Ballmer, the perfect combo for Ritalin and Rogaine jabs at Redmond.

  • 5. Patrick “Gunslinger” Gelsinger Gelsinger actually invented his own nickname in a desperate and wildly unsuccessful attempt to impress college girls. Gelsinger is currently CEO of VMware, which is probably why he wasn’t under serious consideration -- VMware is an actual innovator in the data center, rather than a me-too copycat like Microsoft’s been for the past couple of decades. Plus, he’s an ex-engineer with Intel experience, helping to design the 80286-80486 CPUs, so he’s probably got too much social anxiety disorder in him for the board to manipulate with advanced social interactions like naked coed square dancing -- currently all the rage at Mercer Island’s midnight billionaire bashes.

  • 4. Lucas “BS King” Duplan This 22-year-old has improved on the young tech CEO success story by not only dropping out of college and starting a tech firm in his mom’s basement, but by founding a firm that’s attacted more than $25 million in VC financing while creating nothing. He obviously worships money, is universally despised by his employees, and is in arrogant denial regarding the future of his money-hemorrhaging, stunningly-ill-named corporate baby, Crinkle. All qualities that the Microsoft board was eagerly searching for, but the thought of his future children crawling from their cribs and assassinating him at age 24 probably derailed any momentum he might have had. Oh well, we’ll still be able to flog this guy with ink -- assuming he remains relevant.

  • 3. Bill “The King” Gates Not just the king of tech billionaire-dom, Gates is also secretly king of a tropical island he purchased that’s populated by pygmy Oompa Loompas he had genetically engineered in a Ukrainian lab converted from the corporate offices of a genocidal think tank. Clearly Gates was pushed out of the board because he threw his hat in the ring for CEO, he terrifies everyone in the boardroom as being too sensible, and he owns the mortgages on all their homes. (In fact, he secretly owns the mortgages on all our homes.) He wanted the gig not just because he doesn’t like where his baby’s been going but also because his years as a philanthropist have convinced him that a few more billion would make him feel...

  • 2. George “Lost It” Lucas A little-known dark horse finalist for the job, Lucas is probably the second-wealthiest man in the world unbeknownst to Forbes because most of his money is buried under Skywalker Ranch in a secret vault guarded by steroid freaks dressed as Wookies armed with crossbows and lightsabers. He’s finally admitted to himself that he can’t write a successful book, a winning Star Wars script, or a grocery store shopping list anymore, so he’s looking for another role with which he can disappoint the public. Microsoft CEO would have been perfect. I’m still a bit surprised his garden-gnome facial expressiveness didn’t go over with the board. It would have helped in delivering speeches to the disbelieving press or outraged Windows customers.

  • 1. Robert X. “Ol’ Blue Eyes” Cringely Sinatra gave me the name when we woke up together next to an empty Scotch cask in the summer of ’72. We forged a lifelong bond that day. My suitability for the top Microsoft post is obvious. Blessed with handsome looks, a genius IQ, a complete lack of hubris, and the ability to deal with any kind of pressure or crisis as long as I have access to a wet bar, there really was no better candidate currently inhabiting the planet. So it’s time to admit the hoax, Microsoft. Nadella isn’t your man; I am. If I’m not, and don’t make a few billion soon, Pammy’s going to dump me for an old LPGA girlfriend named Slerma. Microsoft, you’re my last great hope!

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