Anyone who has watched more than a handful of Trail Blazers games this season can see that the team doesn't get much in the way of production from their bench. The backcourt scoring has been almost non-existent, as the combination of Sasha Pavlovic and Will Barton have produced little offensively. Pavlovic is a defensive-minded player, while Barton has shown almost no discretion with the ball, leading to a lot of ill-advised shots.
Eric Maynor has provided the team with some production behind likely Rookie of the Year Damian Lillard, but will have the chance to test the free agent market after the season. Fellow rookie Victor Claver has shown good basketball instincts and awareness on the defensive end, but his size (6'9"), average lateral quickness and lack of a scorer's mentality make him more of a combo forward than a guard.
While there will be plenty of solid guards on the free agent market, perhaps no player is better suited for the Trail Blazers than O.J. Mayo. Mayo has had a career year with the Mavericks, and will likely opt out of his $4.2 million player option for next year. The Trail Blazers have struggled to find any kind of scoring from their second unit this season, and Mayo is instant-offense off the bench. While he's defensively limited due to being somewhat short for a two-guard (6'4"), he has reasonably good ball-handling, and would allow Lillard to play more off-ball.
With Portland having anywhere between $8-$12 million in cap space this offseason, the team could realistically sign Mayo to a multi-year contract starting at $6 million per season, and still have enough money to either re-sign J.J. Hickson or another center. Whether either party has interest in the other at this time is anyone's guess, but it would be wise of Portland general manager Neil Olshey to put in his due diligence.