We followed each other on Twitter, and have mutual acquaintances. I also know personal stuff about Milo that not many people know. If there were meanings that weren't obvious to you, that doesn't mean they weren't there.
It also means those meanings are completely worthless to bring into this discussion as they can't be evaluated - your comment is worded as if it's personal stuff you don't want to get in to.
Maybe it's a cultural thing. Milo is basically an example of British schoolboy humor, and the biggest joke for us, watching it, is that Republicans don't get the joke and take him seriously.
But then, Milo is just riding Trump, and plenty of Republicans take him seriously as well. (Not all, of course. Some have retained their integrity https://goplifer.com/2016/07/22/resignation-letter/ )
The problem is that people who are being taken for a ride obviously don't know they are being taken for a ride, or they wouldn't be. And they definitely don't want to know that: they'll just get angry. So it's much better not to tell them....
What objective facts do you base this on? The tweets themselves are completely innocuous.
And meanwhile, people who post actual harassment and threats are left unscathed (I've personally reported a few myself), and while I'm not privy to what happens in Jack's office, it definitely quacks like it's okay to to harass if you subscribe to one political mindset, but not another.