Bill Gates 2020

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2) he's a Republican or at least used to be, so his opinion on economic issues are likely to the right of hillary, overall he's somewhere between warren buffett and arnold schwarzenegger.

He's been a big supporter of progressive tax reform here in WA, I don't know if I'd go that far.

http://old.seattletimes.com/html/politicsnorthwest/2012959755_microsoft_co-founder_bill_gate.html

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If the Dems are going to nominate a billionaire, it would likely be Mark Cuban or a Hollywood type.

Tbh i can't think of ANY American billionaires of the top of my head that I think would be tough enough on WS/corporations.  We probably have an equivalent of JK Rowling somewhere that I'm not thinking of, but overall I'm pretty skeptical.

Maybe Oprah? She's worth $3 billion.