If Shepard is traded after 20 games, Udoka will definitely choose between Whitehead and Holiday.

The Rockets are basically certain that Shepard will enter the starting lineup and may give him 20 games. If that doesn't work, the Rockets will make a decisive trade. Udoka should prefer White or Jrue Holiday.

White and Jrue Holiday won a championship together with the Celtics. They are both offensive and defensive guards and are suitable for Udoka's system. Jrue Holiday has publicly expressed his unwillingness to play for the Trail Blazers since the trade. If the Rockets want to trade, they still have a good chance to get him.

The Celtics have sent away Porzingis and Jrue Holiday in order to avoid taxes. If next season starts poorly, they will definitely continue to trade and hoard draft picks to prepare for future reconstruction.

In terms of chips, the Rockets can offer VanVleet and Shepard plus 1-2 first-round picks. The former's contract is more reasonable and only lasts 2 years. The other party can choose flexibly after receiving it; Shepard, as the third overall pick, has great potential and can be cultivated slowly.

If the Rockets acquire White or Jrue Holiday, they will fill VanVleet's vacancy and be free to attack the championship.