In the NBA, player movement is at its highest point ever. Remarkable offseason transactions and high-profile free agent additions are customary, causing notable rosters to be reorganized almost every year. Naturally, the League has always been known for its paradigm-shifting trades, and numerous times in the past, the correct decisions made at the appropriate moments have radically altered the trajectory of basketball, for better or ill.

However, what about the deals that were struck out of? What about the behind-closed-door transactions that nearly resulted in one player or another moving to a different location and changing the NBA landscape? What about those who had the opportunity but chose not to? For ardent basketball fans, “what-if” scenarios are a common source of conjecture and conspiracy theories. Each one has a unique explanation for why it almost happened and why it ultimately didn’t.

The Milwaukee Bucks appeared prepared to make huge plays for All-Star player Kyrie Irving as he prepared to leave LeBron James and Cleveland behind. It was widely reported during the 2022 summer that Malcolm Brogdon, Khris Middleton, and a future first-round selection were part in the package that Milwaukee had offered to trade for Kyrie.

Though Kyrie ultimately chose to go to Boston, how could the previous few years in the East have played out if he had joined the Bucks? Despite the rise of Giannis Antetokounmpo and the success of Brogdon and Middleton in Milwaukee, the Bucks have yet to reach the Finals, and Brogdon was ultimately traded. Giannis may have needed Kyrie’s clutch ability and consistent scoring to push his club to new heights. To be honest, Cleveland may have had a little more to work with in 2024 if the Bucks had been traded.