Apparently Dame's dream scenario is Draymond signing in Portland. Personally, I think Dray will stay in Golden State (hard to picture him in another jersey), but if Dame succeeds this might be a scenario that works all around.

For Portland, they obviously can't just sign Draymond, they need to do a sign and trade if they want to get Draymond. The obvious man-out is Simons, who is the fourth guard on the roster now (behind Dame, Scoot and Sharpe), and makes $24M.

For Golden State, Simons is a nice piece, but they don't need another guard, as they already have the Splash Brothers, and just acquired CP3. If Dray leaves, they need a defensive wing to make up his defensive impact.

Who has a defensive wing who could make up Dray's defensive impact, along with a serious need for a lead guard? Toronto.

Toronto apparently talked to the Warriors at the deadline about OG, but talks fell apart. Toronto was apparently interested in Kuminga, while the Warriors didn't want to give up Kuminga. In this deal, if Dray is gone anyways, the Warriors are essentially getting OG for just Kuminga (the package at the deadline would have had many other pieces involved). With the Poole trade, and the Wiseman trade, the two-timeline plan is officially out the window. You've gotta maximize Steph's prime, and if Dray is gone, this is about as good a deal as you will find to replace his impact. There is a loss in playmaking by losing Draymond, but the much better floor-spacing of OG makes up for that. OG and Wiggins will make an excellent defensive wing duo.

For Toronto, this is trading from a position of strength in order to address weaknesses, as well as long term cap planning. OG will get much more expensive after this coming season (likely a $30M annual deal if he signs the extension in October). FVV could leave if the Raps get outbid, but, even if he stays, the Raps are short on guard depth. Simons has lead guard potential, as he has shown in games where Dame has been out (27 ppg and 5.7 assists in games Dame missed this past year). He is also a high volume three point shooter who can shoot off the catch or off the bounce. A potential future backcourt of Simons/Gradey Dick could provide the elite spacing that a Barnes/Siakam/Poeltl frontcourt would need. Meanwhile, Kuminga is a very Raptors-y player, with the physical tools Masai loves. He even showed some reasonable three point shooting potential, with 37%, albeit on low volume, last year. Kuminga, Precious, Koloko and Gradey Dick (or GTJ) would give the Raps the potential to develop a pretty good bench mob to address the glaring weakness of their bench last season (especially if OPJ can stay healthy, too).

Also, at the deadline, Masai reportedly wasn't looking to deal OG for future draft picks. He said any deal had to include a high potential young player. This deal is exactly that kind of package, with both Simons and Kuminga arguably fitting that definition. That makes this seem a much more likely package for Masai to accept than one of the random three-late-future-first packages that are frequently thrown out for OG.

So, in the (admittedly unlikely) situation where Draymond decides he wants to leave the Warriors, who says no here?