Seeing that a tender offer ezpires today with consideration in a range of $27-31/bond for the 6.25% Seniors and a bit less for the ones in the 4% range, I'd say that CC is saying "take the gift or chase us (unsuccessfully) in b/k court".
The fact that the company has committed $100 million to purchase debt at a steep discount is a positive and not a sign of bankruptcy. They may be able to eliminate $350-400 million of debt in this fashion which will reduce future debt service and improve the balance sheet. Companies planning bankruptcy hoard cash so they can operate post petition.
Keep telling yourself that as CCMO goes b/k and you're still waiting to get 100/bond. Tribune did the same thing a few months ago and what is the headline for this week: Tribune may file for b/k. Watch and learn. A true tender would be 100/bond + early redemption premium not a dutch auction for 27 cents (or 21 cents for the 4+%) on the dollar.