Ujiri wants to play the patient, see-what-I-have card. If he thinks he is not getting decent offers for his players currently, there is little risk in holding on to them. If they play well, perhaps their value goes up. And they might win some games, which Raptors fans have heard great things about.
But to pretend there is no risk here is to cover your eyes and ignore the lessons of the past. If the Raptors head into training camp with this roster, a slight improvement from last year’s 34-48 record is perhaps the most likely result. And if the team ultimately decides it wants to “suck to be good,” as Maple Leaf Sports and Entertainment president Tim Leiweke delicately termed it, any early success would run counter to such a philosophy. (Especially since Andrew Wiggins wants to be a Raptor!) Toronto has lost out on some draft slots by winning meaningless games at the end of the season, and a decent start could be the difference between the 11th pick and the fourth pick, which matters quite a bit.
There is a risk of failure with Ujiri’s chosen path, because there is a risk of failure with all paths. By limiting himself to minor moves and preaching patience, the Raptors GM is not putting himself on the spot in the same way he would if he dismantled the roster Bryan Colangelo gave him or significantly added to it. He is betting that some of those pieces, such as Gay and Lowry, will produce either more wins or trade pieces in the future than they would at this point. But even if he is right, he is still opening himself up to risk. In the asset-obsessed NBA, there is always a potential loss lurking; there are no true win-win situations.