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1) No matter what it looks like with the media and their quasi-toughness on Hilary, no, I've said it all along that the skids are greased for her.

Sarah Palin. Here: https://www.yahoo.com/news/ap-interview-palin-warns-gop-leaders-nominee-224145685--election.html

Starting at the 27th second.

OK. I know that she does not speak well and her English leaves much to be desired but I am only interested in this part:

No matter what it looks like WITH the media... and the way 'with' is used there.

What does that phrase mean exactly? What does 'with' mean in that phrase?

Gratefully, Navi.

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    "What it looks like" -- what impressions are given. "With the media" -- with respect to the relationship between Mrs Clinton and "the media". – Hot Licks Apr 15 '16 at 22:47
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What she is trying to say is not a straight forward message but an attempt to evoke a sense that the system is rigged: following the methodology of Trump, his eternal victimhood and his aura of "outsider" she sets up the impression that continues with this invocation of decay and bribery. "The skids are greased" can mean a way to cheat in an iditarod race, won with no friction as opposed to a struggling candidate with integrity. "With the media" is anthropomorphizing media as a group instead of a communication source that is duplicitous and untrustworthy as presenting themselves as tough but giving Hilary a blind eye to her trickery. "No matter how tough the media appears to be with Hilary, they are proven worthless when the system is already set in her favor" Sets up the seed of doubt about the system in which she is part of and glosses over integrity and the plight of the outsider as an authentic fighter for her would be agreers. Media in this case is painted as ambivalent sources of portrayals.

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