The Minnesota Timberwolves currently hold a record above .500 forty-seven games into a season for only the second time in the franchise’s last seventeen seasons.

More impressively, rookie head coach Chris Finch has displayed promise breathing confidence into the NBA’s third youngest team entering the season and leading them to a 24-23 record overall, placing them No. 7 in the West and on track to host a play-in game come April. That includes an 20-12 tally when all of Karl-Anthony Towns, Anthony Edwards and D’Angelo Russell have been active. For reference, if Minnesota’s Big 3 had played every game so far and held that pace, Minnesota would currently be the No. 5 seed at 30-18.

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The Wolves’ current core has exceeded this year’s expectations by powering a team with little national media attention and belief into the thick of not just play-in contention, but playoff contention.

However, raising the bar and setting a new standard for this season — to avoid the play-in entirely and secure at lowest the No. 6 seed — has sent the Timberwolves into uncharted waters.

For years, this franchise has done a better job selling at the trade deadline than they have at the ticket office. This season, the Timberwolves, led by executive vice president of basketball operations Sachin Gupta (who is auditioning for full-time head of basketball operations), will attack the deadline head-on as buyers.

Gupta has a unique set of circumstances in front of him that complicate not only the Wolves’ current position as a somewhat over-achieving young team with little playoff experience, but also their long-term position as a team with a defined core whose key prospects who are making cases to be part of Minnesota’s future plans.

The way in which Gupta steers the ship through these uncharted waters over the next few weeks will speak volumes about how the Wolves will look in the years to come.

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Summer Extensions

The first complicating factor is that it is extremely difficult to manage a team’s plans at the trade deadline when two of said team’s three best players are extension eligible. Towns and Russell are the foundation on which this team has been built since Russell’s arrival in 2020, and it is hard to imagine how a front office leader in Gupta could operate without having a good idea of how those dominos are going to fall this summer. I expect they will both be back at the start of next season with long-term extensions, but anything can happen.

Karl-Anthony Towns

Towns signed a five-year rookie maximum extension in September of 2018, and is in his seventh season in the NBA, which makes him eligible to sign an extension this offseason that could add up to four years onto his existing deal (two years left after this season). His hypothetical next contract (starting in the 2024-25 season) would pay him 35% of the team’s salary cap if he were to make an All-NBA team this season. If he doesn’t, the biggest extension Towns could sign would be a two-year, standard maximum contract (30% of the cap). That hypothetical extension would be added onto his current deal.

Here are the options, using estimated numbers that cannot become official until the salary cap is announced for the corresponding season:

Note that a possible Towns extension would need to be signed by June 30 of this year. If he or the team opts against agreeing to an extension by then, both parties would have to wait until the final season of his existing contract (2023-24) to negotiate a new deal.

That would likely signal he is betting on himself to make an All-NBA team in one of the next two seasons so he could make himself eligible for a supermax extension during the 2023-24 season.

It appears unlikely that Towns would refuse to sign an extension at all and eventually become an unrestricted free agent in 2024. The soon-to-be three-time All-Star made his feelings known about staying in Minnesota long-term in September during an interview with Sports Illustrated.

“My chips are all on the table, so it’s up to the Wolves, you know?” Towns said. “If they give me the chance to stay there I fa’ sho would take it. The ball is in their court.”

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Whatever your opinion of Towns is, you cannot ignore the fact that it would be foolish for the Wolves to opt against signing one of the league’s most talented offensive players — and a perfect fit next to Edwards — to a long-term deal.

At this stage, I would be rather surprised if Towns does not make the All-NBA Third Team and subsequently sign a four-year, $201 million supermax extension to stay in Minnesota through the 2027-28 season.

Towns would have trouble finding a new team, either in free agency or via a trade request, that could bring him in without hamstringing its future and win more than the Wolves have the potential to in the coming years, given that Edwards has superstar written all over him. He has mentioned several times over the years his promise to Flip Saunders — the franchise legend and man who drafted him — to turn the Wolves into a consistent winner, but Towns still has work to do. You can bet he wants to fulfill it.

D’Angelo Russell

Russell is in the third season of a four-year, $117.3 million maximum contract he signed in a sign-and-trade with the Brooklyn Nets that sent him to Golden State in exchange for Kevin Durant. He becomes eligible to sign an extension on July 7.

