Company boss, Peter Morris, has nothing but his "anger" to show for 25 years of marriage after a series of court rulings.
Jane Morris, 52, a stay at home mum, was "criticised" by her high-flying ex for not bringing more money in after they split, having quit her career as a recruitment consultant to keep house for him and their three children for 20 years.
London's Appeal Court heard that Mr Morris, 51, "took credit" for the "high standard of living" the couple enjoyed in their £1.2m cottage in the Chiltern Hills.
But the couple's "extravagant" spending, both during their marriage and after their "bitterly contested" break-up in 2013, brought them "to the brink of financial disaster", reducing multi-million-pound family assets to just £560,000.
Divorce judges have handed Mrs Morris, 52, almost half a million pounds while her husband has been left with nothing, despite him being the only breadwinner in their family for nearly two decades.
Now, in a fresh blow to the software tycoon, his ex-wife is trying to have him jailed for failing to keep up with maintenance payments.
The court heard that the couple enjoyed quarter of a century of married bliss in their four-bedroom detached house, set in extensive gardens in Princes Risborough, Bucks, whilst their two younger children boarded at a £30,000-a-year public school.
Mrs Morris, who was praised by divorce judge, Glen Brasse, as having been a "competent and effective operator" during her pre-marriage career, "stayed at home to look after the home and care for the children by agreement with her husband."
Mr Morris, the managing director of a software company with a seven-figure turnover, who earned up to £240,000-a-year, was said to have "considerable business acumen."
"The wife and family have relied on him considerably in the past for his expertise in producing a good standard of living for them," Judge Brasse said.
They enjoyed "expensive holidays" and showed "exceptional generosity" in lavishing gifts of cars, holidays, horses and expensive birthday parties on themselves and their three children.
When their marriage hit the rocks and they split in 2013 their "extravagant" spending continued unabated.
The husband's lifestyle in particular "continued as a very affluent affair", with Mr Morris "taking himself" on six holidays in the space of nine months,whilst "huge and pressing debts" mounted up.
That care free spending backfired when Judge Brasse ruled that, due to their profligacy, only enough money remained in the pot to meet the core housing and day-to-day needs of the wife and children.
He handed almost half a million pounds to Mrs Morris, whilst giving the husband just £66,000.
In July last year another judge, Judith Hughes QC, ordered the husband to fork out £77,000 for unpaid maintenance and other debts "from his share", effectively leaving him with nothing from the marriage.
"The husband has had the money to pay the maintenance but has failed to prioritise it and has spent sums instead on himself and his enjoyment," Judge Hughes said.
Mr Morris had criticised his wife's own expenditure, and "vented his anger" pointing out that she had spent £5,000 on a 50th birthday party for herself after they split.
He also "criticised her for not earning more, having re-entered the labour market" since they separated.
But Mrs Morris was ruled to be "a sensible woman" who was "probably in need of emotional and psychological comfort" during her own spending sprees.
Judge Brasse at the Central London Family Court agreed he had made a "substantial departure from authority" in handing 90% of the family assets to a stay-at-home wife.
But he said Mrs Morris "needs adequate maintenance" because sacrificing her career had left her with a "low earning capacity...in her middle fifties with rusty skills."
He also pointed to "the husband's very substantially larger earning capacity into the future" and his bigger pension pot.
"It is self-evident that not all the needs of the parties could possibly be met in full, or even substantially, from the available resources so the parties expectations have to be scaled down.
"Some of their needs will have to be prioritised over others. The priority must be given in my judgement to the housing of the wife and children," he concluded.
Mr Morris now has a six-week prison sentence hanging over his head, which Judge Hughes imposed for non-payment of maintenance but suspended to give him a chance to pay up.
He is now challenging that sentence, and the financial outcome of the divorce generally, in the Court of Appeal.
Mr Morris appeared to represent himself in court, but Lady Justice Black adjourned the hearing for him to obtain a legal aid barrister, saying that his "liberty is at stake."
The case will now return to the Court of Appeal at a later date.