Matt Drudge is not a proud progressive Elizabeth Warren-type supporter. He made his name hunting down the Clintons. He loathes the left. So when Matt Drudge seems to turn on Trump, there has been a tremor in the Force and perhaps Drudge is a canary in the coal mine, to butcher some metaphors. It isn’t the first time Drudge has published something detrimental to Trump, but this is the first time it’s gone straight at the only thing Trump ever cared about.
Drudge went right at Trump’s money.
Now, for those unfamiliar with Drudge style, he doesn’t exactly write stories, he links stories from all over the place, generally supporting the main theme. Rawstory has helpfully  put together some of these links and we’ll comment on what it all means:
“LOST MORE MONEY THAN MADE?” reads one headline from the top of Drudge, about the Times’ exposé. “FINANCED EXTRAVAGANT LIFESTYLE WITH USE OF BUSINESS EXPENSES…” reads another.
‘Can you believe how f*cking stupid the IRS is?’
FLASHBACK: Ripped Obama 20.5% Rate…
Said poor should have to pay to ‘be part of game’…
WIRE: National Security Threat…
Biden ad compares to what workers pay…
Sells ‘I paid more income taxes than Donald Trump’ stickers…
Now, again, Drudge didn’t just become anti-Trump overnight, he’s cooled on him over the last year or so. But no one cares what Drudge as an individual thinks. The importance of all this is that Drudge could be representative of voters know as the “Obama-Obama-Trump” voters. (Not that Drudge voted for Obama, but we’re talking about Trump voters that primarily wanted a change and now have buyers’ remorse … like Drudge.)
We have said over and over that this “smart businessman” Trump (as Trump presents himself) inherited $400 million over the years from his father and would clearly have made more money simply putting that money in a conservative mutual fund and golfed twice a day. (The country would’ve made more money, too).
Little did we know that Trump would have “made” more money had he buried the cash in Central Park.
Ultimately, voters will likely care less about the $750 he paid in income tax than the problem they’ll have with the duplicity. He wanted to be the “billionaire” to them, and so he hid his taxes. It forces voters ask “What ELSE is the man hiding?”
American voters have a far higher tolerance for assholes than they do for cons. If one is going to make a mistake with American voters, just be a jerk. There are a lot of jerks that enjoy long careers as politicians (see, e.g. McConnell, Mitch). Do not be a con, Americans hate being fooled – as seen by Drudge’s headlines.
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