Hate him or love him, Colby Covington is arguably one of the biggest draws the UFC has on its hand. His trash-talking skills have rubbed more people the wrong way than most people would imagine, leading him to make many enemies on the roster. However, the enmity Covington has with some of the fighters could have made for some of the biggest fights in promotional history, if only Dana White and Co. had not dropped the ball.

Colby Covington is a former interim champion who failed to achieve undisputed status on three different occasions. As he tries to make way for another shot at the title ‘Chaos’ will be taking on up-and-comer Joaquin Buckley in the main event of UFC Tampa. But before we get to that fight this weekend, let’s a look at the time when the UFC missed the boat on some massive Covington fights, starting with Conor McGregor.

Colby Covington wanted to fight Conor McGregor

The first time Colby Covington ever spoke a word about Conor McGregor was back in 2018. ‘The Notorious’ had just been involved in the infamous dolley-throwing incident, which wasn’t the kind of action that the former interim welterweight champion endorsed. In fact, Covington decided to take a jibe at McGregor, while expressing his disdain for the Irishman’s actions.

“If that fugitive [Conor McGregor] is till on the lam when wheels touchdown in JFK I’ll bring in that c-ked-up leprechaun myself,” Colby Covington tweeted six years ago. This comment could have been an attempt to get on Conor McGregor‘s nerves and hopefully earn a chance at a ‘red panty night’ against the former double champion, but the richest MMA fighter in the world didn’t show too much of an interest.

However, Conor McGregor did hint at making a potential return to the welterweight division to fight for the title with a simple tweet: “145. 155. 170.” For many, this message seemed like an expression of his urge to fight for and win a third UFC title, but that never happened. Meanwhile, Colby Covington would rally for a fight against the Irishman, but Dana White didn’t see any point in it since McGregor never spoke about ‘Chaos’. There was always this promotional aspect of the fight with two of the best trash-talking and entertaining fighters at hand, but the UFC didn’t capitalize on it.

The next big fight that the UFC could have made for Colby Covington had a guaranteed heated rivalry written all over it, which was against Dustin Poirier. As we all know, there’s a rich history between the two former teammates.

Colby Covington vs. Dustin Poirier grudge match

Dustin Poirier and Colby Covington were close associates and teammates when they trained together at American Top Team in Florida from 2012 to 2020. While ‘The Diamond’ has continued to train with the Florida-based team, ‘Chaos’ was the one to leave, but he’d later claim that it was Poirier’s fault that he was shown the door by ATT, because of ego issues.

“When we were training together, he was using me everyday just for wrestling. Never wanted to do anything else but just wrestle with me. I was giving him knowledge, giving him information, obviously toying with him like he was an amateur,” Colby Covington told ‘Submission Radio’ in the past. “Eventually his ego got to him. He started winning some fights in the UFC and I was still coming up. I hadn’t had the name that he had yet, so his ego got to him.”

Colby Covington would add that there was a sudden change in Dustin Poirier’s demeanor when he started making the climb in the UFC rankings and claimed that he treated “people like sh*t.” However, he didn’t want any of that attitude, but he would get that anyway when he started his ascent in the UFC welterweight rankings.

“As soon as I started rising up the ranks and I became the top draw in the company, that’s when he got jealous and envious. He just started bad-mouthing me… Telling the old gym owner, ‘Kick Colby out, he’s a meanie head, he said mean words, kick him out.’ So that’s when the beef started,” Colby Covington added. Thereafter, the Clovis native would proceed to call out Poirier after his UFC 272 win, but yet again, his callout didn’t really materialize at all.

Despite the fact that Dustin Poirier is willing to throw down against Colby Covington “on sight,” he doesn’t want anything to do with the welterweight star, advising him to stick to his own weight class. After his UFC 302, however, Poirier hinted at a potential welterweight move and Vicente Luque appeared to be ready to welcome him. But Dana White and Co. still didn’t take any initiative in trying to set up the former interim lightweight and the interim welterweight champions, given how much of a history there is between the two fights.

The last possible big matchup that we could have seen Colby Covington fight was against Khamzat Chimaev, and both of them actually wanted it.

Khamzat Chimaev and Covington wanted to fight each other

One of the most common problems Khamzat Chimaev had during his welterweight run was to find some opponents to fight. He’d claim that nobody wanted a piece of him, not even Colby Covington. In fact, the Chechnyan-born would boldly claim that ‘Chaos’ is actually “scared” of him during an interview last year, that bore the seeds of a beef between the two fighters.

“They called me four times [to fight Covington]. Why it didn’t happen? They wanted it, the UFC wanted it,” Khamzat Chimaev told combat sports journalist Ariel Helwani. “Someone said, ‘No.’ I know it’s not me… He’s too little a boy. He’s scared.” How do you think Colby Covington reacted to these claims from the undefeated 14-0 star? Well, he denied ducking Khamzat Chimaev, of course. And guess what? He also pointed his fingers at Chimaev for the fight falling off while calling ‘Borz’ an unreliable professional.

“They were looking at setting up that fight with that motherf***er Khamzat Chimaev, but he’s unprofessional, he’s a clown,” Colby Covington told ‘Sports Illustrated’. “He’s out there laughing when he’s missing weight by 10 pounds, making a fool of this publicly-traded beautiful company of the UFC, making a fool laughing while you’re ruining their main event pay-per-view. So, he’s not accountable, he’s not someone they can trust in that spotlight.”

Dana White was actually ready this time to book this fight, but it didn’t come to fruition and Khamzat Chimaev ended up moving to the middleweight division. Besides these failed fight plans, do you have any other possible Colby Covington fights in your mind? Let us know in the comments down below.