Let's start with this: it's rarely a good idea to sell a valuable asset at its lowest value.
If the Toronto Raptors do decide to move on from Pascal Siakam this offseason it'll be on the heels of a tumultuous 2020-21 season as the 27-year-old recovers from labrum surgery that has jeopardized his start of 2021-22 season. Right away, that's not usually a recipe for success when dealing with a former All-NBA caliber player who at the very least has shown he can be the No. 2 player on a very deep championship team.
All that being said, an offer from the Golden State Warriors involving the No. 7 pick, James Wiseman, presumably Andrew Wiggins, and potentially the 14th pick is certainly nothing to scoff at and, according to The Athletic's John Hollinger, something like that may be available for the Raptors if they're willing to move their star forward.
The report from Hollinger raises plenty of questions that Bobby Webster and presumably Masai Ujiri will have to answer.
1. Has Pascal Siakam hit a wall? Is he regressing?
The past 15 months have not been particularly kind to Siakam. After a stellar start to the 2019-20 season, his post-COVID-19 hiatus in the NBA Bubble was disappointing and he struggled as the Raptors' top dog in the playoffs. There was hope that whatever was ailing him was just a minor hiccup, but 2020-21 didn't go entirely as planned either. His scoring dropped to 21.4 points per game on 29.7% three-point shooting and his defense didn't recover to his Most Improved Player season level.
On the other hand, his playmaking was much improved this past season and at times he certainly appeared to get back into a groove attacking downhill and scoring inside the arc. While he's unlikely to ever be a No. 1 in the NBA, All-Star caliber players aren't all that easy to find and Siakam is certainly that kind of player. It's too early to say he's regressing and Toronto might prefer to hold onto Siakam at least until he shows he can put all his skills back together again.
2. Is James Wiseman a bust?
Writing off last season's second-overall pick at 20 years old seems a little premature, especially considering centers usually take a little bit longer to develop compared to their guard counterparts. While he was certainly disappointing this past season, with the right developmental program around him there's still plenty of upside in the 7-foot, 240-pound big man.
3. How valuable is the 7th pick?
By all accounts, the 2021 NBA Draft has a clear top 4 with Cade Cunningham, Evan Mobley, Jalen Green, and Jalen Suggs leading the way. While those four are going to attract a lot of attention, the next group of players is pretty impressive too. It's a list that includes Jonathan Kuminga, Scottie Barnes, Keon Johnson, Josh Giddey, James Bouknight, and Davion Mitchell. These players all have some glaring holes in their game, be it size, shooting ability, athleticism, or rawness, but they all have enough upside to at least pique Toronto's interest.
4. Can the Raptors win now?
Last season didn't really seem like a fair indicator of just how talented this Raptors roster is. Playing at home, without COVID-19 issues, Toronto certainly has enough talent to be an Eastern Conference playoff team and probably a pretty good one. If they can bring back Kyle Lowry, Gary Trent Jr., and Khem Birch next year, they'll have a pretty solid core once you slide in the fourth pick in the draft. It might not have NBA Finals potential, but with some development from Aunoby, Trent, Siakam, and the draft pick, there's enough upside to get close to Eastern Conference contention.
That being said, a healthy Brooklyn Nets team is going to be tough to compete with, the Boston Celtics should be back in contention with a few tweaks, the Miami Heat aren't going away next year, neither are the Milwaukee Bucks or Philadelphia 76ers, and all of the sudden the Atlanta Hawks are among the Eastern Conference's elite teams. Moving Siakam for younger assets would allow Toronto to rebuild on the fly and build around Trent, Anunoby, Malachi Flynn, the fourth pick, the seventh pick, and Wiseman, all with Fred VanVleet leading the way. That's a core group that with the right development shouldn't take too long to be back in Eastern Conference contention.
5. Is it worth it?
Considering Raptors' track record of luring All-Star caliber players to Toronto, moving one they already have isn't an easy decision. It would take a lot to pry Siakam loose, but if Golden State is truly willing to move a bunch of future assets for Siakam, it's a conversation the Raptors should at the very least listen to.