Could the Wolves’ big move to hire Tim Connelly actually … work?

When the Minnesota Timberwolves put on a show at this time of year, the song and dance typically doesn’t age well. 

There are more examples of this than anyone cares to consider. But in the interest of brevity, we’ll limit ourselves to the past eight years:

In June 2014, the Wolves called a presser to announce that then-President of Basketball Operations Flip Saunders was naming himself head coach. Owner Glen Taylor said the team underwent “an exhaustive process” before coming to the conclusion that Flip “was the stabilizing force needed to lead our team.” Except it was an open secret that Flip had come to that conclusion almost as soon as he was hired as POBO 13 months earlier. 

The “exhaustive process” was kabuki theater, meant to wear down Taylor, who frequently remarked that he didn’t want one person running both the front office and the sidelines. Flip’s tragic death disrupted his burgeoning rebuild, which stands as a single 15-67 season “tanking for Towns.”

In April 2016, the Wolves announced the hiring of Tom Thibodeau as both coach and POBO. Concerns about the infamously crusty, veteran-oriented Thibs being able to patiently rear the team’s pair of top overall draft picks were allayed by the story of his “sabbatical” visits to various NBA teams in the year he was off after being fired by the Bulls. “Your view of everything is so much broader,” he said of that period, likening it to a college professor expanding his horizons. 

But if Thibs was turning any pages, it was backwards, to chapters and coursework he sought to resurrect. He stocked the Wolves with his most loyal former players to reinforce the mentoring of the old ways. He took the Wolves to the playoffs that way, but when Jimmy Butler demanded a trade and Thibs seemed more sympathetic to him than the franchise he was running, his exit was only a matter of time. 

Then, in May 2019, the Wolves announced the hiring of Gersson Rosas as the new POBO. With a twin child balanced on each knee, Rosas stated that the Wolves organization would be run like a family. A trip to the Bahamas by players and other members of the organization was thoroughly documented as evidence of these good vibes. Within months, the vast majority of those players would be traded, and while Rosas should be given credit for an upgraded roster, he was undone by an extended dalliance with an underling that repulsed the staff who worked with them both and set the nail on the hypocrisy of his “team as family” vibe. He was let go just weeks before the 2021-22 NBA season. 

Picking some nits

All of which brings us to this week. On Tuesday afternoon, the Wolves announced Tim Connelly as their latest new POBO hire. For those chafed by the trifecta of the aforementioned Saunders, Thibodeau and Rosas pressers, there were nits to pick. 

Asked to describe how it was determined that Connelly was the best person for the job, Alex Rodriguez said “Glen (Taylor) was in charge of the process” and that he and his fellow minority owner Marc Lore were “following his lead.” But it has been common knowledge for weeks now that A-Rod and Lore had been bent on landing a high-profile, “top 5” new POBO for many months. Sure, as majority owner, Taylor was the one with the standing to ask the owners of the Denver Nuggets, Connelly’s employer, for permission to woo him. But Taylor admitted he wasn’t even aware that there was an option in Connelly’s contract with Denver that made him available. And it was only after Lore and A-Rod made real headway in their negotiations with Connelly that Taylor, again as majority owner, was brought in to essentially give his blessing and finalize the details.

For his part, Connelly waxed eloquently about the “special core” of players on the team, how it was “an attractive destination,” and how he could tell that the local populace was really excited about the Timberwolves. He heaped praise on the work head coach Chris Finch and interim POBO Sachin Gupta had in pointing the Wolves in a positive direction and persistently spoke in a self-effacing manner, saying he was “here not to mess it up,” and adding, “There is a real sense here that this team can do something special, and I hope to be a small part of it.” 

But the bottom line is that if the Nuggets had matched the Wolves’ magnanimous offer of a 5-year, $40-million contract (not counting performance bonuses that may or may not give him some equity in the team), Connelly almost certainly would have stayed in Denver. By the same token, the Wolves aren’t paying him that much money to be delicate with his involvement in the direction of the franchise. He will inevitably be responsible for the lion’s share of the credit — or the mess — that ensues.

