Many measures have been taken to counter recidivism into gang criminality, amongst other the efforts to prevent arrested gang members to return to their gangs after imprisonment. Whereas the conditions for successful intervention may be hard to unravel, this article will claim that some efforts may be destined to failure by default, because they do not adequately address issues of social identity as a central part of the problem, e.g. replacing one identity with another when leaving one community to establish a meaningful life in another. This article presents some views on social identity from the standpoint of pragmatism and demonstrates how their application on recidivism into gang-related crime reveals problematic issues for social work. To that end, this article takes departure in outlaw-biker communities as illustrative example and make use of two interviews with former presidents of a well-known club.