Timberwolves who may not last the entire 2023-24 season in Minnesota

Shake Milton

While this name may be a bit more of a surprise for this list, Shake Milton could end up being another victim of the Timberwolves’ deep guard rotation. If Minnesota ends up bringing back Jaylen Nowell for their 15th roster spot, he could be in direct competition for minutes with Milton.

There is certainly a lot of potential for Shake to be a major contributor for this team not only as an off-ball shooter, but as a playmaker as well. His skills will give him the chance to crack Head Coach Chris Finch’s rotation early on.

But there is also the chance that the Timberwolves could sell high on him if he plays well to begin the year. A rejuvenated Shake Milton could be an attractive piece on the trade market come January, and Minnesota would be wise to cash in on him for an upgrade if they get the chance.

With Tim Connelly’s history of ambitious moves, it would not be out of the question to trade Milton before year’s end at all. The reality is that there are several players on the Wolves’ roster with more job security, and that factor alone could lead to Shake’s departure sooner rather than later.