Purpose: This review aims to highlight key advances in the evolution of tracheostomy and tracheal intubation, and contextualise their impact on survival, ranging from ancient legends such as Alexander the Great to standardised modern critical care. Methodology: A literature review was conducted, summarising the historical development of airway management, with a focus on tracheostomy. Results: The origins of tracheostomy trace back to ancient civilisations, with the earliest depictions found in Greek and Roman texts around 2000 BC. Legend attributes one of the first life-saving tracheal incisions to Alexander the Great, who reportedly used his sword to open a soldier’s airway suffocating from an aspirated bone. In the thirteenth century, tracheostomy was formally condemned as a “semi-slaughter and a scandal of surgery.” During the Renaissance, progress continued when anatomist Andreas Vesalius demonstrated maintenance of animal ventilation through a reed passed into the trachea. Italian physician Antonio Brassavola reintroduced tracheostomy in humans in 1546 by performing the first documented successful tracheostomy. Further surgical accounts by French surgeon Nicholas Habicot in 1620 underscored its controversial use, including for a convicted thief who sought a pre-gallows tracheostomy. The 19th and 20th century ushered in significant technological progress in airway management with the development of laryngoscopy. Direct laryngoscopy was pioneered in 1895 by ENT surgeon Alfred Kirstein. Instrumentation improved in 1943 with the introduction of the Macintosh laryngoscope blade by Sir Robert Macintosh. The procedure’s profound, modern impact was exemplified by physicist Stephen Hawking, whose life was prolonged by decades following a tracheostomy necessitated by pneumonia in 1985. Conclusion: The extensive history of tracheostomy demonstrates the evolution of surgical techniques and reflects its trajectory from a last-resort emergency procedure to precise critical care.