1. Toronto would be trying to win with Holiday.
The lack of direction surrounding his team has been the main subject of all the fanbase’s ire, as Ujiri has chosen to hold on to expiring contracts and commit to a core that has some genuine flaws rather than rebuild or go all-in for a Lillard-type player. A Holiday trade says very clearly they intend to win.
A starting lineup that features Holiday setting the tone on both ends alongside Pascal Siakam in his prime and Scottie Barnes continuing to get better would be a very difficult mountain to climb for most of the Eastern Conference, especially if Darkp Rajakovic’s scheme clicks.
The Toronto Raptors can contend with Jrue Holiday.
Holiday will play for $34 million next season, and he has a player option worth $37 million the following season. Due to his age, there is a real chance he picks up that option. Doing so gives Toronto a two-year window that could see them make some playoff runs if all their young guns develop well.
The Raptors are not going to be at the front of the pack for Holiday, and they might find it hard to get a deal done with Portland for Holiday after failing to get Lillard, but Ujiir owes it to himself as an executive and the fans to at least call Joe Cronin and see if he wants to talk.