Well, and also by being a billionaire with the apparatus of a billion-dollar party and the wealthiest PACs in the country behind him. He wasn't suffering any realistic financial deficit and experienced none of the main drawbacks of third party candidates. He's the epitome of an insider who convinced the credulous that he was an outsider.
But overall I definitely see the central point: that the media played into a Heel-Face play-act that benefitted him massively, like the foolish bellends they are.
You're letting "orange man bad" get in the way of facts. In
2016, Hillary's money total was $770m, and Trump's was $433. That's a 1.8:1 funding advantage in Hillary's favor. In
2020, Biden's was $1.6b, and Trump's was $1.08b. That's a 1.5:1 funding advantage in Biden's favor.
To compare these numbers, in
2012, Obama had a 1.3:1 funding advantage; in
2008, Obama had a 2.1:1 funding advantage; in
2004, Bush had a 1.1:1 advantage over Kerry. Metrics before that aren't exactly available, nor reliable when available, due to lack of electronic records-keeping, accurate means to track and estimate third-party expenditure via the internet, and/or sunlight due to public awareness of campaign finance as a political issue. 2008 was a bit of an outlier for a variety of reasons, so indeed Trump's two campaigns faced major financial deficits against his opposition -- both times.
To make it clear, those totals account for hard and soft money, first- and third-party expenditures alike.
The "why" and "how" of it is simple. In 2016,
the Hillary campaign staged a silent coup of the DNC, weaponized it as their personal fundraising apparatus and money laundry, and left the national and state Democratic parties in the financial lurch. And in 2020,
when wealthy neoconservatives backed conservative Democrats (including Joe Biden) in a bid to block progressive candidates threatening to push the US Overton window left, while trying to regain control over the Republican party from tea party and Trump-supporting paleoconservatives.
Say what you will of Trump himself, the money game was bigger than him, and representative of internal party conflict to which he was only periphery. He just happened to show up at the right time to force those internal conflicts -- in both cases, party elites versus populists -- to a head.
Meanwhile, in the field of earned media,
in 2016 Trump received $5.9b worth to Hillary's $2.8b. I'd link the mediaQuant report directly, but unfortunately despite a huge number of citations (of which that Open Secrets article is but one) it vanished from the internet entirely just in time for the 2020 election -- something to my great consternation, as I've searched for it repeatedly over the years and have been unable to find it since. Something on which I've remarked before, on old and new Escapist forums.
Except here's the thing. Earned media is
not estimated by how much a candidate received in that cycle; it's estimated by how much outlets themselves receive for covering that candidate. Outlets covered Trump, ratings/clicks went up, those outlets charged more for ad buys and sold more of them. In other words, Trump was the media's most profitable Presidential candidate to cover in American history.
Now, what you need to ask yourself is, did major media investors and executives -- not the low-level people, the talking heads, producers or editors --
really get fooled by it, or did they knowingly play along, laughing all the way to the bank?