Steyer's wealth will enable him to run more television ads than most of his opponents can afford. He is already spending $1.4 million on advertising over the next two weeks on national cable news networks and in the first four states to hold a primary or caucus.
"Maybe he feels he can overwhelm these questions by spending a lot of money telling his story the way he wants to tell it," said David Axelrod, the architect of Obama's campaigns. "The problem is in the presidential race, the coverage is so intense and social media such a big piece of that, these kinds of vulnerabilities get shared virally very readily, and I'm not sure you can overwhelm that, even with hundreds of millions of dollars."
Steyer could also face questions about spending that much money on himself. "Does all that spending help in the end of the day or does it become an emblem of excess and self-aggrandizement?" Axelrod said.
Asked about his letter to Farallon investors on the British Virgin Islands company that was going to help them avoid federal taxes, Steyer did not address his past actions, but called for new taxes on the rich to reduce inequality.
"I use no offshore tax havens and pay all U.S. taxes in full," he said. "I believe we should have a much simpler and fairer tax code and get rid of all loopholes."
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