#3 vs. Johny Hendricks
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.
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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.