It's remarkable that Trump has consistently been against free-speech but still has the support of a non-trivial number of self-described "libertarians" like Thiel. This is in the 1st amendment sense as saying he wants to open up libel laws in 2016 [0] to his comments on video games [1] and flag burning [2] to in the broader sense in his anger at the kneeling protesters [3].
Or the guns rights activists barely flinching at "Take the guns first, go through due process second". Just trying to imagine their reaction if the previous officeholder had said that.
The anger at the kneeling protestors is especially revealing considering the debate centered around whether the private NFL could interfere with the expression of the players.
public expression, on the NFL's property, under the NFL's name... Nobody believes Kapernick should be denied the right to say and do what he wants to say and do, but if I take actions contrary to my employer's best interests, on company time and property, my company can't restrict my right to speak, but they can sure tell me I can't do it on their property anymore, and they can terminate my employment as well.
As for the gun issue, nobody in the gun crowd liked that comment from him. Some have even argued they're not going to vote for him going forward as a result. But when the alternative is people who literally believe that the second amendment doesn't exist, doesn't say what it says, and don't believe that the SCOTUS rulings that have come down on it have any effect, what choice do they have?
In this instance is he really against free speech though? Seems like the struggle seems to be between his freedom of speech and twitter's. It all comes down to the question of whether twitter is a "publisher" with the freedom to edit/change content users post on its site. Seems like they want to be treated as both when its convenient for them.
His speech is still there it just has a commentary beside it. Nothing in 230 requires a company to be either neutral or hands off with user content to get protection from civil liabilities for moderation.
[0] https://www.washingtonpost.com/news/the-fix/wp/2016/02/26/do...
[1] https://www.nbcnews.com/politics/donald-trump/fact-check-tru...
[2] https://www.washingtonpost.com/politics/2019/06/15/no-braine...
[3] https://www.nbcnews.com/politics/donald-trump/trump-says-nfl...