(Bloomberg) — German financier Lars Windhorst failed to stave off a demand for about 124 million euros ($146 million) plus interest he owes to a Monaco-based cruise ship tycoon, after a London judge called his evidence “unsatisfactory.”

The British lawsuit was brought by Manfredi Lefebvre d’Ovidio’s Heritage Travel and Tourism Ltd. — an investor in Windhorst’s lingerie brand La Perla Fashion Holding. The firm said it was owed the money after Windhorst missed repayments he’d agreed under a prior settlement from February last year.

The case is a window into the high-risk transactions and relationships built up by Windhorst, a one-time wunderkind of German industry who then suffered a series of reversals in the 2000s including personal bankruptcy. He has sought to mount a comeback in recent years with the help of some influential European business figures, including Lefebvre, who was formerly an advisory board member of Windhorst’s Tennor Holding BV.

A spokesperson for Windhorst said he planned to appeal.

The dispute stems from a series of transactions in the shares of Windhorst’s companies that provided short-term loans to him and his connected entities. After his firms “failed to perform their obligations,” Windhorst agreed to a settlement with Heritage Travel.

Despite the settlement, the judgment detailed how Windhorst then sought to avoid the full payout by arguing that he was effectively forced into a “highly disadvantageous” agreement. He alleged that Lefebvre threatened to reveal the confidential terms of the transactions to other investors.

‘Vague’ Evidence

But Judge Richard Salter disagreed, ruling that the financier gave “vague and unspecific” evidence.

“In my judgment, Mr. Windhorst’s evidence is in many respects unsatisfactory,” the judge said Friday. Windhorst has repaid just 15.6 million euros of that total according to the judgment.

The negotiations with Heritage took place as Windhorst attempted to untangle ties with H20 Asset Management, one of the more controversial relationships in European finance. Berlin prosecutors are now investigating Windhorst’s links with the fund, which had been majority-owned by French bank Natixis SA. Windhorst has said that there was no violation of German banking rules.

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Heritage Travel is controlled by Lefebvre’s Heritage Group, which also owns luxury travel operators Abercrombie & Kent and Cox & Kings. The Lefebvre family built their fortune carrying ultra-rich passengers on their Silversea cruise line, which was ultimately sold to Royal Caribbean Cruises Ltd.

Lawyers for Heritage Travel in London didn’t respond to messages seeking comment. Lefebvre didn’t respond to an email sent via Heritage Group.

“The lawsuit was not about principal amounts owed which we do not dispute and are happy to pay but just about interest amounts,” a spokesperson for Windhorst said in a statement. “The case has been ongoing for over a year and we plan to appeal.”

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