Don't forget about inflation dudessss
The MSRP of my SPORT 1999 TJ is $35,069.84 adjusted for inflation. The sticker is $23k(with all options added).
Although I would not buy a new JL. I don't think $45k for a new Rubicon is too far off what these used to be. If I was to compare Sport vs Sport I think they would be similar in price but the JL will have better standard and safety features.
I wouldn't buy a new JL but still.... they are similar in price when you compare new vs new prices at time of release.
I am not sure where you are getting this information, but I bought a brand new 2010 sport with some features out the door for 20K in 2010. I promptly sold it a year later because it was the worst car ever. No way a sport was 35K in 1999. Or if that is really the case, they must have known how much of a piece of shit the JK's were.