Four Big Questions: The Timberwolves have plenty to figure out heading into the offseason

Coming off back-to-back Western Conference Finals, the Wolves fell in the second round to San Antonio, who mostly dominated the series.

Despite the Wolves struggling through some injuries, and a clearly banged up Anthony Edwards, the Wolves went out with a whimper, being blown out in Games 5 and 6.

It leaves this Timberwolves core - Edwards, Jaden McDaniels, Rudy Gobert, Julius Randle - in a spot where change may be inevitable.

Here are four looming issues the team's leadership needs to address:

Will the Wolves keep the "core" together?

Although he likes the core of this group, Wolves General Manger Tim Connelly says everything is on the table when it comes to improving the roster.

"We have a lot of confidence in our guys," says Connelly. "But again, it would be disingenuous to be sitting here in front of this crew and say, 'hey, we're happy we're the 6th seed, we're happy we're not being a home court playoff team, we're happy that our last three closeout games have been lopsided. So we have to be realistic about what we have, which is way more good than bad, but know that we're not good enough right now."

Those last three closeout playoff games referenced by Connelly have been blowouts. This year, it was a 139-109 loss to the Spurs that was so lopsided, Edwards went to the Spurs bench with 8-minutes left in the game to congratulate them.

They were beat 124-93 by the Thunder in the WCF last year, and 124-103 by Dallas in the WCF in 2024.

That speaks to a team that hit a ceiling - hard. And any talk of this meaning the end of head coach Chris Finch is probably misguided. The most successful coach in franchise history is sure to be back.

Edwards is going nowhere. The Wolves have had numerous offers to consider that included McDaniels in the deal, including a trade this year to get Milwaukee star Giannis Antetokounmpo. It appears it would take something pretty dramatic to get Connelly to move McDaniels, but as he said, anything is possible - including Antetokounmpo who the Bucks are reportedly shopping again.

In the 2025 NBA Draft, the Timberwolves selected 6'11" French center Joan Beringer. He saw very limited action this season, but also did show some serious skill and upside in those minutes. Another offseason to add to his game, and put on some NBA-ready weight should pay off in 2026-27.

At this point, it would be pretty surprising if both Gobert and Randle are back in 2026-27. Both struggled against the Spurs, and Randle really fell off after the All-Star Break.

The money the team has committed to both next year and beyond has to be seriously considered. Gobert is due $36,500,000 next year, with a $38,000,000 player option for 2027-28. It's the same for Randle, due $33,333,334 next year, and $35,802,468 in a player option for 2027-28.

Those two players probably have a big effect on question number two.

What about looming free agents?

As for retaining their own free agents, Ayo Dosunmu is a top priority. The Wolves acquired him from Chicago midseason, and until a strained calf limited him in the San Antonio series, he looked like a perfect player for the Wolves - fast, athletic, and explosive.

Connelly wants to keep him, but the problem is Dosunmu is an unrestricted free agent, and has gone on record as saying he's excited to see what the league offers him in his first go-around with free agency.

Still, Connelly thinks this playoff experience will help the Wolves retain him.

"He really enjoyed playing in these moments he hadn't seen the second round of the playoffs," Connelly says. "He loved the fans. He talked about the fans all the time, how loud the building was. So we're pretty optimistic that we'll get something done there, and I think he's everything we thought and more."

Other pending free agents are veteran point guard Mike Conley. He'll be 39 at the start of next season, but showed flashes during the playoffs that there is still more in the tank - and he's said he feels like he can still play. The Wolves could try to bring him back as insurance at a position where they're severely lacking right now.

Also unrestricted is guard Bones Hyland, who became instant offense off the bench for the Wolves. Veterans Kyle Anderson and Joe Ingles are unlikely to be back. The Wolves also have a restricted free agent in Jaylen Clark who has shown promise as a lockdown defender. They can match offers for Clark, who could see interest from other teams.

What kind of player are the Wolves looking to add?

There's no question what is number one on the wish list: a solid option at point guard.

"Basketball IQ and toughness are two attributes we're going to look for to continue to augment the core group," Connelly said Tuesday.

That settling presence on the offensive end is going to be key. Donte DiVincenzo tore his Achilles in the playoffs and is likely down for at least a portion of next season already. And even DiVencenzo isn't a traditional point guard and facilitator.
Conley's age makes it impossible to count on him for the entire season as the starter, as the Wolves found out this seasons. But when Conley was good, the Wolves were great. They need a traditional point guard and facilitator to get the most out of the roster.

Whether that is trade, free agency or the draft is something Connelly has to navigate.

Speaking of the draft, the Timberwolves don't have much coming up. And what they do have is complicated.

They do control their own first-round picks in 2028 and 2032, and their own second-round pick in 2029. Due to various trades—notably the Rudy Gobert and D'Angelo Russell deals—many of their upcoming selections feature pick swaps or are owed to other teams.

If there's good news - and this is a stretch - the Wolves do have a first round pick this year. The Timberwolves hold the 28th overall draft pick this year as a result of a pick swap with the Detroit Pistons in a three-team trade. It's going to be difficult to add a major contributor at that position in the draft, but it's possible they strike gold.

Playoff experience matters but do the Wolves still need to "grow up"?

Short answer - yes. And Connelly knows it.

"Emotional maturity is certainly something we talked about consistently, and basketball IQ and toughness are two attributes we're going to look for to continue to augment the core group," he said Tuesday.

Going to the playoffs, advancing to the Western Conference Finals is great, but this is a team that admitted, and tried to sell their coach on the fact that the regular season doesn't matter. They'll flip the switch during the postseason.

That was sort of true, but it shows that this is not a championship team yet. They were able to out-athletic an aging Denver team with significant weaknesses on defense. But they are way, way, way behind San Antonio and certainly Oklahoma City when it comes to Western Conference supremacy.

Edwards is still young, and was very beat up during the Spurs series, but he needs to take the next step as team leader and show the way forward. That means making the most of the regular season so you are ready for the playoffs, and in better position going into them.

Gobert regularly called out his teammates when they didn't put out the defensive effort, and has been a leader. But it needs to come from Edwards and McDaniels now. And McDaniels especially has to show more maturity. He's too quick to pick up crucial fouls, and take himself out of games.

On a team of admittedly moody players, maybe none stood out as much as Randle. Too often, Randle was inconsistent to be treated as a credible number two option for the team, and Randle's body language too often showed indifference.