“Jim...failed at a run for Senate at the same time David Brat was knocking off Eric Cantor.”
Nope. Gilmore ran for Senate in 2008, the year of Obamalove, and Brat defeated Cantor in 2014.
Then who was running for Senate in 2014?
Not to mention Brat defeated Cantor in the GOP primary (that’s right, Cantor wasn’t a democrat) several months before the 2014 GE when Gilespie was losing a superclose stolen race to Warner (ie not the same time) so even if Gilmore had been the 2014 Senate nominee, I’ve not sure what the heck that would have to do with Brat’s primary victory.