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#2. Tito Ortiz
Tito Ortiz and Dana White were once close friends—in fact, White was once Ortiz's manager. However, things soon soured between the two men who were, at one point in time, as close as could be.
A feud between the two ensued, leading to a range of antics, such as Ortiz's infamous t-shirt describing Dana White in unflattering terms, before culminating in a boxing match that White agreed to partake in. It wasn't the first time White had been challenged by one of his fighters, but it remains the only time White was not only pleased to accept, but also swore that his prior boxing experience would serve him against Ortiz.
The fight never ended up coming to fruition, yet the feud never quite died down. When Lyoto Machida faced 'The Huntington Beach Bad Boy' at UFC 84, it was revealed that Dana White had offered to pay Machida a bonus if he defeated Ortiz. While Machida dominated most of the bout, he was ensnared in a triangle choke towards the end of the fight.
Fortunately for White, 'The Dragon' prevailed, becoming one of the only fighters known to have been paid a bonus by the UFC president for beating a specific fighter.
#1. Cris Cyborg
Not many fighters are as decorated as Cris Cyborg is in MMA. She has won championships across multiple MMA promotions, including the UFC, Strikeforce, Invicta, and Bellator, where she currently reigns as the featherweight champion.
Prior to signing with the UFC, Cyborg was the subject of several dream match scenarios, with many fans yearning to see her face off against Ronda Rousey. In the years prior to her UFC signing, however, Cyborg was the subject of hateful ridicule from both Rousey and Dana White.
White once infamously described Cyborg as resembling Wanderlei Silva in a dress and heels before mocking her gait by stomping in front of the cameras as he accused her of steroid use.
It was a blow from which there was no return, even when Cyborg signed with the promotion. Ultimately, the Brazilian great suffered a premature end to her UFC run after a devastating loss to Amanda Nunes. In the aftermath of the loss, White questioned Cyborg's desire for a rematch despite the latter's public campaign to fight Nunes again.
It culminated in Cyborg releasing doctored footage of a conversation between her and White, falsely portraying White as confessing to lying about her to the MMA media. It was a damning turn of events that forced Cyborg to issue an apology and led White to terminate her contract, stating that the promotion was no longer in the Cyborg business.
