Since its enactment in AD 313, the Edict of Milan (sometimes referred to as ‘the Edict of Toleration’), an edict that freed Christianity from empire-wide persecution, Constantine’s declaration has received a significant amount of attention within Christendom. Most of the discussion has centered on Constantine’s conversion, the precursor to the actual edict (whether the conversion was real or insincere, as some have suggested), with many suggesting that Constantine was acting more as a politician than a Christian. While this line of inquiry is legitimate, perhaps a better approach to the question may be more helpful to present-day Christians. That is, while it is logical to deduce that every prudent politician will ignore the largest religious movement in his/her time at his/her own peril, Christians of every age will be better served if they critically evaluate their reception of each and every major policy that is clearly aimed at their benefit. With this background, this paper will attempt to critically examine the reception of Constantine’s edict by the Church in the years immediately following its enactment. Two early exhibits will be brought to bear here: the Donatist controversy and the Arian controversy. In so doing, the thesis that while Christians had every reason to celebrate the enactment of the edict, down the road, an uncritical adoption of the emperor’s policies and favors towards the church opened a door for an unhealthy marriage between earthly powers and the church that proved detrimental in the ensuing years, will be defended. As such, the Church’s reception of the Edict of Milan continues to be a lesson to Christians of every age in their relationship with the political leadership of their time.