Multiple myeloma is associated with a susceptibility to bacterial infections, specifically for encapsulated organisms such as Streptococcus pneumoniae. However, severe bacterial infection as the initial presentation of this disease has been rarely reported. The most common presenting features are anemia, lytic lesions, hypercalcemia, and renal failure. We report two cases of pneumococcal bacteremia as the initial manifestation of an underlying multiple myeloma. The first case is of a 68-year-old woman with pneumococcal pneumonia and bacteremia, presenting with a white blood cell count of 900/microL and mild anemia. Further work-up disclosed monoclonal IgG kappa and 50% plasma cells in bone marrow. Her course was complicated by acute renal failure requiring hemodialysis. The second patient is a 57-year-old man presenting with acute pneumococcal meningitis and bacteremia. Due to prior bacterial epiglottitis, further work-up disclosed IgG lambda monoclonal spike and 40% plasma cells in bone marrow. Both cases responded to antibiotic therapy without complications. These two cases add to the few patients described in the literature with pneumococcemia as the first sign of multiple myeloma. Features that were common in most of these cases, and that should lead to a suspicion of myeloma in an otherwise asymptomatic patient, are S. pneumoniae bacteremia, leukopenia, mild anemia, history of prior bacterial infections, and indirect evidence of a paraproteinemia, such as increased total protein levels with low albumin.