It was just before Labor Day, and Senate hopeful Blake Masters had spent much of the summer getting absolutely shellacked with negative advertising in Arizona. Thousands of miles away, his financial patron Peter Thiel was enjoying a late summer tour of Europe and planning a decadent party to celebrate the 20th anniversary of PayPal’s I.P.O., the liquidity event that helped introduce a plethora of future tech patrons (Elon Musk, Reid Hoffman, David Sacks, et al.) into the economic stratosphere. But Thiel’s team, based out of his family office in Los Angeles, was nevertheless hard at work, vetting a proposal to drop another $20 million on Masters and J.D. Vance, a fellow Thiel protégé, to boost their struggling Senate campaigns. It would have been a monumental investment, and one that would have transformed the G.O.P. advertising landscape all across the country. But it never happened.