“WE HAD A very loose relationship,” US businessman Jeff Leo told the High Court.

It was his way of explaining the circa $60 million (€52 million) investment dealings he had with wealthy Ohio poultry farmer Mary Wenning and her husband Jim.

“No paperwork, handshakes”; a “trustworthy relationship”, he elaborated.

When he sold the Wennings’ 66% interest in an Irish company called Steelworks to a company fully controlled by him for a nominal sum of one euro in September 2022, it was on her urgent instruction, he said.

By his account, he was to wind up the investment interests, mostly in Irish hotel subsidiaries, sell off the assets, and transfer it all to a Portuguese company to pay off what was due to the Wennings.

“Mary wanted everything out of Ireland,” he said, for tax purposes. When the assets were sold, she would dictate who would get what, the court was told.

Despite the physical distance between Ohio and Ireland— Leo lives at Tullamain castle in Fethard, Co Tipperary — they were close and spoke twice a day, “seven days a week”, he maintained.

But why would the Wennings have agreed to transfer their interest in Irish investment vehicle Steelworks, now in liquidation, to a company fully controlled by Leo?

Mary Wenning needed a Portuguese tax ID before ownership of Pixel, the company set up in Portugal under Leo’s control, could be transferred to her, he said.

“She trusted me. That is what she wanted to do,” he added.

But what the Wennings wanted is hotly contested, not least because they claim they have been left millions out of pocket by Leo’s dealings.

That is what led to Leo, a former Morgan Stanley trader, spending two days this week being cross-examined by Kelley Smith, senior counsel for Kieran Wallace of Interpath, the liquidator appointed to Irish company Wenning Holdings Ltd (WHL) last February.

Wallace’s appointment, replacing an earlier liquidator appointed on a voluntary basis by Leo, was at the behest of the Ohio couple over concerns of alleged fraud and asset stripping in related corporate entities, run by Leo.

They say WHL was set up as a vehicle for the couple to invest over $60 million in hotels and other assets in Ireland through Steelworks, a company they majority owned with Leo, the CEO, sole director and minority stakeholder.

In September 2023, Leo voluntarily wound up Wenning Holdings, and allegedly transferred millions of euro to Pixel, a Portuguese entity owned by him, rather than paying the Wennings a dividend. The couple disputes that this was done with their consent.

Leo’s two days of cross-examination spanned his business relationship with “good friend”, sometime business advisor, and loan provider David L’Estrange to Leo’s hidden stake in Utmasta, which operates the International Protection Accommodation Service (Ipas) centre on the grounds of Dundrum House in Co Tipperary.

The court heard L’Estrange worked on a settlement negotiation with the Ohio couple last summer.

Leo also explained that his friend held shares and crypto assets (Phoenix coin) in trust for Steelwork Investments, due to tax clearance and accounts filing issues with the company. He denied this was done because a winding-up petition was coming down the tracks.

“I didn’t know that,” he said.

Separately, L’Estrange was said to have advanced, with his brother-in-law, in the region of €1.6 million to assist the purchase of 12 holiday homes near Dundrum House in 2023, a loan that had not been repaid, according to Leo. Other earlier loans had been satisfied, he said.

Explanations were sought as to why L’Estrange had been paid €400,000 from the sale of a parcel of land by a separate company linked to Leo. The US businessman said between three and five loans had been advanced by his friend to group entities.

The court heard L’Estrange had also filed an affidavit and sent a message to Wallace, the liquidator, on Leo’s behalf, but seemingly without his authority.

“That’s just David. David is David. He does what he does,” the former trader said, agreeing with Smith that he was a “maverick”, at times.

Kelley Smith, senior counsel for the WHL liquidator, repeatedly sought to challenge the veracity of Leo’s evidence, from financial practices and missing records at the companies he ran to an email he wrote, purportedly at odds with his claim that the transfer of interests to a Portuguese company was done for the benefit of Mary Wenning.

“A much more plausible explanation was that you were hoodwinking the Wennings and you were taking ownership of the entire group,” Smith suggested.

“No,” Leo objected, the move was done for the Wennings to avail of a tax benefit. When counsel said this was not in any of the documentation, he replied that he had “other emails”.

