It was perhaps the cleverest corporate tax strategy ever devised: no matter how much money the company made, neither it nor its shareholders would ever owe a penny in federal income taxes.

“In conception, it was brilliant,” said Robert Willens, a longtime tax analyst who now runs his own firm, Robert Willens L.L.C. “It would have been probably the greatest tax avoidance structure ever devised, had they earned income.”

Instead, the strategy has now backfired on the Tribune Company, the publisher of The Chicago Tribune and The Los Angeles Times, among other publications. The company seems likely to have to pay hundreds of millions of dollars in taxes that it would never have owed had it not tried to be so clever.

In a way, this latest disaster is an indictment of a corporate tax law that allows companies — even encourages them — to play games to minimize their tax bills.

Without the expected tax savings, the numbers probably would not have worked when Samuel Zell, the real estate billionaire, was putting together his 2007 takeover of Tribune. Perhaps he would have dropped the deal, or perhaps he would have been unable to finance it. In either case, everyone involved would have been better off.

As it is, Tribune has come out of bankruptcy and now faces a big tax bill that it had not budgeted for. It says it thinks the Internal Revenue Service is wrong, but Mr. Willens says the I.R.S. has tax court precedents on its side and is likely to prevail.

If so, that will be one more — and perhaps the final — indignity to Tribune caused by Mr. Zell. He is long gone from the company, but his legacy lives on.