Companies can sell subsidiaries in which they have a very low basis through tax-efficient transactions like Reverse Morris Trusts and tax free spins to shareholders, but they usually involve the parent company or its shareholders receiving stock consideration. There are some debt + derivative trades that can allow for tax-efficient monetizations, but it is unlikely you could do it with an asset like this. Since it seems that the Trib needs/prefers cash consideration, I highly doubt they can find a way to make this a tax-efficient sale. The only thing I can think of is doing some kind of securitization of revenue streams or licensing fees as part of the deal. That could be a possibility. You're smarter than me.
Don't. We are still paying the guy. So if we sign him, we don't have to pay anything extra? The money "paid" to him for this stint will just come out of whatever it is we're already paying him? Hmmm............