Lemierre's syndrome (LS) is a rare disease entity, which can be catastrophic if organism-directed treatment is not initiated early. Lemierre's syndrome is frequently caused by Fusobacterium infection which is frequently susceptible to clindamycin. Evidence suggests there is an increase in the incidence of cases of drug resistant Fusobacterium species. Through this case we present a unique case of a 45-year-old Caucasian female with Lemierre's Syndrome due to polymicrobial organisms that were resistant to clindamycin thus developing recurrent infections despite being on antibiotics.