The development of competitive relations in the electricity sector, the increase the number of large-scale systemic accidents in the world that have occurred in market economies, improves the importance of the reliability factor for the electric power system (EPS). In this regard, the tasks of taking into account and analyzing all risks, especially the EPS risk operation due to electrical equipment failures, which currently has a significant level of wear and depletion of resources, are relevant in power industry of Ukraine. To solve these problems, it is necessary to develop models for assessing of technical condition and risk of electrical equipment failures. Equally important are the issues of decision-making on the strategy of operation of defective electrical equipment and emergency risk assessment in the power system when the equipment is disconnected. The conditions of functioning of modern electric power systems are analyzed. The problem of estimating the operation reliability of the power system based on the definition of risk indicators is formulated. The necessity of complex modeling of technical condition and modes of EPS for determination of quantitative indicators of emergency risk of a normal mode of EPS under electric equipment failures is substantiated. A generalized linguistic model is proposed to assess the subjective probability of electrical equipment failure under the presence of a defect. An algorithm of complex modeling of the EPS mode for estimating the emergency risk of the normal mode in case of electrical equipment failures by statistical modeling is proposed. An assessment of the subjective probability of failure of a power transformer actually functioning in the EPS has been performed. A comprehensive modeling of the EPS mode was performed to assess the emergency risk of the normal mode during emergency decommissioning of the power transformer. The advantage of the proposed development is the ability to determine the probability of failure of electrical equipment due to unsatisfactory technical condition based on the use of quality information, to form a priority for decommissioning electrical equipment based on risk indicators in the power system.