Kentavious Caldwell-Pope, Orlando Magic
The Orlando Magic were one of the most aggressive teams during the offseason as they signed Kentavious Caldwell-Pope away from the Denver Nuggets in free agency. As a move that could perhaps help the Magic take another big step forward in the Eastern Conference, this signing was viewed as a huge win for the team. However, at least through the first quarter-plus of the season, KCP's impact with the Magic has been a bit of a question. KCP is struggling on the offensive end of the floor to find any consistency.
KCP is having one of the least productive seasons of his career thus far, averaging just eight points on 40 percent shooting from the field and 30 percent shooting from 3-point range. I'm not sure we've arrived at the point where the Magic are regretting the signing but if there is any second-guessing, I suppose they could also shop him at the NBA Trade Deadline, Officially, on December 15, KCP becomes trade-eligible for Orlando. I wouldn't be on this possibility but I suppose nothing is off the table.
Chris Paul, San Antonio Spurs
As the San Antonio Spurs looked to build around Victor Wembanyama during the offseason, there were many who were expecting them to make a bold move. While that big splash move never arrived for the Spurs, they did make the underrated move to acquire Chris Paul. As a player who would emerge as a key mentor for this young roster, it's hard to say that there is much regret for San Antonio in this signing. In fact, I'd say that both sides have to be pretty happy with how this has all played out.
The Spurs have continued to look better this season and Paul is having a pretty solid season, averaging 10 points and nine assists per game playing next to Wemby. If the Spurs wanted, though, they would be able to trade Paul pretty soon. As he becomes trade-eligible, it will be interesting to see if there is any movement on that front. San Antonio could look to trade him to a contender if he wanted. Considering he signed just a one-year deal with the Spurs, I suppose that can't completely be counted out as a possibility.