Sounds like Dame is basically giving Olshey an ultimatum.....but it may be too late. There isn't a lot to work with, no Draft picks this year for capital, he doesn't have a single significant contributor from the Draft since 2013 (that is downright brutal), and the cap situation of his own doing is going to make it much more difficult to make moves. He had one of the highest payrolls in the league at one point and nothing to show for it.
GS is/was in Cap hell.....but it was certainly worth it. Portland is in cap hell while being irrelevant.