This study investigated a resurgence of Liothrips oleae Costa (Thysanoptera: Phlaeothripidae), an insect pest of olive crops, in a focal Southern Italian olive-producing area (Calabria Region). The young and adult olive thrips feed on the leaves and fruits of wild and cultivated olive trees, producing distortions, necrosis, and premature dropping of fruit. In our study, organic and integrated olive groves were compared for two years in order to establish the relationship between leaf and fruit damage among olive groves managed under different phytosanitary conditions. Sampling techniques were used in order to collect and count leaves and fruits (on plants and dropped premature drupes) presenting symptoms of thrips’ feeding activity. The impact of the thrips was significant in all orchards, and the estimated damage level on drupes and leaves was higher in organic olive management in each year. A morphological description of the adult females of the species is provided, and the first molecular characterization of the Calabrian olive thrips population was performed by using three different genetic regions (cytochrome c oxidase subunit I (COI), 28S ribosomal subunit (28S), and internal transcribed spacer 2 (ITS2)).