Lillard has all but said he only wants to play for the Heat, and the latest rumors seem to suggest that he would be willing to once again demand a trade if he isn’t sent to Miami. Would Toronto give away all of those assets just to call his bluff and see if he’s serious?
Lillard’s game might age well, but it’s fair to be worried about a 33-year-old guard who has a $121 million contract extension that hasn’t even kicked in yet. The financial flexibility Ujiri loves would be gone, as would large components of Darko Rajakovic’s bench.
Could the Toronto Raptors get burned by Damian Lillard?
Trading for Lillard would also make the future very uncertain for Pascal Siakam and Scottie Barnes. For Siakam, would he be willing to sign a long-term contract with a Raptors team that would likely pencil him in as the second fiddle for the end of his prime?
Barnes will also never be more than a tertiary option with Siakam or a secondary one without him. This marks a sharp philosophical change, as they would need to scrap their plans of a future led by Barnes to make sure that Lillard ends up in charge of this ship.