Timberwolves' past mistakes could haunt them this offseason

The Minnesota Timberwolves enter this offseason in a challenging position. This year's playoffs proved that changes are needed to catch up to the San Antonio Spurs and Oklahoma City Thunder. However, their cap situation and lack of draft capital will make things challenging. 

Minnesota's front office has generally done a good job of building a competitive roster. There have been some missteps along the way that could make it difficult to land a legitimate co-star alongside Anthony Edwards, though. 

Recently, ESPN wrote an article about the 10 teams that will define this year's offseason. In this piece, Tim Bontemps wrote that he believes the Timberwolves' past mistakes are starting to haunt them. 

"Minnesota's past decisions are starting to come back to haunt it. Paying above-market contracts to both Gobert and Reid has left the Wolves bumping up against the second apron without a lot of flexibility. It also left them without the financial flexibility to keep  in free agency and he left for the  and promptly won the league's Most Improved Player award after he made it clear he hoped to stay in Minnesota," Bontemps wrote. 

The Timberwolves lack flexibility thanks to their past decisions

Bontemps brings up some good points regarding the Wolves' salary situation. No Timberwolves fan needs to be reminded of the pain of losing Alexander-Walker last summer. As the team searches for a point guard, though, it hurts seeing NAW blossom, and he has the exact skill set they lack.

Reid's five-year, $125 million contract was certainly a notch above market value, which made retaining NAW all the more difficult. It was also a bet on Reid becoming a starter one day, and the Wolves were at risk of losing him in free agency. Still, there's no denying that Reid's hefty contract will hurt their flexibility this offseason, and it's worth wondering if the Wolves could have gotten away with paying him a bit less.

I would challenge Bontemps on his point about Gobert. He notably declined his $46.6 million player option for the 2025-26 season and signed a three-year $110 million extension. Regardless, the Wolves' high payroll will be a major hurdle for them this offseason. 

It's also important to note that the Wolves trading a future first-round pick and a pick swap to draft Rob Dillingham will undoubtedly hinder them as they pursue a star this summer. These picks could be the difference between the Timberwolves trading for a player like Kyrie Irving or striking out.

You could say the same about trading a treasure trove of picks for Gobert, but I'd argue that they wouldn't have made two straight conference finals without him. 

In any event, the Wolves only being able to trade the No. 28 pick in this year's draft and their 2033 pick will hurt their ability to trade for a star.

The Wolves are $30 million below the second apron, or $27.1 million below it if they use their first-round pick. However, they have seven free agents, including Ayo Dosunmu.

The Wolves could dip into the second apron this summer, but given how much it limits roster construction, that would be risky, that is, unless you can become clear-cut title contenders.

Finding a move that can get them to this level is difficult, though, due to their lack of draft capital and high payroll. 

Given how close they are to the second apron (particularly after re-signing Ayo), it will be difficult for the Wolves to pull off a needle-moving trade. Kyrie is the dream trade target, but he makes $6.1 million more than Julius Randle and $2.9 million more than Gobert. 

With Randle and Gobert being the team's top two trade candidates, the Wolves will likely have to save money in one of these possible deals. Doing this while finding moves to be more competitive will be incredibly challenging.  

Tim Connelly will certainly have to work his magic as the Wolves try to make a leap to true title contention. If the Wolves strike out on landing a co-star for Ant, it will be hard not to think back on the decisions they made in the past two offseasons. 

These decisions are already plaguing the Wolves' flexibility, and there's a reality where they end up haunting the team for the rest of the decade.  

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