Detroit Pistons: The 7 Worst Offseason Moves of the 2000s

Emily Dickinson wrote: “Hope is the thing with feathers.” 

If this is true then the NBA offseason is a peacock perched on the naïve soul of the fan. 

For some teams, the offseason is the only part of the year that offers hope, potential, some payoff for the suffering months when you cheered for your team to lose just for a better shot in the draft lottery.

The offseason is a time of belief and high risk, argument, conjecture, and judgment. 

With a new decade underway, what better time to look back on the last one, specifically those moves that didn’t work out, the ones that still make you angry, the ones that left the team looking like a plucked chicken. 

Here are the seven worst offseason moves made by the Detroit Pistons in the 2000s.

7. Mateen Cleaves

Drafting Mateen Cleaves in 2000, OK, can’t kill them on this one. 

Not a good draft and you can’t blame Detroit for taking a local hero. 

That local hero should have been Morris Peterson.  He was on the same team and a better player.

6. Larry and Flip

Buying out Larry Brown and hiring Flip Saunders in 2005. 

Brown may be overrated and Saunders led the team to 64 wins and their most successful regular season, but something changed when Brown left. 

The Pistons signature defense got soft and it showed in the playoffs. 

Brown certainly didn’t help his own cause with constant rumors of new jobs, but after two-straight appearances in the finals, it would have been nice for one more run.

5. Curry and Kuester

I’ll combine two here, hiring Michael Curry (2008) and John Kuester (2009). 

Both were overmatched and never really had the team largely due to a constant shuffling of lineups.

Let’s hope Lawrence Frank isn’t the next name on this list.

4. Jason Maxiell and the Rise of Mediocrity

Extending Jason Maxiell's contract through 2013.  I like Jason Maxiell.  Most Pistons fans do.  He hustles and occasionally has a dynamic block or dunk, but one of the reasons that the Pistons, as well as the NBA at large, are in trouble is contracts like this. 

You don’t give undersized backup power forwards four-year, $20 million extensions. 

Ridiculous contracts for mediocre players is the No. 1 reason why there isn’t going to be an NBA season this year.

3. Allen Iverson and Chauncy Billups

Trading Chauncey Billups for Allen Iverson in 2008. 

Technically this happened two games into the season, but the writing was already on the offseason wall.

The logic was to clear up cap space with Iverson’s expiring contract, and hey, maybe he would play well.  He didn’t. 

The Pistons chemistry was ruined by Iverson, who stunk and ended up sulking on the bench while Chauncey went on to lead the Nuggets to the Western Conference Finals. 

Hamilton was alienated and the locker room has never been the same.  The Pistons got their coveted cap space, but at a steep cost, which only got steeper with No. 2.

2. Ben Gordon and Charlie Villanueva: 90 Million Worth of Suck

Signing Ben Gordon and Charlie Villanueva in 2009.  This almost got No. 1 just because I nearly vomited writing the sentence. 

I will rationalize these signings by saying Dumars was under a lot of pressure to keep the team decent while they were shopping for a new owner.  The economy turned horrible, and Detroit was desperate to keep the team in the playoffs, even as a lower seed. 

This was a huge mistake for many reasons, the first being that the Pistons have a smart fan base who knew it was time to rebuild. We would have waited. 

Secondly, I am not a business mogul, but I have to believe that a young team with potential and no huge salary obligations would be more attractive than a team full of underachieving, mediocre, young veterans who are all making $10 million a year. 

I never thought we had a chance at any of the marquee free agents of the Summer of LeBron, but why not just sit on the cap space, bottom out, hope you get lucky in the draft, and start to rebuild with a young core of Stuckey, Monroe and Jerebko? 

Oklahoma City has provided the model.  Instead, the Pistons are now stuck with two one-dimensional bench players who can’t defend their positions.  All for $90 million. 

Whatever the new CBA is, it has to include something that protects owners and GMs from themselves, something that stops mediocre players from getting paid like superstars. 

These two have both stunk and are now untradeable, which is why the Pistons are hovering in NBA purgatory, trapped in that awful area of fighting for the eighth playoff seed.  Not a good place to be.

1. Darko Milicic: The Dynasty Killer

Darko.  The name alone brings dread to the soul.  It sounds like the name of a despot, a marauder, a creepy count who lives in a castle and drinks blood.  I don’t know if I’ll ever get over this one. 

I can’t blame Dumars.  Everyone was high on this teenage phenom;  if the Pistons hadn’t gotten so “lucky” to get the No. 2 pick, some other sucker surely would have went all-in on Darko’s potential. 

The Pistons were in a unique position in 2003 in that they were good.  They were fresh off the Eastern Conference Finals.  They didn’t need Darko.  He was a luxury which probably made it easier to fall for his siren song, but when I think of how achingly close the Pistons were in 2005 and beyond, I can’t help but conclude that Wade, Melo, or Bosh would have been more than enough for a three-peat. A dynasty. 

Sure, the Pistons won a title, and they did it with this disease known as Darko, but he was the beginning of the end, the first symptom of what we are now praying is not a terminal illness. 

Darko was the plague that ended an era, and will go down in lore as the worst offseason move the Pistons will ever make.  At least I hope.