#2 Randy Couture
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Randy Couture and Dana White have been through the ups and downs of the business relationship they shared, which ultimately culminated in having a bad personal relationship. There were many factors that led to this beef, many of which are understandable differences while others are rather mundane and even downright silly.
In the early days, Couture was disappointed as many, including Dana White didn't see much potential in him. They undermined his promotion, not seeing him as a viable and marketable personality, something that really hurt Randy's sentiments. The UFC instead chose to promote Pedro Rizzo as the Heavyweight Champion.
Randy took this personally and demolished Rizzo in two back to back fights, claiming to be the rightful face of the company. After his retirement, Couture declined a job offer from Dana White to work for UFC on FOX and called the salary "peanuts", publicly disrespecting White in the process.
While White always claimed that Couture was particularly hard to work with, there are always two sides to a coin and what really happened will probably always remain a mystery.