Injectable thermoplastic oligomers represent a promising biomaterial for drug delivery provided they possess a melting point at or very near physiologic temperature, as well as a low melt viscosity. One approach would be to prepare an oligolactone. In this paper, we examine the role of different alcohol initiators used in the ring-opening polymerization of epsilon-caprolactone oligomers on the melting point and melt viscosity of the resultant thermoplastics. We found that the initiator used plays a significant role in the final properties of the final oligomer. For primary alcohols, the longer the chain length of the oligomer the lower its melt viscosity, until a chain length of 8 carbons, after which there was no noticeable effect. There was no significant effect observed of primary initiators on the melting point. The use of secondary alcohols produced oligomers with higher viscosities but with reduced overall crystallinity. The use of an unsaturated alcohol, oleyl alcohol, not only reduced the melting point and overall crystallinity but also reduced the melt viscosity of the oligomer. The oleyl alcohol initiated oligomer appears to be a promising vehicle for localized, sustained drug delivery applications.