Could this work? 

Just two weeks ago, I wrote that one of the three ways the Wolves could improve on their breakthrough 2021-22 season was by giving Sachin Gupta a two-year contract to ensure a unified chain of command and sustain the uncommon harmony that boosted this team into the playoffs. When news broke that Lore and A-Rod were seeking that “top 5” POBO to work alongside Gupta, I updated the column to reflect that the meddling was ratifying my fears that Gupta would be alienated by the disrespect and that the synergy wrought by the Gupta-Finch collaboration would be disrupted. 

In other words, it felt like the Wolves’ wretched history with POBO hires was about to be extended. 

But the past doesn’t have to be prologue this time around. Skepticism doesn’t have to harden into cynicism. Sure, for a long time now, when things are not what they seem with this organization, that usually means they are worse than you could have imagined. This time, a dispassionate view, one less marred by scar tissue, would indicate the opposite: that things are better. 

It is open to debate whether Connelly does indeed rank among the “top 5” POBOs in the 30-team NBA, but his credentials are solid enough. Denver has made the playoffs the past four seasons in Connelly’s nine-year tenure determining personnel for the Nuggets, including a trip to the Western Conference Finals in 2019-20. Recently, injuries have stalled the team’s development arc around two-time MVP Nikola Jokic, and Connelly’s signing of the injury-prone forward Michael Porter Jr. has hindered future flexibility. But even if you concede that landing Jokic in the second round turned out far better than anyone could have predicted, and was greatly abetted by Connelly’s assistant at the time, Arturas Karnisovas (now the POBO in Chicago), Connelly has a track record for getting good value out of the draft, especially outside the lottery, where the distinctions between players become finer. 

But the best reason to be excited about Connelly is his fit with the existing personnel in the front office and the coaching staff, and the way that could extend into the eventual transfer in ownership from Taylor to Lore and A-Rod. In that sense, all those nit-picks from Tuesday’s press conference become reassurances instead. 

Connelly’s faux self-effacement wasn’t disingenuous; it was meant to send a signal to Gupta and Finch that the timing of his hiring and the groundwork they have laid developing the roster are not taken for granted. By almost all accounts, Connelly is a “team player” in the true sense of the words; someone who seeks and values input from his colleagues. Like Finch, he has the reputation for being a straight shooter able to be congenial while not mincing any words. His transparent, blue-collar style was popular among the media and the fan base in Denver. When he noted that the first meeting with the minority owners occurred “in Marc’s palatial condo in New York City,” the dry humor in the class-conscious description rolled out of his mouth. But so did the sincerity in his voice when he said to the three owners, “Thanks for the transparency. Thanks for taking a chance.” 

Meanwhile, Lore and A-Rod seemed keenly aware of the circumstances, that they are minority owners engineering the hire of a new POBO at reportedly twice the size of his former salary. Time will tell if they will now exercise restraint and be content to bask in the refracted credit from anything Connelly accomplishes. But their targeting of Connelly feels like good judgment, and their deference to Taylor at the press conference, again, felt more like solidifying bridges than engaging in false modesty. The money quote from Lore on how things will proceed: “It’s not ‘trust but verify,’ it is just ‘trust.’ We have full trust and confidence in Tim.” 

A (potentially) great scenario

It is probably unreasonable to expect Gupta to stay on with the Timberwolves indefinitely, but it is hard to imagine a better scenario for the organization this season than having Connelly, Gupta and Finch working in tandem through the June 23 draft and the July free agency period. 

Like Finch’s right-hand man, assistant coach Micah Nori, Connelly’s roots in the game came as a scout and he is a hoops junkie who enjoys eye-testing personnel. Denver’s draft slot is the 21st pick this June, just two behind the Wolves, who select 19th, so a lot of Connelly’s draft prep and intel is transferable. And despite all his talk about not messing anything up, there was real joy in his voice as he envisioned everybody getting in a room together and arguing about the pros and cons of potential draft picks, only to emerge unified once the decision has been made.

