The 2021 NCAA Basketball Tournament and season have come to a close, but a new season always provides new data and new stories to tell about that data. In the 2021 Tournament, one story line was the apparent ease at which No. 2 seed Houston was able to reach the Final Four. The Cougars' path to the final weekend went through a No. 15 seed (Cleveland State), a No. 10 seed (Rutgers), a No. 11 seed (Syracuse), and finally a No. 12 seed (Oregon State). This marked the first time in history that a team had reached the Final Four without facing a single-digit seed. By some measure, this implies that Houston had the easiest path in history to the Final Four. But, for me, this type of discussion always begs the question of how to quantify something like the difficulty of a given NCAA Tournament path. My approach to try to answer this question is to try to define a benchmark or reference team and to then calculate the odds that this hypothetical team would reach the Final Four given any ar...