Abstract: This Commentary is part of a dealmaking symposium on the Oracle-PeopleSoft contest from 2003-2004. The facts of the case are described in Millstone & Subramanian (2005). This Commentary examines Oracle's alternatives and PeopleSoft's potential responses in the fall of 2004. I demonstrate that certain defects in the design of PeopleSoft's poison pill made a deliberate pill trigger a plausible course of action for Oracle at this critical juncture. This radical maneuver becomes even more attractive because Oracle had made the negotiated acquisition route extremely expensive for itself by revealing that it had $26 per share in its pocket nine months earlier. Even if Oracle had not actually triggered PeopleSoft's poison pill, threatening this maneuver would have given Oracle bargaining power that it could have used to pay a lower price in its negotiated acquisition. The Commentary closes with implications of this analysis for practitioners, boards of directors, and the Delaware courts.