The 24-year old signed with the Timbers in December but a deal has yet to be finalised due to legal red tape.
Gilbert, who has also played for Cardiff City, Southend United, Leicester City and Peterborough United in England, has a few alcohol-related incidents on his record and it was believed to be too difficult to officially get him onto the club’s playing roster for the 2011 season.
But Timbers owner Merritt Paulson revealed that things had taken a turn for the better and that there was still a chance of adding Gilbert.
“I would have said, ‘No way,’ if you asked me two weeks ago,” Paulson told MLSsoccer.com.
“It’s all coming to a head this week. With this new information, there’s still a chance we get him. But we need validation one way or another on the history, and we take character very seriously.”