More likely to leave - Monte Morris
The Timberwolves have enjoyed extremely solid point guard play in their starting lineup ever since the trade for Mike Conley back in February 2023. Previously, D'Angelo Russell was a touch inconsistent with his performance, and Minnesota was happy to gain an older and more steady veteran presence in Conley.
Mike's play has undoubtedly elevated this roster's ceiling, but the issue of needing another high-level scoring threat alongside Anthony Edwards still remains. Conley's catch-and-shoot ability is still great, but he is not able to create off the bounce consistently. At the deadline this past season, the Wolves opted to make a play for a backup point guard, and they ended up with Monte Morris.
Ultimately, Morris was solid but was never really a difference-maker for Minnesota in the regular season or the playoffs. The Timberwolves still need that extra scoring threat to come off the bench, and Monte is more of a game manager than a "go get it yourself" scorer. His salary this past season was around $9 million, similar to what the Wolves were paying Kyle Anderson. For that price and considering his productivity, it feels more likely the team will move on and find a cheaper option.