Ranking the Best GMs in Minnesota Timberwolves History

The history of the Minnesota Timberwolves is chock-full of off-court drama, lottery misfortune, and stars and superstars coming and going over the team's relatively young 37-year history. Still, the franchise can be summed up relatively simply.

This is an expansion squad that began play in 1989 and was consistently bad until drafting a future Hall-of-Famer in 1995. The Wolves made their first playoff series less than two years later but somehow only managed to get out of the first round of the playoffs once in the first 34 years of the team's existence.

The current era of the Wolves, under President of Basketball Operations Tim Connelly and coach Chris Finch, has already included three seasons advancing past the first round, including two Western Conference Finals. There had only been one of each in the entire history of the franchise— and the feats occurred in the same season.

A couple of quick clarifiers before we get started. First, we're using the term "general manager" liberally here. The Timberwolves have often employed presidents or vice presidents of basketball operations with a general manager underneath the head executive. The intention here is to evaluate the person who led the basketball operations effort, and in many cases, the actual title was not GM. However, we'll use the term to cover all heads of basketball operations we're ranking in this article.

Additionally, we are not ranking the four general managers who carried interim tags after their predecessors were fired but prior to the role being filled on a "permanent" basis. Jim Stack (2008-09), Milt Newton (2015-16), Scott Layden (2019) and Sachin Gupta (2021-22) all held the job for multiple months, but none of them made consequential trades or signings. Therefore, they aren't on this list.

Let's dive into the gnarly world of Timberwolves general managers...

1. Tim Connelly (May 2022 to present)

Sure, there's no draft capital in the cupboard. But as already established, the Wolves advanced beyond the first round of the playoffs once in 33 years prior to Connelly's hiring and have already done it three times since he took the job.

Yes, Anthony Edwards and Jaden McDaniels were drafted by his predecessor. But Connelly immediately got to work after he was hired, trading for future Hall-of-Famer Rudy Gobert to raise the floor of the team's defense and support a young Edwards.

The move, along with the free agent signing of Kyle Anderson, virtually guaranteed that he would be presiding over a playoff team. Later that same season, he traded for Mike Conley and Nickeil Alexander-Walker in a steal of a move, shoring up the Wolves' backcourt for the next few seasons.

He went on to re-sign Alexander-Walker to a bargain contract the following summer, re-signed Naz Reid, and reworked the contracts of Gobert and Julius Randle to open future opportunities based on the realities of the NBA's cap restrictions.

Connelly has already spun the Wolves through two contention windows and iterations of the team built around Edwards: the Gobert and Karl-Anthony Towns pairing and the Gobert and Julius Randle pairing. The team made the conference finals with each frontcourt duo, and now, the Wolves are on the third version of the team under Connelly and Finch with the acquisition of LaMelo Ball.

The team has gone 196-132 (.598 winning percentage) with Connelly at the helm, easily the best mark in Wolves franchise history.

2. Gersson Rosas (May 2019 to September 2021)

Gersson Rosas took over following the firing of Tom Thibodeau and a few months of Scott Layden leading the charge. He was handed a roster that had been largely gutted to A) acquire Jimmy Butler, and B) send him to Philadelphia with very little in return (more on that later). The Butler saga cost Thibodeau his job, and the cupboard was bare when Rosas took the job, outside of Towns, who was the No. 1 overall pick and Rookie of the Year in 2015 and was already a two-time All-Star.

The first move Rosas made was to trade up to the No. 6 pick in the 2019 NBA Draft. The rumored target was Darius Garland, which would have been great. Instead, he ended up with Jarrett Culver, who was out of the league by 2023—easily the worst move of Rosas's tenure.

But that summer he also inked undrafted free agent Naz Reid to a two-way contract. Reid quickly earned a partially-guaranteed deal with a fantastic performance in Las Vegas Summer League and famously turned into a Sixth Man of the Year Award winner and eventually land two lucrative contract extensions from the Wolves.

