I returned my 2017 Ram Express 6 months early on a buy out.
Let me guess. You got a letter from the dealer saying they were looking for used trucks and your truck was a candidate for a buyout. It's likely you had put on less miles than the lease allowed, making the truck attractive to the dealer's used car lot. Usually this means the dealer intends on buying the vehicle from the bank, in this case Chrysler Finance and resell it.
There was normal wear and tear. I asked the sales rep to take a look at the car and I pointed out one dent in the tailgate that was concerning to me. He said I should be fine. I placed my drivers license over it and my drivers license covered it.
Usually, when you get to about three months left in the lease the bank sends letter explaining what sort of damage may be subject to repair charges. They typically include a template with examples of the sizes of acceptable damages. I've leased many vehicles (nine) over the years and the usual standard for dent damages is an area about the size of a half-dollar. Unless your sales rep is new, he/she should have known this. In any event, the sales rep is not the decision-maker on damages, it is the bank, in your case Chrysler Finance. Also, dealerships typically have designated people that look at the condition of lease return vehicles and don't leave it up to the sales rep. Not only that, the dealership is not the final authority on this, the leasing bank is the final authority.
When I've reached a lease end the bank sends out a representative from a company not associated with the bank, that is in the business of assessing damages to leased vehicles. They spend about half an hour inspecting the vehicle, taking pictures, measuring tire tread depth, driving the vehicle, etc. Then you get a written statement of their findings. The ONLY time I did not go through this process was the one time I did an early return, buy out type of deal.
I went home with my new 2019 Warlock. Today Chrysler Financial sent certified mail a bill for $687 and cited 2 dents no scratch and one dent with scratch. I was told if I stuck with a new Chrysler I was going to be alright and they usually don't bill for minor things if you stick with them. I have 7 days to dispute and 10 days to send in a new estimate from another repair shop. I don't even have the car and live 60 miles away from the dealership. What would you do if this were you?
I would start with Chrysler Finance. Tell them you turned the lease in early to the dealership and the dealership said there would be no damage charges incurred to you since you were writing a new lease with Chrysler Finance. I would also mention that you never received the lease end information kit regarding damages from them since it was an early lease return. The only thing you knew about damages was what the sales rep at the dealer was telling you and the rep assured you there would be no damages assessed.
I would also complain to the dealership's new car manager. Don't bother talking to anyone below this level. Play dumb, maybe hint that you are looking to turn in your vehicle and have questions about dent damages. Ask them if there is anyone qualified at the dealership to assess damages or if someone at the bank needs to look at it. Once you get an answer you can decide how to proceed. If he says only the bank can decide this then you can tell your story about how you did a new deal with his dealership based on the sales rep being the person claiming there would be no damage. If the sales manager says he is qualified to assess damages then you can say that only the sales rep looked at your vehicle and based on his recommendations you proceeded to do a deal on a new lease.
The best outcome would be for the dealer to pay Chrysler Finances for the damages to your old truck. That should be your negotiating stance. The dealership misrepresented the severity of the damages and you were stuck with the consequences. Meanwhile, the dealership wrote a lease deal based on the misinformation.
Finally, if possible, I'd find out what happened to your truck. I bet the dealership bought your old truck from Chrysler Finance and resold it, without fixing the damages. If that is the case, why were you charged for the damages?