In respect of Dundrum House, the court heard that following a “lucrative” arrangement to house Ukrainian refugees, it became an Ipas centre under a purported lease with Utmasta, an Irish company controlled by a single shareholder, a Spanish woman based in Palma.

However, it was put to Leo that he and his wife held, in trust, a 50% beneficial interest in Utmasta, a fact he had sought to conceal. He replied that there had been violence involved, his wife had been run off the road, and rocks had been thrown.

He claimed the shares were never assigned and that all the funds had rolled through a corporate entity, Brogan Capital Ventures.

Finally, it was put to Leo that significant portions of his evidence were untrue. Asked if he accepted that, he replied: “No”.

-Reporting by The Currency

Tuesday in the High Court

Yesterday, the court heard that the companies behind Dundrum House Hotel in Co Tipperary failed to file accounts for six years.

Leo accepted that accounts were not filed for 2018 to 2023. He said he had “assumed everything was being done” to ensure financial records were being kept up to date for the multimillion euro companies, Wenning Holdings and Steelworks Investment Ltd.

Dundrum House Hotel came to national attention last August when it was provided to the state for temporary use to shelter people seeking asylum.

During Tuesday’s hearing Leo also told the Mr Justice Michael Quinn that he disagreed with evidence given by his former accountant and auditor that he had “repeatedly” asked Leo for information to complete the accounts, only to find it wasn’t forthcoming.

Leo outlined to the court how he came to know Mary and Jim Wenning, the Ohio family who are now pursuing him for €60 million.

The Wennings were Leo’s former business partners, and the court heard how they first came to know each other in the US in 2006.

“They had a poultry company, they were egg layers,” Leo said, adding that they had faced problems with local environmental regulators due to water pollution issues.

At the time, Leo was a shareholder in a water treatment company. 

“Their machine wasn’t fit for purpose on the farm and that’s how our relationship began,” he said.

Leo had intended on setting up a company which would be focused on “stock loans”, but moved away from the plan after seeing that it might face regulatory issues in Ireland.

After hearing about the work of Nama following the financial crash, Leo “saw an opportunity to buy properties at a significant discount”, the court heard.

Around 2012 to 2013, the Wennings agreed to advance money to the businessman to acquire properties including hotels in Ireland.

Steelworks Investments was established, with a third each owned by Leo, the Wennings and Dublin businessman Bernard Brogan senior, a former football star for Dublin in the 1970s. The court heard the business relationship between Leo and Brogan ended in 2017.

Kelley Smith, counsel for Arthur Cox solicitors, asked Leo how accounts weren’t filed as required for 2018 to 2023.

“At the time, I assumed everything was being done,” Leo said.

“It wasn’t until Covid that I realised there was a problem here with the accounts. It was one of the first times ever I had times to sit there, in the office and go through that,” he added, confirming this applied not only to Wenning Holdings but also to Steelworks.

Leo further told the court that he had emails showing that he had queried this with his former accountant and auditor.

Smith queried why Leo did not provide these emails, pointing to a High Court order made last April “obliging you to disclose documents about Wenning Holdings” to the liquidators.

“The breadth of that order captured emails that you’ve suggested were sent by you. It appears they were not provided,” Smith told Leo.

In response, the businessman said, “I don’t know”, but added that he “assumed that accountants would have books and records” in relation to the company.

Leo also confirmed that he was found to have committed a “violation” of financial industry regulations in the US, leading to reprimands by an industry body.

While he first disputed this with Smith – arguing that he wasn’t working in the area at the time – he later accepted that he had faced a “statutory disqualification” in 2002.

Dundrum in the headlines 

Dundrum House Hotel hit the headlines in September this year after the operator of the site’s golf course and leisure facilities – Brogan Capital Ventures – announced it was closing with immediate effect. This resulted in 48 people being laid off.

At this point, Leo had already began using Dundrum House to house Ukrainian refugees and people seeking asylum following the outbreak of the Ukraine war.

The subsequent move towards extending the use of the hotel as an Ipas accommodation centre was met with major demonstrations in the local area throughout the summer of 2024.

Later that year, a contract was signed between the Department of Integration and the then newly established company Utmasta to rent a section of the property for three years to house people seeking international protection.