We present a detailed study of the heavy flavor content in the W + jet data sample collected with the CDF detector during the 1992-1995 collider run at Fermilab. Rates of heavy flavor jets, identified via the observation of secondary vertices or semileptonic decays of b and c quarks, are in good agreement with a standard model simulation including production of the top quark. An exception is the number of events in which a single jet has both a secondary vertex and a semileptonic decay tag. In the W + 2,3 jet data, we expect 4.4 +/- 0.6 and we find 13 such events. The kinematic properties of this small sample of events are statistically difficult to reconcile with the simulation of standard model processes.