Gupta made his bones through analytics and salary-cap management more than scouting, and is thus a perfect complement for Connelly, who might be criticized for overpaying some players that have come up through the organization. Along with pick 19, the Wolves will have three second-round choices, in slots 40, 48 and 50; just right for cheap but relatively lengthy contracts known as “Gupta specials” that bet on committing small but guaranteed money for players whose skills can be developed beyond that value. At least three Timberwolves — Jaylen Nowell, Jordan McLaughlin and Naz Reid — were on the roster that way last season, and the bargain signing of power forward Jarred Vanderbilt followed a similar pattern. 

Free agency will be a different sort of challenge. It would be a shock if the Wolves didn’t sign KAT to a “super-max” contract extension over the off-season, a choice for stability that will make it difficult to extend D’Angelo Russell at a price he is likely to deem acceptable. Not extending DLo also gives the Wolves a brief window to make a sizable free agent investment before KAT’s extension kicks in and the rookie contract of Anthony Edwards is torn up; but that in turn also limits how big of a plunge the Wolves can make upgrading the roster this offseason. The expiring contracts of Taurean Prince ($13.3 million) and Jake Layman ($3.9 million) provide some wiggle room, and Patrick Beverley will earn a million less on his one-year deal this season. Not extending a qualifying offer to Josh Okogie is another cost-saving measure. 

But then significant questions remain. Can DLo and the Wolves co-exist productively if he isn’t extended this offseason, and if not, what is the least painful and least destructive way to resolve the situation? How much cap space does the team husband for that sweet spot period before KAT and Ant both get massive raises, and how much do they spend now and hope to finagle later? Again, having the complementary skills of both Connelly and Gupta in the room, with significant, potentially decisive, input from Finch is a great scenario for the franchise. 

“100 percent alignment”

The relationship between Connelly and Finch is the most important one for the entire Wolves organization moving forward. The fact that they seem so temperamentally similar cuts both ways, especially if Gupta isn’t around to provide diplomatic grease. Connelly is under contract through the 2026-27 season, a year longer than Finch. The two were together for a single season in Denver, where Finch was an assistant coach and Connelly was general manager. 

Asked why Finch wasn’t retained, Connelly drew laughs by replying, “I have to be honest on day one?” Then he explained, “Chris was coveted and a team wisely targeted him. He went to New Orleans and did a great job.” 

Finch spoke with reporters off the side after the press conference for Connelly was over. He spoke of the potential synergy in the skill sets of Connelly and Gupta, approved of the way Connelly challenges people, and later expounded more broadly on the need for harmony. “We have a lot of really qualified and talented people in this building. There’s been 100% alignment. That’s the key with this, alignment from the ownership all the way down to the star talent. Surround that with the right like-minded talent — whether that be players or basketball ops staff — and you have a chance to keep building.” 

Finch also revealed that greater physicality among the frontcourt personnel would be a priority for the Wolves during the offseason, correctly noting that KAT’s versatility provided some flexibility in how those frontcourt tandems could be fashioned. But he also sounded an appropriate warning: “With a young team, there is maybe an inclination that we are going to pick up where we left off. That’s not going to be the case.”

And that is where Connelly, aided by Gupta as long as he’s here, can supplement with brawn, maturity and more options in general for Finch to wield. 

“There is no real plan yet,” Connelly flatly stated when asked about how we might address personnel needs. “I’m going to get here, get to know the team, understand what really allowed the team to be successful this year. Pick people’s brains and figure out how to fill some of those voids that allows this team to take the next step. 

“I have known Finchy since he was coaching overseas. He is a guy that has had diverse experiences on the bench and it has allowed him to become one of the best tacticians in the NBA. So I’ll rely on those guys; some really bright minds. But again, if I had to answer right now, it would just be a sound bite.” 

For the first time in a long while, however, the Wolves have people at the POBO and head coaching positions locked in for the long term who inspire enough confidence to surmount the entrenched cynicism from a dozen or more springtime press conferences gone bad.