The same rules as Towns’ extension apply, except they are moved up a year because Russell has one season left after this one, whereas Towns has two. The biggest difference between the two is the All-NBA escalator; Towns is in the mix to achieve that, while Russell is not.

Here are the options:

It is important to keep in mind that Russell chose Golden State over Minnesota in restricted free agency in 2019 so he could make every penny possible. In what has been a resurgent season, it is entirely possible Russell will expect a maximum contract extension in July — one worth $164 million over four years.

It wouldn’t surprise me to see the Wolves opt against offering Russell a maximum extension in July; it seems unlikely another team would offer it to him in 2023 free agency, and Wolves brass won’t want to bid against themselves, in a sense.

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If Russell wishes to remain in Minnesota — an environment in which he is relied upon heavily as a leader and connecter, and has spoken very highly of in recent weeks — it is in the best interest of both sides to work out a deal. Russell cannot earn any extra dollars on a deal with Minnesota next summer by hitting incentives in the 2022-23 season; therefore, his best chance to lock up long-term money is by playing lights out basketball for the rest of this season (which he has gotten a head start on post-COVID-outbreak) and signing a multi-year deal.

Honestly, I’m not sure what a Russell extension will (or should) look like, because there is so much basketball left to be played this season. But given D-Lo’s glove-like fit alongside Towns and Edwards — and taking into account the success the trio has had thus far —, and that the value of the Wolves’ return on the Andrew Wiggins trade is growing by the day, I don’t think you will have to sell your Russell jerseys anytime soon.

Russell’s contract will be a barometer of how ownership feels about paying the luxury tax next in the 2023-24 season and beyond. Remaining under the luxury tax through the trade deadline and this conclusion of the league year is paramount in preventing Minnesota from being a repeater team next season, the first season the team should realistically expect to win a playoff series.

Expect Jake Layman (along with one of the team’s three second round picks in the 2022 Draft) to be moved — if Minnesota makes a deal that sends out one of Taurean Prince or Malik Beasley — in order for the Wolves to stay under the tax line.

Jaylen Nowell

At the start of the season, many expected that Nowell could be waived prior to his 2021-22 salary guarantee date (1/10/22). Now, he’s primed to cash in during restricted free agency this summer.

What does restricted free agency mean?

Essentially, it allows the Wolves to match any contract offer Nowell may receive from another team. If the Milwaukee Bucks signed him to a three-year, $21 million deal, the Wolves could match the offer sheet and sign him to that contract to stay in Minnesota.

This route is the best option for both parties. It allows Nowell, a former second-round pick, to get long-term money locked up and play in an environment where he has been needed and has truly thrived, while also rewarding the Wolves for betting on his talent as the Pac-12 Player of the Year coming out of Washington.

He is very likely seen as a core piece of the team moving forward, and I fully expect the Wolves to try and sign him to a four-year extension come this summer.

Here’s what his maximum contract would look like:

Despite there not being a whole lot of money to spend this summer around the league, it wouldn’t surprise me at all if Nowell signed a contract averaging over $10 million annually. At 22 years old, he possess coveted skills around the league as a legitimate bench engine and shot creator with massive scoring upside. With Prince’s and Layman’s contracts coming off the books after this season, Nowell could theoretically slide into a more expensive deal without pushing Minnesota into the luxury tax.

Note that the Wolves could also exercise Nowell’s option for next season at $1.93 million and Nowell would then enter unrestricted free agency next summer. Minnesota would be unwise to go in that direction.

Naz Reid

Reid is also extension eligible for the same contract as Nowell is. Given his underwhelming play this season, he could very well be a trade chip for Minnesota to push into the middle of the table in an attempt to upgrade the front court at the deadline. At this stage, it seems unlikely he would sign an extension this offseason, but anything can happen.

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Pending Free Agents

Locker room Patrick Beverley headlines the Timberwolves’ pending 2022 free agents, a list that includes Prince, Layman, Josh Okogie, Nowell, Reid and two-way players McKinley Wright IV and Nathan Knight.

Beverley has taken hold of a young locker room in need of a veteran alpha with playoff experience, and helped to transform the Wolves’ identity into a scrappy defensive team that plays relentlessly hard on both ends of the floor. He also played a crucial role in a meeting after the team’s 10th game of the season that Towns credited — after Sunday’s win over the Nets — for role players answering the call when their numbers have been dialed.

