These days it never rains but it pours on Lord Conrad Black.

The erstwhile media baron is facing further legal entanglements as Toronto-headquartered Hollinger Incorporated [H-Inc], a company in which he holds most of the shares, sues him for C$636 million ($524m, €405m, £279m).

H-Inc, the holding company that controls Chicago Sun-Times publisher Hollinger International, is pursuing its former ceo and his privately held company, Ravelston, for financial misconduct.

Black, who was forced out of the ceo role at H-Intl in 2003, and former henchman David Radler are currently subject to a criminal investigation by the US Attorney's Office in Chicago. They also face civil fraud charges filed by the US Securities and Exchange Commission.

These relate to $85 million of company funds allegedly diverted into their own pockets - a charge vigorously denied by both men who insist the payments were authorized by the H-Intl board.

The latest twist in this scandal-beset tale comes shortly after Canadian financial regulator, the Ontario Securities Commission stopped Black's attempt to buy the 22% of H-Inc he does not already own.

Ravelston spokesman James Badenhausen dismissed the latest lawsuit as a rehash of existing litigation adding: "We are confident that, as with those other suits, we will prevail in this case."

Data sourced from New York Times; additional content by WARC staff