Multiple primary malignancies (MPM) are an increasing trend seen in oncology due to factors of increased survival time of patients, environmental exposures and hereditary risk factors. The increase of diagnoses is also seen with more screenings as well as longer life expectancies. We present a 70 year old female who initially presented with trouble swallowing. It was revealed she had squamous cell carcinoma (SCC) of her epiglottis. PET scan work up revealed uptake in her left breast. Bilateral mammogram, ultrasound and biopsy revealed her left breast had invasive ductal carcinoma (IDC) and her right had invasive lobular carcinoma (ILC). With her smoking history and strong family history of cancer, she was highly susceptible to developing multiple primary malignancies She did not continue routine health screenings including mammogram and low dose CT chest which may have prevented or discovered her malignancies at an early stage. This is an emphasis on the importance of routine health surveillance and screening especially in the primary care setting.