The Toronto Raptors’ 2017-18 NBA season came to another disappointing end at the hands of the Cleveland Cavaliers. However, it is a fate that could have potentially been avoided had general manager Masai Ujiri been able to pull off the deal of a lifetime.

Ujiri has long sung the praises of Milwaukee Bucks forward Giannis Antetokounmpo even before he became one of the biggest stars in the NBA. According to ESPN’s Adrian Wojnarowski, Ujiri had attempted to trade up to select Antetokounmpo at the 2013 NBA Draft:

“Masai had a deal in Toronto,” Wojnarowski said Friday. “I remember Masai was working with Oklahoma City on a possible trade. I think Oklahoma was at 10 that year and they took Steven Adams. Ten or 11 or 12, somewhere in there. And once Adams made it to the Thunder, there was no trade. But I think if Adams had gotten taken ahead of them, Oklahoma City may have traded out of there, and Toronto would’ve gotten (Giannis).”

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The NBA is chalk-full of stories like these where a team’s future could have been drastically impacted by the countless scenarios that could have taken place during the draft of free agency. Unfortunately, most of the time they are left with a number of questions beginning with “What if?”

That is certainly the case for the Raptors. Despite all their success in the regular season, Toronto has inevitably fallen victim to small forward LeBron James and the Cleveland Cavaliers. Although it is unclear as to what Ujiri would have had to give up to make the deal, it is safe to say that having a player like Antetokounmpo would have undoubtedly helped alleviate the dominance from James in the Raptors’ favor. Instead, Toronto is now left with more questions than answers despite coming off their best regular season in franchise history.