Anthony Smith is all set to ride into the sunset. The former light heavyweight title challenger will have his retirement fight this Saturday at UFC on ESPN 66 co-main event against a formidable Zhang Mingyang. Smith kicked off his career way back in 2008, mostly fighting in small shows around the Midwest. Since then, he’s seen it all—wins, losses, wars, comebacks. Now, 59 pro MMA fights later, he believes it’s time to close the book. The 36-year-old will look forward to ending his journey with style.

‘Lionheart’ has had his fair share of highlights inside the UFC cage. Ever since he showed up in the Octagon back in 2016, he’s been throwing down with some of the toughest names in the light heavyweight division. He’s given fans a bunch of fights that were just pure scraps. It’s also true that many fights didn’t go his way, but the championship mindset was always there. So, let’s take a look at three moments from his career that’ll remain forever in the promotion’s history.

First-Round KO of Rashad Evans (UFC 225, 2018)

Anthony Smith kicked off his UFC journey as a middleweight. Things looked good at first, but after getting stopped by Thiago Santos at UFC Fight Night 125—thanks to some nasty body kicks and punches—‘Lionheart’ decided he was done with the 185 division. The weight cuts weren’t doing him any favors either. So, he made the move up to light heavyweight, and none other than former champ Rashad Evans welcomed him into a new division.

Rashad was already 38 when he stepped in to face Anthony Smith at UFC 225 in Chicago. ‘Suga’ was on a rough patch too, coming off four straight losses. Meanwhile, the younger Smith was hungry and looking to make a serious statement in his light heavyweight debut. And, he did exactly that! About a minute into the fight, Rashad pressed Smith against the cage, hunting for a takedown. But he forced it a little too much and left himself wide open. Smith timed a clean knee straight to the face, followed by some ground and pound to seal the legend into his record book.

Submission Victory Over Alexander Gustafsson (UFC Fight Night 153, 2019)

This one hit different. By the time Anthony Smith stepped in to face Alexander Gustafsson, he wasn’t just some rising contender anymore—he was a former title challenger. A guy who went five rounds with Jon Jones. He’d already proven he belonged with the best. But this fight? It was another big test. Gustafsson had also pushed ‘Bones’ to the edge back in the day, so the stakes were clear. For the Texas native, it was a chance to show he still had it—and that he was right there, just below the GOAT.

Anthony Smith came out pressuring Gustafsson right from the jump, so much that the Swede couldn’t really push forward at all. Smith landed some nasty leg kicks early, and at one point, Gustafsson was backing up so much it almost looked like he was running. They traded a few shots to close out the first round, but Smith definitely set the tone.

Round two had a similar vibe. ‘Lionheart’ kept walking him down and landed some solid right hands. But near the end, Gustafsson managed to drag him down with a body lock takedown. Smith, though, stayed active off his back, probably eyeing an armbar. By the third, Smith stuffed a takedown, chased Gustafsson to the cage, took his back, and locked in a rear-naked choke. Just like that, another legend was in his win column.

Triangle Choke Submission Against Devin Clark (UFC Fight Night, 2020)

After that Gustafsson win, things didn’t go too great for Anthony Smith. He lost two in a row, and it started to look like he was slipping a bit. Then came Devin Clark, an up-and-comer, making noise in the light heavyweight division that ‘Lionheart’ once did. On top of that, his opponent was on a two-fight winning streak over Dequan Townsend and Alonzo Menifield. The UFC organized a main event bout inside the Apex.

Clark came out swinging wild right from the jump. He pushed Smith up against the cage and went for a clinch, but honestly, it was kind of a sloppy move. That opened the door for ‘Lionheart’ to slam him to the mat from the clinch position. From there, Smith had full control—cool, calm, and dangerous. Clark did manage to scramble on top for a second, but it didn’t last long. Smith locked in a slick triangle, and that was pretty much all she wrote

It’s definitely bittersweet to see a legend like Anthony Smith step away from the sport. But hey, everyone has their own finishing line, and it seems like Smith feels he’s reached his. What about you? What’s your favorite ‘Lionheart’ moment? Drop a comment below.