Just before the COVID-19 pandemic hit, Rosas took a huge swing across two separate trades, sending seven players out, including Andrew Wiggins, and bringing back All-Star guard D'Angelo Russell and six additional players. Russell was close with Towns, and Rosas envisioned a dynamic pick-and-roll duo coming together.

The pandemic disrupted the season, pushing the 2020 NBA Draft to November. The Wolves won the lottery and selected Edwards while Rosas also swung multiple draft night trades, bringing Ricky Rubio back to Minnesota as a mentor for Edwards and landing the No. 28 pick, which became Jaden McDaniels.

Rosas eventually fired head coach Ryan Saunders and replaced him with Finch, and, just prior to being fired, traded for Patrick Beverley, who played a significant role in bring the Wolves to the playoffs the following year. Rosas was fired just prior to the 2021-22 season in part due to an inappropriate relationship with a team employee.

Signing Reid, hiring Finch, drafting Edwards and McDaniels, and making enough moves on the edges to allow the Wolves to field a perennial playoff contender absolutely outweighs the Culver misstep, and Rosas is a fairly obvious No. 2 on this list.

No. 3 Kevin McHale (May 1995 to December 2008)

This is a tough one. McHale is by far the longest-tenured Wolves general manager, but he also grossly mismanaged the roster around a Hall-of-Famer for more than a decade.

McHale ranks this high for one reason: he drafted Kevin Garnett. The selection of a Hall-of-Famer and top-25 all-time player in the first draft that he ran meant that McHale made the playoffs in eight consecutive seasons starting in 1996. However, the Wolves only advanced out of the first round once, and that 2003-04 season was also the only time that Minnesota held a top-two seed in the West.

There were plenty of missteps along the way, and the Joe Smith contract scandal led to many of them. The Wolves lost three first-round draft picks and missed badly on most of the ones they did make: Paul Grant, Ndudi Ebi, and Rashad McCants were three of the Wolves' five first-round picks from 1997 to 2005.

He did pick a solid regular (Rasho Nesterovic) and a one-time All-Star (Wally Szczerbiak). But in 2006, he inexplicably drafted and traded Brandon Roy to Portland for Randy Foye. His 2007 selection of Corey Brewer was fine, and the decision to trade for Kevin Love on draft night in 2008 aged incredibly well.

Overall, the Wolves were 527-526 (.500) with McHale in charge. The drafting of Garnett was the most significant move in franchise history, and his selections of Szczerbiak and Love were solid, too. But the mismanagement in trades and free agency were undeniable, and the Wolves only ended up with one playoff run to show for having one of the best 25 players to play in the NBA on the team for 12 seasons.

4. Tom Thibodeau (May 2016 to January 2019)

Following the passing of Flip Saunders in fall of 2015, Milt Newton led the front office during the 2015-16 season. He was replaced by Tom Thibodeau, the hard-driving former head coach of the Chicago Bulls and former top lieutenant to Doc Rivers in Boston when the Celtics won a championship in 2008.

Thibodeau was a solidly above-average coach, that much was clear. But owner Glen Taylor also gave Thibs the keys to the front office, and that came with a significant amount of risk.

Thibodeau drafted Kris Dunn over Jamal Murray in his first draft and led the Wolves to a 36-win season. The following summer, he swung a draft night trade to land three-time All-Star Jimmy Butler, who played for Thibs in Chicago.

To complete the trade, Thibodeau moved down in the draft, passing on Lauri Markkanen and landing Justin Patton, who would only play in 22 NBA games due to recurring injuries. He also sent out Dunn and Zach LaVine.

The Wolves won 47 games that season, earning Minnesota's first playoff berth in 17 years. But Butler did not mesh well with Wiggins or Towns and made life miserable for everyone in the organization leading into the 2017-18 season.

He gave the infamous interview with ESPN's Rachel Nichols and plenty of carefully-crafted messaging was leaked via Butler's camp that painted Thibodeau, Layden, and Wiggins and Towns in a less-than-positive light. Butler played in just 10 games that fall before he was sent to Philadelphia, and Thibodeau did not exactly get requisite value in return.

