No. 2: Josh Okogie
It's time to go even further back in time than college, to when Immanuel Quickley was a member of the 2017 FIBA U19 Basketball World Cup in Egypt. A stacked Canadien roster led by current Toronto teammate RJ Barrett won the gold medal, their first FIBA gold in any event, and the United States and Quickley finished with the bronze after losing to Canada in the semifinals.
One of Quickley's teammates on that team was Josh Okogie, who would go on to play for Georgia Tech and enter the NBA in the 2018 NBA Draft. The Minnesota Timberwolves took Okogie 20th overall, and he has established himself as a tough defender and rebounder with inconsistent offensive ability.
Okogie has spent the last two seasons on the Phoenix Suns and seen inconsistent playing time. Some games he starts and is a crucial part of the rotation, and on other nights the Suns spin the roulette wheel and try someone else at the expense of Okogie's minutes.
The jumpshot is a problem, but it also means he will be available at a discount if he declines his player option and leaves the Suns this summer. The Raptors would offer a lower-stakes environment with a touch more ball movement to allow Okogie to recoup his value, and at the same time play alongside Quickley once more.
A contract at either the veteran's minimum or a touch more to entice him to decline his option for a larger role makes a lot of sense for both Toronto and Okogie.