I think the first significant one would have been D.Johnson after 2015 season. He knew at best he would be a 2nd round pick and go to the G-league. But his family was in such a financial situation that he felt he had to go for it. He wouldn't have gotten rich off NIL, but he would have done well enough that his family wouldn't have been struggling. Then he returns in 15-16 season as the missing piece for that team with 2 AA's at guard (Ulis & Murray), a hard-nosed defender in Briscoe, Poythress playing at 80%, Lee, Willis, Matthews, Hawkins. Maybe Skal doesn't join us knowing DJ is returning, but in retrospect that would have been more than ok (Ulis, Murray, Briscoe, Poythress, Johnson - bench of Lee, Willis, Matthews, Hawkins). Probably takes us from 2nd round loss to E8 or maybe F4. And raises his stock to possibly late first round pick status, while banking a few hundred K w/ NIL.
Then Ulis! He had to leave when he did, while his NBA stock was as high as it was going to ever get. If he waits another year, even playing at same AA level, he probably falls out of 2nd round. But no doubt had he had NIL he would have seen Oscar like NIL $, making as much (or more) in JR & SR years at UK as he did in the NBA total. But...would Fox have came then? Did Monk come because of Fox? So a lot of uncertainty how that would have affected the 16-17 team. Then in 17-18 we had a boat-load of FR, but not top 15 FR except maybe Knox. So maybe we don't get Green, but I could see the rest of those FR coming to join Ulis and Gabriel. Maybe SGA doesn't get the opportunity to emerge as a FR, backing up Ulis & Diallo (or maybe Cal plays him over Diallo at the SG/2 or goes 3G lineup again). Ulis, SGA, Diallo, Knox, PJ w/ bench of Gabriel, Vanderbilt (when healthy), Richards. But that steadying SR pressence may have been just what that team needed to reach a F4.
Then Ulis! He had to leave when he did, while his NBA stock was as high as it was going to ever get. If he waits another year, even playing at same AA level, he probably falls out of 2nd round. But no doubt had he had NIL he would have seen Oscar like NIL $, making as much (or more) in JR & SR years at UK as he did in the NBA total. But...would Fox have came then? Did Monk come because of Fox? So a lot of uncertainty how that would have affected the 16-17 team. Then in 17-18 we had a boat-load of FR, but not top 15 FR except maybe Knox. So maybe we don't get Green, but I could see the rest of those FR coming to join Ulis and Gabriel. Maybe SGA doesn't get the opportunity to emerge as a FR, backing up Ulis & Diallo (or maybe Cal plays him over Diallo at the SG/2 or goes 3G lineup again). Ulis, SGA, Diallo, Knox, PJ w/ bench of Gabriel, Vanderbilt (when healthy), Richards. But that steadying SR pressence may have been just what that team needed to reach a F4.