I don't know about towed, maybe Ranger SVTs old dually loaded with scrap to the scrap yard. I think total weight on that one was 19,000 lbs.
Pulled=Here's a recent shot out at Lake Travis of a 36,000 lb (empty, but it wasn't) trash truck that buried so deep in the sand, only half the frame was showing from in front of the rear axles back. Snatch block on the Champion Power equipment 10,000 winch, a big rock under the driver's front tire=NO luck! Hook the second trash truck to the rear for an anchor and pick my Ranger up off the ground, while I winched out the other one!! SUCCESS! A guy with a dually drove up right as climbed in the cab and said "want me to get that." Told him just a minute, let me give it a tug. I started winching, my truck came off the ground and the trash truck started moving. He said "never mind, I'm embarrassed and out of here!"
My Brother Steve does some logging and has had me hook to several old oaks or cedars to keep them from falling on a house or shed. Sometimes when I start winching the tree starts moving and I just keep winching till them fall over! The 1st time a tree started moving, he runs up "let me make a cut." I told him "what for, I'll just winch it over." He just shook his head. Then said "well that saved a cut on the chain!"