Through a comparative analysis of two recent Tanzanian lawsuits concerning pastoralist–farmer disputes over land, this article argues that the judicial system is being employed as a vehicle for legitimizing dispossession. Wealthy elites who find their efforts to acquire vast tracts of land thwarted by protective mechanisms in the Land Act No. 4 of 1999 and Village Land Act No. 5 of 1999 are turning to the courts to get what they want. Having access to deeper pockets and being able to out-lawyer and out-manoeuvre their poorer and often less-educated opponents enables elites (including the government itself) to avail themselves of the judicial system and acquire land through illegitimate means. Yet our analysis also illustrates that Tanzanian courts at times act independently of political influence and secure property rights for at least some of the dispossessed. An unusual mix of conflicting pressures and key personalities in these two cases coalesced to produce unexpected outcomes in favour of the Maasai defendants, whose land and legitimacy were on the line. Winning, however, came at considerable cost.