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Anthony Smith’s greatest UFC win came over Jon Jones’ ‘toughest challenge yet’

Fresh off five rounds with Jon Jones, Anthony Smith captured the highlight of his UFC career in 2019.

Last weekend, the 60-fight MMA veteran marked the end of his run in the Octagon, deciding to retire in the co-main event of UFC Kansas City.

There, Smith unfortunately went out on his shield, suffering a bloody TKO loss to Mingyang Zhang, a Chinese finisher who’s shooting straight for the top of the light heavyweight division.

Smith’s retirement fight came with mixed reactions. The UFC world paid tribute to Smith with a retirement video while others like Dillon Danis and Conor McGregor seemingly kicked him while he was down

The 35-year-old may not have had a hall of fame worthy career in the UFC but he did have his moments, including back-to-back wins over former UFC Champions and a perennial contender who pushed Jon Jones to the absolute brink.

Just three months removed from his title fight loss to Jon Jones at UFC 235, a fight he could’ve won by disqualification but opted not to, ‘Lionheart’ found himself in another main event, this time in enemy territory.

UFC Fight Night: Gustafsson v Smith
Photo by Jeff Bottari/Zuffa LLC/Zuffa LLC via Getty Images

Anthony Smith retired Alexander Gustafsson in their first fight post Jon Jones

In June 2019, Smith was booked against former UFC title challenger Alexander Gustafsson in his backyard of Stockholm, Sweden.

Gustafsson is most famous for his five-round war with Jon Jones back in 2013 in a title fight many believe the Swede had won on points in the first 3 rounds.

However the judges didn’t see it that way, scoring the fight in favor of Jones, despite Gustafsson’s lead in the strike count.

Gustafsson was 32 years old at the time, the #2 light heavyweight in the world coming off a loss to Jones in their long-awaited rematch at UFC 232 several months prior. In the opposite corner, Smith entered the fight as a 2-to-1 underdog, applying forward pressure right away on Gustafsson. 

UFC Fight Night: Gustafsson v Smith
Photo by Jeff Bottari/Zuffa LLC/Zuffa LLC via Getty Images

Across three rounds, Smith was able to tag Gustafsson with shots and even broke his hand in the process. Gustafsson had his moments as well on the feet, fighting a decent third round.

However, the tide quickly turned in the championship rounds. A little more than a minute into round 4, Smith took Gustafsson down to the ground, masterfully grabbing ahold of his back. 

Landing damaging elbows from the top, Smith flattened Gustafsson out before locking in a rear-naked choke. In 7 seconds time, Gustafsson tapped out, suffering his second submission loss in the Octagon.

Gustafsson threw down his gloves post-fight, signifying what would be a short-lived MMA retirement as the Swede came back a year later.

Alexander Gustafsson gave Jon Jones a run for his money in 2013

Gustafsson may not have been a former champion on Smith’s resume such as Mauricio ‘Shogun’ Rua or Rashad Evans, but the 32-year-old had only lost to Jon Jones, Daniel Cormier, Phil Davis and the late Anthony ‘Rumble’ Johnson at that point.

Gustafsson was the first-ever fighter to take down Jon Jones in the UFC and defended 10 out of 11 takedowns from his greatest rival, making Smith’s finish on the ground all the more impressive.

‘The Mauler’ also drew first blood against Jones in their first title fight at UFC 165, outlanding him in total head strikes.

Jones found his footing in the championship rounds, nearly finishing Gustafsson with spinning elbows in round 4 and having him on the ropes in round 5.

Despite his best efforts, Gustafsson lost in a controversial split decision with one judge scoring the fight 4 rounds to 1 for Jones.

UFC commentator Mike Goldberg, who has called much of Jones’ career, says Gustafsson was Jon Jones ‘toughest test yet’ – a feat that may still hold up today as the world awaits the UFC Heavyweight Champion’s title unification with interim champion Tom Aspinall.

Only a few fighters have come close to dethroning Jones over the years such as Vitor Belfort, Thiago Santos and Dominick Reyes