Presidents sometimes "push the envelope" on their powers, but that is not what Trump has been doing:  normal Presidents "push the envelope" where the law is not settled or ambiguous.  Trump is just a brazen lawbreaker.   Here's one account by a law professor from more than a week ago!  The list has gotten longer since.  Almost all of these are not close cases.  As I remarked the other day, Trump is the proverbial "Holmesian Bad Man," who recognizes neither legal nor moral obligations:  the only relevant question concerns a cost-benefit analysis about whether it "pays off" to violate those supposed obligations.    

What's important to understand is that this is how Trump has always acted.  When I was a litigation associate at a law firm in New York City in the late 1980s, Trump was just a local butt of jokes.  No serious law firm would work with him, and NYC is populated by real estate law firms who learned that lesson the hard way, and dropped him as a client.  Back then, of course, his propensity to breach contracts and fail to honor his legal obligations took place against a ledger that had some potentially serious costs (at the extreme, jail or massive financial penalties).  But now he is President of the United States, and most of the costs that would be imposed on a Holmesian Bad Man cannot be imposed on Trump any longer.  That's why this is such a dangerous situation.  Between his first term and his current one, he has figured this out.  He is breaking laws right and left to figure out when the cost-benefit calculation will work to his disadvantage.

The Democrats have one point of serious leverage, the looming government shutdown unless the debt ceiling is raised.  Trump wants the debt ceiling abolished (it should be), and he can't get it abolished without many Democratic votes, since there are hardline lunatics in his party (the "Freedom [sic] Caucus") who will never vote for that.  So he has a reason to cut a deal.  But by breaking the law basically every day or every other day, he has effectively lowered the expectations of the opposition.  If the status quo on January 20 would require him to rescind two dozen illegal actions, by now it will look like a victory if he rescinds ten.  That's yet another danger.  And once the debt ceiling is lifted, if it is, why wouldn't he start all over again?  He will.