In recent years electrification of agricultural machinery vehicles is gaining interest from the manufacturers point of view to meet the emission reduction targets set by several authorities. Some studies have already investigated the topic, however, none of them have dealt with the challenges of agricultural machinery electrification in a general and methodical way. This paper presents a method to evaluate the economic feasibility of tractor powertrain electrification based on life cycle cost analysis. For a parallel hybrid, the best combustion engine downsizing, among some discrete values, was evaluated. The methodology was applied to three case studies with different power levels and operating cycles: a 76 kW orchard tractor, a 175 kW row crop tractor with medium duty use, and a 210 kW row crop tractor with heavy duty use. Fuel and electrical energy consumption were estimated through simulation. A range of powertrain components prices and fuel and electrical energy prices was taken into account, in order to cover price uncertainty and to show its effects. The results show that operating cost savings decrease when more power-intensive operations are performed. Considering a combination of system and energy prices deemed realistic by the authors, the operating cost savings, respectively for orchard, row crop medium duty, and row crop heavy duty, are approximately 8%, 3%, and 0.5%, which result in 6%, 1%, and 0.1% life cycle cost savings. Thus, powertrain electrification of high-power tractors should probably be avoided.