The Wolves went 15-12 following the Butler deal and had a record of 19-21 on the season when Taylor opted to fire Thibodeau and install Ryan Saunders as interim head coach.

Thibodeau's legacy is that of acquiring Butler and ending the playoff drought, but also allowing Butler to burn everything to the ground—including his trade value—on his way out the door. With a Butler-less roster, the Wolves went 19-45 in the pandemic-shortened 2019-20 season before Rosas ushered the organization into the Anthony Edwards era.

5. Flip Saunders (March 2013 to October 2015)

Flip Saunders was Kevin McHale's head coach for the vast majority of the Kevin Garnett era, and until Finch came along, was by far the most successful coach in franchise history.

He was unceremoniously fired during the 2004-05 season and immediately hired by the Detroit Pistons, who he took to the Eastern Conference Finals in three consecutive seasons. A couple years after an unsuccessful stretch with Washington, Saunders ended up back in Minnesota but this time in the front office.

This Saunders era may be remembered for his re-acquisition of Kevin Garnett, but the totality of his moves were actually fairly solid. He quickly traded for Kevin Martin to pair with head coach Rick Adelman and slot in next to the burgeoning pick-and-pop duo of Rubio and Love; the team won 40 games but was in playoff contention prior to Rubio's torn ACL.

Saunders also presided over the trade of Love to Cleveland in exchange for the 2014 No. overall pick, Andrew Wiggins, an unavoidable move that at least netted the Wolves a high-upside potential future star.

After Adelman retired and Saunders named himself to the bench to preside over a bottom-out season with no Love, Saunders selected Towns No. 1 overall the following summer. He then brought in veterans Tayshaun Prince and Andre Miller to help with the development of Wiggins, Towns, and Rubio. Sadly, Saunders became ill and passed away that fall just prior to the season.

6. Jack McCloskey (June 1992 to May 1995)

Trader Jack McCloskey was the architect of the famed Detroit Bad Boy Pistons and was brought in to stabilize a young franchise that went wayward quickly. Things didn't work out, however.

His biggest moves were trading away original Wolves Tony Campbell and Sam Mitchell. He also drafted Donyell Marshall No. 4 overall in 1994 and shipped him to Golden State in exchange for Tom Gugliotta less than a year later. Overall, the Wolves went 60-186 (.244) during McCloskey's tenure.

7. David Kahn (May 2009 to May 2013)

There's far more to unpack here than we have space. Let's just say, the first move he made was unquestionably the best move he made during his tenure: trading veteran role players Mike Miller and Randy Foye to Washington in exchange for the No. 5 overall pick in the 2009 draft.

Infamously, Kahn drafted Rubio and Jonny Flynn with the No. 5 and No. 6 picks, passing on Steph Curry. Kahn's post-draft media tour only made things seem worse, and he apparently had some pretty off-the-wall ideas about how the roster construction could work.

There was the 2011 trade-back saga, when Kahn continually traded down on draft night, presumably to raise funds for a buyout of head coach Kurt Rambis. Hiring Adelman later that offseason and signing Andrei Kirilenko were strong moves, but Love broke his hand (remember knuckle push-ups?) and was limited to just 18 games. The team went 31-51, and Kahn was out.

8. Billy McKinney (1988 to November 1990)

McKinney was put in charge of the Wolves front office as an expansion team. The selection of Pooh Richardson in the draft and the initial roster was fine. Not much else that happened was consequential, and his exit was unceremonious.

9. Jim Brewer (December 1990 to June 1992)

Brewer took over after McKinney left and presided over one draft, selecting Luc Longley at No. 7 overall in 1991. Longley played 2.5 seasons in Minnesota before he was traded to Chicago in exchange for Stacey King.

His only other move was to fire Tyrone Corbin and replace him with Jimmy Rodgers, who proceeded to put up a 21-90 (.189) mark and get fired only 29 games into his second season on the bench.