The Chicago Cubs aren’t going to win anything this year despite having one of baseball’s largest payrolls. But their bankrupt owner, Sam Zell’s Tribune Co., may be about to hit a home run — at taxpayer expense.

Zell is trying to get around the problem he created when he converted Tribune from a standard C corporation to an S corporation to avoid taxes. Firms making that switch owe corporate gains taxes if within 10 years of the change they sell assets, such as the Cubs, in which they had “built-in gains.”

The proposed Cubs deal, involving a “leveraged partnership” using lots of borrowed money, is so aggressive that a leading tax expert, Robert Willens expects the IRS to challenge it.

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