If Jose Aldo vs. Conor McGregor ends up being the biggest, or even just one of the biggest money fights in UFC history, it's almost apropos that it happening is the result of a huge gamble.
The entire company was built on high-stakes gambles by Lorenzo and Frank Fertitta, along with Dana White. The gambles started from just buying the company, as well as later decisions made to keep it alive through very lean times. After the company was established as a viable sports franchise in 2005 with its television deal with Spike, and the pay-per-view explosion of 2006, some of the biggest gambles taken have involved matchmaking.