Microsoft’s New Hot Shot Likely Cost Hillary Clinton the 2008 Election

There’s a lot of hullabaloo today over the new team Microsoft has assembled. The Seattle Times writes breathlessly in this morning’s banner story that this is “the most sweeping reorganization in years” and that CEO Steve Ballmer’s personnel realignment will, says Ballmer “make the company faster-paced and more collaborative.”

One of the newly chosen is none other than Mark Penn, whose responsibilities at the software giant will include marketing strategy, while taking the co-lead on advertising and media.

No mention in the local coverage that Penn probably cost Hillary Clinton the presidential election in 2008.

It was Penn, Clinton’s long-time political confidant and chief strategist, who made the colossal and unforgivable mistake in failing to understand party rules as regards delegate selection to the Democratic National Convention.

By not understanding the rules, and not realizing that California was not a winner-take-all state and that it allocated delegates based on a candidate’s proportion of the vote, Penn screwed the pooch.

Here’s how then-Time magazine reporter Karen Tumulty explained the devastating error, which has become legendary in political circles.

Clinton picked people for her team primarily for their loyalty to her, instead of their mastery of the game. That became abundantly clear in a strategy session last year, according to two people who were there. As aides looked over the campaign calendar, chief strategist Mark Penn confidently predicted that an early win in California would put her over the top because she would pick up all the state’s 370 delegates. It sounded smart, but as every high school civics student now knows, Penn was wrong: Democrats, unlike the Republicans, apportion their delegates according to vote totals, rather than allowing any state to award them winner-take-all. Sitting nearby, veteran Democratic insider Harold M. Ickes, who had helped write those rules, was horrified -- and let Penn know it. “How can it possibly be,” Ickes asked, “that the much vaunted chief strategist doesn’t understand proportional allocation?” And yet the strategy remained the same, with the campaign making its bet on big-state victories.

Penn resigned from the Clinton campaign in April 2008. He was not missed and will have no role in any future presidential campaigns Hillary may be contemplating.

Good luck, Microsoft.

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