It's not that hard to understand really.
The MSM are still stuck in their default mindset. And that mindset is "To take down a Republican we need to find the Scandal" or failing that just harp on anything and everything. After all thats what worked on Bush '43, McCain and Romney.
The same goes for all of Trump's opponents. The media and the DC establishment can't find a way to fight Trump effectively because they refuse to learn or adapt to how Trump operates.
Yep, the playbook on how to beat back resurgent Republicanism was 1. Paint him as racist, 2. Paint him as sexist 3. Paint him as out of touch to common Americans. 4. Make fun of his religion and that devotion to Christianity makes him a backwards gay-hating theocrat. 5. Find the unsavory monetary shenanigans in his background and paint them as proof he's in the pocket of big business. 6. Find the character scandals (sex and drugs) and viciously contrast those to all the smarmy I love Jesus stuff he said (from point 4) and paint him as a hypocrite.
Problem,
NONE of these work on Trump.
4 and 6 are out the window because he's not religious.
5 is out the window because he was, ironically, rich enough to pay for his own campaign without the usual neocon backers, the way the left wanted his tax returns, and were so utterly shocked he paid just shows how they can't believe there's
nothing there to find. They're guilty of projection on that one "All businessmen are corrupt, how do we know? Because the real successful ones pay us grey-area bribery with PAC funds, so how can this guy have NOTHING?! It's not POSSIBLE!!!!"
And 1, 2 and 3 don't work because they require the targeted individual to have a history of votes and statements on the floor of Congress to dig up and smear him with. An oft-hand "chicks dig me" comment at a fundraiser, a poor taste joke about "chinamen" told to an intern, votes on record AGAINST hate crime legislation or gay rights... Trumps got a clean slate, he's a Washington outsider, there's no history to haunt him with.
Even if he did, they only work if you can force a guy to backtrack, deny and get into endless debates over qualifying things, which puts them on the defensive and the media just keeps pushing "See? He's dirty, if he wasn't he wouldn't spend so much time denying it!" .
Trump never once got on his back heels, he either said "That's fake" or "Yeah, I did it, so what?" and after years of slimy establishment politicians, people actually find this candor APPEALING. Who knew?
And they have no answer, instead of brainstorming up better ideas, they only pound on what doesn't work LOUDER.
A much bigger problem with the left, however, is not that they can't figure out why Trump is so appealing, the much bigger handicap they suffer from is an inability to see their message, when it's not "we aren't Trump" isn't APPEALING at all.
Identity politics, open borders, free handouts for non citizens generated directly from taxing actual citizens, globalizing everything and telling those affected "Sorry, but the future doesn't include you, it belongs to the oppressed masses, Lilly white middle-class suburbia is a relic that needs to die" making gender snowflakism the next great social cause.... they can't figure out why such compassion and progressiveness can't excite people.
They dont' get a broke person doesn't care about the number of trannys in a comic book.... they care about where they might get a paycheck. Only to have leftist tell them that complaining about not having a paycheck is "dogwhistling racism"
They're so out of touch they don't even realize there's another side out there, there's only The Democrats and the Forces of Evil.