Getting worse isn't pain-free. It alienates a fan base that can only take so much, especially when there is nothing close to a guarantee that said losing would net Canadian proto-legend Andrew Wiggins. It can build bad habits among unmotivated players. It can cause friction between the coaching staff and management, which is why Casey wisely stays out of the entire discussion.
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Ujiri understands the downsides of tanking, a strategy he explicitly avoided in guiding Denver through the post–Carmelo Anthony world. "You play ball to win," Ujiri told Grantland. "It's difficult to teach winning by losing. There is value in winning. If it comes to a point where you feel like the team is not what you felt it was, then I think you can react. But I think the team will dictate where we go."
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Several teams, including the Rockets most recently, have shown that careful asset accumulation can serve as an alternate road map to a franchise-level star.
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Winning a title in the NBA generally requires a top-10 or top-15 overall player...The best way to acquire such a player is to draft him, and the best way to do that is to pick at or near the top of the right draft. That's why teams still tank today. Tanking doesn't always work, but for a certain species of team and ownership group, it can be the quickest and easiest way to transform a franchise. That's why Toronto thought about it, and why it might do so again if this run turns out to be fool's gold.