That crazy guy who's spending all his money in San Antonio

As with the previous post, looking at how Trump was perceived as a candidate is ... interesting. Here's a summer 2016 New York Times discussion of how Republican insiders thought he was a lost cause and they need to conserve their money for Congressional races:

The party is in turn providing much of the fund-raising expertise and technological backbone, including up-to-date donor lists and systems that will send roughly a billion emails by Election Day. A third of the party’s digital team is now embedded at the San Antonio firm that formerly built websites for Mr. Trump’s properties and is now leading his campaign’s online efforts. Payments to that firm, Giles-Parscale, amounted to $8 million in July, most of which was paid out for online advertising to reach grass-roots supporters and donors, according to party officials. “The R.N.C. has built the most efficient and effective ground game in the party’s history,” said Lindsay Walters, a party spokeswoman. “No other campaign, committee or organization has been doing this for as long as we have. We are the infrastructure for the entire G.O.P. ticket. And the Trump campaign has embraced that.”

Giles-Parscale was the then obscure firm, identified by Jared Kushner and run by Brad Parscale, managing the campaign's digital strategy. Subsequent events made them look like geniuses.