Our Detroit Pistons have a long, storied history, full of champions and chumps, thrilling moments and doldrums better forgotten. I believe in focusing on the positive and doing everything one can to maintain a glass-half-full sort of mentality in life. Luckily, for much of my time as a fan, the Pistons have made it easy enough to maintain such an attitude. However, recent times have been unkind to the old faithful like me, let alone, newer, younger fans.
Here’s a glimpse of the most disappointing seasons in franchise history, may we raise our glasses to only good times ahead.
The 5 most disappointing seasons in Detroit Pistons’ history
#5: 2022-23 Detroit Pistons
We’re going to suffer through some fresh memories as it was just last year when Pistons fans had a modicum of optimism entering the season. We were still on a vibe from the Jaden Ivey-Jalen Duren-led draft class that had most of us feeling like GM Troy Weaver was some kind of magician. Besides Ivey falling to #5 (most mocks had him gone at #4), Detroit also managed to trade back into the lottery and land a young big to build the frontcourt around in Duren. A core began to take shape, with former #1 overall pick Cade Cunningham being the centerpiece. There was a lot of chatter about making it into the play-in tournament. But all that happy talk stopped when it was announced that Cunningham would undergo surgery for a tibial stress fracture.
Just twelve games into Cade’s sophomore year, one in which the fanbase held some hope to see a meaningful game or two in the spring, it was clear that we had another long season ahead of us, and boy, did we ever. Without the captain there to steer the ship, the seas got choppy in a hurry. As a matter of fact, despite the recent influx of talent, the Detroit Pistons took six more “L’s” than they did the season before. All that losing, while nearly unbearable, did position Detroit well in a lottery that would determine where one of the most hyped prospects (Victor Wembanyama) in the history of the NBA would be headed.
Of course, the Pistons didn’t win that lottery, nor did fare particularly well in it. Instead, Detroit endured a freefall back to the 5th pick, and while the Pistons seem to have lucked out by getting Ausar Thompson with it, lottery night was the perfect end to a disastrous season – one of the most disappointing seasons in Pistons history, in fact.
The 5 most disappointing seasons in Detroit Pistons’ history
#4: 1986-87 Detroit Pistons
For those of you who can remember how glorious the NBA was throughout the 1980s, you’ll also remember what a gut punch it was to see Isiah Thomas’s intended pass to Bill Laimbeer get intercepted by a dazzling Larry Bird late in the fifth game of the ’87 Eastern Conference Finals.
With five seconds remaining on the game clock, the Detroit Pistons had a one-point lead and possession of the basketball following a great blocked shot by Dennis Rodman that fortuitously ricocheted off of Boston’s Jerry Sichting before going into the stands and out of bounds.
Thomas, well aware that the Pistons were on the verge of stealing an important victory in Boston Garden and heading back to Detroit with a 3-2 series lead, managed to make a blunder for the ages when he somewhat lazily lobbed the ball toward Laimbeer, giving Bird the opening he needed to steal the ball and hit a streaking Dennis Johnson for an easy go-ahead basket that ultimately propelled the Celtics back to the NBA Finals for one last dance during the Bird-era.
The Pistons had to wait another year before getting their shot at the Lakers, leaving fans like me to rue a mistake that may have prevented the Pistons from winning the first of four NBA championships had we had a bit more luck on our side.
The 5 most disappointing seasons in Detroit Pistons’ history
#3: 1999-2000 Detroit Pistons
This is an odd duckling given the other teams on this list, but it represents the culmination of an era. Specifically – The Grant Hill Era. When Hill was drafted 3rd overall in 1994, some were of the opinion that the 22-year-old Duke grad should have been taken with the 1st pick by Milwaukee. Instead, the Bucks took Glenn Robinson, the Dallas Mavericks formed the “J-Team” upon adding Jason Kidd with the 2nd pick, leaving Hill to fall into the lap of the Detroit Pistons.
