It goes back to the overthrow of the monarchy, illegally, in the 1890s. Queen Liliuokalani abdicated the thrown and white plantation owners imprisoned her in the palace as they declared a new Republic of Hawaii, with the sole point of joining the Union as a territory. As Robert Remini pointed out (I think) in his book on the House of Representatives, the U.S. was divided even during this time of high imperialism. Eventually Speaker Thomas Brackett Reed, who allowed the House not to become the morass that the Senate is, let the Annexation Bill through during McKinley's time, even though he opposed it. Soon American imperialism outright annexed Hawaii.
Oddly though, there was always a question as to whether Hawaii would become self-governing within the U.S. as a territory expanded or whether we would hold it solely as an imperial possession like the Philippines, with the hopes of one day turning it loose. On the one hand, it did have a lot of non-whites that people thought could not self govern. On the other hand, the Congress did during the annexation incorporate Hawaii, allowing the Constitution to follow the flag, unlike Puerto Rico, Guam, and the Philippines (See Downes v. Bidwell, 182 U.S. 244 (1901)). Interestingly though, there was a period where the Constitution did not follow the flag to Hawaii, but Congress's incorporation around 1903 (I think) solved that problem.
So, what was Hawaii? A colony to be governed from the metropole? Or some sort of entity that we hoped to groom to join the insoluble union of states? The question has never really been sufficiently answered.
In the intervening years, the territory saw some level of self-governance with the legislature, and an appointed but powerful governor. The Homestead Act of 1928 granting certain lands (bad ones at the time) to Native Hawaiians for rent at a very low rate. There was Pearl Harbor and the military bases. Sugar and pineapples drove the economy, but on the dawn of statehood, the new industry, tourism started to take grasp.
After World War II, the United Nations, which the U.S. helped create (something we often forget), created a little list of imperialist trust territories. These territories had to become either independent or incorporated. Hawaii made the list of territories.
The push was on. However, Southerners were no fan of a majority minority state. Meanwhile, back home a great deal of consternation arose among strange bedfellows. The Native Hawaiians saw an illegally taken state. White plantation owners feared of course the minority workers gaining control as they had more numbers.
However, a bill did move, and eventually a plebiscite was held with over 90% of Hawaii residents approving of statehood. Hawaii joined the union on August 21, 1959. It was removed from the UN list. This happened many years one should not too after having the U.S. Constitution follow the flag to Hawaii, and many question if the U.S. really moved out of self interest in holding the territory as a possession. One cannot say for certain what actually led to Statehood itself.
Yet, in some ways, the questions still remain. The State of Hawaii under the Admissions Act had to handle Native Hawaiian Affairs pending some resolution. That resolution still remains. The cloudiness of the territory, and the speed at which it was admitted post-UN Trusteeship, and most importantly the status of self-determination for Native Hawaiians (NB: I am not one myself) continues to raise questions for the future of the state as a whole. Will the Homestead Act survive? What is the future of the Native Hawaiians and their self-determination that the Admission Act itself implies? What will become of the last state to enter our union? Will others too finally follow or be set free?
As readers and friends may know, I have supported the Akaka Bill. My own personal feelings is still that statehood was right, and the only way for a state to leave is for consent of the American people as a whole through their representatives (states seceding on their own was answered in the period 1861-1865 though again Hawaii presents some unique questions since the overthrow and annexation was sort of more recognized internationally as a violation of customary international law). Still these questions dog me as someone who grew up in Hawaii and still cares for it.
Let us celebrate the past 50 years, let us look toward the future, and let us reflect deeply on the troubling questions too that history presents us.
Update: Paul Theroux's take (he once said "Hawaii is not a state of mind; it is a state of grace").
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