A (not very) definitive ranking of Tom Thibodeau’s major moves with the Minnesota Timberwolves

On a Sunday afternoon full of news, from Patrick McCaw’s continued journey to Cameron Payne replacing McCaw with the Cleveland Cavaliers to the drama surrounding Chandler Parsons in Memphis, the Minnesota Timberwolves “won” the news cycle, announcing their firing of head coach and president of basketball operations Tom Thibodeau. Thibodeau signed a five-year deal worth a reported $40 million in April 2016, leaving roughly $20 million on that deal for owner Glen Taylor to pay out, on top of whatever he’ll pay to Thibodeau’s replacements in the front office and on the bench. They will hire two separate replacements for Thibodeau’s combined job, as the league as a whole has moved away from the president/coach combination after some high-profile failures. Thibodeau was among a very small fraternity that seemed to lose members every year, from Stan Van Gundy in Detroit to Mike Budenholzer in Atlanta. Now, the sole remaining member is Gregg Popovich in San Antonio.

Thibodeau, the once innovative and modern defensive coach with the Boston Celtics and Chicago Bulls earlier in his career, had seen the rest of the league catch up to his creative schemes and wasn’t able to continue to think up new ways for his team to stay ahead of the competition. The result was a Minnesota team that was inexplicably unable to truly unlock the full ability of one Karl-Anthony Towns, who should see a nice bump in production as a result of a regime change. Whether it will be enough for him to make an All-NBA team (and thus earn an estimated $31.6 million more on his five-year extension) remains to be seen.

Now that Thibodeau has been relieved of his duties with the Timberwolves, it’s worth taking a look back at his major draft picks, signings, and trades over the last two and a half years with a bit of hindsight and some thought to what he and his staff were thinking at the time of each one.

Tier 1 – no-brainer positives:

The aforementioned Towns extension is going to be essentially the entirety of Thibodeau’s positive legacy in Minnesota. Despite some of their struggles to put him in the best position to succeed and his defensive struggles under a coach with a strong reputation on that end of the floor, Towns is one of the great young players in the league right now and still has significant time to improve upon his weaknesses. One of the best offensive big men in the league, signing Towns to a full five-year max extension was the top of the Timberwolves’ priority list over the summer. While it took a couple months longer than they initially wanted (mostly due to the Jimmy Butler saga), they did eventually get the deal done. Thibodeau was also able to put together a five-year deal with no player option for Towns in the final season, which gives the team a bit more control over their superstar.

Despite how it worked out in the end, the initial trade for Jimmy Butler has to be included among the best moves Thibodeau made while in charge. Pretty much everything Butler-related that happened after the trade, most of which is on Coach Thibodeau, turned the move into a black eye on the entire organization, but President Thibodeau deserves credit for making the initial deal to bring a second superstar to Minnesota during the 2017 draft. Getting back the No. 16 pick was icing on the cake for the Timberwolves, who had to part with Zach LaVine, Kris Dunn, and the No. 7 pick in 2017 to make the deal they thought would solidify a partnership between Butler and Towns for the next several years. We all know how it worked out, but the thinking at the time was that the move was fantastic.

Tier 2 – clear positives:

Speaking of the mercurial Butler, Thibodeau’s patience in making a trade and ability to wrangle multiple useful players out of the Philadelphia 76ers has to go down as a solid move on his ledger. What pushed Butler to the point that he wanted out and pushed Towns to threaten to not sign the extension until he was sure Butler was on his way out is going to be Thibodeau’s overriding legacy in Minnesota, but once those two things were established, the deal to obtain Robert Covington, Dario Saric, Jerryd Bayless, and a 2022 second-rounder for the same package they received from Chicago about a year after making the initial move was admirable. Nobody involved, from Butler to Towns to Thibodeau to Taylor, came out the other side of the situation looking good, but the move to strengthen their depth and get back a two-way wing in Covington was strong.

Unfortunately for Thibodeau, two of the three best moves he made essentially offset one another. In hindsight, Minnesota is in a worse position now than before the Butler trade happened, as the package of Lauri Markkanen, whom the Bulls selected No. 7, LaVine, and Dunn would be much better than the Covington-Saric-Bayless-pick quartet that arrived from Philadelphia. Covington is probably the best player of the non-Butler pieces involved in these two trades, but Markkanen has the highest ceiling and the best contract situation and Dunn has looked the part of a competent starting point guard and fits their long-term timeline with Towns. Whether LaVine still picks up a massive offer sheet from Sacramento last summer or not if Minnesota never moves him is unknowable, but even if he had and the Timberwolves let him walk (as Chicago should have done), the Markkanen-Dunn combination would likely be preferable to the Covington-Saric duo.

