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Roundtable: What Should We Make of the Timberwolves Power Play Hiring of Tim Connelly?

Change is afoot at the highest levels of the Minnesota Timberwolves organization.

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The Minnesota Timberwolves have for years been searching for long-term stability and a plan to surround franchise cornerstone Karl-Anthony Towns with the the right people on the court, on the bench, and in the front office.

Yesterday’s hiring of former Denver Nuggets President Tim Connelly to run Minnesota’s front office was the biggest step to-date towards that goal of long-term franchise stability, after of course the selection Anthony Edwards at No. 1 to be KAT’s running mate and hiring Chris Finch as head coach last February.

A big win in all of this is that the Timberwolves stated in a press release that “Connelly will work closely with Timberwolves Executive Vice President of Basketball Operations Sachin Gupta, as well as Head Coach Chris Finch, whom Connelly worked with in Denver during the 2016-17 season.”

It was widely speculated that Gupta could leave the Wolves if an external President of Basketball Operations hire was made, but Gupta appears to be staying in Minnesota, at least for now.

Our Canis Hoopus staff got together to share their thoughts on specific questions regarding the hire and where the Timberwolves go from here.

2022 NBA Playoffs - Minnesota Timberwolves v Memphis Grizzlies Photo by David Sherman/NBAE via Getty Images

What is your biggest takeaway about the Tim Connelly hiring?

Jack Borman: The new ownership tandem of Marc Lore and Alex Rodriguez are cashing checks they wrote soon after the announcement of their limited purchase of the Timberwolves and Lynx. They vowed to be aggressive in going after the best possible people (in their view) to run their team and they have followed it up by signing one of the league’s most well-respected executives just as the biggest offseason in the franchise’s recent memory is heating up. They still are not majority owners of the team, yet may be asked to pay luxury tax from the get-go next season. Majority owner Glen Taylor has been apprehensive about paying the tax for a team not in serious playoff contention, but he may ultimately decide next season’s team is worth it on his way out, if that means more success. Taylor’s willingness to foot the first bills for Connelly’s contract shows he is willing to back his minority partners, but the bigger question becomes how comfortable Lore and Rodriguez will be spending their own money, not Taylor’s, when it comes time to pay the tax in 2022-23.

Gabe Schneider: Lore and Rodriguez aren’t afraid to go after it. They’re clearly serious about turning the Wolves around, and take another big step in that direction by doling out $40 million to Connelly. It’s so atypical for the Wolves to go after big fish (Masai Ujiri, Connelly, etc), that it feels a bit weird. Makes me wonder: if Lore and Rodriguez weren’t involved, would Connelly even consider taking this job? Ant’s a big factor there, but Glen probably doesn’t make it happen. It’s really exciting that having those two in ownership has already changed how the Wolves are perceived (maybe it’s because they’re now a good team, but still, Lore/Rodriguez have to be more intriguing/better to work with than Glen).

Logan Alten: I started out this process a little trepidatious of the whole thing. The Wolves thing to do would be have it aired, have it blow up in their face, lose Gupta, and have to start the offseason in a weird spot. Thankfully that isn’t the case. As Gabe said, the new ownership duo isn’t afraid to go for it and, in A-Rod’s case, have some fun while doing so. They seem very committed to a complete overhaul of what the Timberwolves are as an organization. They brought in Marquise Watts to be the Chief Experience Officer, they are making a change in the broadcasting booth by (unfortunately) letting Dave Benz go, and now Tim Connelly is the latest domino to fall. I am very excited to see what the future holds for the team.

