Campaigning in Hawaii

[Schiff for Senate]

Nixon visited every state during his 1960 campaign, this is often seen as contributing to his loss since he didn't focus enough on the swing states.

Interestingly, this was the first presidential election for both AK and HI (the last two states added to the Union), and both were quite competitive in 1960. As it turned out the 1960 election determined those states' political leanings. Ultimately, HI went narrowly Democratic (foreshadowing a legacy where it would become a rock-ribbed blue state) and AK went narrowly red (it'd vote Democratic only once, in 1964, thereafter).

[Schiff for Senate]

Cheney thought Hawai’i was winnable for Bush.

Not too unreasonable. HI took a massive turn and shift to the left in 2008, shifting 36 points leftward (more than most counties did in 2020 and 2016). Since 2008 HI has shifted slowly rightward, but still, it's not nearly as competitive as it was in 2004. In 2008, HI went blue by 45.27%; in 2004, by 8.75%. In 2004, HI was a blue state just out of reach for the GOP no matter how well they did nationally, so it going Republican would've required a great night for Bush and Cheney, but wasn't impossible. Today, HI is one of the bluest states and one of the states and the core of the Democrats' electoral math (that is, HI is one of the most reliably blue states). But still, Cheney expecting HI to flip blue is like Biden expecting AK to flip in 2020 - not happening, though the state is still only Likely, not Safe, for the opposite party.