Simmons Advocates For A Dame-For-Towns Trade Again

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.

Simmons started by discussing Portland GM Joe Cronin’s point of view.

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.