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Mark Penn, dropped by the 2008 Hillary Clinton campaign well after it was clear she would lose, landed at Microsoft, where he's been running the company's marketing efforts against Google. According to tech site Recode, Penn is on the bubble with the company's new CEO, which might help him avoid the same fate he saw six years ago: bearing the blame for defeat.

Penn, a long-time political strategist, joined the company in July 2012. He's the guy behind Microsoft's anti-Google ad campaign, "Scroogled," which has alternated between criticizing the search giant for selling user data to advertisers and critiquing products like the Google Chromebook laptop. Its most recent push involves introducing the Chromebook to the not-particularly-tech-savvy stars of Pawn Stars, a campaign which said hit a "new low" for the company.

Here's an example of one of Penn's anti-Google spots. For lack of a better description, it's an attack ad, highlighting the negative aspects of the competition in somewhat sketchy terms.

Compare that ad to the Clinton campaign's famous "3 A.M. Phone Call" spot from February 2008.

There's a lot in common between the two. Who do you trust, the inexperienced upstart or the established player? In fact, the two roles themselves see a lot of similarity: Penn rising to the defense of the obvious frontrunner against the challenger, using fear of the unknown as his sales pitch.

Whether or not Penn continues that gig at Microsoft isn't clear. Recode's Kara Swisher reports that Penn was closed tied to former Microsoft CEO Steve Ballmer. With Satya Nadella stepping into the role, Penn "is currently matched in a classic and problematic two-in-a-box face-off with EVP of marketing Tami Reller." "According to many," Swisher writes, "the set-up has been uncomfortable and, increasingly, untenable, with sources noting that some big change in this key area for Microsoft is expected very soon."

In 2008, Penn drove the Hillary campaign from the start. Clinton was Microsoft, Obama the data-smart, hip, young rival. And Penn lost, badly. Clinton's poll numbers are red on the graph below.

By the time of that "3 A.M." ad, the writing was on the wall. Obama was already well into that big spike. By April 2008, after Obama was ahead, Penn was out.

In comparison, here's how Microsoft is doing against Google, in terms of quarterly revenue. (Quarters indicated are Microsoft's.) Again, Penn's client is in red.

Not quite the same, and, of course, there are literally millions of extenuating circumstances in the corporate examples that don't apply in a political campaign. But regardless, Penn's efforts have clearly not done much to slow Google's ascent.

Microsoft's new CEO doesn't want that revenue graph to look like the 2008 Democratic primary polling. The question he faces is: Is Mark Penn the best bet to keep that from happening?

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