Is It Time For A Front Office Shakeup?

After a lackluster off-season from Toronto, is it time to put some pressure on the front office?

You’ve probably heard that insanity is repeating the same mistakes and expecting different results. A saying that is often attributed to genius scientist, Albert Einstein. It wasn’t from Einstein though, but rather a 1981 document published by Narcotics Anonymous. We as a culture like to attribute things to who we deem as geniuses, and that applies to sports executives as well. With a good reputation, lateral moves can be viewed as progressive; good moves, as great. The question now is how we view another attempted move by Masai Ujiri and the Raptors front office. After showing significant interest, trying to hammer out details, and a now deleted tweet from Shams Charania that said the Raptors had won the Damian Lillard sweepstakes – Milwaukee is running on Dame Time. The Raptors have been in this situation repeatedly. 

Masai Ujiri is known as a front office mastermind, savvy businessman and deal negotiator. He cut his teeth as the GM of the Denver Nuggets where he facilitated the Carmelo Anthony trade which ultimately netted Denver Jamal Murray who was an integral part of the Nuggets recent championship run – in addition to a collection of pieces that kept the Nuggets competitive over the years. Masai’s most successful trade to date though, is undoubtedly the Kawhi Leonard deal which led to the first championship in Toronto Raptors franchise history. These two moves went against public opinion at the time, as did drafting Scottie Barnes at fourth overall. The list goes on, but the point is that Ujiri has a sizable treasure chest of great moves as a GM. However, these moves all have one thing in common: they’re years in the past.

The NBA is a what have you done for me lately league, and lately Ujiri has not steered this team in a way that will lead them back to contender status. There have been questionable decisions made for this franchise under Ujiri and while some of these things were ultimately out of their hands, many of them were conscious decisions that will surely have serious ramifications in the near future. For starters, during last year’s trade deadline there were many suitors for Fred VanVleet and OG Anunoby. At the time, Fred VanVleet was an upcoming unrestricted free agent who could simply leave the Raptors for nothing if they didn’t find a deal for him. Instead of dealing him at the trade deadline and getting any sort of value back for him, Ujiri decided to roll the dice and allow him to hit free agency where he promptly joined the Houston Rockets, leaving Toronto with a hole at point guard. He also decided against trading OG Anunoby at the deadline despite Anunoby having the chance to leave for nothing this upcoming offseason, with a heavy dose of reporting indicating Anunoby’s wishes for a different role, and potentially a different team.

The Jakob Poeltl trade was another example of a confusing move.  Masai and company decided to bring back Jakob Poeltl and it cost them Khem Birch, a top-6 protected 2024 first round pick, and two second round picks – one in the 2023 draft and one in the 2025 draft. This package seems innocuous upon first glance, until you see the protections on this 2024 first round pick. That top-6 protection means that in order for them to keep it they would have to be bad enough to get the 6th pick in the draft. In some eyes, this move makes it harder for the Raptors to choose a direction, because you are essentially handicapping your draft capital in a move where you don’t improve astronomically. Additionally, there is now a league climate where most non-superstar trades can net more conservative protections on picks, sometimes even getting firsts to eventually convey into seconds.

Last summer there were two great players available in Kevin Durant and Donovan Mitchell, both of whom Toronto were reportedly interested in and made offers for yet they wound up with neither. Kevin Durant, the All-NBA superstar who is one of the best scorers in NBA history – who would have surely supercharged Toronto’s offense and given necessary aid to Pascal Siakam – was turned down in lieu of keeping Toronto’s assets. For reference, Durant averaged 29 points per game and had a 67 percent true shooting percentage and shot 40 percent from three. Not only would he have made life easier offensively for every member on the Raptors, he would have also catapulted them to contender status. Donovan Mitchell is a similar case as well, a bonafide star who put up averages of 28 points per game with a true shooting percentage of 61 percent and a three point shooting percentage of 38 percent, and one of the most electric pull-up jumpers in basketball. In both of these cases these stars were available and would have provided a major boost to an offense that stagnates at times because of the lack of scoring punch and advantage creation outside of Pascal Siakam.

Masai has garnered a reputation for consistently low balling teams during trade negotiations which has led to Toronto striking out on many stars – we saw this play out once again with Damian Lillard. Toronto reportedly never offered Scottie Barnes which to some degree makes sense, but they also never offered OG Anunoby who Portland has had interest in, in the past and who is also on an expiring deal. Lillard could have not only filled the void left by Fred VanVleet’s departure, but was yet another chance for this team to become a serious contender. Similar to Kevin Durant and Donovan Mitchell, Lillard is a masterful scorer who is quite simply an offensive engine. Lillard averaged 32 points on 64 percent true shooting and shot 37 percent from three. Lillard also averaged 7.3 assists last season, so he also adds an element of high level passing that is more than needed on the Raptors. If OG Anunoby or Scottie Barnes were put in the Lillard package then Toronto would have almost certainly obtained him but once again, the apprehension of the front office held Toronto back from obtaining one of these life-changing players.

Now Toronto heads into the 2023-24 season with so many things up in the air. Pascal Siakam seeks an extension which the Raptors have not given him, and according to Michael Grange of Sportsnet the Raptors are waiting to see how Siakam fits into Darko Rajakovic’s system. You’d be hard pressed to find any organization that would show this level of hesitancy with an All-NBA player, or promote an unforeseen offensive system over them. It’s virtually unprecedented. OG Anunoby who has reportedly been unhappy with the Raptors is scheduled to be a free agent this summer, and Scottie Barnes may be forced into a role he’s not quite ready for. The state of this team surely makes a shakeup in the front office worth considering as the team is seemingly in limbo. It is time for Masai to pick a direction, two timelines on one team never works and if the front office doesn’t realize that soon, then Toronto is in for a painful next few seasons.