Eric Watson is attempting to keep himself out of prison after a United Kingdom court sentenced the New Zealand businessman to four months behind bars.
Meanwhile, his partner Lisa Henrekson has seemingly been enjoying the Spanish Mediterranean island of Ibiza.
A London judge earlier this month found Watson in contempt of court for withholding information about his assets from Kiwi philanthropist Sir Owen Glenn. He was sentenced to the prison term overnight.
Watson's legal counsel has requested to apply for an appeal and also asked the sentence not be imposed immediately.
Henrekson, however, posted several photos on her Instagram overnight.
One photo from Ibiza was at what appeared to be an open-air market and was published with the caption "love this lifestyle".
The High Court in England and Wales ruled Watson committed acts of contempt by failing to comply with court orders after being found to have deceived Glenn during their business dealings.
In Lord Justice Christopher Nugee's judgment, Henrekson is also referenced in relation to a Swedish property she owned with Watson.
Watson's sentencing marks the latest chapter in the bitter dispute with Glenn.
After a lengthy trial, Watson was declared liable in 2018 for £43.5m ($85m) and interest compounding at 6.5 per cent per annum in compensation to Glenn's company Kea Investments (Kea). He was ordered to pay an interim sum of £25m ($48.8m) plus costs of £3.8m ($7.4m).
Watson, who formerly owned the Warriors league club with Glenn, appealed against the ruling, which was dismissed by the UK's Court of Appeal in October 2019.
Kea, however, accused Watson of being "deliberately reticent" over providing information about his assets as part of a strategy to frustrate compensation recovery efforts.
It sought three orders of contempt against Watson over suspicions about interests, including those held by his mother Joan Pollock and the Swedish house.
In his decision, Justice Nugee said it was "demonstrated how blatantly Mr Watson lied to the Court of Appeal" about the state of his assets.
Justice Nugee said there were "strong grounds" for believing Watson tried to arrange his affairs after the trial to "put himself in the best position to make it difficult for Kea to enforce any judgment".
While the judge said he had "no confidence that [Watson] is telling the truth" he only found him guilty of contempt over withholding a statement of transactions about a "Rainy Day account" in Pollock's name.
Formerly one of New Zealand's wealthiest men, Watson also claims he is now impecunious. He said in a court statement the "small amount I spend on living is given to me by my mother".