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John Risley, co-founder of Clearwater Seafoods stands out front of the giant lobster sign in Bedford, N.S., in August, 2022.Carolina Andrade/The Globe and Mail

For decades, John Risley seemed unstoppable. The Nova Scotia entrepreneur struck it rich off a seafood business, repeated his luck with a fish oil company, then made out like a bandit selling a cable and wireless company in the Caribbean.

Along the way he became a billionaire, was invested into the Order of Canada and earned a reputation as one of the country’s top philanthropists.

So it was a surprise to many when his primary holding company, CFFI Ventures Inc., sought a judge’s approval in February to restructure US$776-million in debt.

Mr. Risley had taken out a loan in 2017 from HPS Investment Partners, an American private credit giant, and by 2019 he’d broken some of the debt’s covenants. That meant he hadn’t followed the financial rules the lender had put in place.

Three years later, in 2022, CFFI defaulted altogether, and Mr. Risley was directly affected because he had personally guaranteed the loan. The seafood magnate is now piling up unpaid interest on that debt at an annual rate of 28 per cent.

And that isn’t all he owes. A restructuring plan proposed by HPS revealed that CFFI also faces a $331-million tax bill from the Canada Revenue Agency.

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In late February, Mr. Risley put this 6,400-square-foot Halifax home, which he recently built, up for sale for $14.9-million.Darren Calabrese/The Globe and Mail

In all, CFFI’s liabilities, which include related-party debt, total $2.04-billion, according to court filings. The value of its equity is negative $914-million.

With the restructuring now before the Supreme Court of Nova Scotia, the CRA bill is shaping up to be a lightning rod. Under the current proposal, HPS plans to take control of everything inside Mr. Risley’s holding company. If approved, that could leave nothing for the CRA, which HPS argues is an unsecured creditor.

HPS declined to comment for this story. In an e-mail, the CRA said it does not comment on matters that are currently before the courts.

Mr. Risley, meanwhile, told The Globe and Mail he can’t disclose much because of the court process, but in a phone interview he said he has “substantial assets and projects that are not in any way related to or connected to CFFI.”

The mystery in all this is where Mr. Risley’s money went. Some entrepreneurs have only one big win in their lifetimes, but he’s had multiple home runs.

The company that made him a household name is Clearwater Seafoods, which was founded in 1976 and harvests shellfish off the coasts of Atlantic Canada and Argentina, then processes it and markets it around the world. Clearwater went public on the Toronto Stock Exchange in 2002, and at the time, CFFI’s majority stake was worth $250-million.

A decade later, in 2012, Mr. Risley sold Ocean Nutrition Canada Ltd., which made its name supplying Omega-3 fatty acids from fish oil for $540-million. The business was co-owned by Mr. Risley and Richardson Capital.

His largest deal of all came in 2015, when Mr. Risley and his partners sold their Caribbean and Latin American telecom company, Columbus International Inc., for US$1.85-billion. Mr. Risley owned 53 per cent of the company, giving him US$980-million in cash and stock of the acquirer.

Yet even after all those gains, Mr. Risley borrowed US$250-million from HPS in 2017 for working capital and acquisition financing purposes. He agreed to pay 8 per cent annual interest in cash, plus an additional 5 per cent annually “in-kind,” which gets added to the debt total each year.

In 2019, when Mr. Risley breached the loan’s covenants, he chose to add continuing unpaid interest to the loan balance, at an annual interest rate of 20 per cent. The hope, according to court filings, was that he’d soon sell one or more of CFFI’s larger investments and use the proceeds to pay the debt back.

The problem: These sales never happened. CFFI is still sitting on a number of assets that can’t find buyers. “CFFI does not believe that its assets can be monetized in the near term, nor that the value of its assets are sufficient to address the quantum of the debt outstanding” from HPS, according to court files.

These assets include 30 per cent of World Energy GH2, a family of companies and partnerships based in Newfoundland and Labrador that are developing renewable energy; a minority stake in World Energy LLC, a Boston-based producer of biofuels for airplanes; and 47 per cent of Mara Renewables Corp., which delivers Omega-3 products derived from algae.

Because HPS, a secured creditor, is owed so much and isn’t being repaid, the company has proposed taking ownership of everything in CFFI. However, a judge will have to decide whether that’s possible, because the CRA has been fighting with Mr. Risley for years and says it is owed $331-million related to unpaid taxes from the sale of his Barbados-based telecom company, among other things. HPS has labelled the CRA as an unsecured creditor.

A curveball in the saga is that as the debts piled up, Mr. Risley racked up more investment wins. In 2020, publicly-traded Clearwater was sold to Premium Brands and a coalition of Mi’kmaq First Nations for $1-billion. Mr. Risley took home $116-million for his remaining stake in the company.

He was also an investor in MDA Space Ltd. when it was brought back under Canadian ownership in 2019. In August, 2024, Mr. Risley sold three million MDA shares for $45-million, and he continued to sell down more holdings, leaving him with no common shares by January, 2026.

But it still hasn’t been enough. CFFI kept selling what it could, including a Cessna plane for $2.7-million in 2024 and a Global 5000 private jet and equipment for $25.8-million, but the unpaid interest kept piling up, blowing a hole in CFFI’s financials. The company lost $270-million over the first nine months of 2025. Its largest expense, at least on paper, was interest payments.

In January, Mr. Risley’s tax lawyer, Jenny Mboutsiadis at Fasken Martineau DuMoulin LLP, dropped him over unpaid bills, according to a CBC report. (She did not respond to questions from The Globe.) And in late February, he put a 6,400-square-foot home he recently built in Halifax’s South End up for sale for $14.9-million.

As the walls closed in, HPS and CFFI filed their restructuring proposal on Feb. 17. Other creditors will now get their say, and a judge is expected to rule on the matter by the end of April.

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