Leo Sun: It’s time for us to get serious. I was lamenting to my best friend, who writes for The Kings Herald, about how awful I feel that the Timberwolves are going all out to hire a #Top5POBO while the Kings are hiring the owner’s 29-year-old daughter to be an assistant general manager of their G-league affiliate (I’ll save you the time - She does not have any professional basketball or management experience). It wasn’t so long ago that Glen Taylor may or may not have given our former POBO a mandate to hire the son of a former head coach/minority owner as the new Wolves head coach. But I digress. It feels like Minnesota is no longer “allowed” to just toil in the doldrums of the league and make silly mistakes which everyone laughs at, as we continuously kick the proverbial can down the road. The young stars developing, an elite head coach, a true postseason berth, making headlines in the media circuit, and now this. It feels like winning is no longer going to be a pleasant surprise, but a serious expectation.

Brendan Hedtke: The Wolves are a franchise that saw a path to sustainable success this past season, which has been a vision they’ve lacked since Kevin Garnett had the trees tied around his waist. Now, that same team decided to change course and pursue another lead man in the front office. From the outside looking it, that does not make much sense. One might say to let Sachin Gupta continue to drive the boat, but that is not what is going to happen. Gupta did a good job righting the ship after Gersson Rosas was fired before training camp. He didn’t do anything flashy in order to try to win the job. Instead, he did what he thought was best for the franchise: standing pat. Now Gupta gets to (likely) work alongside Tim Connelly.

Now, I haven’t really made a point yet, so I’ll say this. I think Tim Connelly did a fantastic job for the Denver Nuggets. There were things that he was very good at as well as things that he was not so great at. I think he is a fantastic talent evaluator and a great #vibes guy. He has had a couple warts of paying guys too early before they’ve proved anything, but it hasn’t been catasprohic to the Nuggets. Overall, my biggest takeaway is that Alex Rodriguez and Marc Lore are not going to sit around and be okay with “doing good enough”. They want to do great, which is nearly always done by taking risks. We will see if this one pays off, but as of now I give it a stamp of approval.

Andrew Carlson: Something we don’t see often and are often weary for Minnesota sports in general as fans and followers; capitalizing on momentum. The safe, non-risky, cost-effective play was rolling with Sachin Gupta moving forward, and who knows? That could have worked! But I’ll do you one better - keeping Gupta AND luring over a top-ten decision maker in the league to boot. When the news first broke, there was a large adverse reaction to getting risky and making a big play. Why? Because it’s uncomfortable, uncharted waters. We haven’t experienced this before and making the risk for the hire itself, paid off. This is not the Tom Thibodeau hire. This is Alex Rodriguez and Marc Lore doing their best Sam Cassell impersonation.

As for Gupta? A win-win, in my opinion. If the Wolves continue success moving forward under Connelly, he’s in for a bigger payday and a surefire chance to run his own ship soon enough. Oh and also Connelly won’t lock him out of the facility.

Western Conference Semi-Finals - Portland Trail Blazers v Denver Nuggets Photo by Garrett Ellwood/NBAE via Getty Images

What excites you most about what Connelly will/can bring to Minnesota?

JB: The respect of the rest of the NBA. There are certain executives who can immediately grant a team a level of certain level of credibility that can drive winning and by all accounts Connelly appears to be one those executives. Whether it is in trade conversations alongside NBA Collective Bargaining Agreement and trade maestro Gupta or in free agency conversations with the likes of Zach LaVine or whomever it may be alongside Chief Experience Officer and former Klutch Sports executive Marquise Watts, the hope is that Connelly’s presence will make the Wolves more serious players in spheres more commonly reserved for big market teams.

GS: Finding someone that excels in scouting/finding talent through the draft is crucial for this team. Historically speaking, players aren’t looking at Minneapolis as a desirable place to be. Therefore, finding talent through the draft becomes even more important. If Connelly can find a few gems during his time in Minnesota, in combination with an exiting new ownership group and this young core, they might just be able to become a semi-intriguing destination for free agents.

