Acquired in 2010 by the Blazers, Wesley Matthews was originally supposed to be a sixth man off the bench. As injuries to Brandon Roy decimated his career, Matthews stepped in as a starter and has never looked back. He is a prototypical 3 & D player. He is limited by his lack of handles, and his lack of quickness compared to other players at his position. Matthews currently plays in one of the weakest positions in the NBA in terms of depth, which makes his abilities more attractive right now.
Wesley Matthews is the best perimeter defender on the Blazers currently, but becomes redundant on the roster when playing next to Batum. Lillard becomes the only ball handler on the floor and gets trapped constantly, because of the lack of respect defenders give Batum and Matthews with the ball in their hands. Matthews deserves to be a starter on this team currently because of the leadership he has and the consistency you get from him.
This season puts Matthews in a unique position. The past few seasons there has been little depth at his position, but this season he has plenty of teammates that can play his position. Matthews may see the biggest reduction in minutes played this season because of the depth at his position. Mo Williams, Lillard, Dorell Wright, and CJ may eat into his minutes which isn't a bad thing, but if CJ proves to be capable at SG for the future Matthews may not see a new contract with the Blazer in 2015.
Furthermore, if any of the young SG's (CJ, Crabbe, Barton) prove to be a capable starter it would make Matthews a good trade asset to have. The Blazers could package a deal of Lopez and Matthews for an upgrade at center if this is the case. The Blazers could also open up cap space by not re-signing him.
Matthews is one of the most well-liked players by the front office, and is a coaches dream because he goes all-out every single game. If he is able to accept a role off the bench on a slightly smaller contract the door for him might be open for him to stay with the Blazers, but it far less likely Matthews would accept that role after starting for several years.
If Matthews was younger, or was able to handle the ball effectively he would have a new contract by 2015. If McCollum turns out to be a bust it would improve Matthew's chances, but if CJ has the ability to start by 2015 then it may be the last time we see Matthews in a Blazer uniform.