5 Ben Askren fights that we missed out on in the UFC

The MMA world was rocked yesterday by the news that former ONE FC and Bellator MMA Welterweight champion – and current UFC star – Ben Askren has decided to hang up his gloves, citing a need for a hip replacement as the biggest reason for his decision.

Askren was on a two-fight losing streak in the UFC, but his acquisition in an unprecedented ‘trade’ with ONE FC, with former UFC Flyweight champion Demetrious Johnson going the other way, was still one of the most noteworthy moments in recent MMA history. Who could’ve expected him to have just three fights in the promotion?

The former Olympic freestyle wrestler will leave the MMA world with an impressive record of 19-2, and while he’s seemingly leaving the sport with few regrets, many fans will wonder what could’ve been had Askren entered into the UFC a little earlier.

Due to such a long time competing outside the world’s biggest MMA promotion – practically a decade in fact – MMA fans were robbed of seeing some of the most intriguing fights involving ‘Funky Ben’. Here are 5 potential Ben Askren fights we never got to see.

#1 vs. Georges St-Pierre

Could Askren have outwrestled the great Georges St-Pierre?

When Askren left Bellator MMA as their undefeated Welterweight champion in the summer of 2013, many hardcore fans suggested that the former Olympic freestyle wrestler was the best grappler in the 170lbs division – and even if that wasn’t the case, he was probably the best pure wrestler. Of course, at that time, one man who could’ve disputed both was then-UFC Welterweight champion Georges St-Pierre.

‘GSP’ fought twice in 2013, lastly defeating Johny Hendricks to defend his UFC crown that November, after which he would take a leave of absence from the sport that lasted almost four years. But had the UFC been able to sign Askren when he left Bellator, a fight between the UFC’s champion and the undefeated champion of their biggest rival promotion would’ve been practically impossible to ignore.

How would a fight between the two have gone? Based on the evidence we’ve seen recently, GSP most likely would’ve won in impressive fashion, but it still would’ve been fascinating to see if he could’ve prevented Askren’s takedown, particularly as he’d always proved himself to be a superior MMA wrestler than even great amateur wrestlers like Josh Koscheck and Jon Fitch.

Askren would’ve been the perfect foil for GSP’s white-meat babyface persona too, as his intelligent trash talk would’ve built the fight into one of the biggest challenges in St-Pierre’s career. It’s a massive pity we never got to see it.

#2 vs. Nick Diaz

Could Nick Diaz have stopped Askren's takedown?

Any time Nick Diaz is involved with a fight, it automatically becomes noteworthy, and a fight between the Stockton bad boy and Ben Askren definitely wouldn’t have been the exception to that rule. Can you imagine the kind of trash talk that could’ve occurred between the wise-cracking All-American wrestler in Askren and the marijuana smoking, almost permanently angry Diaz? That alone would’ve made the fight worth booking.

Even more intriguing though would’ve been the clash of styles inside the Octagon. How would Askren – an amateurish striker at best – have dealt with the boxing-heavy, volume-based attack of Diaz on the feet? And on the flip side, could Diaz have ever dealt with Askren’s wrestling, given his penchant for giving up takedowns to hunt for submissions from his back?

Gut feeling tells me Askren likely would’ve won this fight had it taken place; a look at Diaz’s record would tell you that traditionally, he always struggled with fighters who could take him down and keep him there, and despite being submitted by Demian Maia in his final fight, ‘Funky Ben’ was always a tremendous grappler.

Regardless of the result, this one would definitely have been awesome to watch – both in the build and in execution.

#3 vs. Johny Hendricks

Prime Johny Hendricks would've been a fascinating match for Askren

By the time that Askren arrived in the UFC to make his debut in early 2019, former UFC Welterweight champion Johny Hendricks had already retired following a string of terrible showings from 2016 to 2017 that saw him post a record of 1-5. The reasons for his decline are still debatable, but when Askren first left Bellator in 2013, ‘Bigg Rigg’ was a certified monster.

At that stage Hendricks had been destroying everyone in his path – from Carlos Condit and Martin Kampmann to Jon Fitch and Josh Koscheck – as he cut a swathe of violence en route to an eventual Welterweight title shot against Georges St-Pierre. And although Hendricks lost his fight with GSP, he would claim the vacant title with a win over Robbie Lawler in early 2014.

A fight between Askren and Hendricks in 2013 or 2014 – in the prime of Hendricks’ MMA career – would’ve been absolutely fascinating, simply due to the wrestling pedigree of both men. Hendricks had won the NCAA Division I wrestling championship in 2005 and 2006 at 165lbs, while Askren also picked up two NCAA Division I titles at 174lbs in 2006 and 2007.

One can only imagine the kind of grappling exchanges we could’ve seen between the two, and although Hendricks’ powerful striking likely would’ve given him the win, it would’ve been interesting to have seen him against an opponent who could potentially outwrestle him – and so it’s a pity we missed out.

#4 vs. Kamaru Usman

Kamaru Usman is the most dominant Welterweight on the planet

Of all the fights on this list, we were probably closest to seeing this one. Had Askren been able to overcome Jorge Masvidal at UFC 239, rather than being knocked out in five seconds flat, the likelihood is that the UFC would’ve granted him a shot at their current Welterweight kingpin Kamaru Usman. And boy would that have been a fascinating fight.

Usman defeated Tyron Woodley for the title this past March – coincidentally on the same show that Askren made his UFC debut with a win over Robbie Lawler – and currently boasts a record of 15-1. He’s the most feared 170lber on the planet today, purely because thus far into his UFC career, nobody has been able to do a thing to prevent his powerful grappling game from allowing him to dominate inside the Octagon.

But despite showing almost superhuman strength at times, Usman’s record as an amateur wrestler actually pales in comparison to that of Askren; ‘The Nigerian Nightmare’ won an NCAA wrestling championship as a collegiate athlete – but only at the Division II level, whereas Askren won two titles in Division I.

Could Askren have been the one to impose his own wrestling game on Usman? And if that were the case, how would Usman have reacted to being taken down in the Octagon for the first time? We’ll never find out now that Askren has retired, but it’s hard not to wonder what might’ve been had he avoided that flying knee from Masvidal!

#5 vs. Colby Covington

Colby Covington could've turned Askren from a villain into a hero with his trash talk

Throughout his MMA career, Ben Askren’s outspoken demeanor made him a villain in the eyes of most fans, and it seemed like the former Olympian was more than happy to play the role of antagonist, particularly when it came to talking trash on potential foes in the UFC. But if one opponent could’ve turned Askren from villain to hero in the eyes of the fans, it would’ve been the current top contender for the UFC Welterweight title, Colby Covington.

Covington’s polarising trash-talk – braggadocios in the style of Conor McGregor, but with a disturbing undercurrent of quasi-racism and pro-Donald Trump politics – has made him arguably the most hated man in MMA, and in comparison to ‘Chaos’, Askren’s smart mouth would practically have made him seem lovable.

A fight between the two would’ve been fascinating from an in-cage perspective, too; an NCAA Division I All-American, Covington’s amateur wrestling credentials don’t come close to Askren’s on paper, but few fighters have been able to parlay their wrestling game into MMA quite so well as ‘Chaos’, who has been able to essentially outwrestle anyone he’s faced in UFC action thus far.

Could Covington have taken Askren down? Or would he have been forced to use his wrestling in reverse – and looked to use his improving boxing game instead? And what would’ve happened had Askren planted Covington on his back? They’re all fascinating questions, but they’re also ones that won’t ever be answered, sadly.