LA: This may be a weird takeaway but I’m pretty excited for the extra level of patience that ownership will likely have with Connelly. One of my biggest concerns with not landing a big fish was that the ownership team may have put Sachin Gupta (or a different GM) in a tough spot by wanting a superstar. This could’ve resulted in Gupta’s hand being forced in an overpay or a trade that would’ve produced a weird fit culturally or on court. Even though A-Rod and Lore remain in pursuit of home runs, having Tim Connelly will hopefully allow them to strike the superstar trade market in a more organic matter and land their guy when the time is right.

LS: Though I agree with my colleagues above, I’m actually most excited that Connelly opens the door for us to create cool new headlines like, “TC Brings *insert All-Star* to TC.” It’s just too perfect. Sure, the PRosas thing was neat. Sachin Gupta has a dope background and we got to meme the ESPN trade machine. But those won’t hold a candle to our new head decision-maker. “No Cons Here, Connelly is the Real Deal.” “Whoa Nelly, Tim Con Signs *insert future HOF*.” Alongside the charismatic quote-generator, Anthony Edwards, Tim is only going to help the Timberwolves further assert themselves as the media sweethearts.

BH: His talent evaluation. I won’t say the Wolves have never found talent later in the draft. I mean, they drafted Jaden McDaniels 28th overall. But Connelly’s track record in that area has been very impressive. If the Timberwolves hope to bring in quality players through the draft for years to come, they will have to do so in the later portion of the first round as they’ll likely be out of the lottery for quite some time.

I’m also excited to see the relationship that he and Chris Finch build here. They both seem like guys you’d drink a beer with, which is far and away not a typical trait for NBA executives and coaches.

Plus, at least for now, Tim Connelly and Sachin Gupta will form one of the best 1-2 front office punches in the NBA, which isn’t nothing.

AC: Echoing everyone above on talent evaluation, something this organization has been hit and miss on, with more misses. Just think, in the same draft Connelly snagged the heralded Jamal Murray pick, Tom Thibodeau took Kris Dunn just two picks earlier! But more than anything, I’m looking forward to the guarantee of competence in the Timberwolves organization. Ownership will not get in his way, nor will he or Chris Finch get in each other’s way. In fact, they sound like they’d even get a beer together!

Tim Connelly may or may not work out as the president of basketball operations for the Minnesota Timberwolves. But I look forward to Minnesota no longer being the laughing stock of the league with how it treats players/agents/its approach to the roster.

LA Clippers v Minnesota Timberwolves - Play-In Tournament Photo by Jordan Johnson/NBAE via Getty Images

Do you have any concerns about the move? Do they outweigh your excitement?

JB: I initially had concerns about the potential of Connelly being a guy who would want to make his own imprint on the team right from the jump and bring in a mostly new front office, but The Athletic’s Jon Krawczynski reported on that front on a Monday evening appearance on KFAN.

If Connelly decides to trust the team in place and keep those who have experience working with Gupta, while bringing on a few hires of his own, I will have next to no concerns, outside of the obvious one that Gupta could leave this time next year.

GS: I have no idea what the ownership stake part of Connelly’s deal means or what that will look like, so that’s on my mind. Other than that, I’m thinking about Sachin Gupta. It was just confirmed that he’ll remain with the Wolves as Executive VP, but I’m still curious to see how that shakes out. My concerns aren’t horribly serious, so I’m more excited than concerned.

LA: Not really. It’s not a concern but I am definitely curious about who Darren Wolfson is alluding to here:

LS: I don’t have any real concerns. My only concern is that I’m too unconcerned. Unlike Logan, I’m actually excited for TC to bring back Canis Alumnus, VJL, back home. As Kevin Garnett once said, “If LeBron can go home, why can’t I?” For those of you who aren’t as long in the tooth here at CH, VJL was an invaluable member of our comments section who created his own NBA draft models that were so impressive, he ended up getting scooped up by the Denver Nuggets staff around 2016. I’m 1000% of the belief that Connelly is going to bring our prodigal son back home, so I can’t quite say my excitement can be outweighed.

