With the trade deadline coming quickly on the 2017 NBA season, we at DSN took a look back at the trade history of the Detroit Pistons. Many times, the trade deadline proved to be extremely beneficial for the Detroit Pistons under “Trader Jack” Jack McClosky and Joe Dumars. Other times, the trades left many fans of Detroit’s basketball team scratching their heads. Below are the the six worst trades in the history of the Detroit Pistons in their unique and painfully obvious failed glory:

#6: August 4, 2004 – Acquired Derrick Coleman and Amal McCaskill from Philadelphia in exchange for Corliss Williamson.

This trade isn’t higher on the list largely due to it not dismantling any hopes that Detroit had. The trade came in the midst of the impressive run of the 2000s Pistons but it does have us curious of what could’ve been. Williamson was a beast on the block and proved to be a valuable asset off the bench during the Pistons’ 2004 title run. The trade included Derrick Coleman, who only played through the 2004-2005 season when he was cut by Detroit, and another player clearly none of us know of outside of his inclusion in this trade. The teams in 2005 and 2006 could’ve greatly benefited from Williamson bolstering the bench if Detroit had retained him.

#5: July 31, 2013 – Acquired guard Brandon Jennings from the Milwaukee Bucks in exchange for guard Brandon Knight, forward Khris Middleton and center Viacheslav Kravtsov.

This trade has a lot of hindsight behind it, but it still hurts dangit! Despite his issues with injuries, Khris Middleton is a talent the Pistons had seen and still shipped away. A product of the last efforts of the dying tenure of Joe Dumars, this trade was made to rejuvenate a roster with a bona fide scorer in Brandon Jennings. Knight and Middleton have gone on to be at the least serviceable in their respective careers, while Jennings departed the Motor City after a brief time of succes in Detroit. The most iconic moment for Jennings in Detroit was his drive against San Antonio during the “Form a F#*$ing Wall” days of 2014. Questions will always be asked whether shipping Middleton was premature or just hindsight in full view.

#4: November 3, 2008 – Acquired Allen Iverson in exchange for Chauncey Billups, Antonio McDyess and Cheikh Samb.

This trade holds so much emotion with it. The city of Detroit never embraced AI and the decision to trade away a beloved player was painful for everyone, even Joe Dumars. Billups would go on to have a successful career in Denver and Los Angeles that extended to 2013. Many view this trade with obvious negativity but it should be mentioned the Pistons were in the midst of resetting the organization and viewed AI at the time as the solution. We can lement it now, but there’s a reason Mr. Bigshot was shipped back in 2008.

#3: July 13, 2009 – Acquired second-round draft choice from Denver in exchange for Arron Afflalo, Walter Sharpe and cash considerations.

Shipping Arron Afflalo is higher on the list than moving Mr. Bigshot solely on the value of this trade. Not only did Joe Dumars decide to ship him out of Detroit, but also packaged another player AND more cash because apparently Afflalo on his own wasn’t enough. The pick clearly wasn’t even with the value of the trade and Afflalo’s lasting career since being moved adds to the sting. He has proven to be a valuable utility shooter for many teams and this trade seems simply perplexing due to the lack of value Dumars must have had for Afflalo at the time.

#2: August 28, 1975 – Acquired Kevin Porter from Washington Bullets in exchange for Dave Bing and Pistons’ 1977 first-round draft choice.

The Wizard was great for the Pistons back in the day. This trade simply makes no sense and shows a microchosm of the problems that Detroit had back in its early years. Not only did Detroit throw away a future Hall of Famer, but they also packaged a first round pick for a player they would trade away in 1978. In his second season, Kevin Porter would have a knee injury that had him only play 19 games. The returns Detroit got from Porter ridiculously diminished any value they could’ve gotten by trading away one of the franchise’s best players and a future first round pick. It may have happened awhile ago, but it is still just as eggregious.

#1. December 19, 1968 – Acquired Walt Bellamy and Howard Komives from New York in exchange for Dave DeBusschere.

Dave DeBusschere is considered one of the best 50 players in NBA history. Debusschere hailed from Detroit not only in his high school days at Austin Catholic Prepatory School but also as an alltime great at the University of Detroit Mercy. He tried his hand as a player-coach for Detroit but was traded to the New York Knicks where he became a defensive anchor on two world championship teams. Detroit received nothing near the same value that they gave away and saw Debusschere play on some of the NBA’s greatest teams while they saw their investments amount to nothing. Despite retiring in 1974, there would’ve beena chance to build around the two man combo of two Hall of Fame guys named Dave. Alas, we can only speculate now after Detroit management committed the worst trade in Detroit Pistons history.