I'm nearly 40. This is the earliest Chrysler I remember.
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I had no idea when the 300 came out that it was trying to evoke the 50's 300 and wasn't a baby Bentley.
The 300 I remembered looked like this and it was owned by my girlfriend's grandmother.
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The Chrysler I pined for growing up was a 95 New Yorker even then they were primarily sold to people in their 60's and 70's. Most people who aren't enthusiasts that I ask about Chrysler know its Michael Scotts car from the Office. Why did he have a Sebring? Because the joke was the flawed character with his limited budget would think it was a fancy car and a good deal.
Being nearly 40, I'm likely already outside of the primary demographic these companies are aiming for so in a way, yep its a clean sheet. The Pacifica is actually doing a decent job keeping the limited reputation decent. Everyone I know who's seen and touched one admits its very nice, but "they don't like minivans". If they can keep that formula in the Airflow or some sort of EV wagon or car and fast, they could pull it off. But they have to beat all the other auto makers to market with good quality product.
Dodge's reputation is starting to suffer from cool brand to bad credit specials for guys who need attention. Dodge is going to have to evolve too if wants to survive as well. What kept it well rounded and ground ironically enough was the Caravan, Journey, and Dart. IMO Dodge can have both in the EV space. You can make a round of EV's (cars and CUV's and even a minivan) optimized for performance with muscular styling (Dual Motors), Chrysler with the same platforms with softer styling, optimized for EV and PHEV range (Single Motors), and let Jeep be Jeep. Small, Medium and large trail runners.