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Retiring in the world of the UFC is always a tricky thing to time. While some fighters choose to walk away at the perfect time, many others end up completely mistiming their decision.
Over the years, we’ve seen numerous fighters in the UFC either hang on for far too long, or seemingly step away far too early.
Sometimes, these fighters could’ve gone onto far more success had they stuck around, while others ended up damaging their legacy by fighting when they had no business doing so.
Here are five of the most badly timed retirements in UFC history.
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#5. Donald ‘Cowboy’ Cerrone – former UFC lightweight contender
Donald ‘Cowboy’ Cerrone is undoubtedly one of the most popular UFC fighters of recent years. In fact, there’s probably an argument to suggest that he ought to be inducted into the promotion’s Hall of Fame in the near future.
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However, it’s also inarguable that the former lightweight title challenger mistimed his retirement by leaving it a little too late to hang up his gloves.
More to the point, not only did he only choose to walk away after failing to win any of his last seven bouts inside the octagon, but his final appearance came on the preliminary card of a major pay-per-view, something that would’ve been unheard of a couple of years ago given his status as a big star.
To be fair to ‘Cowboy’, he did take his final bout with Jim Miller on late notice, but the promotion could easily have moved the clash to the main card of the event when another big fight, Miesha Tate vs. Lauren Murphy, fell through.
However, Cerrone vs. Miller remained on the preliminary card, meaning that what should’ve been a major retirement ended up flying under the radar somewhat.
The truth is that ‘Cowboy’ probably should’ve stepped away after his 2020 loss to Conor McGregor in what was the highest-profile bout of his career. By choosing to stick around, his retirement ended up lacking the impact it should’ve had.
#4. Zabit Magomedsharipov – former UFC featherweight contender
For every fighter in the UFC who seems to stick around longer than they ought to, there’s another who seems to retire a little too soon. One such example from recent times is former featherweight contender Zabit Magomedsharipov.
The Dagestani burst onto the scene in 2017 and quickly reeled off four impressive wins in the octagon, winning three of the bouts via submission. From there, it didn’t take long for him to break into the featherweight rankings, as he defeated Jeremy Stephens before overcoming Calvin Kattar in his first headline bout.
However, from there, things turned disastrous for the featherweight contender, just as he appeared to be on the cusp of genuine title contention.
After seeing a fight with Yair Rodriguez fall through due to an injury to ‘El Pantera’, Magomedsharipov practically dropped off the face of the Earth and was eventually removed from the rankings in April 2021, when it was revealed that he was suffering with multiple health issues.
Despite his coach suggesting he’d be ready to return in 2022, the Dagestani then announced his official retirement last month, writing on Instagram that while he was recovered from his issues, he just didn’t feel the same way about fighting.
While it’s probably harsh to completely slate his decision, it’s probably fair to suggest that it was also somewhat mistimed, as had Magomedsharipov stuck around, particularly with current featherweight champ Alexander Volkanovski cleaning the division out, he’d have almost certainly been granted a title shot at some stage.
But ultimately, if a fighter's heart isn't in it, it's perhaps best to step away.
#3. B.J. Penn – former UFC lightweight and welterweight champion
Former UFC lightweight and welterweight champion B.J. Penn is undoubtedly a legend of MMA, and it should come as no surprise that he’s part of the promotion’s Hall of Fame, having been inducted in the summer of 2015.
However, it’s also fair to say that ‘The Prodigy’ stuck around for far too long in the end. His eventual retirement, which was in fact forced, was woefully mistimed compared to the way that his career should probably have ended.
Penn first decided to walk away from MMA following his loss to Nick Diaz in 2011. While the decision seemed somewhat rushed at the time, in hindsight it was probably the right call for the Hawaiian to make.
Even then, had he remained on the shelf following ill-advised comeback losses to Rory MacDonald and Frankie Edgar, his legacy probably would’ve been firmly intact.
Unfortunately, Penn returned for a third time in 2017 and promptly went on a horrible slide, losing his final four fights in the octagon to end his UFC run with seven straight defeats. Worse still, outside of Yair Rodriguez, his last few losses weren’t even against elite-level opponents.
Incredibly, were it not for the intervention of the promotion, who cut him from the roster in 2019 after his ongoing legal issues outside the octagon, ‘The Prodigy’ may well have continued to taint his legacy further.
As it was, though, his retirement essentially slipped by unnoticed, something that would’ve been unthinkable at one time.
#2. Georges St-Pierre – former UFC welterweight & middleweight champion
When legendary former UFC welterweight and middleweight champion Georges St-Pierre retired for good after claiming the 185lb title from Michael Bisping in 2017, few fans could’ve argued with his decision.
After all, GSP signed off on the back of a ridiculous 13-fight win streak dating back to 2007 and had basically accomplished everything he’d ever dreamed of. In fact, he’s still widely recognized as the greatest fighter in UFC history today.
However, there is an argument to suggest that St-Pierre’s first retirement, which came in 2013 following his welterweight title defense against Johny Hendricks, was somewhat mistimed.
The Canadian cited burnout as the major reason for hanging up his gloves, but he also had a number of issues with the UFC, most notably the holes that he felt existed in the promotion’s drug testing program.
However, given Hendricks’ sudden slide following his title challenge, it seems unlikely that he would’ve overcome GSP in the rematch that Dana White wanted to book in 2014. More to the point, less than two years after St-Pierre walked away, the promotion decided to bring in far more stringent drug testing with their USADA program.
With that considered, there’s every chance that had he stuck around and perhaps taken a little longer away after the Hendricks bout to deal with his burnout, he could’ve put together even more title defenses, breaking the UFC’s record of 11 in the process.
#1. Khabib Nurmagomedov – former UFC lightweight champion
Okay, so on the one hand, Khabib Nurmagomedov arguably retired at the perfect time. He always intended to walk away from the UFC at the top of his game rather than tainting his legacy, and after promising his mother that he’d hang up his gloves after his October 2020 bout with Justin Gaethje, he did just that – and appears to be sticking to that promise.
However, it’s hard for fans not to have a nagging feeling that ‘The Eagle’ could’ve achieved even more had he continued to fight for just a little longer. With that in mind, it’s definitely fair to suggest his retirement was mistimed.
After all, for all of his greatness – few fighters retire from the UFC undefeated, let alone with 29 victories to their name – Khabib only defended his lightweight title successfully on three occasions.
While those wins were undoubtedly three huge ones – his victory over Conor McGregor famously setting the UFC’s pay-per-view buyrate record – in comparison to the likes of Anderson Silva, Demetrious Johnson and Georges St-Pierre, his record is lacking somewhat.
More importantly, it wasn’t like the Dagestani was slowing down, either. He appeared to be at the top of his game against Gaethje and it’s hard to imagine that he’d have lost to someone like Charles Oliveira or Michael Chandler had he continued to fight.
With that in mind, then, particularly when you consider his final bout did not come in front of a capacity crowd thanks to the COVID-19 pandemic, it could definitely be argued that Khabib mistimed his retirement, and should’ve stayed around for at least a few more fights.
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