It's never a good sign if you feel like you need to roll up to a meeting with your mother with your lawyer in tow.
On Thursday morning, Prince Andrew, disgraced former working member of the royal family, disgraced former trade envoy and general all-round disgrace, turned up to Windsor Castle for a 90-minute session with mumsy, or as you and I know her, Queen Elizabeth II.
While it is not known if she served him her favourite Earl Grey and a plate of jam pennies while she kneecapped what was left of his royal career, what is known is that while the historic meeting was happening outside, Andrew's lawyer Gary Bloxsome, waited in his client's Range Rover. Billable hours are billable hours, after all.
(Already, the Duke of York is said to have spent more than $3.9 million on lawyers and advisers.)
While thus far it has been Andrew's own abysmal judgment, pomposity, hubris, love of a free holiday, and willingness to open the doors of Buckingham Palace to a Libyan gun which has landed him in hot water.
Now, it is the legal strategy he has chosen to pursue to fight the civil sex abuse case he is facing in New York which is seeing him come for a drubbing.
Last week, a judge in New York threw out Andrew's motion to dismiss the suit brought by Virginia Giuffre, nee Roberts, who alleges that the Duke of York sexually assaulted her on three occasion when she was a teenager.
Andrew has vigorously and repeatedly denied the claims.
This ruling fired the starting gun on the pre-trial process for both sides who are now set to begin the process of collecting sworn depositions in the coming months.
And on the list of people facing an on-camera, under-oath grillings, are Giuffre's psychologist Dr Judith Lightfoot and her husband, Robert Giuffre.
In court documents, Andrew's lawyers reportedly allege that Giuffre, "may suffer from false memories" and want to interview Dr Lightfoot in regards to this, along with being given access to notes she took and want to ask about prescriptions she might have given her patient.
It's a gambit that was nearly immediately met with gobsmacked horror in the UK.
"It's the ultimate in victim blaming. A lot of victims of abuse understandably reach out for therapeutic support," Dr Charlotte Proudman, a barrister and Cambridge academic specialising in violence against women, has told The Times.
"Defence lawyers used to always try to put forward evidence of sexual history, and some of that has been closed off legally," Clare McGlynn QC, a professor of law at Durham University and expert in sexual violence, has also said.
"Now it has moved from 'sl*ts' to 'nuts': instead of framing women as sl*ts, they try to claim they are nuts."
The choice to go down this route has shocked many.
It was the now 61-year-old's apparent lack of sympathy for the victims of convicted sex offender Jeffrey Epstein during his catastrophic 2019 Newsnight interview that ultimately led to him being sacked from frontline royal duties.
(Sure, he technically "stepped back" but numerous reports have painted a picture of the Queen, Prince Charles and Prince William forcibly making the decision he needed to go and giving him no choice in the matter.)
Not once during the nearly hour-long sit-down did he express a jot of concern or even interest in the young women's lives irrevocably damaged by Epstein.
Instead we were treated to Andrew pompously telling the world he thought at the time it was "the honourable and right thing to do" to end his friendship with Epstein in 2010 in person during a five-day stay at the financier's gargantuan New York home, even though by then the financier was on the sex offenders' register.
There are no bones about it: Andrew is a man whose judgment has proven, time and again, to be spectacularly horrible. Still, even for the Duke of York, who is far from grand and not that old, to now go down this path is stunning.
Andrew's attempts to deploy questionable tactics are nothing new.
In August 2019, pre-Newsnight, his supposed "closest supporters" raised the preposterous allegation that the infamous photograph of the Duke with his arm around the waist of a 17-year-old Giuffre was a con job.
"The picture is a fake, and the girl's story is a fantasy," a source told The Telegraph. "Sadly – it seems to us – this girl is simply out to make a name for herself."
Their proof? Andrew's fingers are "much chubbier in real life".
(Andrew also sought to cast doubt on the shot during his TV interview offering up the arguments that the image shows him wearing his "travelling clothes" and that "I don't believe it's a picture of me in London because when I would go out to … When I go out in London, I wear a suit and a tie." He also argued that members of the royal family don't hug and that "public displays of affection are not something that I do".)
Likewise, in October last year, in one court filing, his lawyers attempted to have a newspaper report that called Giuffre a "money-hungry sex kitten" taken into account by the court. (In December, District Judge Lewis Kaplan rejected the move and dismissed it as a PR stunt.)
While Andrew obviously has every right to vigorously defend himself in court, of all the various tactics to deploy, choosing to highlight the issue of memory seems particularly hypocritical.
Memory is, after all, something that Andrew himself has long had issues with.
Quizzed by Newsnight's Emily Maitlis about the notorious photo showing him with his arm around Giuffre along with former pal and now convicted sex trafficker Ghislaine Maxwell, the royal said, "I have no recollection of ever meeting this lady. None, whatsoever."
The most obvious question is, why?
Pursuing Giuffre's psychologist, a source close to the Duke has told The Times, was a similar move to something out of "the Maxwell playbook". However, given that she now faces 65 years behind bars having been convicted on five charges of sex trafficking, that seems a bit like getting sailing lessons from the captain of The Titanic.
Then there is the fact that strategy will only further alienate the public, though perhaps this does trouble him given he is already reviled by the public in the UK, the US and anywhere with basic access to the internet.
Andrew appears to be trying to save his own skin by attempting to sell himself to the public as a white-as-snow victim of malignant forces out to get him rather than say, providing hard evidence in the form of security logs that he was tucked up in bed in Buckingham Palace on the night the Virginia photo was taken.
If there is one thing to take away from the Andrew cataclysm of the last two and a bit years is that the cocktail of ego, lifelong privilege and surrounding oneself with a clutch of yes men and women is disastrous. That and his lawyers are getting very, very rich right now even if they are only being left waiting in the car.
• Daniela Elser is a royal expert and a writer with more than 15 years experience working with a number of Australia's leading media titles.