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.
The pitch, formulated by a trusted, well-regarded Thiel-backed operative named Luke Thompson, was to put $20 million into a nonprofit that would then disburse about $4 million to a pro-Vance super PAC, $4 million to a pro-Masters super PAC, and split most of the remainder on “issue ads” boosting the two candidates in the states. Part of the strategy was to preserve Thiel’s anonymity—the provenance of the nonprofit’s money wouldn’t be disclosed, and the nonprofit could run the issue ads as long as they aired before mid-September. But by late August, Thiel’s team ultimately passed—and the proposal, which hasn’t previously been reported, fell apart.
It may have been a fateful decision: While Vance won his seat in Ohio, where he was always the favorite over Democrat Tim Ryan, Masters appears unlikely to win in Arizona, trailing incumbent Mark Kelly by 5 points as of Wednesday afternoon. Thiel had intervened early and emphatically in both G.O.P. Senate primary races, where he invested some $30 million total to elect Vance and Masters, both former employees of his venture capital empire. In the general election, however, Thiel retreated financially, mostly resisting entreaties to top off their campaigns. While he continued to stump for them at fundraisers in Miami and L.A.., he grew frustrated with the demands of Republican leadership, and Mitch McConnell in particular, that he pull them across the finish line.