Mud Sligger, what type of trailer are you pulling? You driving on the hiway? Do you have a trailer brake controller? If the pin weight isn't to heavy the truck will be ok pulling a trailer if you take your time at it (the truck will be slow anyways). 37in tires will kill your transmission regardless.

I own a 2001 5.2 1500 4wd 3.55 (32in tires) trucks as well, it is totally gutless but on flat land I probably could pull a dump trailer with total weight around 6000-8000 lbs, but it will not be fun. Worst thing will be stopping, so crank up the trailer brake response.

I own a 2010 3500 6.7L set-up for pulling trailers and has no issue pulling over 20000lbs

fyi- I hauled 2000 lbs of gravel in the 2001 bed, the truck was dead slow and took forever to stop.

 

With no stickers how would any law enforcement know your legal towing capacity? As long as you are within reason you will be fine, a 5.9 with 3.55 gears is gutless when towing much more than 5K anyway so you probably wouldn't want to go over about 7K.

 

Well I was going to buy a big ol camper trailer but I don’t feel like getting another truck I already got 2, so I’m just going to do my camping the more fun way in tent and a fridge in the truck