By Michael Oneal | Tribune Co. on Wednesday asked the judge in its bankruptcy case to approve a 2010 incentive bonus plan that could pay out $30.8 million to $42.9 million to about 640 managers, including the company’s top nine executives.

The range is based on the degree to which the company meets or exceeds its cash-flow targets before the end of the year. At the top level, the nine senior officers would split approximately $5.7 million, the document said.

Since Tribune Co. entered Chapter 11 proceedings in December 2008, the judge has approved similar bonuses totaling $57.3 million, including a payout of $42.1 million for 2009 performance.

On Monday, Tribune Co. inserted two bonus plans in its proposed restructuring that would grant an additional $14.9 million to the Chicago-based media conglomerate’s top 35 executives, related to the company’s 2009 restructuring efforts.

Tribune Co.’s bonus requests have incited a storm of protest from various creditor constituencies and the company’s unions, which have argued that management’s performance targets were set too low, allowing the company to beat them easily.

William Salganik of the Washington-Baltimore Newspaper Guild said, “This is more than they paid out in most of the good years,” when revenue and cash flow were sharply higher. He said the Guild would formally contest the plan following a protest Wednesday of the $14.9 million proposed payout to senior executives.

Tribune Co., which owns the Chicago Tribune, argued in its motion that the company has paid such bonuses for years and that Mercer Inc., the compensation consultant management hired to vet the plan, believes “the incentive opportunities provided under (the plan) are well within reasonable market ranges.”

If the company meets its target for 2010 operating cash flow of $425 million, the plan would pay out $30.8 million to 640 managers, including $2.2 million for the nine top executives.

At 119 percent of planned performance, or $505 million in cash flow, the payout would be $38.1 million, or $4.4 million for the top nine. At 149 percent of planned performance (cash flow of $635 million) for top management and 132 percent ($560 million) for others the top payout would be $42.9 million, or $5.7 million for the top executives.

In 2009, the plan paid $42.1 million for hitting a top target of 200 percent of projected results. Actual operating cash flow in 2009 was $494 million.