Before I begin, this post is directly sourced from one man, whose information I am still going through to verify for integrity myself.  The man is Thomas Wictor; here is a link to his Twitter account: https://twitter.com/ThomasWictor
Take this with a grain of salt, but realize that it may be possible, given that the information is correct.
Edit: Information has been reviewed, sources at bottom of post.

In 2012, Supreme Court Chief Justice John Roberts was the deciding vote on the constitutionality of ObamaCare, or the ACA. Roberts claimed that the ObamaCare penalty is a tax. The only body of government that can levy a tax is Congress.

What Justice Roberts implied in his ruling was that it is the duty of the Supreme Court to find unconstitutionality, but that it is also their job to find ways save a statute from unconstitutionality.

Roberts said, “The question is not whether that is the most natural interpretation of the mandate, but only whether it is a ‘fairly possible’ one,” the chief justice said, citing a 1932 precedent. “As we have explained, ‘every reasonable construction’ must be resorted to, in order to save a statute from unconstitutionality” [citing an 1895 precedent]. The government asks us to interpret the mandate as imposing a tax, if it would otherwise violate the Constitution. Granting the act the full measure of deference owed to federal statutes, it can be so read. … The exaction the Affordable Care Act imposes on those without health insurance looks like a tax in many respects.”

This is where I would like to point out the caveat to certain White House personnel’s own words, in that this essentially means that the President or Congress can use “alternative facts” to pass a penalty as a tax, in that it looks like a tax. As Thomas Wictor states, “Precedent REQUIRES that the Supreme Court twist itself into “every reasonable” contortion in order to save a “statute”.”

Thomas continues to explain that “Presidential executive orders are equivalent to laws, another word for “statute”.” There are many Executive Orders that have been passed which manipulated existing law. So long as an Executive Order does not create NEW law, the President has the power to adjust existing legislation. Thomas Wictor explains, “As long as Trump doesn’t MAKE law in his executive order(s), he can tinker with ObamaCare until it no longer exists.”

Now here is the fun part… Trump has already began doing this.

https://www.whitehouse.gov/the-press-office/2017/01/2/executive-order-minimizing-economic-burden-patient-protection-and

He is slowly attacking each point where ObamaCare is to fail, by expediting the process in legal ways through EO’s. When the process is adequately moved along, and more faults of the plan begin to show, Trump will be able to outline the issues in his EO’s.

Essentially, Wictor argues that President Trump’s plan is to “tackle each and every deliberate failure of ObamaCare.” Since ObamaCare was designed to fail, Trump will be able to point these failures out in his future EO’s, stating as Wictor puts it that Trump “has the duty and authority to act.” His EO’s will be solid in that they do not make NEW law, but simply clarify existing law. Because the clarifying of existing legislation, such as ObamaCare, is minuscule in comparison to EO’s from previous Presidents’, The Supreme Court will ultimately be forced to rule that the EO’s are constitutional. This first thing the Supreme Court does when determining constitutionality is reflecting back on previous rulings. Here is a list of major EO’s that continue to exist today:

  1. The Manhattan Project that created the atomic bomb.
  2. The Emancipation Proclamation that ended slavery.
  3. The internment of Japanese-Americans.
  4. The suspension of habeus corpus.
  5. The creation of the Federal Emergency Management Agency (FEMA).
  6. The New Deal.
  7. Nationalizing the steel industry.
    -An important note on this one: The Supreme Court did eventually rule against Truman’s EO that put all U.S. steel mills under Federal control. They ruled that Truman had overstepped his reach by attempting to create NEW law, instead of clarifying existing legislation.
  8. The confiscation of gold coin, bullion, and certificates nationwide.
  9. Restricting access to presidential papers.
  10. Creating the Warren Commission to investigate the assassination of John F. Kennedy.
  11. Banning assassination.
  12. Desegregating the armed forces.
  13. Desegregating public schools.
  14. Creation of the Peace Corps.
  15. Creating equal opportunity in hiring for government jobs.
  16. Requiring that the government do a cost-benefit analysis of each regulation.
  17. Creating the Department of Homeland Security.
  18. Creating the current American flag.
  19. Defining lawful versus unlawful interrogation techniques.Compare these Presidential Executive Orders to the one we are considering today… As Thomas Wictor put it, “Repealing ObamaCare by EO will be a walk in the park”.

Sources:

List of Presidential Executive Orders:
http://www.presidency.ucsb.edu/executive_orders.php

Supreme Court Chief Justice John Roberts on Constitutionality of ACA Penalty/Tax
http://www.upi.com/Under-the-US-Supreme-Court-What-Roberts-actually-said-about-healthcare-tax/35241341732600/

EO Minimizing the Economic Burden of the Patient Protection and Affordable Care Act Pending Repeal:
https://www.whitehouse.gov/the-press-office/2017/01/2/executive-order-minimizing-economic-burden-patient-protection-and

A Look Back at how ObamaCare was Signed into Law:
https://www.forbes.com/sites/physiciansfoundation/2014/03/26/a-look-back-at-how-the-president-was-able-to-sign-obamacare-into-law-four-years-ago/#3e792ae1526b

Thomas Wictor:
https://twitter.com/ThomasWictor/
thomaswictor.com

Thomas Wictor on ObamaCare repeal by EO theory:

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