So, yes, the playing field is tilted, but it’s tilted in Trump’s favor; he’s been running downhill. You can see this in the table below, which shows Trump’s percentage of the vote in each state compared with the percentage of the delegates he won there. In a perfectly “fair” system, the two numbers would match perfectly.
Trump has won a higher share of delegates than votes in 24 of the 35 contests studied (67 percent), most notably in winner-take-all contests. Winner-take-all statewide contests are less democratic than winner-take-all by congressional district (in the sense that the delegate allocation mirrors the vote). And winner-take-all by district is less democratic than simple proportional allocation. Trump benefited most in South Carolina, which awarded all 50 of its delegates to Trump even as he won a little less than a third of the vote. He also took all the delegates in the winner-take-all states of Arizona and Florida, while earning less than 50 percent of the vote in each. In 40 percent of the contests, Trump did at least 10 percentage points better in the delegate race than in the actual voting.