BH: The biggest concern I have is the potential loss of Sachin Gupta in the near future. The press release mentioned that Connelly and Gupta would be working together, but that doesn’t mean it will be a long-lasting thing. Gupta has had chances to run teams in the past and he surely will again soon. The reason losing Gupta is worrisome is due to his extensive knowledge of the Collective Bargaining Agreement. He’s likely had his fingerprints all over some of the bargain contracts that the Timberwolves have. If there isn’t someone who could replace that when he’s gone, well then I’d be a bit concerned.

Does this move raise the ceiling of the team? Why or why not?

JB: That should be the expectation. Like I said previously, the credibility Connelly brings in, combined with the front office team in place, should raise the ceiling for what is possible in Minnesota. At minimum, this team needs to win a first-round series next year. There is too much talent on the roster and too many assets available to the front office for this roster to not be markedly better next season.

GS: Certainly. I’d assume under Connelly that this team continues to get better via the draft, which should be more than enough to improve the ceiling of the team. Connelly’s hits have been good (MPJ, Jamal Murray, Nikola Jokic, etc.), but he’s also missed on guys like Emmanuel Mudiay.

Allowing Connelly to deal with draft/scouting stuff and Gupta to deal with salary cap/financial stuff seems like a really logical choice. It’s natural, allowing each of those two to do what they’re best at. Not forcing them into other responsibilities could turn out to make for a really strong group.

LA: In theory, yes. While Sachin Gupta is great at his job, Connelly is more renown and has a fantastic track record. If you can pair them together (which sounds like it’ll be the case for at least this year) then you’re really cooking with a duo that seem to cover one another’s weaknesses. If Minnesota’s cap flexibility for the 2023-24 offseason remains the same, they’ll have a brilliant front office to handle max cap space.

LS: Absolutely. Though recency bias may have us thinking the Nuggets haven’t had significant postseason improvements (2021 they were swept by an NBA finals Suns team, 2022 they were injured-ravaged and lost to a likely NBA finals Warriors team), it’s hard to argue that Connelly didn’t build on the Nuggets success during his tenure there. If you take a look at when he took over as their head decisionmaker to start the 2017-2018 season, they ended up finishing with a record of 46-36. Do you remember what the 2021-2022 Timberwolves record was? That’s right. 46-36. Spooky. TC was able to build on that first season and subsequently get Denver to the WCSF and WCF. If that’s the future for this Wolves team, sign me up.

Connelly took over as POBO for the Denver Nuggets in the summer of 2017.

BH: I think it does. How much? I’m not really sure. The cornerstone pieces seem to already be in place, so most of that ceiling has already been set by the skill level of Anthony Edwards and Karl-Anthony Towns. I think the biggest key to raising the ceiling of the team is continuity. I know that this is yet another chance during the KAT era, but Connelly and Finch both have multi-year contracts and it seems that those two would have to royally screw something up to lose their jobs.

AC: 100%. Not even in just making marquee moves, but Connelly has clearly shown the ability to grow an elite bench pretty much out of the ground. I would expect more ideal supporting pieces to around the already-selected cornerstones in Karl-Anthony Towns and Anthony Edwards. The difference in Minnesota? Connelly will have one of the league’s most elite trade facilitators alongside him.

How would you evaluate the moves Marc Lore/A-Rod have made so far?

JB: 9/10 thus far. The aggressive mentality to change what is possible and what the external perception of this franchise is has been a pleasure to watch. Taylor has essentially accepted the status quo, which makes this infusion of energy and ambition a joy to see.

GS: Considering what Glen has done (or not done) during his time, they’re killing it. I’m honestly not even thinking about the moves that they’ve made so far as much as I’m thinking about them just being pleasant. Posting on social media, having a good time at games, getting involved with fans, etc. is just cool to watch. They’ve brought some life to the organization (along with Ant, of course), which just makes things so much more fun. Even if they end up making a few questionable moves, I like seeing them doing things and just not being Glen.

