Wait what, you could get more for flipping Bozak than you could for trading Glendening. This favours Detroit easily.
In a vacuum yes, Bozak is worth more. But if you take into account bargaining position, then Detroit has no reason to value Bozak in a trade to his fair market value since they can go after him as a UFA and not have to worry about giving up assets to get him.
Conversely, Toronto IS incentivized to value Green/Glendening because they’re both valuable additions to the Leafs’ roster (well, after Plekanec Glendening isn’t AS valuable, but if Bozak goes the other way maybe...) so the Leafs would have to pay FMV to get those assets.
Still, I can’t see Toronto dealing a 1st to make this happen.
Far more likely is they thin the prospect pool and include SJS 2nd.