Has he admitted to being red pilled yet?

Without saying it outright, yes.

He has pretty much indicated will vote for Trump, without it meaning some lasting Republican vote in the future.

I've always liked Pool but has almost become TOO pro-Trump lately.

I know that sounds ridiculous, but I've always enjoyed listening to people that are more neutral third party types like him, Weinstein, Harris, sometimes Shapiro, or Clay Travis because they just point our the insanity of the progressive moment, without being on either team. Mainly not being overt Trump sycophants. I mean I'll easily vote for the guy as of now but I'm not madly in love with the idea.

Most of those guys are liberal mainly but recognize the modern democrat party has moved over so far left that common sense comes off as right wing these days. I will say that Harris and the Weinsteins go a little too far and have TDS and say dumb things like " Trump is a threat to our democracy."

I've noticed this as well but considering the multi front attack trump is dealing with and the incredible bias in the standard media story, a guy who reacts to the news as written could easily end up speaking positively of trump almost without trying.

That said I'd also argue there's not much for him to use to balance right now. The democrats have done so little lately that is newsworthy. It's truly embarrassing that they are able to do literally nothing and get a pass while the country burns and they hold a house of Congress.