The population of the Earth is moving towards urban areas forming smart cities (SCs). Waste management is a component of SCs. We consider a SC which contains a distribution of waste bins and a distribution of waste trucks located in the SC sectors. Bins and trucks are enabled with Internet of Things (IoT) sensors and actuators. Prior approaches focus mainly on the dynamic scheduling and routing issues emerging from IoT-enabled waste management. However, less research has been done in the area of the stochastic reassignment process during the four seasons of the year over a period of two years. In this paper we aim to stochastically reassign trucks to collect waste from bins through time. We treat this problem with a multi-agent system for stochastic analyses.