Now up against the 2nd apron of the NBA luxury tax, Minnesota’s expected to mostly run it back from here. But that doesn’t mean Tim Connelly isn’t moving in the shadows down at Mayo Clinic Square. If the Wolves president of basketball operations does have an offseason trick up his sleeve, what could it be?

Well just in case you hadn’t heard, there is a new point guard on the market, after 7x All-NBA point guard Damian Lillard was released Tuesday by the Milwaukee Bucks, a move that cost them over $100 million in salary cap penalties over the next handful of years. And now, one NBA team’s sunken cost will become another team’s dirt cheap treasure.

Could Minnesota Timberwolves be a favorite to land Damian Lillard?

At some point soon, Lillard will sign a minimum contract with his next NBA team, an imminent reality that has driven national NBA talk shows all day. Which brings us to Wednesday’s episode of NBA Today on ESPN, where league insider Marc J. Spears prepared a list of top landing spots for Dame. And at number one… were your Minnesota Timberwolves.

Where could Dame go next? #nba #nbatoday pic.twitter.com/3B9AOJsRK5

— Marc J. Spears (@MarcJSpears) July 2, 2025

“Number one is the Minnesota Timberwolves. They would be an amazing pick. With all due respect to Michael Conley, if they brought [Lillard] in running point next to Ant, imagine the shooting in that backcourt, imagine the boost Minnesota would get. Imagine Mike coming in behind him…He and Ant-Man have a relationship.”

Michael J. Spears – NBA Today (ESPN)

The other panelists on NBA Today erupted in surprise and excitement over Spears’ No. 1 landing spot for Dame. Brian Windhorst seemed to be in utter disbelief, admitting “that’s something I hadn’t considered”. In 2024-25, Lillard averaged 24.9 points, 7.1 assists and 4.7 rebounds per game (58 games).

Is this Damian Lillard’s best moment as a Buck?
pic.twitter.com/CtqkFnmAhl

— Bucks Lead (@BucksLead) July 2, 2025

Does Lillard to the Wolves make any realistic sense?

Let’s be honest, Damien Lillard would be a really good fit for the Minnesota Timberwolves, in a lot of ways. They need point guard help and they have no money to buy any. When healthy, Dame is one of the best point guards in the league, even at 34-years-old, and now he basically comes free.

Of course, there’s one major issue with signing Lillard. He isn’t expected to play at all in 2025-26, after suffering a torn achilles tendon during the Bucks’ latest playoff run. So whoever signs him will have to wait a full season before seeing him take the floor in his new uniform.

Related: Minnesota Timberwolves Hang Onto Popular Coach

By then, Rob Dillingham will be in year three of his rookie contract and Mike Conley may very well be out. In all reality, going from Conley to Lillard would be a nice little veteran PG upgrade, even if Dilly has taken the next step in his development by then.

Alright Minnesota Timberwolves fans. We need to sit down and chat some things out. I know we’re desperate to see our favorite NBA franchise climb its way back into a playoff conversation. Hopes are as high as they’ve been in this basketball town since the Jimmy Butler era was still on the upswing and everyone who’s still paying attention wants to start seeing their time, money and decade+ of disappointment finally payoff.

But trading away everything you’ve built for a proven NBA star isn’t always the best way out of a hole and that’s a road we’ve already traveled, as Wolves fans. Yes this is a much different situation than what we encountered with Jimmy Butler, but let’s be honest, that’s not the only transaction that’s gone sideways for this franchise.

But on Sunday, SKOR North and Ch. 5 insider, Darren Wolfson, reported the Wolves as very interested in Ben Simmons, which would certainly stand as the next franchise altering move to reshape this organization. How much does Gersson Rosas want Simmons? “Badly”, according to the source who texted Wolfson.

Remember, Simmons is available because he’s being driven out of Philadelphia by a fanbase (and some inside the organization) that’s sick of watching him melt down in the playoffs.

How badly do the #Timberwolves want to trade for Ben Simmons?

“Badly” pic.twitter.com/owYhhydPMQ

— SKOR North (@SKORNorth) June 27, 2021

Ben Simmons in the playoffs

How bad is Ben Simmons in the playoffs? Well, he’s a primary ball handler who can’t shoot. That includes free throws. Simmons was so afraid of throwing the ball toward the rim by the end of the 2021 playoffs that he hoisted just 45 total shots in 7 games, before being eliminated by Atlanta. That’s less than 6.5 attempts per game. For context, Damian Lillard shot 134 times in 6 games (or 22.3 times per game) before being bounced by Denver.

It gets worse. Damian Lillard, who’s admittedly the polar opposite of Simmons when talking shooting acumen, had an average shooting distance during this playoffs of 19.4 feet from the basket, a career high. Ben Simmons’ was 2.6 feet, a career low. I mentioned free throws earlier. If you can’t shoot the ball from the outside but you can get to the rim like Ben can, you’d better be able to make free throws. Simmons shot 45 free throws in 7 games vs the Hawks, which matched the number of field goals he attempted. He made just 15 of them (33.3%). Maybe that’s why he likes to shoot from 3 feet and in.

A lot of Ben Simmons’ playoff woes have built up in his head over time. In the first playoff series of his career (2018 vs Miami), Simmons shot 66 times in 5 games. That, to this day, stands as his career high for any playoff series. He’s played in two series that have gone to 7 games. Ben also shot 71% from the free throw line in his first ever playoff series back in 2018 vs Miami.

Here are his year-over-year playoff shooting stats. If you get nauseous easily, think about skipping this part.

Other red flags

But, those “in the know” with Jimmy Butler (like Chicago sportswriter Joe Cowley) tell a Ben Simmons’ story that goes much deeper than any physical or mental playoff block. Both Butler and Joel Embiid grew frustrated with Simmons’ refusal to improve his shooting and work on his game like they felt he needed to, according to an interview that Cowley did with KFAN yesterday.

