According to a report from the New York Times' Marc Stein, Drake is planning to put together his own personal and independent recruiting pitch to try and convince Leonard to stay with the Raptors.
3. The Raptors haven't backed off one centimeter and Drake is said to be mounting his own recruiting campaign on top of whatever the freshly minted champions are doing to convince him to stay— Marc Stein (@TheSteinLine) July 2, 2019
Much like the rest of Leonard's free agency process, there aren't many details to work with in terms of what Drake is planning. But knowing how much he loves the Raptors and putting on a show, he'll likely spare no expense to try and convince Leonard to remain in Canada. Also, per Stein, this will be separate from whatever the Raptors themselves are planning.
It seems a bit unlikely that Leonard, a notoriously simple and private person, would be swayed by Drake's opulence, but it probably can't hurt. At worst, putting together this pitch will make Drake feel important, which, to be honest, is also an important factor to consider here.
To this point, it seems like no one really has any idea which team Leonard will decide to play for. He's set to meet with the Raptors this week, as well as the two Los Angeles teams, the Lakers and Clippers. All three teams have the cap space and can make a case that Leonard's presence would put them at the front of the NBA championship discussion for 2019-20. Regardless of where he decides to play, his decision will shape the future of the league.