In this research, the Caribbean part of the Kingdom of the Netherlands is examined as an example of an autonomy arrangement that has been subject to change, but is at the same time inflexible due to its robust constitutional entrenchment. With special reference to particular timeframes and conflicts, this research compares the autonomy arrangement of the former Netherlands Antilles to the Åland Example. All autonomies evolve in their unique directions. The ones embedded in a relatively stable and democratic environment maintain longest over time, and contribute to the organisation of a state. As of now, the autonomy arrangement of Aruba, Curaçao and St Maarten seems to be constitutionally stable as it is domestically entrenched in multiple ways that are comparable to the Åland Example, and safeguarded by the international community that advocates the right of self-determination of former colonies. The relations within the Kingdom of the Netherlands are, however, not completely exempted from the ghosts of the colonial era, as is visible in the authority of the country of the Netherlands within the Kingdom relations, both institutionally and in its structural parenting role when it comes to law enforcement and finances. In the right words of the fox in The Little Prince, the Netherlands still maintain a certain responsibility for their `tamed´ territories in the West.