In 2011, realizing it desperately needed to offer a competitive product to Airbus’ A320neo, Boeing embarked on a project to upgrade its legendary 737 aircraft to match the A320neo’s efficiency. Limited by the constraints of the 737’s original design and their desire to minimize training needed by pilots to fly the new aircraft, Boeing made multiple critical compromises in the aircraft’s design. 346 deaths and $87 billion later, we have all been reminded of the importance of rigorous design processes and the need to engineer systems for the realities of the end users and their environment. This talk dives into the motivations for the design compromises, the human factors considerations that were disregarded, and how a Fortune 100 company’s prioritization of profit over good design practice led to its stunning fall from grace.