Jon Krawczynski of The Athletic has already reported that the Wolves and Beverley have had preliminary discussions about a deal and that both sides are interested in Mr. 94 Feet returning to Minnesota on a new deal this summer.

Beverley, 33, still has multiple years of high-level basketball ahead of him and can absolutely drive winning team on a team in need of hard-nosed defense and 3-point shooting like the Wolves are. If Gupta believes Beverley will back in the fold next season, that will allow him to cross off any back court needs and instead pursue the Wolves biggest needs at the deadline: interior defense, rebounding, and perimeter shooting.

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If his $13 million salary isn’t used at the trade deadline, Prince would be a solid player to bring back next season at a more team friendly price. The veteran forward from Baylor has enjoyed his time in Minnesota in large part because of what he described on Sunday as the team’s collective character and how together they play on both ends, as well as how well the team gets along off the floor.

Every time he rises up to shoot, the Wolves bench rises with him; it is obvious how revered Prince is in the locker room because of how eager his teammates are to support him. Winning NBA teams need veterans who are willing to buy into their roles and lead younger players even if they aren’t playing every night. Prince is a guy who fits that mold and can be a solid rotation player for years to come. He’s only 27 and has plenty of hoops ahead of him.

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Okogie is the most interesting player of the group not up for an extension. He has displayed a defensive ceiling that no one other than Beverley has hit before as an NBA player. His defensive track record includes shutting down the likes of Luka Dončić and James Harden, and that type of weapon can be extremely valuable in a playoff series. The Wolves declined to offer him an extension last summer and it may come back to bite them.

The former Georgia Tech stopper is the type of player I could see signing a veteran’s minimum contract with a contender and shine in the playoffs as a guy capable of swinging a game solely with his defense on the opposition’s best offensive player. For as good as Jaden McDaniels and Jarred Vanderbilt have been, they don’t have the same ability to absorb contact and hold their ground quite like Okogie does, although McDaniels has shown flashes of it. Plus, if either of those two get into foul trouble, Okogie is a seamless stopgap. The Nigerian National Team standout is the longest tenured Wolf not named Karl-Anthony Towns and is beloved in the locker room. Whether he will return or not remains to be seen, but Okogie’s potential as a defender in the playoffs is too high to concede without making a competitive offer to keep him this summer.

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A Struggling Trade Centerpiece

Entering the season, Beasley was expected to play a significant role as a high-volume 3-point shooter that can get hot at a moment’s notice and tip the scales in Minnesota’s favor on any given night. The front office likely viewed him as its best trade asset (that is not part Minnesota’s Big 3), too.

That vision is yet to materialize, because Beasley hasn’t found a rhythm shooting the ball and his role has fluctuated wildly as a result of both Nowell becoming the team’s best player off the bench, and Vanderbilt emerging as a 25-plus minutes per game starter whose rising has moved McDaniels to the bench.

The former Florida State standout, a career 38% 3-point shooter, has connected on 34.9% of his triples and only 37.4% of his field goal attempts this season. Beasley is averaging 12.2 points per game this season after scoring a career-best 19.6 points per game in 37 games last season.

Beasley’s struggles this season have likely altered his view around the league as a “positive asset” (meaning teams would give up assets to trade for him); that development is unfortunate for the Wolves, who would like to hold onto as many first-round picks as they can given they are not a free agency destination for the league’s most impactful players.

His value may never be lower than it is right now, which certainly flames an argument to be made about holding onto Beasley and betting on him to return to form as a premier shooter in the NBA.

But, whether or not they like it, netting a significant upgrade at backup center or on the wing will require the Wolves to move not only Beasley (or Prince), but likely also a first-round pick, and potentially move second-round picks, or even McDaniels as well, depending on the target.

A key question to answer when surveying the market for potential trade targets is whether or not the Wolves would be willing to move a young player with as high of a ceiling as McDaniels, a hyper-fluid 7-foot wing who possesses the defensive versatility to successfully guarding 1 through 4 and intriguing scoring upside on offense. The best part? He’s on a very team-friendly rookie scale deal as the No. 28 pick.

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There’s no doubt a player like that piques the interest of teams looking for value in return for players like Jerami Grant, Harrison Barnes, or Myles Turner, to name a few. But will the player Minnesota can net from a potential McDaniels deal make it worth cashing in that potential now, before it can be fully realized? Time will tell.

