The Constitution was written so as to have checks and balances between the Congress, the Executive and the Supreme Court. Their individual powers were clearly spelled out but were drastically altered by one of the first acts of the Congress, the act that established the Judiciary. If the Judiciary was to be the final judge in all disputes between the parties named in Article 3 Section 2, then it should not have taken over 40 pages to describe the court's powers to settle disputes.
True to form, it was Chief Justice John Marshall, the one who in McColloch versus Maryland 17 US 316 opined that Congress could do most anything that was not specifically prohibited while saying the Constitution has prescribed limits, is again the culprit in giving the Congress the power to delegate law making to the executive provided it is within prescribed limits as defined by the Supreme Court.
The case in question was Waymand versus Southard and brought to the court because the plaintiff objected to a state marshal's actions that exceeded those of the legislation he was enforcing. How this was not settled in the state court I have no idea but Marshall took the opportunity of siding with the plaintiff while at the same time stating the state legislatures could not delegate law making to the state's executive branch, but the Congress of the United States could within the limits imposed by the Supreme Court. Of course they could not impose such limits unless a dispute arose between the parties affected by the abuse of power.
If the executive issues Executive orders that have the force of law, that order is prima facie an unconstitutional assumption of power not granted to the executive. In muddying the waters, Marshall opened the door for the Supreme Court to make the decision as to what can be delegated. The plaintiff does not even have to have standing in order to bring such a suit if he is not personally harmed by the law. The ACLU and other special interest groups including the States themselves have used this mechanism when it suits them and the lower courts will acquiesce as they have in the past for matters that have high profile.
As Judge Robert Bork has said, if the courts followed the Constitution all of the Fair Deal and New Deal legislation as well as Social Security, Medicare and Medicaid would never entered the lexicon of US law.
Thomas Jefferson and James Madison in the Virginia and Kentucky Resolutions tried to get the northern states to adopt the stance that it was the States who were the sole determiner of what was Constitutional but they would not. Why should they when the Constitution was written to favor the mercantile classes.