June 22, 1918, Alonzo Sergent fell asleep while conducting a train that plowed into another train killing 86 passengers and injuring another 187. 17 days later, July 9, 1918, two passenger trains collided head on in what became known as The Great Train Wreck of 1918, killing 101 people and injuring 171 people. The investigations and analysis of failure in both accidents can be attributed to a single person. During this month, the single person failed to operate the company’s train properly, which lead to a colossal disaster which affected numerous lives, loss of business revenue, loss of credibility, and had a huge social impact. Similar to an analysis of a colossal train wreck, this report focuses on the complexities behind colossal business failures, analyzes the reasons for failure and the role of the CEO, and proposes recommendations that can be used to guard future businesses against colossal failure. / text