This tricks people because it doesn't start out in static equilibrium. For it to look like this, the weights would have to be resting on a table to relieve the tension in the rope.
If the man does nothing, the heaviest weight will fall and the lightest will rise. If it's frictionless and he starts pulling, the same thing will happen, only the lengths will lessen.
Could it not be in a meta stable equilibrium like this if the weights were of equal mass? The numbers of the weights are unit-less. We assume they represent the mass, but for all I know the number is the serial number of the weight.
For all we know, it could be in space, they could be heavily magnetized, 100m/s wind, .5 CoF in the pulleys, the rope could stretch, and the system could be traveling near the speed of light.
If the man does nothing, the heaviest weight will fall and the lightest will rise. If it's frictionless and he starts pulling, the same thing will happen, only the lengths will lessen.