Minnesota owns all of its first-round draft picks and has a plethora of second-round picks to go along with it, which is a positive; however, diving into that treasure chest of assets may be frowned upon by ownership given Gupta is trying out for the full-time head of basketball operations job.

With that said, Gupta’s specialty lies in finding value on the trade market by concocting complex deals that comply with the NBA’s Collective Bargaining Agreement. The inventor of ESPN’s Trade Machine has his work cut out for him, but Beasley taking a major step forward shooting the ball in the coming weeks may take some pressure off of Gupta and his staff.

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New Ownership

This is by far the most complicating factor and biggest wildcard in not only how the Wolves approach the next two-plus weeks ahead of the trade deadline, but also how its core may look beyond this season.

First and foremost, we have yet to see any indication of whether Gupta will stick long-term.

The Timberwolves recently hired former Klutch Sports Executive Marquise Watts as Chief Experience Officer, which was first reported by The Athletic.

That type of news isn’t broken by The Athletic unless it has potentially large ramifications on the organization. The Athletic called the position “unique” and that the Wolves and Lynx “plan to make Watts’ position and initiatives one of the biggest priorities in their vision of where they want to take the franchise.”

Given Watts’ connections from his time as a sports marketing maven who reportedly represented several NBA stars on the brand and sponsorship side during his time at Klutch, adidas, and Under Armour, and the way his role was described by The Athletic, it seems like, at least on the outside, that Watts could be included in talks about roster decisions.

Although The Athletic reported that Watts’ position “is separate from the head of basketball operations,” I don’t understand how it feasibly could be. Based on how his job was described, it seems Watts would need to work closely with the head of basketball operations of both the Wolves and Lynx in order to maximize his impact, especially if minority partners Marc Lore and Alex Rodriguez plan to make his position one of the biggest priorities in their vision.

In order to personalize the player experience, you have to know who you are working with, the player’s history, and how that player and the player’s history may align with your organization; Watts has the experience to help on that front, and it is certainly part of a player’s evaluation before bringing them into the fold.

What that means for Gupta in his quest to become the Wolves’ head of basketball operations is still unseen, but it may muddy the waters ahead of a trade deadline the Wolves are approaching as buyers in an effort to buoy their playoff viability. Gupta is well-respected around the league as a front office veteran deserving of the opportunity to run a team’s basketball operations.

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Cleaning the Glass founder Ben Falk, a former colleague of Gupta’s with the Philadelphia 76ers, wrote an incredible column in September describing Gupta’s empowering leadership style.

“Sachin listens more than he talks. He’s not a manipulator, playing political games or figuring out how to get people to fall in line. He’s genuine and transparent. But rather than cut against his ability to lead, those traits enable it,” Falk wrote. He continued:

That type of leadership is needed in Minnesota, because it has already proven to work here. I wrote on Sunday that Finch’s strong communication skills have helped him get the most out of his players and fostered an environment all of his players have sung praises about throughout this season.

Gupta and Finch are, at surface level, a match in terms of leadership styles and personality; perhaps more importantly, they understand how each other operates from their time together with the Houston Rockets. That relationship matters, especially when it is shared by the those who perform the most important roles in the organization outside of the players.

The more aligned an organization can be, the better. What Falk describes falls in line with Lore’s well-marketed business credo of “Vision, Capital, People,” or “VCP” for short.

Vision

Gupta’s vision, of well-thought-out moves that position the Wolves to capitalize on Edwards’ rookie contract and the primes of Towns and Russell, is one that should excite Lore given Gupta’s experience and the Wolves’ primary avenue of seismic improvement — the trade market.

Capital

Minnesota owns all of its first-round picks and has developed multiple intriguing young players, which constitute the needed capital to make a splash — often a priority for new ownership.

People

Finally, based on Falk’s essay, it’s clear that Gupta is the kind of person the Wolves should seek out to run basketball operations: one whose action inspires work, leadership brings people together, and mind engages people intellectually to elicit collaborative, diverse thinking.

Until a final decision is made on Gupta’s long-term status by ownership and, ultimately, by Gupta himself, Gupta in the mean time will navigate what is sure to be an eventful two-plus weeks ahead of him.

A smooth sea has never made a skilled sailor, but Sachin Gupta’s shrewd executive skills have been forged by rough seas throughout his time in the NBA, and he is one of the most well-equipped people Wolves fans could ask for to steer the collective ship through these uncharted waters full of organization-changing potential.