After WWII and the UN was created, the UN got down to the business of making a list of non-self-governing territories that it immediately began to push colonial powers to incorporate or give independence. The list still exists and is, as back then, very political (the PRC took Hong Kong off the list years before they took over; and of course somehow Tibet is not on the list but Pitcairn Island and its 37 people are).
Hawai'i and Alaska were both included. Now, both being strategicly placed and Pearl Harbor still a major base, the Cold War precluded the possibility of independence, imagine if the Soviets influenced either nation as they would later do in Cuba, and dont forget the Japanese took Aleutian Islands and did bomb Pearl Harbor to start the war, and the Battle of Midway of course. So statehood was the only solution. And they came in together because, opposite of today, it was thought that Alaska would be Democratic and Hawai'i Republican.
With whatever PoD after 1900 is there a way to make it where both remain US territories, or that Hawai'i is given independence? Bonus points if it is post wwii.