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What should be at the top of new Timberwolves boss Tim Connelly’s to-do list?

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Tim Connelly has yet to make public comments since being named the Timberwolves’ president of basketball operations on Monday. His initial press conference is expected to be held this week.

That will provide the first real insight into Connelly’s views on the roster and basketball operations structure over which he now resides.

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Tim Connelly, president of basketball operations of the Denver Nuggets, is in a press conference on April 29 at Ball Arena in Denver, Colorado.
Hyoung Chang / TNS

He will face a number of questions about key players ranging from Anthony Edwards, Karl-Anthony Towns, D’Angelo Russell and beyond, head coach Chris Finch, executive vice president of basketball operations Sachin Gupta and more.

All are pertinent, all will have a major impact on the Timberwolves’ direction for years to come. Because while Minnesota took leaps forward this past season, simply maintaining this level of success would only be viewed as a failure. Growth has to be the expectation. The level to which that is achieved will, largely, be determined by Connelly, starting with the moves he makes this offseason.

Here’s a look at what should be at the top Connelly’s agenda as he gets started in Minnesota:

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Minnesota Timberwolves executive vice president of basketball operations Sachin Gupta on Nov. 5, 2020. Gupta was thrust into the role of basketball boss last week following Gersson Rosas’ firing and is not operating under an interim title.
Carlos Gonzalez / Minneapolis Star Tribune / TNS<br/>

Sachin Gupta

Sachin Gupta, by many accounts, would have been a great hire for the job Connelly just took over. He was credited for deftly handling a rocky and sudden leadership change back in September, shrewdly handling Patrick Beverley’s contract extension negotiations and fighting the urge to make a move just to make a move at the trade deadline, going with what he thought was best for the team’s future, even if making a splash was more likely to please an ownership group that would determine his future just a couple of months later.

At the end of the day, team owners went with the bigger name with the stronger resume.

Still, it’s clear the Timberwolves have designs on Gupta maintaining an integral role in the team’s front office, even including him in the press release announcing the hiring of Connelly.

Connelly has a scouting background, while Gupta, currently the team’s executive vice president of basketball operations, is known for his work in analytics.

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If the two are able to coexist, Minnesota may have one of the NBA’s most formidable front office tandems.

There certainly will be some awkwardness at the outset of the relationship, with Connelly coming in to take the job Gupta for all intents and purposes held for the past eight months and certainly desired to hold on a permanent basis.

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It’s on Connelly to make sure the partnership gets off to a smooth start to benefit himself and the organization. Because as the man who has been running things, Gupta is best equipped to ensure a smooth transition into Connelly’s tenure, which in turn will set the Timberwolves up for a successful offseason.

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Minnesota Timberwolves head coach Chris Finch looks on against the Phoenix Suns during the first half March 19, 2021, at Phoenix Suns Arena.<br/><br/>
Joe Camporeale / USA TODAY Sports<br/><br/>

Chris Finch

The relationship between bench boss and basketball boss is critical within an NBA organization. Synergy between the two positions leads to stability and, often, success.

Finch and Gupta seemed to establish that in short order last season. Now it’s up to Connelly and Finch to move in similar lockstep, starting this offseason.

Connelly is walking into a situation in which he likely has opinions about Wolves players, but Finch has worked with a number of these guys for nearly a season and a half, and has a good idea of their specific strengths, weaknesses and how they fit — or don’t fit — into what he wants to do.

Finch and Connelly do have a previous relationship, with Finch having served as an assistant coach for a season in Denver during Connelly’s tenure. The two spoke during Connelly’s hiring process, as well.

Quickly building a relationship of trust and collaboration should help Connelly hit the ground running this offseason.

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Minnesota Timberwolves guard D'Angelo Russell (0) shoots against the Memphis Grizzlies center Xavier Tillman (2) in the third quarter on April 29 during game six of the first round for the 2022 NBA playoffs at Target Center in Minneapolis.
Brad Rempel / USA TODAY Sports

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D’Angelo Russell

D’Angelo Russell certainly had moments this season — chief among them was his heroic play-in game performance against the Clippers that helped move the Timberwolves into the playoffs.

But the downs were just as prevalent as the ups.

The offense didn’t always necessarily flow when Russell, Anthony Edwards and Towns shared the floor, and Russell has a low ceiling on the defensive end.

How does that balance out his at-times clutch shot-making and abilities to stretch the floor, pass the ball and hit tough buckets in the mid-range? Probably not enough to justify Russell’s robust salary.

But it’s on Connelly and Co. to determine if it’s best to have the point guard play out the final year of his contract, try to negotiate an extension that gives Russell more long-term security on a team-friendlier salary or attempt to trade him.

Whatever that decision is, it will be the biggest domino to fall this offseason.

NBA: Playoffs-Memphis Grizzlies at Minnesota Timberwolves
Minnesota Timberwolves center Karl-Anthony Towns (32) blocks Memphis Grizzlies guard Ja Morant (12) in the fourth quarter on April 29 during game six of the first round for the 2022 NBA playoffs at Target Center in Minneapolis.
Brad Rempel/USA TODAY Sports

Karl-Anthony Towns

Karl-Anthony Towns’ well-deserved third-team All-NBA recognition means the center is eligible this offseason to sign a four-year, $210.9 million extension that would be added onto the two remaining years of his current deal.

It sounds like a no-brainer to keep the all-star in Minnesota as long as possible, no matter the terms. That could very well be how Connelly feels.

But the final year of that extension would pay Towns $58 million toward the cap. Does Connelly believe Towns is a championship-caliber building block? If not, it may be difficult for him to come to grips with such a hefty extension, which would constrain management’s roster maneuvers two years from now.

Things could get awkward between team and star center if the Wolves put an extension for less money than that max number in front of Towns. But it could be a risk worth taking if, after assessing the big man, Connelly determines Towns would need a lot of help to lift Minnesota to title heights.

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Minnesota Timberwolves guard Malik Beasley (5) drives to the basket as Boston Celtics guard Payton Pritchard (11) defends during the second quarter in this 2021 file photo at Target Center.<br/><br/>
Nick Wosika / USA Today Sports<br/><br/>

Malik Beasley

Connelly already has traded two players on the current Timberwolves roster. He dealt Malik Beasley and Jarred Vanderbilt to Minnesota in 2019, as part of the three-team deal that sent Robert Covington to Houston.

In retrospect, that wasn’t one of Connelly’s more prosperous moves. Denver didn’t get much in return for trading away its wealth of role players. There’s little question he’s happy to have Vanderbilt on his roster again. The young forward has proven to be a valuable piece playing on a team-friendly deal.

But what about Beasley? The guard seems to be largely the same player he was in Denver, and Connelly decided to move him versus paying him back then. Well, Beasley has since been paid. Does Connelly think a player of Beasley’s caliber — along with any off-court issues — is worth the $15.5 million he’s due this season?

If not, the sharpshooter is potentially another trade chip on a potentially expiring deal — there is a team option for the 2023-24 season — the Timberwolves could use to continue to try to revamp and elevate their roster this summer.

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