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For a candidate whose first foray into elective politics was met with an enviable raft of prominent endorsers (Mitt Romney, former Governor Pete Wilson, and John McCain) and a ton of free media, the past two weeks have been absolutely brutal for California Republican Meg Whitman. The alleged frontrunner for the GOP nomination for Governor in the Golden State, her introduction to the political stage has been pure amateur hour.

It started with a Sacramento Bee investigative story, which outlined an almost comically sparse voting history for the first-time candidate. The same weekend as that revelation became known, Whitman was blasted in a straw poll at the state GOP convention by state Insurance Commissioner Steve Poizner.

Then, last week, Whitman tried to explain her proclivity for electoral absenteeism, and dug herself in deeper, making the rather silly excuse that she was too busy raising a family to register to vote.

Now, as the vetting continues, Whitman is going to have to answer questions about one of her first forays into California politics--her 2004 endorsement of U.S. Senator Barbara Boxer, no one's idea of a Blue Dog Democrat.

"Whitman contributed $4,000 to Boxer in the 2004 reelection campaign -- and endorsed Boxer as a part of Technology Leaders for Boxer,'' confirmed Boxer aide Rose Kapolczynski today.

And, she signed an "open letter" appealing for support from the California technology executives, touting Boxer as a "dynamic and courageous leader" on the tech front.

Whitman went into spin control on this one quickly, claiming that it was Boxer's stand on internet taxation that pushed her to make the endorsement.

Indeed, there are actually quite a few reasons why a Silicon Valley executive might have warm feelings for Boxer, who has also promoted things like R&D funding for tech companies.

That explanation, though, probably will not carry the day with the right-wing in California, which can out wingnut the best of them despite California's reputation as a blue state. Some on the right here were already getting twitchy because Whitman was a DTS (Decline to State--a reference to being independent of party preference) voter as recently as just two years ago.

The contribution-tracking website Newsmeat says that Whitman has donated nearly $300,000 over the years (with contributions dating back to 1994). 71% of those donations have gone to Republicans, but there are several prominent progressive Democrats on that list, including Senators John Kerry (MA) and Maria Cantwell (WA), as well as Congressmen Mike Honda (CA) and Gerry Gary Ackerman (NY).

While it is not unusual for businessfolks to cross party lines to curry favor with critical members of the Congress, that line of reasoning will be very hard to explain to an ideological primary electorate who will see any consorting with the enemy to be treasonous.

Whitman has a lot of work to do to win the GOP nomination, but all of her early moves have only succeeded in doing is making the mountain she must climb exponentially larger.

Originally posted to Daily Kos on Wed Oct 07, 2009 at 06:22 PM PDT.

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