Malignant transformation of wounds is a rare complication that if missed can lead to loss of life or limb. This case report presents a rare invasive variant of squamous cell carcinoma presenting in the setting of a chronic wound complicated by osteomyelitis. This aggressive form of squamous cell carcinoma has a high growth rate and a high propensity for metastasis and recurrence. Early intervention greatly decreases the risk of metastasis and recurrence. We present the systematic evaluation and surgical management of an aggressive primary tumor occurring in the forefoot.