How the Pistons, one of the NBA’s most storied franchises, cratered

The Detroit Pistons are one of the NBA’s most storied franchises. Yes, the same Pistons who have done nothing but toggle back and forth between mediocre and putrid for 15 years. Yes, the same Pistons who, on Tuesday night, set the NBA’s single-season record for most consecutive losses (27).

Yes, those Pistons.

Detroit has three NBA championships. Only five franchises have hoisted the Larry O’Brien trophy more. The Pistons won their three titles over three decades, starting in the late 1980s before briefly falling off and then coming back in the early 2000s to do it again. All different players from the first go-round. A whole new mantra and vibe. The true signs of a healthy organization. Do it, come back and do it again. Detroit also has five Eastern Conference titles. Only three rivals (Boston Celtics, Chicago Bulls, Miami Heat) have more.

This current iteration of Detroit basketball is on pace to be its worst over the last 15 years of meh-to-bad basketball. Let’s go a step further: This current iteration is on pace to be the worst NBA team ever.

A lot of things had to go wrong this season for the Pistons to achieve such an embarrassing milestone. But what you’re seeing now in Detroit has been 15 years in the making. Nearly two decades worth of poor drafting, poor roster decisions, poor management, injuries and restlessness, and too much reliability on luck.

This is how the Pistons got to today.

The most natural starting point is Nov. 3, 2008, when general manager Joe Dumars came to the conclusion that a shake-up was needed.

The Pistons of the 2000s were one of the NBA’s most consistent and dominant franchises. From the 2002-03 season to the 2007-08 campaign, Detroit’s season never ended any sooner than the Eastern Conference finals. The Pistons won a title in 2004 and nearly won again in 2005. However, after making it to the Finals in 2005, Detroit stalled out a bit. Stalling out to the franchise at that time was three straight trips to the Eastern Conference finals and no NBA Finals appearance to show for it.

With a starting group that referred to itself as “The Greatest Five Alive”— Chauncey Billups, Richard Hamilton, Tayshaun Prince, Rasheed Wallace and Ben Wallace — Dumars felt the squad’s inability to get back to the pinnacle signaled that change needed to come. Things were stale. So, on that day in early November, the Pistons traded Billups and Antonio McDyess to the Denver Nuggets for Allen Iverson.

Billups became the second core piece of the “Goin’ to Work” era Pistons to leave, as Ben Wallace had signed with the Chicago Bulls in 2006. In trading Billups, and failing to get back to the NBA Finals yet again, Dumars and company prepared the organization for a transition to its next phase.

That was never more evident than in the postseason of 2009, when Detroit was swept in the first round of the playoffs by the Cleveland Cavaliers after a 39-43 season with Iverson running the show. After the season, Iverson signed with the Memphis Grizzles, and Rasheed Wallace went to Boston. Detroit handed over the keys to the organization to Rodney Stuckey, the 15th pick in 2007, and “big-time” free-agent signings Ben Gordon and Charlie Villanueva.

From the 2009-10 season until the 2014-15 season, the latter being the first season of Stan Van Gundy as both head coach and general manager, the Pistons never won more than 32 games in a season. The franchise had five head coaches during that span. Detroit was bad but not bad enough — or lucky enough — to secure even a top-five pick in the NBA Draft.

These were Detroit’s first-round picks from 2009 to 2015: Austin Daye (No. 15, 2009), Greg Monroe (No. 7, 2010), Brandon Knight (No. 8, 2011), Andre Drummond (No. 9, 2012), Kentavious Caldwell-Pope (No. 8, 2013) and Stanley Johnson (No. 7, 2015). Four of those six were out of the league or barely hanging on by the age of 28. Drummond signed a max deal with the Pistons in 2016 but was never the franchise-altering player his money suggested (more on this later).

Caldwell-Pope went on to have a great career — he’s still going, lately as a key role player on title teams in Los Angeles and Denver. The Pistons did draft Khris Middleton (2012) and Spencer Dinwiddie (2014) with second-round picks in that time. However, the team grew impatient and moved both. Middleton, after his rookie season, was traded to the Milwaukee Bucks, along with Brandon Knight, for Brandon Jennings in a move the organization thought would help it get better quicker. Dinwiddie bumped heads with Van Gundy and was traded in 2016 for a guy who played 36 career NBA games, Cameron Bairstow.

