Masai Ujiri, President of the Toronto Raptors, is still reflecting on the departure of players he had a strong connection with, such as Pascal Siakam and Fred VanVleet, among others. Siakam and VanVleet were integral members of the Raptors, with Ujiri sharing a warm bond particularly with Siakam, evident from his emotional reaction when announcing Siakam’s trade to the Indiana Pacers mid-season. However, Siakam wasn’t the only valued player Ujiri bid farewell to, as VanVleet also departed during the off-season to join the Houston Rockets, citing a desire for a change of scenery.

Looking back on the absence of players like Siakam from the team, Ujiri admitted to Raptors analyst Blake Murphy that he may have been a bit unfair to former players and regrets any harshness that may have been perceived. Despite this, Ujiri explained that his approach was fueled by a desire to aggressively push the team to return to their winning ways and maintain the same attitude that led to the Raptors’ 2019 NBA title victory.

However, Ujiri’s efforts to rejuvenate the team ultimately resulted in missing the playoffs in 2021 for the first time since 2013-14. Alongside this disappointment, Ujiri faced the notable losses of two-time NBA All-Star Siakam and Fred VanVleet. During his conversation with Murphy, Ujiri hinted at the importance of identifying future All-Stars in each draft, indicating his ongoing search for players to fill the void left by Siakam’s departure.

Aside from Pascal Siakam and Fred VanVleet, the Toronto Raptors have also seen the departure of other significant players. DeMar DeRozan, a longstanding franchise icon, dedicated nine seasons to the Raptors and played a pivotal role in their success. Notably, he contributed to the team’s record-setting 59-win season in 2018. However, DeRozan was traded to the San Antonio Spurs in exchange for Kawhi Leonard, a move that reshaped the Raptors’ roster. Leonard’s impact was profound, leading the team to their first NBA title in 2019 and earning the Finals MVP title.

Despite their success with Leonard, the Raptors faced another setback when he departed to join the LA Clippers in 2019. Speculation suggests his decision was influenced by a desire to be closer to his hometown of Los Angeles, California. The loss of key players like DeRozan and Leonard was described by Masai Ujiri as challenging and even “unwatchable at times” during his conversation.