1. Lack of direction
Ultimately, every issue the Raptors are facing right now can be traced back to Ujiri and the front office not defining any clear strategy. They haven't done enough to go all-in and try to win, and they have also failed to start a more honest rebuilding effort despite being given multiple attempts to do so.
The Raptors' inability to win close games this year wouldn't be as bad if Rajakovic was brought on to mastermind a rebuild with Barnes at the center. Growing pains would be expected. The team's lack of future draft capital and pending free agents also wouldn't be troubling if the Raptors were competing for a top postseason seed.
The Toronto Raptors need to make some tough choices.
Ujiri will get another chance to take one of the paths at this fork in the road, and the constant influx of logical Siakam trade rumors makes it seem like he is eventually going to be forced to take the second option. Winning would be harder to come by in the near future, but at least they wouldn't be stuck in the middle.
Raptors fans are smart enough to know that being stuck as a perennial play-in team is the worst spot a team could be in. Trading Siakam and turning the page on this era of basketball simply makes the most sense, but it remains to be seen if Ujiri will come to that conclusion.