In the case of Kalanianaole v. Smithies, Trustee of Cockett in 1912, Prince Jonah Kuhio Kalanianaole filed a lawsuit against William O. Smith as trustee for Helen Kinau Wilder and Mary E Foster to recover land that he claimed was his by right of inheritance from Queen Lili'uokalani's estate. The Supreme Court ruled against Prince Kalanianaole stating that there was no evidence supporting his claim to the lands in question and affirmed the decision made by lower courts which had also ruled against him. The court held that under Hawaiian law, a will must be probated within six years after death or it is considered void unless an exception applies such as fraud or mistake; none were applicable here since Queen Lili'uokalani's will had been probated more than six years after her death without any allegations of fraud or mistake being raised at the time.

In the dissenting opinion for Kalanianaole v. Smithies, Trustee of Cockett, Justice Holmes disagreed with the majority's interpretation of Hawaiian law and its application to this case. He argued that under Hawaiian law, a life tenant could not be held responsible for improvements made by a remainderman without their consent or knowledge. In his view, it was unjust to hold Princess Ruth Keelikolani liable for improvements she did not authorize or benefit from during her lifetime. Furthermore, he believed that the lower court had erred in interpreting "waste" as including both voluntary waste (i.e., destruction) and permissive waste (i.e., neglect). According to him, only voluntary waste should have been considered in this case since there was no evidence suggesting any form of neglect on part of Princess Ruth Keelikolani towards her property.