It's a really tricky situation because if the fan base perceives that the team is waiving the white flag, that's going to drive down ticket sales. As Hurl pointed out that perception is at least as important as the actual W-L record when it comes to impacting revenue. So while a retooling that still has the franchise fielding competitive teams seems like an ideal compromise between the team's need to get younger and what Rogers wants, it's not necessarily going to work out that way. Shapiro could make a perfect Donaldson trade, one that includes a huge return with great future assetts and some controllable pieces that the team can use right away to field a decent team now and the average fan wouldn't care. They would see it as a personnal affront and the Rogers bottom line will feel that.
That being said, the team doesn't have much choice but to make some unpopular decisions at some point. Despite some signs of life lately, the overall picture shows a team that is in a downturn. What Rogers will want if for the team to get back on the upswing as quickly as possible.