In captivity, intact male horses, due to their sexual drive, are usually socially isolated from other horses. This lifestyle strongly contrasts with that experienced by horses living in free-roaming, feral, or semi-feral conditions, where adult stallions have several roles in their social group, with successful reproduction being their primary drive. Reproductive skew in wild populations is high; many stallions will fail to reproduce at all, while others achieve high levels of reproductive success, siring a large number of foals. Successful stallions are those with particular characteristics and abilities that facilitate harem formation and tenure, allowing them to successfully take over a harem or establish a new one, protect mares from rival stallions, employ appropriate social behaviour to maintain group cohesion, and avoid kin-mating, for example through kin recognition mechanisms. Whilst the life of free-living stallions is far from stress-free, they retain ancestral adaptations to selection pressures (such as predation and competition) exhibited by their natural environment over thousands of years. Here, we discuss the challenges faced by free-living horse stallions, the roles they play in social groups, and their resulting social needs. By understanding these pressures and how stallions react to them, we highlighted the importance of the social environment for the stallion. It is hoped that a better understanding of wild stallions’ lives will lead to their needs being more clearly met in captivity, reducing stereotypical behaviour and improving welfare.