There’s a reason why Butler beefed with both KAT and Simmons while playing with them. He thought they were soft and lacked the drive it took to win championships. Should the Wolves build their team based on the thoughts of Jimmy Butler? No, but do we really want to put both dudes on the same team?

Elite everywhere else

Simmons’ struggles in the playoffs all come back to his poor shooting ability. When he’s playing in the regular season, teams aren’t game-planning for him like they do in the playoffs. Getting to the rim is easier. He gets fouled less often and the pressure is mostly off. That allows the rest of his game flourish.

Ben does everything else at an elite level. He’s like Ricky Rubio on steroids and he’s one of the best and most versatile defenders in the NBA. At 6-11, he’s able to shut down a very large percentage of NBA offensive talent, especially all of the wing players who give other defenses headaches across the league.

Just look at the individual hardware Ben Simmons holds. He’s is a 3x All-Star, 2x All-Defensive Team and he was named All-NBA in 2019-20. Ben has more individual accolades than everyone on the Wolves combined.

Getting LSU Alum on the right team, where he doesn’t have to be a primary scorer, could be a franchise-changing move. And we all know how desperately the Minnesota Timberwolves need everything else Simmons does so well, especially the defense.

So, what’s the price?

At the end of the day, there’s not a basketball fan on the universe who doesn’t think Ben Simmons could help the Wolves climb out of their (pretty much) 15-year playoff drought. He’s a walking triple-double who would immediately improve this team in every aspect they crave.

But, then you see the price tag and want to turn around and walk right out of the store.

I’ve heard it would take multiple first round picks for the Timberwolves to even get into the conversation when it comes to a Ben Simmons trade negotiation. pic.twitter.com/x8fbKPRo7q

— Dane Moore (@DaneMooreNBA) June 25, 2021

RECKLESS SPECULATION: D’Angelo Russell and Malik Beasley for Ben Simmons? ESPN’s Zach Lowe makes the case. #Timberwolves #76ers pic.twitter.com/6ftCBVGsis

— SKOR North (@SKORNorth) June 22, 2021

What would be the starting point in a Ben Simmons-#Timberwolves trade? ????@DWolfsonKSTP has your scoop! pic.twitter.com/WJea1H6fqs

— SKOR North (@SKORNorth) June 25, 2021

If the Wolves refuse to give up Ant or KAT, which everyone is assuming, then they’ll need at least three of four out of [D-Lo, Beasley and TWO 1st-round picks]. So, Gersson Rosas could save a 1st-rounder (or two) if he sends both Beasley and D-Lo out to the right team. But, if they insist on keeping D’Angelo Russell in a Minnesota uniform, then they have to be willing to lose AT LEAST two 1st-rounders in the deal (probably three).

Does Rosas prefer to trade all of his current shooting for Ben Simmons or all of his future draft picks? He’d have to deal one or the other.

Is it worth it?

Getting back to the playoffs would be great and Ben Simmons would make this team a legitimate 5-8 seed in the West. With the play-in tournament expected to come back for 2022, the Minnesota Timberwolves would be a bona fide playoff team following a trade for Simmons.

But, unless Ant becomes the next NBA great (which is certainly possible), the Wolves aren’t going very far with Ben Simmons and Karl-Anthony Towns as their main offensive pieces. I worry about KAT in the playoffs because of how fast teams play and I’ve now spent most of my day researching Ben Simmons’ obvious flaws.

Giving up Russell and Beasley for Simmons would be putting a limit on this team’s future and way too much pressure on Anthony Edwards becoming a top-10 NBA player. If the end-goal is the playoffs then dealing for Ben Simmons will check that box. If the goal is to become a real contender in the West, then Rosas will wait patiently for something better.

Eric Strack | Minnesota Sports Fan

The basketball season isn’t over but the NBA and much of its following probably feels like it is. Viewership numbers continue to fall and now LeBron James is out of the playoffs after a game-6 1st round knockout by Devin Booker and the Phoenix Suns.

Let’s talk more important matters, though… like Minnesota Timberwolves trade rumors. That’s usually a more enjoyable exercise for Wolves’ fans, though it may not be the case today. On ESPN’s First Take Friday morning, Stephen A. Smith and Max Kellerman were discussing the likelihood that Damian Lillard stays in Portland long term, after he sent some cryptic tweets Thursday following his own playoff elimination.

That’s when Stephen A Smith received a text message he felt compelled to read on-air. It was apparently from someone who “has incredible credibility when it comes to basketball”. Well, that incredibly credible person mentioned Karl-Anthony Towns joining Lillard in Portland.

Here’s the exchange.

"I just got a text from somebody … and they mentioned to me Karl-Anthony Towns maybe in Portland."

???? @stephenasmith pic.twitter.com/Lnpcf0sUEp

— First Take (@FirstTake) June 4, 2021

I don’t know who this “nameless” insider is, who texted Stephen A Smith, but the back and forth felt more like a speculative pipedream than it did actual steam. But this is something we’ll have to get used to when it comes to KAT.

That’s not all bad. It’s clear that Karl-Anthony Towns is building his rep back up within NBA circles. When rattling off Trailblazer players it would take to pry KAT from the Wolves, Smith led off with both Yusuf Nurkic and CJ McCollum, just to get the conversation started. That perked my interest, slightly.

Now, Karl has emphatically stated his intent to win with the Minnesota Timberwolves and I believe there’s ZERO chance Rosas trades him away before the start of next season. But, it’s nice to see his stock rising, if nothing else.

Eric Strack | Minnesota Sports Fan