Tier 3 – slight positives:

Drafting Dunn was Thibodeau’s first move as the head of the club’s decision making, and while hindsight doesn’t exactly view that move as favorable, the pick was perfectly fine at the time. Looking back now, Minnesota would have been much better off with Buddy Hield or Jamal Murray, taken with the next two choices after Dunn, but there’s really no use in grading drafts in hindsight. In the moment, Dunn looked like a great choice for Thibodeau team. There were certainly experts who clamored for Murray to be taken higher than he was in that draft, but Dunn was a consensus top-five pick and was viewed as a good pick for Minnesota at the time. His eventual inclusion in the initial deal for Butler helps seal the deal as making his pick a positive move for Thibodeau.

Two years later, Minnesota were choosing further down the board in both rounds but picked up Josh Okogie and Keita Bates-Diop. While much, much too early to judge either player, there was little negativity surrounding each guy in their respective draft slots in the immediate reaction to draft night. Okogie has been a consistent rotation piece for the Timberwolves this year and while Bates-Diop hasn’t quite gotten his shot for the big club, he’s flashed a lot of what made him an interesting prospect in the G League, where he’s putting up 18 and 9 for the Iowa Wolves.

As divisive as he is on and off the court, it has to be said that the Derrick Rose signing this past summer has paid dividends for the Timberwolves. The morality of giving Rose a platform to continue his career after his significant off-court transgressions is not for me to judge in this space (I’ve been plenty vocal about that on other platforms), but purely in an on-court sense, he’s been a very nice piece for their team this year. Only making the league minimum on this one-year contract, Thibodeau’s ability to coax the most out of Rose’s remaining skill set was admirable.

Another 2018-19 signing, Anthony Tolliver was coming off the best year of his career with the Detroit Pistons when the Timberwolves signed him to a one-year deal worth a good portion of their mid-level exception. The thought of Tolliver bombing away from the perimeter while Towns went to work on the block was an exciting one, but this was another situation in which Coach Thibodeau worked against what President Thibodeau did just months earlier. Tolliver hasn’t appeared at all in about 40 percent of Minnesota’s games this season as Thibodeau favored playing Taj Gibson or Gorgui Dieng ahead of him in the rotation for reasons that remain unclear. Tolliver’s acquisition and immediate burial in Minnesota’s rotation is a massive indicator of Thibodeau’s internal fight between catching up to the modern NBA and sticking with the things with which he’s most comfortable, especially defensively, despite all data to the contrary.

Tier 4 – slight negatives:

Now that we’ve gotten through the good moves Thibodeau has made, it’s time to start in on the bad side of things. Nothing in this tier was likely part of the calculation that ended in his termination, but rather moves that created small negatives for the Timberwolves during his tenure.

In a vacuum, picking up a lottery-protected first-round pick for Ricky Rubio in 2017 would have been listed among the positive moves. At that time, Rubio had two years left on his four-year, $56 million deal he signed under the previous regime and his time had run its course in Minnesota. The future was in Towns and the freshly-acquired Butler, who had arrived about a week before Rubio was shipped to Utah. The move also opened significant cap space for the Timberwolves to use on the open market to add to their core.

The problem is that just hours after agreeing to the Rubio trade, news broke that Thibodeau had agreed terms with Jeff Teague on a three-year deal worth $57 million, with a player option on Year 3 to boot. Given the tight window between these two transactions, it feels more correct to treat it as one big deal. To his credit, Teague had just completed a solid year in Indiana in which he posted per-100 averages of 23.6 points and 12.0 assists, the latter being a career high for the veteran point guard, and played in all 82 of the Pacers’ games. Meanwhile, Rubio had stagnated slightly in a Timberwolves jersey and likely didn’t have a lot more upside to explore under Thibodeau. He’s thrived in Utah, which just twists the knife on the deal for Minnesota, but it’s unlikely that he would have been able to produce as he has for the Timberwolves.

The negative side of this deal has to do with the financial outlay. Would you rather have Rubio on a deal that pays him $14 million through 2019 or Okogie and Teague on a deal that pays him $19 million through 2020? It’s very close and could easily be viewed as a positive, but I think the best outcome for Minnesota was somewhere in the middle; trading Rubio for the pick that became Okogie was a great deal for them, but then using that extra cap space on Teague (and Taj Gibson, whose two-year, $28 million deal also belongs in the “slight negatives” tier) was a poor use of their newly-available resources.

The Rubio-Okogie-Teague swap could really come down on either side of the ledger, but the $28 million move for Gibson, when they already had Dieng on the books for an extended period and had just drafted Justin Patton, was as perplexing at the time as it is now. Gibson’s a fine player and has held up better than I had expected over the last two years, but the higher dollar figure makes this a negative move.

Another of Thibodeau’s favorites from his Chicago days, Luol Deng signed with the Timberwolves after being let go by the Los Angeles Lakers earlier this year, but has played just 32 minutes and is essentially just taking up a roster spot they could use on a younger player who might fit better in their team long-term. With Thibodeau ousted, it’s worth wondering whether Deng is not far behind his old coach. On the other hand, the Timberwolves may value his veteran leadership behind the scenes in a way that makes an impact on the floor even if Deng himself doesn’t see a ton of playing time.

