Trouble in Chicago: Tribune, Playboy

Ill winds are blowing in the Windy City. Tribune Co. has hired bankruptcy advisers to help it reckon with the possibility of an imminent default of its debt covenants, although it's uncertain as of now whether the company is actually planning a bankruptcy filing. (The Journal says a filing could come this week; the Times says bringing in advisers could be "a just-in-case move." Oh, yeah, and Mark Cuban, who represents Tribune's best chance at fetching a high price in its auction of the Chicago Cubs*, now has his hands full with insider trading charges. Portfolio.com's take on what it means is here.

Meanwhile, Christie Hefner is stepping down after 20 years as CEO and chairman of Playboy Enterprises. Hefner, daughter of Playboy founder Hugh, makes it sound like reaching the milestone triggered her decision, but it can't be ignored that the iconic men's magazine has been struggling lately: Ad pages are down 5.7 percent for the full year, and in October the company announced plans to cut 55 jobs and leave 25 more unfilled.

*Whoops! As noted on Portfolio.com last week, Cuban's no longer in the running for the Cubs.