Caldwell and Ige benefited from the fact that the alternative candidates that ran against them was even more detested by the voters. Both Djou in the Mayor's race, and for Abercrombie in the primary and Aiona/Hannemann in the general were hobbled by the fact that the vast majority of voters who actually went to a booth or put their ballot into the mailbox didn't really like the alternatives to the "ho hum" candidates that actually won. 

And this is the crux of the real problem with elections in Hawaii. We have candidates that are either at or a little below the common denominator. And what does the opposition do to counter that...they put even weaker, less likable candidates out there! Whose fault is that? Well we can start with the such-low expectation voter who votes these guys in. But further you can blame the political parties that put these candidates up. I swear sometimes the candidates they put up are literally strangers dragged off the street and told "you da man/woman".