Luke Rockhold will root for Dan Henderson at UFC 204, but wants to settle things with Michael Bisping

Luke Rockhold is in a complicated position when it comes to the middleweight title fight between Dan Henderson and Michael Bisping. He is longtime friends with the 46-year old Henderson, whom he has trained with on multiple occasions at Team Quest in Murrieta, and it’s not lost on him that Henderson could beat Bisping (again) and retire as the UFC’s 185-pound champion.

Then again, he just lost his title to Bisping at UFC 199, and a rubber match with "The Count" is the fight he covets the most. So when it comes to his rooting interest, it’s can’t win…and in some ways, can’t lose.

"I’m on both sides," Rockhold told Ariel Helwani recently during an in-studio appearance on The MMA hour. "I mean, of course I would love to fight Bisping. I would love to beat him.

"It sounds appealing, going out there and getting to finish that one. I put him away fairly easily the first time and I got caught the second time, and so I would love to go solidify who the better fighter is. And so, that would be nice, but I’m not going to hold onto it. I’m not going to hold onto that and make that be my dying desire, to have that fight. I hope Dan goes out there and wins. I’m a friend of Dan’s and I don’t really care if I get that as much. I’d rather have Dan go out there and put him to sleep. It would be sweet both ways."

Rockhold said if he could find the time, he would definitely go out and help Henderson prepare for his title shot, which takes place in Manchester on Oct. 8 as the main event of UFC 204.  Right now Rockhold is dabbling in other interests. Namely, launching his own business (Grapes) and entering into a modeling career.

When asked if he was surprised the UFC would grant Henderson a title shot — out of all the contenders at 185 pounds from Renaldo Souza to Yoel Romero to Chris Weidman to himself — he said he was a little but. Especially with Henderson vowing to retire win or lose.

"Yeah, I guess," he said. "I was surprised, I thought that might deter them from making that choice, but he stood firm to what he was saying and they granted him the shot, so good for Dan."

Another name that the 31-year old Rockhold has long had on his mind and remains there to this day is Anderson Silva, the longtime middleweight kingpin who was on top of the fight game back when Rockhold was the Strikeforce champion.

He said that’s still a fight that interests him, even after his AKA training partner Daniel Cormier won a unanimous decision over Silva at UFC 200.

"It’s a fight I’ve always wanted," he said. "Even at this stage, I think [Silva]’s still kept somewhat relevant in that [Cormier] fight. I still think he proved he’s dangerous. He went in there and hung with DC, hurt DC a little bit in the fight, and DC couldn’t finish him, and that’s the light heavyweight champion right there.

"He had a controversial fight with Bisping, so I go out there and out him away, I think that makes a big statement. And it’s a fight he wanted. He called me out when I was with Strikeforce, and I tried to make it happen but they made me fight Vitor first, and so I got set back from that. Of course Anderson’s not going to be around for much longer, and it’s a fight I’ve always wanted."

Asked if he had made that request known to the UFC, Rockhold said he had.

"I inquired about it, and they have other ideas," he said. "I didn’t hear them say anything back."