Jonathan Mogbo was a questionable pick
This wasn't a case of Anthony Bennett going first overall, but it was a reach for our board and most public boards. Jonathan Mogbo was usually mocked in the late 30s or throughout the 40s by most draft experts, and he was certainly ranked well behind prospects such as Filipowski, Kolek or Furphy, all of whom met a need for the Raptors.
It's hard to argue that Mogbo did, even if the Raptors thought more highly of him than most teams and draft analysts. He is an undersized big in the mold of P.J. Tucker or Draymond Green in that he doesn't have the skill to play anywhere but center but is undersized for that position at 6'6". Perhaps his 7'2" wingspan and strength will allow him to play as a smallball 5, but he certainly isn't going to be an obvious fit at the 5.
Kevin O'Connor of The Ringer summed it up well, saying of Mogbo that he "Possesses the size of a forward, the handle of a guard, and the shooting of a throwback center." Mogbo's strengths are as a ball-handler, playmaker and rebounder.
To unlock that skillset he would need to play alongside a big who can both space the court and protect the rim. That's the exact problem that the Raptors are already dealing with, because in many ways Jonathan Mogbo is just a lower-level version of Scottie Barnes himself.
That means in both strengths and weaknesses - Mogbo is a truly terrible shooter with poor touch and has a lot of work to do to even reach passable in that area - Mogbo duplicates the Raptors' best player, so even if he adds the necessary skill to earn a spot on an NBA court, he will be relegated on this team to playing only when Barnes does not.
Perhaps there is a sliver of a path to a different future, to Mogbo developing as a shooter and thriving as a smallball 5 alongside Barnes, but it's a small path. And what is so painful about a Raptors team trying to convince themselves of that path as being worth walking is that the true reason the pick was made doesn't seem to be his skillset or that sliver of upside.
Jonathan Mogbo was Scottie Barnes' childhood friend and the two have stayed close ever since; Barnes was present at Mogbo's draft watch party to celebrate with him when he was drafted. Did he know Mogbo was likely to be drafted by Toronto? Was that something worked out ahead of time as a part of Barnes signing his extension?
Those questions are largely unable to be answered, but it's hard to look at the situation and not think that connection played into it. Sometimes those kinds of connections work; the New York Knicks are thriving by scooping up former Villanova teammates around Jalen Brunson, and the Sacramento Kings re-signed Malik Monk at a discount to play alongside college backcourt partner De'Aaron Fox.
Most often, however, those familial connections cause a team to make a decision they would not otherwise have made. The history of these types of reaches are much more often mistakes justified by making a star happy.
All of this was known at the time of the draft, even if it's become more clear with a few weeks to process. What has happened since is that Kyle Filipowski, the player the Raptors passed on, has been rubbing the front office's nose in their mistake.