Your post is vague, but I will ASSUME that you are not referring to the trailer safety chains.
In my oh so humble opinion...
ASSUMING all things are equal (same U bolt, same chain & brackets parrallel on trailer frame) Both sides of a WDH should be hooked to an equivalent chain link. Otherwise you risk one bar being tight, the other being a bit loose....which means the tight chain is taking the brunt of the load (maybe exceeding it's limits).
My driveway is less-than-level, and I have to lift the trailer higher in order to get the passenger side on without overly straining myself. Try lifting the nose of the trailer in order to get the high side first....should make the low side real easy to attach.
Check to see if you are aligned to the trailer when hooking up. Having your TV slightly ****-eyed will mean that one bar is being pulled forward, while the other is being pushed backwards. It may not seem like much of a difference, but those chains are under extreme loads. If your brackets are set up in a fashion that the chains are less than verticle (pulling a bit forward or backwards)this could align one chain, while making the other further away. AGAIN...raise trailer high enough to safely attach the tighter of the two, the other one should be easy.
Hope this makes sense....hope it helps.
EDIT: Guess I shouldn't have said ****-eyed. In future post I must remember to use crooked, not stright, bent....or anything besides ****-eyed.
Will it work without the hyphen... cockeyed.
MORE EDIT: IT WORKED. Must have been the hyphen that was being BANNED.