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After the massive integration of distributed energy resources, energy storage systems and the charging stations of electric vehicles, it has become very difficult to implement an efficient grid energy management system regarding the unmanageable behavior of the power flow within the grid, which can cause many critical problems in different grid stages, typically in the substations, such as failures, blackouts, and power transformer explosions. However, the current digital transition toward Energy 4.0 in Smart Grids allows the integration of smart solutions to substations by integrating smart sensors and implementing new control and monitoring techniques. This paper is proposing a hybrid artificial intelligence multilayer for power transformers, integrating different diagnostic algorithms, Health Index, and life-loss estimation approaches. After gathering different datasets, this paper presents an exhaustive algorithm comparative study to select the best fit models. This developed architecture for prognostic (PHM) health management is a hybrid interaction between evolutionary support vector machine, random forest, k-nearest neighbor, and linear regression-based models connected to an online monitoring system of the power transformer; these interactions are calculating the important key performance indicators which are related to alarms and a smart energy management system that gives decisions on the load management, the power factor control, and the maintenance schedule planning. [ABSTRACT FROM AUTHOR]