While all three players would go on to have good if not great careers, Hill immediately turned heads with his athleticism and began to draw the inevitable “Next Jordan” refrain from both fans and pundits alike. Hill won Co-Rookie of the Year with Kidd, and from there would rack up eye-popping stats and other various accolades that would seem to indicate that he was on a Jordan-like trajectory.
In time, other comparisons would be made, with many arguing that Hill’s game resembled Magic Johnson’s or Larry Bird’s more than it did MJ’s. The question was whether or not he had the same killer instinct that the greats he was compared to were known for. Doubters questioned his toughness, competitiveness, and whether or not he had the proverbial “clutch” gene that set His Airness apart from so many others.
Sadly for Pistons fans Hill was so competitive that he played on an ankle so badly damaged he was never able to recover from the injury. His career was effectively ruined. But watching Hill hobble through the first game and a half of the postseason, before sitting out the rest of a first-round sweep at the hands of the Miami Heat was soul-crushing.
Those with a clue realized that for the past six years we were privileged with a front-row seat as one of the most talented basketball players ever to lace them up represented our franchise with great poise, yet failed to win a single playoff series during his time with the Pistons – and that his time in Detroit had come to a mind-bogglingly disappointing and sudden end.
The 5 most disappointing seasons in Detroit Pistons’ history
#2: 2008-09 Detroit Pistons
There are a couple of ways to look at this. In the first place, the season is a disappointing one because in it, we traded away Mr. Big Shot himself, Chauncey Billups. That alone didn’t make any sense. Even if we had acquired two Allen Iversons instead of one, it still wouldn’t have made sense. Billups, along with Ben Wallace, was the heart and soul behind that era of Pistons basketball.
Ben was already gone, having gotten his bag from the Chicago Bulls. Then we added a head coach with no coaching experience to the mix. From there, we swap Billups for Allen Iverson. It was clear that the Goin’ to Work Pistons were dead, and that the team had blown up…but there was excitement around adding a future Hall-of-Famer the likes of A.I. The only problem with that was, Iverson clearly didn’t want to be here.
He spent more time gambling in the casinos than he did practicing, I’m quite sure. His 17.4 points per game was easily the lowest number of his career as it became clear that he was no longer capable of the sustained brilliance that could carry a franchise. The Pistons went 39-43 that season before bowing out in the first round of the playoffs. Iverson never played another game for the Detroit Pistons after that. Head Coach Michael Curry was also one and done. The end of an era happened slowly at first, but all the remaining bricks in the wall came toppling down on fans that season.
The 5 most disappointing seasons in Detroit Pistons’ history
#1: 2004-05 Detroit Pistons
For as long as I’ve been a Pistons fan, I can’t think of a single moment that sucked the air out of me quite like Robert Horry’s 3-pointer for the San Antonio Spurs in Game 5 of the 2005 NBA Finals.
The Detroit Pistons were down 3-2 when they took flight for San Antonio to finish out the series for better or worse. Not many national pundits were predicting the Pistons to win even one more game in the series, let alone two. But sure enough, the Goin’ to Work Pistons, as led that night by Richard Hamilton, who scored a game-high 23 points, defied the odds with a 95-86 Game 6 victory in San Antonio, forcing a decisive Game 7. Back then, the Pistons motto was something akin to, “If it ain’t rough, it ain’t right,” so forgive those of us fans who deeply believed in inevitable triumph.
But they didn’t. As a matter of fact, Game 7 concluded in lackluster fashion with the Spurs coming out on top 81-74. There isn’t much to remember about that particular game, which is somewhat unusual for a game of its magnitude. Instead, many of us think back to the game that got away and wonder what might have been had the Pistons gone back to San Antonio up 3-2 instead of down 3-2.
We’ll never know, but to me, the ’05 team is the most disappointing Pistons team ever because it was on the cusp of winning back-to-back championships and perhaps even chipping away at the belief that they were a squad without a superstar.