.....theoretically,is an equality relation,if we have in mind a closed loop of an one only mass,or the complete trajectory,inside the gravitational field,between two levels.
As you know,the course of reasoning,is decided by the energy conservation law,in a potential field/gravity.
The positive work causes a mass to accelerate,to speed up.
The negative work causes a mass to decelerate,to slow down,to put the brakes on.
When we play a binary,two coupled masses (the classical first class lever/unequal arms,equally masses),this unapplies question "case" (yet!),and maybe more,as a practical subject to trial (especially !),can have a diverse ourcome...
We have a single assumption,premise : "H">>>"h"
-"h" is the arm's difference (and the up- path of the negative work).
- "H+h" is the free fall height of the positive torque difference.
All the best! / Alex