1. If you read the Constitution, it looks like it was written with the expectation that candidates wouldn't usually get a clear majority in the Electoral College -- and presidents would usually be elected in the special elections in Congress for those cases.
2. It wasn't until the 1920s before all of the U.S. states selected Electoral College electors through popular votes. Before that, electors were selected through different measures -- including state legislatures, popular votes, etc.
People like winning, though, which is why we have our party oligarchy.