I dont see a problem, just make sure you have a long enogh chain because once you tighten that chain his lift will give him a slight leverage on you. Second just do this 4x4 low 1or 2nd gear, hold the brakes and spool up a little, once he brakes loose his tires trying to get you to move, let off the break and take him for a ride!
Hey, safety first... put a towel over that chain/rope in case it does snap.
Now, you should drag him around like a ragdoll.
Like Ryan said, longer chain should be a bit better. You'll be pulling his rear end down, effectively giving him traction. Likewise, I suppose he'll be pulling your rear end up, limiting your traction.
It's all about weight and traction to win these things. Do what Ryan said about letting him break traction first and you'll win hands down.
I don't know your mods in terms of lift and/or tires but you should beat him pretty easily. You have tons more power than he does.
It's all going to come down to traction. OR who breaks something first. I'm with the rest, I don't know what tires you have.
Personally, I think people are giving you the win a little too easy, unless they know what tires you have and I don't.
If you are doing this off-road, either in mud, dirt, or grass, if you have some stock-*** street tires he's going to drag you around. Pavement would be a different story, but even then, if his tires are gripping and yours aren't, nothing else matters.
You have the weight advantage, that's a big part of it, also, but I think the proper tires for a specific application is more important (unless you are talking about 5,000 pounds vs 50,000 pounds).
Also, like mentioned, don't use a short rope. If he's a lot higher than you, you'll be pulling his tires down and he'll be pulling your tires up.
Chevy 1500? It it one of those 88 and up "rail dragger" style trucks? If he still has stock axles, he'll break something for sure before he even moves you. A 1/2 ton with 38s... some peoples kids especially if he still has the IFS front end on it. If he is running the set up I think he has, he will be leaving broken driveline components on the pavement. When are these Chevy boys gonna learn
u should be able to beat him. i hooked up to my buddy in his 91 chebby scotsdale 2500 on 33's. i was in my Powerstroke"details in sig" i did have a 4x4 fourwheeler in my bed but i did beat him when he was in 2wd and 4 wd. my 75 highboy had a harder time pulling him around and thats on 39's.
just wait till he spins and you will get him.