A political wrestler, now fighting Google for Microsoft

In Washington, Penn is a lightning rod. He developed a relationship with the Clintons as a pollster during President Bill Clinton’s 1996 re-election campaign, when he helped identify the value of “soccer moms” and other niche voter groups.

As chief strategist for Hillary Clinton’s unsuccessful 2008 campaign for president, he conceived the “3 a.m.” commercial that raised doubts about whether Barack Obama, then a senator, was ready for the Oval Office.

But his approach has ended up souring many of his professional relationships. He left Clinton’s campaign after an uproar about his consulting work for the government of Colombia, which was seeking the passage of a US trade treaty that Clinton, then a senator, opposed.

Hiring Penn demonstrates how seriously Microsoft is taking this fight, said Michael A. Cusumano, a business professor at MIT. “They’re pulling out all the stops to do whatever they can to halt Google’s advance, just as their competition did to them,”

Penn has had a long consulting relationship with Microsoft going back to the late 1990s. He is said to be close with both Steven A. Ballmer, Microsoft’s chief executive, and Bill Gates; all three attended Harvard together in the mid-1970s. Frank Shaw, a spokesman for Microsoft, said the company’s willingness to go after competitors predated Penn’s arrival, pointing to a video criticising Google for scanning Gmail users’ messages so it could deliver related advertising.

Microsoft executives now concede that they did

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