Raptors: 3 offseason regrets Toronto is currently having

The Toronto Raptors might be in the middle of their longest sustained streak of quality basketball in 2020-21, but that doesn’t change the fact that they are still a fringe playoff team at this juncture, with the unusual 2020 offseason really doing a number on how Masai Ujiri was able to build this team in free agency.

The Raptors had to let some key contributors go in free agency, all the while trying and failing to potentially add another star to complement the dynamic inside-out duo of Pascal Siakam and Kyle Lowry. Failures in the summer and fall are biting Toronto in the butt during the season.

Losing players like Serge Ibaka and Marc Gasol, drafting players nearly a year after some of them last played a game, and watching their Eastern Conference rivals all strengthen around them has proven to be a lethal concoction for the Raptors.

If Ujiri and Bobby Webster were given one more crack at the offseason, they would almost assuredly do some things differently, as having a better offseason could’ve prevented Toronto from starting the season off so poorly.

These are the 3 biggest regrets the Toronto Raptors are having right now

Toronto Raptors offseason regret No. 1: Failing to sign a veteran point guard

The Raptors were put in a bit of a bind, as Fred VanVleet’s play and new four-year contract meant that he couldn’t be the proverbial Robin off of the bench to Kyle Lowry’s Batman. Instead, the Raptors assumed that rotation Lowry and VanVleet in different lineup combinations while using a first-round pick on a developmental guard like Malachi Flynn could solve their issues.

Unfortunately, it was Flynn who has destroyed this arrangement, having been sent to the G League after really struggling on the offensive end. Considering how guards like Theo Maledon and Desmond Bane, both of whom went after Flynn, are starring, Toronto has to be concerned about their future.

Several veterans that can provide leadership, defense, and incisive passing changed hands in the offseason, so the Raptors can’t say that a lack of supply led to their demand going unfulfilled. Lowry is getting a little long in the tooth, and having someone behind him Nick Nurse could trust to eat up minutes at PG would’ve helped matters.

Instead, the Raptors are twisting in the wind after Flynn proved to be rawer than anticipated. Adding a George Hill or Jeff Teague via free agency or a trade could’ve solved this issue.