Timberwolves: How they could win a Ben Simmons for Damian Lillard trade

Mar 13, 2021; Minneapolis, Minnesota, USA; Portland Trail Blazers guard Damian Lillard (0) shoots between Minnesota Timberwolves center Karl-Anthony Towns (32) and forward Jarred Vanderbilt (8) in the third quarter at Target Center. Mandatory Credit: Bruce Kluckhohn-USA TODAY Sports
Mar 13, 2021; Minneapolis, Minnesota, USA; Portland Trail Blazers guard Damian Lillard (0) shoots between Minnesota Timberwolves center Karl-Anthony Towns (32) and forward Jarred Vanderbilt (8) in the third quarter at Target Center. Mandatory Credit: Bruce Kluckhohn-USA TODAY Sports /
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If you’ve never seen a messy breakup before, chances are you’re about to see one this offseason, and the Minnesota Timberwolves could be the perfect intermediary.

The situations surrounding both Damian Lillard of the Portland Trail Blazers and Ben Simmons of the Philadelphia 76ers are tense, and it looks like things are about to blow off in a big way. Two superstars that, as early as this year for Simmons and two years ago for Lillard, said they were set on staying are now the subject of the biggest trade rumors of the offseason, and two organizations that once stood behind those superstars are now questioning both of their future.

Just a few years ago all seemed right between these two superstars and their organizations. But since then, Portland “mutually agreed” to part ways with Terry Stotts (in a conversation that almost certainly wasn’t started by the coach), who had been Lillard’s head coach for his entire career, then they overlook the two candidates who Lillard has publicly endorsed for a head coaching position in David Vanterpool and Jason Kidd, both of whom were available this offseason for head coaching positions (in fairness, Kidd removed himself from the search).

If Damian Lillard is traded for Ben Simmons, how could the Minnesota Timberwolves facilitate that trade and come away happy?

On the Sixers side, the organization was so high on Simmons that just earlier this year was adamant that Simmons was not being traded. A lot has changed since then, however, and now president of basketball operations Daryl Morey is saying he wants an “All-Star talent” in return for Simmons. After his playoff failures, Sixers head coach Doc Rivers publicly questioned whether or not Simmons can be a starting point guard on a championship contender, and as a result of this fallout, the organization is now openly having trade conversations (Athletic paywall) centering around him.

With all of this coming to a head right before an incredibly shortened NBA offseason, tempers are sure to rise this summer.

From the player’s perspective, though Simmons has remained quiet on the most recent round of trade speculation, Lillard seems to have changed his tone from 2019 when he said he was loyal to Portland. Lillard declared that he thought there was more to the game than championships, but now is openly questioning his future and saying he wants to win a championship, and questioning whether or not that can happen in Portland.

For their part, the organizations of these two stars are likely to take a lesson from history: trade your disgruntled star before things get ugly. The LA Clippers benefited from this when they sent Blake Griffin away in a shocking move, which would set them up to trade for Paul George and Kawhi Leonard in the near future. On the other hand, the Minnesota Timberwolves have shown the league all too well what happens when an organization can’t move a disgruntled star, specifically with the situation that surrounded Jimmy Butler.

But, if these two organizations are going to swap stars, could the Minnesota Timberwolves get in on the deal and help to facilitate? And if so, what could they get out of it?