He has consistently denied all the sexual allegations made by Virginia Giuffre, and he had relied on his astonishingly expensive lawyers to find a way to prevent her lawsuit from progressing. They claimed it a settlement she reached with convicted pedophile Jeffrey Epstein meant she could not take action against Prince Andrew.
But Judge Lewis Kaplan was not convinced that the case should be thrown out. The case will go ahead and the possibilities for the Prince are now there try to reconcile out of court, or defend themselves before a jury.
Whatever the outcome, and whether or not a jury finds that Prince Andrew did, as Giuffre claims, the damage to his reputation is unmanageable and irreparable.
It is more than a decade ago that rumors first began circulating about his unpleasant friendship with Epstein. And his relationship with Epstein’s former lover, Ghislaine Maxwell – now even convicted sex offender – goes much further back. If nothing else, it seems clear that the prince has made some extremely dubious judgments about his choice of friends.
But the broader question is how much damage this inflicts on the monarchy itself. After Andrews Disastrous Newsnight Interview where he showed no remorse for Epstein’s victims, the queen was left with no alternative but to fire her son from his job. He has not performed any royal duties since. Now it seems that this may not be enough to dampen public opinion. There are calls from the military for him to be stripped of his regimental titles. And there have even been suggestions that he should lose his duchy.
All of this is extremely embarrassing for the Queen at the start of what was to be a year of celebration for her platinum anniversary. It must also be deeply awkward for a 95-year-old mother to have to ask her favorite son about his sex life. But she definitely needs to know the truth.
The legal bills are sky high and will continue to do so in the coming months. The prince is financially dependent on his mother. This could cost her millions, and although she would finance it from her private income, it has already called into question the total cost of the monarchy.
In the coming months, Prince Andrew faces the insurmountable prospect of appearing before Virginia Giuffres lawyers his claim that he had a medical condition that prevented him from sweating at a nightclub. He is also asked to provide evidence that he was actually on Pizza Express in Woking that night where he is said to have had sex with her. He will then have to take an oath before a trial or try to reconcile out of court.
But a settlement will not be enough to clear his name in court of public opinion. His reputation is well and truly defiled, and though he is innocent until proven guilty, the Duke has created a real, very unconventional mess.
Jennie Bond is a Royal BBC correspondent