The Portland Trail Blazers missed the services of superstar Damian Lillard a ton last season. The speculation was the front would eventually trade all their core pieces and start from scratch with youthful guys like Anfernee Simons and Shaedon Sharpe. However, they did not execute a complete rebuild as it was more of retooling their roster for the last run during the prime years of Lillard.

Portland added Jerami Grant and Gary Payton II in the offseason, which are incredible additions but surprising as well. Grant might have been a rental because he is currently in the final year of his deal and possibly not re-sign with the Blazers, and Payton II has been having trouble staying on the court this season.

Lillard and Simons have been remarkable this year, but the Blazers are in an unenviable position right now which is a franchise that has no chance of winning the championship, but they will likely not receive a top 3 or top 5 picks next year's draft. Their organization is in a dilemma in what to do for their future, but first, these are the guys they must move by February 9th.

Jerami Grant

One could argue that it was a buy-low opportunity for the Blazers to add Jerami Grant because the Detroit Pistons were willing to move him for almost anything because they knew Grant would not return after his contract expires. The Blazers did not need to let go of any of their core pieces to get Grant, but the continuous challenge is for them to retain him because he may tend to choose an organization that will consistently contend for championships.

Grant's salary is close to $21 million, so he will likely demand a multi-year contract, which the Blazers may regret if they reward him with the big. The smarter decision may be moving Grant for any future assets or draft capital because this will open up more minutes for Shaedon Sharpe at the 3 position and also open up more opportunities for youngsters like Nassir Little and Keon Johnson.

Even if the Blazers bolster their roster before the trade deadline and give it one last hurrah with Jerami Grant, they will not even be close to contending with the West powerhouses, so they must maximize the value they can receive from him.

Justise Winslow

Similar to Jerami Grant, Justise Winslow is on an expiring contract and continues to receive sufficient minutes at the 3 and 4 positions. Winslow showed flashes of his potential in his early days with the Miami Heat, but he has lost his rhythm and confidence after incurring a ton of injuries. Winslow was acquired last season in the Norman Powell and Robert Covington trade, but he has been massively disappointing in his tenure with Portland.

The expectation was for Winslow to regain his terrific days with the Heat, but he has been inconsistent with the Blazers. The rationale for moving him even if he does not hold a ton of trade value is to open up more minutes, touches, and opportunities for guys like Sharpe, Little, and Johnson. Head coach Chauncey Billups would give Winslow around 20-30 minutes before he sustained his ankle injury last month, so that would keep their inexperienced guys as relievers of both Grant and Winslow.

It seems the Blazers' front office does not want to execute a full rebuild because they do not want to waste the prime years of Damian Lillard. It is unfortunate for them, but this might be the year wherein they need to revamp their lineup and focus on the draft.