Former GM Kevin Pritchard commented after he was unceremoniously fired in 2010 that when you're hired by Allen you have a ticking clock dangling from your neck, counting down the minutes. Olshey must hear the tick. He knows the salary and title came with an expiration date, one that feels a couple of cycles away. Olshey's hair isn't built for rain. Also, he knows how this ends.
So the hunch here is that Portland isn't his forever place. And you just can't built winning culture while simultaneously posturing for the rest of the league's owners.