James Toney had a disastrous start to his career in the UFC, but it could have gone much worse had he gotten the fight of his choice.
The three-weight champion is a legend in boxing, with James Toney almost winning world title gold after jumping up from Middleweight.
However, in 2010, he swapped the boxing ring for the octagon for a face-off against all-time MMA great Randy Couture, which was a bad move by Toney.
He was destroyed by Couture, who mercifully put him out of his misery with a triangle choke in the third minute of the first round, proving how out of his depth Toney was in the fight.
Couture handily beat Toney in that fight, although the boxer initially wanted to face a much bigger and scarier fighter instead.
James Toney wanted to fight Brock Lesnar instead of Randy Couture
Couture wasn’t Toney’s first choice, as he had three names ahead of the former UFC Champion for his maiden voyage into the octagon.
Toney called out Brock Lesnar before his fight with Couture was booked, and in a later interview with Ariel Helwani, he revealed that Lesnar was his first choice.
However, due to the UFC Heavyweight champion’s battle with diverticulitis, he wanted to fight either Chuck Liddell or Kimbo Slice before settling on the Couture fight.
“I told Dana when I first came to the UFC, I don’t want to fight any of these bums. I want the best.
“I wanted Brock Lesnar. I wanted this man, right here, but he was sick. I didn’t know that.
“So I said, Chuck Liddell. He was sitting there, all scared, nervous. Then, Kimbo Slice, they didn’t want that.”
Toney was one-and-done after the Couture fight, although he almost stepped into the octagon with another UFC legend two years after his debut.
A fight between James Toney and Ken Shamrock was planned, but never happened
Despite the abject failure of his MMA debut, Toney signed up to face Ken Shamrock in what was set to be his second outing in the octagon.
The legends of their respective sports had agreed to a bout in 2011 in a unified rules bout, which was expected to go a similar way to the Couture fight.
However, it was soon delayed to the following year, despite Toney getting in shape for the bout and looking much better in his training.
In late 2011, the event was cancelled altogether for unknown reasons and the bout was never rebooked, either inside the UFC or otherwise.
Shamrock was well past his prime at the time, but would have handily beaten Toney. Thank God he never got the Lesnar fight. It would have been a bloodbath.