Kawhi's departure
Kawhi Leonard choosing to remain in Toronto after the 2019 title would have likely resulted in consecutive championships and prevented the franchise's subsequent decline.
Vince's graduation
Vince Carter attending his university graduation on the morning of a crucial Game 7 against Philadelphia remains a polarizing moment in franchise history.
T-Mac stayed
The loss of Tracy McGrady in free agency due to an obscure CBA loophole fundamentally altered the trajectory of the franchise, separating a potential superstar duo of him and Vince Carter.
Giannis miss
The front office's failed attempt to acquire a draft pick to select Giannis Antetokounmpo represents one of the most consequential missed opportunities in organization history.
Draft what-ifs
The franchise experienced several historic draft disappointments, including losing the top pick and failing to select superstars like Allen Iverson, Kobe Bryant, or LeBron James when positioned for them.
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