Bill Simmons had Ryen Russillo on his Monday podcast to go over Summer League happenings and discuss Damian Lillard trades. After talking about Victor Wembanyama’s debut and praising Scoot Henderson, Simmons and Russillo went over potential Lillard trades.
Russillo offered Minnesota as a dark-horse destination.
“If you were Tim Connelly, and you’re running the Timberwolves,” he said. “And you’re like, ‘Alright, we actually can agree with [Joe] Cronin here on a deal.’ KAT’s out, Lillard, and there’s other pieces flying around. Okay, so they’re gonna say yes to this package.
“And granted, Portland’s looking at it like, ‘As soon as he’s traded, we don’t care.’”
“This trade makes the most sense,” Simmons agreed. “I’m with you.”
Russillo continued his thought, laying out the stakes for Connelly.
‘We don’t care if he doesn’t play for you.’ He’s not our problem anymore, and now we have a legitimate scoring big who, again, is not my favorite guy ever. But if you’re looking at floor balance offensively, there’s something there.
Would you, again, if you’re Connelly, go, ‘Alright, he doesn’t want to play here, but I’ll make that deal.’ And bet that you could talk him into that. Would you do that as a GM?
Simmons started by discussing Portland GM Joe Cronin’s point of view.
I think I could because he asked for the trade. You know? And at some point, like that guy, Joe Cronin, this is his one chance to be a GM, right?
We watch TV, or we listen to radio, and there’s former GMs, former executives, they’re on all the time. I don’t want to be one of those guys if I’ve got the Portland job and I’ve got Scoot Henderson. Because I’m like, ‘If I can f–ing figure this out, I’m good. I’m gonna be here for 10-12 years.’
And I would make the trade, and then if he didn’t want to go to Minnesota, Minnesota could figure it out. Minnesota would probably be happy they got rid of Towns anyway, right?
Russillo clarified that he was asking if Connelly would do it.
“I’m not talking about Cronin’s perspective,” he said. “To me, if you get another team that says ‘yes’ to it, and you like the package, then that’s everybody else’s problem. I’m talking about if you’re Minnesota, and you’re picking him up at the airport, alright? And you’re going, ‘Hey, welcome to Minnesota, Damian.’”
“Well, it’s like, ‘Here’s Rudy Gobert. Here’s Anthony Edwards,’” Simmons countered. “You’re saying, if he’s going, ‘I don’t want to be here. Get me out.’”
“His agent is like, ‘I heard the deal, don’t do it. He’s not gonna play there,’ Russillo clarified. “Would you still do the deal?”
“If you’re Minnesota, I think I would,” Simmons concluded. “I’d roll the dice with it because I still feel like I could spin him. First of all, he likes basketball too much. Second of all, I feel like I could spin him in December or January, probably for more than I could have spun Towns for. So I would do it.”
It would be a risky deal for the Timberwolves. Karl-Anthony Towns has stated that he wants to stay in Minnesota, and Lillard’s agents are telling everyone he wants to go to Miami. But an Edwards-Lillard backcourt would be intriguing, and the Wolves are all-in with a deep roster.
Given that Minnesota will never be a free-agent destination, sometimes executives have to take a risk. However, this would be back-to-back years that Connelly made a risky blockbuster trade for a player on the wrong side of 30.
