Your post does touch on an important distinction between two different types of "conservative" judges: originalists and textualists.
An originalist like Antonin Scalia would look at this case and apply this question as part of his legal approach: "How would the authors of the U.S. Constitution apply the original founding principles of this nation to the case?"
A textualist like Clarence Thomas would apply this question: "I'm not going to try to decipher what the authors of the U.S. Constitution would have thought about this case. What did the plain language of the applicable statute and/or Constitutional provision mean when it was drafted?"
At some point the plaintiff in a case has to be seen as an incompetent misfit who had every chance in the world to remedy a situation amicably under the letter of the law but refused to do so.
One would hope when you are 94 and ‘incompetent’ you feel differently.