Twice, although more so the first time. I was living in Texas at the time, and when he lost the first time, I realized that the majority of Texas voters are crass, unpleasant people. He went to hundreds of small towns and met people up close, demonstrating great knowledge, not to mention a strong affection for the people he met, but the voters he met still often chose a despicable human being for another 4 years of mendacity. I also thought the waves of Californians moving in would make the state more purple. But the Californians who arrived were mostly libertarian gamer gate bros. The progressives went to Oregon, I guess.