To be fair, he didn’t win his first election by getting the most votes, and neither did Trump.
The Republicans realized during the Reagan administration that they would soon be unable to win the presidency with a majority of votes and took many steps to undermine the Democratic process. Voter suppression, purges, intimidation, voter ID laws, all of that began with Reagan.
Bush the elder was the last to win a “democratic” victory. If it weren’t for 9/11, Bush wouldn’t have been able to win his second election either. That fact always blows my mind. Like people rallied around the incompetent fool who managed to ignore warnings and let a terrorist strike happen only to then go on and invade the wrong country multiple times and spend trillions of dollars on nothing.