As organizations grow and become multi-national, distributed work, that is, work where members are located in different sites, cities, or countries usually follows (Meyerson, Weick, & Kramer, 1996; Jarvenpaa & Leidner 1999; Zolin & Hinds 2002; Hossain & Wigand 2004; Panteli 2005). Yet such teams and groups have fewer opportunities to build social networks as is common in traditional groups, such as time spent together and frequent informal interaction. The “paradox of trust” in distributed work then, is that while trust is a need-to-have asset for distributed work groups, in particular for knowledge work, it is also difficult to foster due to the lack of physical co-location (Handy, 1995). This chapter argues that one way to deal with the paradox is to recognize the importance of trust as generated through individuals that have trustful ties that cross central boundaries, that is, trust brokers. Based on a relational approach to trust in groups as well as empirical studies of distributed work groups, we argue that trust brokers can help to establish trust quickly and make the group operate in more robust and sustainable ways.