Wrapping up this tier is the long-ago signing of Jordan Hill, who was given a two-year, $8 million contract in the summer of 2016 to add to the team’s center rotation. Hill played just 47 minutes in his lone year in Minnesota before Thibodeau moved on from him with no future cost, as the second year of that deal was non-guaranteed. In keeping with the theme of Teague and Gibson (but at a much smaller value), the issue with taking the flyer on Hill isn’t the fact that they did it at all, but the value they placed on him with that contract.

Tier 5 – clear negatives:

In addition to Hill, Thibodeau brought in another big man in his never-ending quest to play as many of those guys as possible. Cole Aldrich signed a three-year, $22 million deal with Minnesota in the same summer as Hill; Taylor will be paying Aldrich through 2021 after the team decided to stretch his final partially-guaranteed year this past offseason. Aldrich, who never lived up to his pre-Minnesota days with the Clippers, was an immense flop for the Timberwolves.

Later that summer, Gorgui Dieng agreed terms with Minnesota on a four-year rookie scale extension worth $64 million. With three years (including this one) left on that behemoth, Dieng joins the pantheon of his center brethren on massively negative contracts signed in 2016; the only problem is that Dieng’s deal runs one year longer than some of his compatriots. All of Timofey Mozgov, Bismack Biyombo, Ian Mahinmi, Meyers Leonard, Joakim Noah (already stretched) will or would have seen their contracts expire in 2020, but because Dieng’s was a four-year extension, Minnesota won’t see his salary disappear until 2021, unless they’re willing to move multiple first-round picks or equivalent assets to move him.

Circling back to the initial Butler trade, the separate decision to draft Justin Patton at No. 16 has to be the worst pick of Thibodeau’s tenure in Minnesota. The overarching theme of overvaluing big men struck again with this pick; instead of trying to fill out the roster with players who fit around Butler and Towns, Thibodeau went with yet another big guy to add to a roster that already had Towns, Dieng, and Aldrich and would go out into the market to sign Gibson to his deal about a week later. Even if Aldrich and Gibson weren’t long-term pieces in Minnesota, Towns and the recently-extended Dieng certainly were and using a mid-first on another center was really poor.

Of all of Thibodeau’s major moves while in charge of the Timberwolves, the signing of Jamal Crawford to the full Room Exception with a player option for Year 2 in 2017 was perhaps the most inexplicable. Crawford had turned 37 during the 2016-17 season and had long, long seen his usefulness wane; he hadn’t been a positive contributor for his team since at least 2013. A defensive sieve throughout his career, he was never worse than his one year in Minnesota, when his team was more than 10 points per 100 possessions worse with him on the floor than when he sat. That was a trend that permeated his entire career; it’s not as if he was a once-good defender who fell off a cliff at the wrong time. On the other end of the floor, Crawford’s ability to hit difficult shots always outweighed all the misses. He hadn’t been a member of an above-average offensive unit since his last year in Portland, way back in 2011-12. All told, the Crawford signing was about as useful to Minnesota as lighting more than $4 million of Taylor’s money on fire. The only saving grace was that the club was such a mess internally that he opted out of his $4.5 million contract for this year to go play for the minimum in Phoenix.

Tier 6 – the franchise killer:

Is it unfair to slap Thibodeau with the full brunt of the Andrew Wiggins extension? Probably. That deal was just as much about ownership as it was about Thibodeau, but given how much power he had within the organization, he still gets significant demerits for not throwing his body in front of what was widely thought to be the worst contract in the league the moment the details were released publicly. For the most part, Wiggins has lived up to every negative pre-extension expectation; he’s a volume scorer in an age that values efficiency above all else and brings essentially nothing else to the table. He hasn’t been able to translate his athleticism into above-average defense and does nothing offensively to make his teammates better. An inefficient scorer in the best of circumstances, Wiggins is just halfway through the first year of a five-year max extension that will pay him more than $147 million before it comes to a merciful end in 2023. There have been other contracts which have joined Wiggins in the Stratosphere of Terribleness, but it’s hard to imagine that even John Wall can surpass the massive chasm between player and salary that exists between Wiggins and that $147 million.

Purely from the perspective of his work in the Timberwolves’ front office, Thibodeau had some good days, some bad days. The initial move to get Butler from Chicago looked like a winner right up until the player forced his way out, but Minnesota was able to salvage that situation and get a pair of quality role players who fit their current roster. Towns will outlast just about everybody in Minnesota and Thibodeau closing the deal on the full five-year commitment was positive for them. On the other side, massive extensions for Dieng and Wiggins put a major cloud on his reign, as well as the handful of smaller deals he handed out to his former players from his more successful Chicago days. All in all, Thibodeau won’t be remembered as much for his front office work as president of basketball operations as he will for his on-court work as head coach, which was a more spectacular failure in man management and modern inventiveness, but the final conclusion on his two and a half years in charge will not bring a ton of new offers to lead another franchise’s basketball operations in the near future, if I were to guess.