Milwaukee Bucks: Trading Giannis Antetokounmpo
To be perfectly honest, the Milwaukee Bucks are in a very difficult position heading into the NBA offseason. Without a clear pathway toward retooling the roster around Giannis Antetokounmpo, it's going to be increasingly difficult for this team to reemerge next season as a contender in the Eastern Conference. Because of that, it would make sense for the Bucks to explore Giannis' trade market.
At the same time, if the Bucks were to trade Giannis, it would effectively set the franchise back years. It would effectively send the Bucks back into a rebuilding phase and complicate their future much more beyond Giannis. But, again, the Bucks may not be able to field a competitive group around Giannis if they keep him. It's a situation no other team desires to be in.
Minnesota Timberwolves: Re-signing Julius Randle
Even though the Minnesota Timberwolves didn't enter the postseason with much expectation, they have effectively made another deep run. The Wolves find themselves back in the Western Conference Finals for the second straight season. Anthony Edwards is the superstar for the team that often gets all the credit, but the Wolves wouldn't be in the conference finals without their strong supporting cast.
One part of that strong supporting cast is Julius Randle. Even though he's played a big role for the team, I also don't believe the Wolves should make the mistake of re-signing him to a long-term extension. With all due respect to Randle, he's not a player who is going to help this team make a championship jump, especially if he's getting paid top money, which he'll probably be seeking when he hits free agency.