In 1986, Andrew Knight, then Editor of The Economist, advised Black an investment could be made in the ailing Telegraph Group (London, U.K.), and Black was able to gain control of the Group for £30 million. By this investment, Black made his first entry into British press ownership. Five years later, he bought The Jerusalem Post, and by 1990, his companies ran over 400 newspaper titles in North America, the majority of them small community papers. For a time from this date he headed the third-largest newspaper group in the Western World. Control of Australia's leading newspapers, the Sydney Morning Herald, Melbourne Age, and Australian Financial Review, albeit in a minority stockholding, was acquired in 1992. Initially in association with Sydney Billionaire Kerry Packer and Future Prime Minister Malcolm Turnbull. In 1994 Black and Radler bought Chicago's second newspaper, the Sun-Times.

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