This essay addresses the carboxylesterase redundancy in the male reproductive tract seemingly conserved across phyla. Evidence is provided which suggests that carboxylesterases are recruited by the male reproductive system in certain animal groups. These provide advantageous metabolic capabilities to sperm protection, sperm maturation, and sperm use. Rather than an archival record of the available data, we seek possible answers to the central question: Why is carboxylesterase over-expression adaptive with the functioning of the male reproductive tract with respect to male fertility? We discuss patterns of carboxylesterase over-expression and accumulation in different compartments of the male reproductive tract. We also provide evidence of how these patterns are associated with a long sperm path to egg through different local effects. The hyper-expression of carboxylesterases can play different physiological roles depending on its localization in the male reproductive system. However, all the "acquired" functions can serve the same purpose; creating conditions which maximize the fertilizing potential of the sperm. To confirm our concept and more clearly illuminate "moonlighting" roles of carboxylesterases in the male reproductive tract, requires a more extensive comparative analysis of a variety of carboxylesterases in a larger number of species.