The Eocene tectonic evolution of the easternmost Caribbean Plate (CP) boundary, i.e. the Lesser Antilles subduction zone (LASZ), is debated. Recents works shed light on a peculiar period of tectonic duality in the arc/back-arc regions. A compressional-to-transpressional regime occurred in the north, while rifting and seafloor spreading occurred in Grenada basin to the south. The mechanism for this strong spatial variation and its evolution through time has yet to be established. Here, using 3-D subduction mechanical models, we evaluate whether the change in the trench-curvature radius at the northeast corner of the CP could have modulated the duality. We assume asymmetrical CP boundaries at the north (from east to west: oblique subduction to strike-slip) and at the south (subduction-transform edge propagator-like behavior). Regardless of the imposed trench curvature, the southern half of our modeled CP undergoes a NW-to-W-oriented extension due to the tendency of the southernmost part of the South-America oceanic slab to rollback. In contrast, the tectonic regime in the northeast corner of the CP depends on the trench-curvature radius. A low radius promotes transtension-to-transpression, with a NE-oriented compressive component of the principal stress. A high radius largely reduces the compressive component and promotes an extensional regime similar to that in the south. We thus propose that an initially low-curvature radius of the NE-LASZ triggered the tectonic N-S duality in the Eocene and led to an ephemeral period of transpression/compression at the north. However, an additional mechanism might have been required to locally enhance compression.