Background: This paper presents the outcomes of employing the inferiorly based rotated sternocleidomastoid muscle flap in complex tracheal reconstruction/repair scenarios, focusing on the key objectives of ensuring stable airway, functional digestive tract and patient survival. Methods: A retrospective analysis was performed for patients treated at two medical centers (A.O. San Camillo Forlanini, Rome, and A.O.U. Careggi, Florence) from 2011 to 2023, in which the sternocleidomastoid muscle (SCM) flap, detached from the mastoid and basicranium, was rotated on the lower pivot directly onto the repair site and pedicled to the sternal origin to ensure the continuity of the airway. Average postoperative hospital stay, follow-up period and patient survival were analyzed. Follow-up assessments encompassed bronchoscopies and CT scans conducted at intervals of 15 and 28 days, and subsequently at 3 and 9 months. Results: A total of five patients were enrolled in this study. These cases included one patient with anterior tracheal wall lesions with abundant tissue loss, one patient with an anterior wall necrosis due to descending cervical mediastinitis and three patients with extra-long tracheoesophageal fistulas (TEFs) (greater than 4.5 cm or >30% of the total tracheal length). In the case of the direct repair of a TEF with a proximal tracheal stenosis, the sternocleidomastoid muscle was used to reconstruct the tissue deficit caused by extensive loss of substance in the left lateral side of the tracheal wall. In case of repair through exclusion of the TEF, the sternocleidomastoid muscle was interposed between the visceral sutures after exclusion of the TEF by an endomechanical device, in one case even substituting the membranous part of the tracheal wall. Our technique allows rotation on the sternal head of the sternocleidomastoid muscle with the lowest rotation radius, pedicled to the sternal origin, detached from the mastoid process and superior nuchal line, thus providing optimal vascularization from the superior thyroid artery/external carotid artery and accessory vasculature from the suprascapular artery. Patients exhibited uneventful postoperative recovery concerning airway and digestive patency. The mean postoperative hospitalization duration was 41 days. The follow-up assessments were negative for postoperative complications. Conclusions: The use of sternocleidomastoid muscle flap was proposed to ensure repair and protection of the suture margin or to constitute a portion, as a scaffold, of the wall by leveraging the muscle’s vascularization and thickness. This technique may be considered a leading component in managing complex situations in tracheal surgery.