Damian Lillard – Portland Trail Blazers

Damian Lillard has stated numerous times that he is not going to be leaving Portland and that he is there to stay long-term, but the Trail Blazers are currently facing what could be a long rebuilding process. 

At 31-years-old, Damian Lillard needs to be thinking big picture, and should the Blazers fail to add other high-level talents around him heading into next season, the All-Star point guard could have second thoughts about staying with the Trail Blazers. 

Jumping from Portland to New York is pretty much a lateral move for Lillard looking at how both teams are constructed right now, but playing for a big market team is definitely something that would be appealing to Damian Lillard near the end of his career. 

Not to mention, the Knicks are not far off from being a true threat. They were just the 4-seed in the Eastern Conference a season ago and they do have key pieces in play in Julius Randle, R.J. Barrett, and others in Alec Burks, Evan Fournier, and Derrick Rose. 

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This team is just one superstar talent away from taking the next step and cementing themselves as a true contender in the Eastern Conference, which is why Damian Lillard could view New York as a potential destination for him if he was to request a trade.