Mistake after mistake piled up. Misfortunate after misfortune.

It eventually got better in Detroit, starting in 2015, but even a return to playoff basketball wasn’t enough to get the storied organization back to where it desired.

In fact, with time, it only got worse.

Early in Van Gundy’s tenure as team president and coach, the future finally began to look brighter. At the trade deadline of the 2014-15 season, the Pistons landed point guard Reggie Jackson from the Oklahoma City Thunder in a three-team trade. The backup to Russell Westbrook, Jackson earned an opportunity to run the show in Detroit, and it was worthwhile for both sides. Detroit missed the playoffs in 2015, but Jackson looked every bit the part of an above-average point guard.

In the summer of 2015, with the blossoming pick-and-roll chemistry between Jackson and Drummond looking like something worth building around, Detroit traded for Marcus Morris to help round out its starting lineup. At the trade deadline of the 2015-16 season, the Pistons added a 23-year-old Tobias Harris to its core. Detroit went on to have its first winning season (44-38) since 2007-08 and made the playoffs for the first time since 2008-09. While each game was competitive, the Pistons were eventually swept in the postseason by LeBron James and the Cavaliers. However, even though Detroit didn’t win a postseason game, the Pistons seemed to have a little something brewing.

Until, well, they didn’t.

There was a salary-cap spike in 2016, and that offseason, the cracks started to show in Van Gundy’s ability to be a team builder. The Pistons signed Jon Leuer to a four-year, $42 million contract, Langston Galloway to a three-year, $21 contract and Boban Marjanović to the same deal as Galloway. Those three, along with Harris, Johnson and Morris, as well as Jackson’s five-year, $80 million deal and Drummond’s max, meant Detroit was locked into its core for the foreseeable future.

The next season, in 2016-17, Jackson ended up missing 30 games due to knee problems as Detroit finished with a 37-45 record, missing the playoffs. The following season, the Pistons started off hot with a then-healthy Jackson, going 14-6 through their first 20 games. A losing streak in early December brought Detroit back to reality, but then its season took a huge blow in late December when Jackson suffered a grade-3 ankle sprain that would sideline him for three-ish months.

By early February, Detroit was hovering around .500. That’s when the Pistons decided to take a massive swing to try to get out of mediocrity.

The previous summer, Blake Griffin had signed a five-year, $173 million contract to stay with the LA Clippers. Los Angeles elected to pivot shortly after signing Griffin to the deal, and the Pistons, desperate to be playoff mainstays, were one of few — if not the only — teams interested in the oft-injured 28-year-old. Detroit gave up Harris, Avery Bradley, Marjanović and a first-round pick in a trade for Griffin. It surrendered any flexibility it had to go all in on a Jackson-Drummond-Griffin core to try to be playoff regulars.

While Griffin came to Detroit and immediately impressed to close the season, the loss of Jackson was too much for the Pistons to overcome. By the time Jackson came back, Detroit was 31-39 and pretty much out of the playoff picture. Van Gundy’s trade for Griffin was, essentially, for the following season. However, the coach wasn’t around to see it through.

After the Pistons missed the playoffs for the second straight year, Van Gundy and Detroit decided to part ways. In four seasons running the show in the Motor City, Van Gundy had just one playoff appearance. In signing Jackson and Drummond to those deals, and trading for Griffin, Detroit’s finances were tied up for the next few years. Furthermore, the Pistons’ draft misfortunes of the past continued under his watch.

In 2015, Detroit was deciding between Johnson and Devin Booker. It took the former. In 2018, the Pistons selected Henry Ellenson. He was out of the NBA by the age of 24. In 2017, Van Gundy and company decided to go with Luke Kennard over Donovan Mitchell. To put a cherry on top, the pick Detroit sent to the Clippers as part of the Griffin trade ended up being Miles Bridges, who was then traded to the Hornets for Shai Gilgeous-Alexander.

