Bowman's (1980, 1982) widely quoted papers have reported the existence of a risk-return paradox for strategic management. In this paper the authors examine the dynamic behavior of the risk-return relationship and analyze whether the risk-return paradox is stable across time. The analysis involves tracking Bowman's so-called negative association ratio across time. Using accounting measures of risk and return, it is demonstrated that while the paradox holds during the 1970s, the finding does not hold in the environment of the 1960s. Further, the paradox disappears if market-based risk measures are used. Some implications for strategic management are then discussed and attention is directed towards the meaning of risk in the context of strategic management. In addition, possible explanations for this paradox are evaluated and directions for further research are suggested.