Tribune Co. took a calculated risk when it purchased Times Mirror Co. in 2000, acquiring newspapers in markets where it already owned TV stations despite federal rules barring such combinations, the Los Angeles Times reports.

Tribune executives expected the restrictions to be gone by now. That they are not has posed an obstacle to the Chicago-based company’s sale.

Tribune has been allowed to operate the Los Angeles Times and KTLA-TV Channel 5, along with newspapers and TV stations in four other markets, through a complex web of loopholes, waivers and grandfather clauses that would vanish if the company changed hands, forcing a new owner to sell assets.

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