LA: If we’re giving them a grade, I’m going to have to cop out and say incomplete. Many ownership groups seem to be fine with buying the team and more or less standing pat. Marc Lore and A-Rod clearly had a vision and it’s very intriguing to see it unfold in real time. I wouldn’t be shocked to see the experience of being a Minnesota Timberwolves fan totally change in a good way.

LS: In true Timberwolves fashion, I evaluate their moves more from a “What have they done wrong?” lens. From that perspective, I’m happy. If I’m remembering correctly, they canned an ethically suspect POBO, “empowered” Gupta, got fans taking their shoes off, brought in Tim Connelly, and like the others said, are just having a good time. That’s grounds for at least a “Pass” until things shake out in the coming years.

BH: I’d give them a 8/10, I think. Giving Sachin Gupta the ability to re-sign Chris Finch to a multi-year contract was a good move. Bringing in a well-respected POBO is, at least in theory, a feather in their caps as well. Overall, I like the change of pace they’re bringing with the aggressiveness and desire to be great. However, I had to knock one point off for each of Marc Lore’s shoes that get taken off his feet early in a blowout.

Los Angeles Lakers v Minnesota Timberwolves Photo by David Berding/Getty Images

What needs to happen next?

JB: Connelly needs to nail the use of the team’s draft picks. Obviously there is some “learning on the fly” that will happen — and there’s only a month left until the draft — but Connelly made his way as a scout and has been prepping for this draft, as has his new colleagues at Mayo Clinic Square. The Wolves have four selections in this year’s draft (one first-round pick and three second-round picks), including two in the top 40 (No. 19 and No. 40). That is plenty of ammunition to either move up draft a high-ceiling rookie on the fringes of the lottery and/or package the pick(s) with a player on the roster to net an impactful veteran player. Regardless of what path front office takes, they cannot afford to mess this up.

GS: I was going to say figure out the Sachin Gupta situation, but looks like they got that nailed down (hopefully for more than just one year). Next on the list would be the draft/free agency, which I’m hoping Connelly does something with the Wolves draft capital (No. 19 and three SRP’s). Hitting on/making a beneficial move with those picks is absolutely huge, as this is a really important summer to add to this roster and take another step forward.

The D’Angelo Russell situation is also on my mind, not as something that needs to be addressed immediately, but just as a tough situation that Connelly will likely have lingering in the back of his mind from the moment he gets moved in.

LA: I’d imagine Tim Connelly, Chris Finch, Sachin Gupta, and the ownership group sit down for some Arby’s and have a chat about who on this team is going to stay and who is going to go. There are plenty of dominos that need to fall this offseason. Karl-Anthony Towns has a max (potentially super-max if he makes an All-NBA team) contract extension looming, a potential D’Angelo Russell trade, and/or a different potential trade (or draft pick) that would bolster the teams front court. There are many different ways this offseason could go.

LS: I like Logan’s Arby’s scenario. As mentioned above, maybe invite KAT & D’Lo in to discuss their next contracts over a couple Beef ‘N Cheddars and curly fries. I think those big dominoes are the most pressing things to figure out this offseason so that there isn’t a weird looming “Is D’Lo working for the weekend until the trade deadline?” cloud that hovers over every 4/15 shooting performance he has early next season. I know it sounds cheesy and a bit overplayed, but the whole “alignment” thing is important. Make sure Sachin, Finchy, Ant, and the rest of the gang all understand what the game plan is moving forward for the next couple years. The last thing we want to see is another reaction tweet if Connelly & Co. trade for say... Jimmy Butler.

BH: The draft. The Timberwolves have four picks, but I find it hard to believe that they’ll leave draft night with 4 rookies on the roster. I think that Connelly and Co. need to find value to move up on draft night or get themselves a useful rotation player with a couple of those picks. The Wolves need to make a positive step this offseason, because it seems the Western Conference will be healthier and tougher next season. Make a meaningful move with the picks and get ready to roll.