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If the President has the ability to write and rewrite legislation through EOs then I can see how he can effectively be more damaging than a president who declares a national emergency in a more restricted way. But this is an assumption which compares a president who is unrestricted in issuing EOs to a president who has self-control after he declares national emergency
It is not an assumption - it is a description of what has happened. We had one President grab the power to rewrite Legislation through Executive Action, effectively nullifying any Legislative restraints on his power, and we had a second who, because he is acting within the constraints of the authorities granted to him by Congress, remains constrained (however loosely).
The proper comparison is to see which president is more abusive and dangerous as a result of the power he has accumulated?
Hm. I would be inclined to not give that metric much weight for a couple of reasons.
1. "Who I think is more dangerous" is going to be heavily dependent on my personal preferences. People will argue that Trump's actions aren't dangerous, because he's just trying to protect America. Obama's actions, similarly, (his supporters will argue) weren't dangerous because he was just protecting children. First Citizen Trump is just trying to protect us from an Insidious Conspiracy Of Deep State Internationalists And Foreigners, And So Of Course He Has To Imprison Journalists - He's Not Dangerous, They Are (etc. so on and so forth) Whether or not you perceive that a President's use of his power is abusive or dangerous will be heavily colored by one's opinion of the policies he used that power in pursuit of. That is why the granting of any power is a fraught enterprise, which necessitating deep consideration of all the ways it could be abused, and how mechanisms can be put into place to check them.
*This, for example, is the situation we find ourselves in with the Emergency Powers Act, which seems to grant the President quite broad Authority, and which probably should have been thought through a bit better when written and passed. At the very least, probably, it should be time-limited, like the War Powers Act (though, again, under Obama we saw that the War Powers Act timeline wasn't really a limit either, as he blew through it).
2. In terms of how power accumulates to the Executive, every power that a President seizes is a precedent that can be used by those who come after him. When Nancy Pelosi threatens that the next Democrat President can use Trump's expanded vision of a National Emergency to put major parts of the Green New Deal into place, she's not wrong.
*For example, if Trump were to follow Obama's precedent, he could issue an Executive Order telling the Defense Department that they were to now assume that their budget included the direction to build and man a wall along the Southern Border, and build it that way. Or, he could issue an Executive Order directing the entirety of the Executive Branch (including the Treasury Department) to just assume that Congress had granted him $8 Bn for the project, and to go ahead and build it.
Alternately, he could issue an Executive Order instructing the IRS to no longer collect Corporate Income Taxes above a rate of 5%, or telling the Social Security Administration Trustees to privatize Social Security. The precedent that Obama set - that, if the President really believes in a particular public policy, but Congress doesn't give him what he wants, that he can therefore just go out and do it anyway - is much more vast an expansion than Trump's expansion of how the President defines a National Emergency, especially given that it was the Congress gave him the authority to define what a National Emergency was or was not, whereas it never gave the President the authority to alter Immigration, Tax, or Entitlement law.
Alternately, he could issue an Executive Order instructing the IRS to no longer collect Corporate Income Taxes above a rate of 5%, or telling the Social Security Administration Trustees to privatize Social Security. The precedent that Obama set - that, if the President really believes in a particular public policy, but Congress doesn't give him what he wants, that he can therefore just go out and do it anyway - is much more vast an expansion than Trump's expansion of how the President defines a National Emergency, especially given that it was the Congress gave him the authority to define what a National Emergency was or was not, whereas it never gave the President the authority to alter Immigration, Tax, or Entitlement law.
Is it one who is repeatedly using EOs or is it one who is repeatedly using declarations of an Emergency Power? Notice by the way, that no matter how many EOs a president is issuing, he can not use an EO to redistribute funds to boost his pet projects
Sure he does. If the President has the power to rewrite Legislation through EO's (which, per the Obama Administration's precedent, he does), then he can do anything (short of violating Constitutional limitations on the power of Congress) he likes.
TL/DR:
Trump is arguing: "I can use the specific powers given to me by Congress in ways of which they disapprove."
Obama argued: "I can take whichever powers I want from Congress without their permission, and use them however I please."
One of these is more dangerous than the other, and it's the second one.