Masai in the last 3-4 years has been average. He’s made some questionable trades+Transactions:

Jakob Poeltl from San Antonio for Khem Birch, 2024 1st rd, 2023 2nd rd and 2025 2nd rd pick.

Jakob Poeltl signed 4yr-$78 million contract

Thaddeus Young+Drew Eubanks from San Antonio for Goran Dragic+2022 1rd Draft Pick

Goran Dragic+Precious Achiuwa for Kyle Lowry

Otto Porter Jr signed 2 yr-$16 million contract

Not trading Fred Vanvleet in 2022-2023

Not trading Pascal Siakam

Masai seems to over-value some of his key players. Masai seems to get a reputation across the league that no other executives would like to deal with him due to the fact that they’re never serious during trade negotiations.

We’ll see how the Pascal Siakam situation plays out but if he walks out during free agency and the Raptors lose out by not trading him than maybe it’s time we fire both Masai and Bobby Webster and look to hire another exec with a new perspective.