I feel that when it comes to Chrysler, this forum has regulars that try far too hard to go back to the glory days of the K-Car and 300M, and FWD platforms and stuff.
I think they could try making another attempt at the "Bentley for the middle class" like the 2005 300c was. If there's one thing we still really need right now with EVs, it's distinctive looking ones. Everyone's trying to make a pseudo Model S, or add too much tacky black plastic, or trying way too hard with the aero look.
At the end of the day, Bentley and RR have not given up on upright grilles and tall body panels. I think they could get pretty far with design language like the Flying Spur or Bentayga or the RR Ghost. Heck, when you look at the front end of the Ghost, it kinda looks like they copied Chrysler - it even has the C -shaped DRLs lol.
That, and a kickass RWD convertible like the Dawn would be worth it.
I think people still want large, comfy cars that can scoot. It's just that with so much focus on aerodynamics and stuff, cars have gotten too confined. We have a Cadillac at home and driving that isn't as comfortable as the 300 it replaced - the windshield is way too close! I can see why people would buy an Escalade.
I think the biggest thing holding Chrysler as a brand back, is the presence of Alfa Romeo and Maserati. Like, FCA wouldn't let Chrysler sell a luxury car because Maserati is supposed to be the luxury brand. But I don't think either of those brands would be able to pull off what Chrysler still can.
The funny part is, if they didn't want to commit to EVs and a new platform just yet, they still have a hell of an engine portfolio! You could do a very minor refresh on the 300c, give it a new interior and that giant screen the ram has, and stuff the hellcat V8 under the hood and some new tech and you've got a pretty solid contender.