No, Trump did not "roll back" any transgender law...

So review the facts:

• Affordable Care Act was passed with no mention of "transgenderism". 
• Affordable Care Act  provides protection based on sex, rather than gender.
• President Obama signed an executive order to amend ACA to include gender.
• Courts ruled against the executive order as being inconsistent with the law.
• There was never any "rule" legally in place that protected by gender.
• The Health & Human Services is following the law as it is written in the ACA.

So I am not exactly what is really expected here. Whether or not President Trump agreed or did not agree with Obama's executive order is a moot point. If the executive order did not pass court muster in 2016, then what makes anyone think it would be any different in 2020.

The only other option would be for HHS to ignore court rulings on the subject and follow an executive order that has no legal validity. While many people are suggesting differently, this simply appears to be a clarification of the rule (not a change). The HHS is stating that it was a "finalization" of a rule (that was previously under court review). By all accounts, they had been following the law since ACA was passed (not the executive order). 

This is just another blatant example of Democrats openly lying about something, trying to turn it into something racial (when it's really a legal issue). Of course, it's also another example of their minions in the MSM coming to their illogical aid. If they want to take issue with ACA because it's written to protect by sex (rather than gender) than they should have either written that way, or they could amend the law in Congress (as the constitution allows).

What the constitution does not allow (and for good reason) is for everyone on all sides of Congress and the Executive Branch coming to an agreement about a law, then once everything is signed the President goes ahead and makes unilateral changes to the agreed upon law via executive order. This was actually common practice within ACA, with different groups getting different promises of executive orders of clarification for portions of the law that they took issue with... because Congress could not take ACA back through the Senate to make any actual changes (Scott Brown election).

Btw... the left would shit themselves blind if Trump ever did something like that.

But as we have found out over the past couple of decades. The rule of liberalism is supposed to trump the rule of law. Liberals want judges who follow their political views rather than the constitution or legal precedents. Occasionally that actually has worked. It just didn't in this case, right, wrong, or indifferent.

Update: It's possible that new court challenges could be in play in the wake of the USSC ordering that gay and transgender people are protected from being fired under the civil rights act. Although the difference between being fired for being gay or trans and not distinguishing between sex and gender as it pertains to things like transgender surgery and hormone treatments are likely a different legal question. Either way, I would expect someone to use the Civil Rights Act ruling as a basis that ACA should also include gender (not just sex) as their basis.