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 I would like to better understand this. I've heard a number of people say stablecoins can help prop up the dollar during the transition by continuing to purchase treasuries, but I am having a really hard time gaming that out mentally or what you wrote above for that matter. 

As with most things in bitcoin I find that I can't grasp the initial explanation fully, but as it seeps into the scene and I hear it explained several different ways it'll click.  
 1) If the free market is deflationary…..Ie - prices are supposed to fall…..then…what is a “stable” coin? 
2) A “coin” that gains it “stability” by losing value at the exact same rate as a currency. 
3) Which is by very definition, the system that we have today that stops the free market by manipulating money. 

Hope that helps. 
 Thanks, that part I understand totally. Stability is an illusion in a universe that's constantly in flux.

What I can't quite see yet is how the transition will take place. Gradually vs suddenly or what the final warning signs will be. 

The gradual route seems more ideal/peaceful, but historically speaking technology is not adopted that way. 

Most days I am still shocked more people don't see it.