Daimler actually started all this with the Patriot and Compass and watered down Grand Cherokee, as David S reminded me the other day. All that was about increasing volume on the brand that had premium pricing.
I did go back and found that Chrysler’s failure to command premium prices dated back to around 2001, when it took over Plymouth. No surprise there. The USA spec Chrysler Voyager was bad enough but you can't expect Town & Country to be considered a premium vehicle when the base model has the same price and trim as the base Dodge, when the line starts with a stripper PT Cruiser, and so forth. The 2007 Sebring wasn’t too bad for the time but the base models were not luxury by any stretch.