Nightshade

Easy to get jeep parts, PITA to find 70+ year old Cadillac engine parts

Bluelight

So will your Cherokee with that load behind it. Brakes on the tow dolly?

Up I-25? I made the round trip from Alaska to Louisiana a few years ago in the late fall. In no rush to see Wyoming again. I did it with a Jeep load of stuff and more stuff in a utility trailer (3000 lb gross). Before the trip I had a brake controller installed in the Jeep and a brakes put on the trailer. Not a huge load, but with some of the mountains along the way, it definitely helped.

andrewmp6

Uhaul rents pickups or you can buy a cheaper 90s f150 or chevy truck and use it to pull the caddy on a car trailer.

salad

An XJ will pull it just fine, but...

1. Sway
2. Braking

XJs are little sheet metal boxes. The heaviest things in them are the engine, transmission, and any humans. They have a comparatively small wheelbase. Once sway starts it takes weight, a good track, and traction to control a load well, three things XJs don't have.

Early XJs have pretty bad brakes. Assuming the hardware is new, the booster is of an old single-diaphragm design that was replaced a few years later. They can barely stop themselves compared to a modern vehicle. Hooking 5000lbs of uncontrolled mass to one is NOT a recipe for a good time.

When my '99 was stock I towed a 6'x12' UHaul trailer with around 1500 lbs of stuff. If I recall correctly the trailer worked out to the 3000-3500 lbs range. I loaded it properly and secured everything inside. Never got any sway and the XJ pulled it fine along the freeway (65 MPH) but with the giant box the Jeep was batted around in the wind pretty easily. Luckily I didn't have to pass anyone so mirrors weren't an issue. When I got to my destination it was raining, suddenly the lane I was in slowed waaaay down and I stood on the brakes. Luckily the surge brake kicked in full-force, but I came very close to slamming some truck in the bumper.

My other close call was with a 5'x9' UHaul cargo trailer. 2000 lbs with 1000 lbs of crap in it. Just a dump run. Going through the city, at what would be about 38 MPH (speed limit 60 KM/H on this one road), came over a small rise and there was a surprise lineup of stopped cars for some reason. I had plenty of notice to stop but the trailer just pushed the XJ. I am very lucky there was a gravel shoulder to the right or I would've been out of a Jeep that day. By the time my XJ stopped I was looking into their rear seat.

That's in my stock 1999 with admittedly "mediocre" brakes (old ceramic friction, but drums adjusted) and the dual-booster diaphragm hauling FAR less than the max rated...

Technically yes the XJ can move that much. However with more weight the risk goes up SUBSTANTIALLY. After towing with an XJ, and then towing with a pickup, I will never tow more than 1500 lbs behind the XJ ever again. It's not safe enough unless you eliminate all other cars.

Fred/N0AZZ

This works fine but I have duel brakes on my race car trailer and a lot more going on in my GC to pull it greater GVWR/4.7HO engine/Towing package. Would not consider doing it the other way around.