Van Gundy was replaced as head coach in Detroit by then-reigning Coach of the Year Dwane Casey. Ed Stefeanski took over the Pistons’ front office as a buffer until the organization found its next lead decision-maker.

In Casey’s first season, the Pistons made the playoffs, but it took, arguably, the best season of Griffin’s career for Detroit to squeeze in on the regular season’s final day. Griffin made an All-NBA team and put together one of the better player transformations in NBA history, going from a rim-twisting athletic freak to a point forward who made 36 percent of his 3s. Griffin had one of the best individual seasons in Pistons history in 2018-19.

In the end, it was all for nothing.

Griffin’s knee started to fail him as he carried the entire organization to the playoffs. He missed Detroit’s first two playoff games against Milwaukee and returned for the final two games only for the Pistons to get swept.

Griffin was never the same player again, and Detroit learned that early into the following season. The last of his superstar juice was used getting the Pistons to a 41-41 record and just their second playoff appearance in the decade. That’s when the Pistons and all of their decision-makers came to the conclusion that it was time to pivot to a true teardown rebuild.

The start of the 2019-20 season was the final straw for Detroit. The Pistons were 12-20 by Dec. 30 with a somewhat expensive payroll and aging, often-injured roster. Griffin missed 14 of the team’s first 32 games due to the effects of the knee injury the season before, and he was never the same player when he did play. Griffin eventually elected to get surgery in January and missed the rest of the year. He played in only 18 games.

At the February trade deadline of that season, the Pistons officially kicked off the rebuild. They traded Drummond, who still had another year left on his deal and little value around the league, to the Cavaliers for expiring contracts and a second-round pick. Jackson was eventually bought out that season too.

Most teams are able to get a kickstart on their rebuilds. Detroit started from below ground zero.

The Pistons finished the 2019-20 season with a 20-46 record (shortened season due to COVID-19), their lowest win total since 1993-94. In June, Detroit hired Troy Weaver, who had spent a decade in Oklahoma City as assistant general manager, to be its new general manager. The Pistons, one of the worst drafting teams in the NBA, identified Weaver because of his scouting and drafting background. The organization, for the first time, wanted to rebuild the right away, through the draft and getting financial flexibility.

In Weaver’s first draft, in 2020, the Pistons went into draft week with just one first-round pick but left with three — Killian Hayes (No. 7), Isaiah Stewart (No. 16) and Saddiq Bey (No. 19). It was the beginning of a new era.

Detroit signed Jerami Grant in the offseason, as well as Mason Plumlee, to try to put veterans around their young players as the “restoring,” as Weaver calls it, got underway. Griffin was still in the fold but a shell of the player he once was.

The Pistons had just 10 wins by February of that first season with Weaver in charge. In March, the team and Griffin agreed to a buyout to open up more minutes for young players and to start the process of getting Griffin’s contract off the books. The team stretched his remaining $75 million over that season and next. In all, the return the Pistons got for moving on from their three pillars of the previous iteration — Jackson, Drummond and Griffin — were Knight, John Henson, a second-round pick, some cap space and dead money.

Detroit finished the season, though, with optimism given that the young players showed promise down the stretch. However, the franchise finished, again, with just 20 wins. And as can be the case when teams purposely tank, the Pistons were rewarded.

Detroit won the NBA Draft Lottery in the summer of 2021 and, in turn, landed Cade Cunningham out of Oklahoma State with the No. 1 pick, the organization’s first top choice in 51 years. Cunningham, by all accounts, was considered one of the most well-rounded prospects of the past several classes. Many evaluators considered him a “can’t miss” talent.

Cunningham’s rookie season got off to a rough start due to an ankle injury in camp. He missed the first few weeks of his rookie season because of it. By Dec. 29, the young Pistons were 5-28. Like the year before, the end of Cunningham’s rookie campaign built up optimism for the following season. Detroit won nine games in the final month and change, and Cunningham had some big performances along the way.

