Many Raptors fans know this story all too well by now: a disgruntled star asks for a trade to a specific team, and then reports start flooding in that Toronto is trying to swoop in with all its young assets and steal said superstar, despite the player having no interest in heading north of the border.

Just go back to last season when The Raptors were deep in discussions to acquire Kevin Durant after he asked out of Brooklyn, who eventually ended up forcing his way to the team he actually wanted to go too.

It’s certainly a risky game, gunning for players who are totally disinterested in playing for your franchise that is, but can you blame them? After all, it worked out pretty well in 2019 when they went all in for Kawhi Leonard and ended up with a title.

But this Damian Lillard situation is a little bit different.

First of all, this isn’t the stacked Raptors team from 2019 coming off a 59 win season with a bench that ran 11 deep.  tLeonard was shoe-horned into a perfect win-now situation.  This current iteration on the other hand has major question marks in terms of their depth, not to mention they’re coming off of a .500 season in which they missed the playoffs.

If they were to bring in Lillard, it's a fair question of whether or not it would even be enough to move them into serious contention.  Lillarts is also a 32 year old point guard who has never made an NBA finals, and has a checkered injury history.

Then there's the very real question of whether or not he would actually show up.  He’s made it clear in the media that he doesn’t intend too if a trade were to go through.  Here’s the thing though, he’s under contract for the next three years, so he wouldn't really have a choice unless he decided to just sit out and forgo three years at the end of his prime not to mention over 140 million dollars in salary. A move that would be hard to fathom under any circumstances.  Maybe that fact is the reason why Masai Ujiri doesn’t seem deterred by his disinterest.

Now, Lillard does remain one of the premiere scorers in the game.  Last year he averaged 32 points per game, and is the most lethal 3 point shooter in the league besides Steph Curry, an area the Raptors desperately lack in.  Plus, his sup-par defense would be masked on a roster with Scottie Barnes, Pascal Siakam and Jacob Poetle (Assuming OG Anunoby would be included as the centerpiece of the trade.

It would certainly be a gamble to bring Lillard in, one that the Raptors might be better off letting go, and waiting until the next star asks for a trade (Giannis, maybe?)

But with Masai Ujiri at the helm, you just never know what’s next