Abstract.A new species of leafcutter bee, Megachile (Litomegachile) droegei Sheffield & Genaro, new species, is described from Guantanamo Bay, Cuba. Megachile droegei is one of 12 species in this New World subgenus, and is part of the M. brevis species group (with M. brevis Say, M. onobrychidis Cockerell, and M. pseudobrevis Mitchell). This is the first record of the subgenus Litomegachile from the Antilles. A diagnosis for distinguishing this species from other species of Litomegachile, and full descriptions of the female and male with illustrations are provided. In addition, the male of M. pankus Bzdyk is described, and M. cleomis Cockerell is recognized as a valid species (new status) based on 1.45% divergence in COI (cytochrome c oxidase, subunit 1) from M. texana Cresson, and eastern (M. texana) /western (M. cleomis) distributions. Based on morphological data and COI sequence data, four distinct species groups are recognized within Litomegachile. Putative synapomorphies that support the monophyly of these groups are also discussed.