Despite finishing with only 23 wins, the Pistons would land the No. 5 pick in the 2022 draft. They’d leave the night, though, with Jaden Ivey, who was selected fifth, and Jalen Duren, who went No. 13. A young Detroit squad was getting even younger, but for the first time in a looooong time, it had intriguing, young talent that, surely, would have the future far more recognizable.

Then, the following season, more bad luck. Cunningham had been dealing with a nagging shin injury since high school, and it started to flare up again during training camp going into his second season. After playing 12 games to start the 2022-23 campaign, Cunningham sat out and elected to get season-ending shin surgery.

The absence of Cunningham put a damper on any collective development the Pistons hoped to get. It forced them to, again, focus on individual development. As the lost season played out, Detroit elected to take fliers on young players elsewhere to try to build up assets. The most notable came at the trade deadline last year, when the Pistons traded Bey, who was looking for a higher dollar extension than Detroit wanted to give him, to the Hawks and received 2020 No. 2 pick James Wiseman from the Warriors in a four-team trade. Detroit did this in hopes of unlocking Wiseman, who had struggled to find both playing time and consistency in Golden State. However, the Pistons already had three young centers on the roster whom they were trying to develop — Marvin Bagley III, Stewart and Duren. As for building a cohesive roster, the Wiseman move is one that would come back to bite the Pistons this season.

Without Cunningham, Detroit finished the season with an NBA-worst 17 wins, which was the franchise’s lowest win total since the 1979-80 season. The good news, though, was that the Pistons secured the best odds at landing the No. 1 pick, which this past summer was French phenom Victor Wembanyama, whom many considered the best prospect since LeBron James.

The bad news was that Detroit found itself picking fifth … again. It ended up selecting the talented Ausar Thompson at No. 5, but not being able to land Wembanyama was a kick below the belt for an organization that endured a lot of losing. In the same draft, the Pistons also moved up from the second round into the late 20s to grab guard Marcus Sasser. This past summer, Detroit also moved on from Casey as head coach and backed up the Brinks trucks to entice Monty Williams to come to the Motor City after he was let go in Phoenix.

With Williams now at the helm and everyone tired of losing at that level, Detroit came into this season with hopes of turning a corner. Weaver told the media that the Pistons want to play meaningful basketball all the way until the end of the regular season. However, Detroit was trying to do that with an even younger roster than the season before, veterans who would end up being injured during training camp and Cunningham returning to NBA action for the first time in nearly a year. The Pistons had over $30 million in cap space this summer and decided to kick the can down the road for one more offseason. It’s biggest additions were veterans on expiring contracts, including Joe Harris and Monté Morris, both of whom, for different reasons, have given Detroit very little to nothing so far.

That’s how we got to this point today … 27 consecutive losses.

The young Pistons, after starting the season 2-1, looked up and saw those two losses quickly turn into 10, then 14 and so on. No one on this roster knew how to win because no one had done it before at this level. Injuries early cratered any chance of chemistry. Prioritizing flexibility, which was something previous regimes hadn’t done, didn’t allow Detroit to upgrade the way it needed to in order to climb out of the NBA’s basement. Williams has taken a while to learn his team. Weaver and his staff haven’t put together the most cohesive roster as it pertains to proven shooting and defensive depth, particularly on the wings.

Detroit does have promising talent on its roster, but it would be shining even brighter if Tyrese Halliburton was the selection over Hayes in 2020. Detroit had Bruce Brown and traded him for a second-round pick and a player no longer in the NBA. He could help. The future might be a bit more vibrant too if there were more veterans to help put wins on the board so that so much responsibility isn’t put on these handful of 22-and-under players so soon.

Under Weaver, the Pistons decided to prioritize youth for the first time in decades. They wanted to build through the draft, do it the right way. The reason Detroit took this route over the last four seasons is because of what happened the previous 10.

It hasn’t worked so far and, in fact, it’s worse than ever on the court.

There still might be a path forward in the Motor City. There are solid young players, and Detroit does have flexibility. It might be hard to see all of that, though, because the journey for the last 15 years has been a cluttered mess, and the present hasn’t been any better.

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(Top photo of Cade Cunningham: Mitchell Leff / Getty Images)