Tracheal tumors remain one of the most interesting and challenging respiratory tumors. Usually, with the more invasive histologic subtypes, cancer has already invaded surrounding structures at the time of diagnosis. We present an unusual case of primary tracheal squamous cell carcinoma with an extensive mucosal spread at the time of diagnosis without any invasion of surrounding organs or distant metastasis. We discuss the unique features and our treatment approach to this unusual presentation. We also discuss the various epidemiologic, diagnostic and treatment aspects of upper airways tumors of the hypopharynx, larynx, and trachea that can help patients achieve more favorable outcomes.