No matter the sport, it’s always unfair to grade a trade immediately after it happened. It usually takes a few years for teams to benefit from the trade or look back at it and regret it. This is certainly the case in the NBA when so many trades are made based on the potential of players (including draft picks) and not what they are right now. Fortunately, we have the benefit of 20/20 hindsight, allowing us to look back at the worst NBA trades that have been made since the year 2000.
5. Pistons Swap Chauncey Billups for Allen Iverson
Billups was a legend and an icon in Detroit, and when they traded him in November 2008 along with Antonio McDyess and Cheikh Samb, he still had plenty of good years ahead of him. It was utterly foolish to part ways with him given his status, especially if only did it to get Iverson and his expiring contract from the Nuggets. Predictably, Iverson was worth less than the sum of his parts for the Pistons and probably caused more trouble than he was worth before his season ended early due to a back injury. Using that cap space on Charlie Villanueva and Ben Gordon didn’t exactly pay off, as the Pistons haven’t won a single playoff game in the decade since trading away Billups and company.
Meanwhile, Denver got plenty out of Billups in his three seasons with the Nuggets. Billups helped his new team reach the Western Conference Finals the season the trade was made. He even averaged a career-high 19.5 points per game during the following season. In retrospect, there’s little doubt the Pistons would have been better served to hang onto Billups, especially in a city that had embraced him so much over the years.
4. Thunder Send James Harden to Rockets
It’s not just that Oklahoma City traded away Harden, but it’s that they did it because they weren’t willing to give him a max deal of $60 million. Despite losing to Miami in the 2012 NBA Finals, it was clear that the Thunder had a good thing going and needed to do more to keep the core of the team together, regardless of the luxury tax implications. Who knows how the next few years could have been different had Oklahoma State just paid Harden rather than trade him away.
In fairness, the Thunder got Steven Adams out of the draft picks Houston sent them. Kevin Martin also had a decent season coming off the bench for Oklahoma City during the 2012-13 season, so the Thunder got something out of the deal. But that’s little solace when you look at what Harden has done with the Rockets, including back-to-back seasons averaging over 30 points per game. There was also the whole losing Kevin Durant in free agency gaffe that could have gone differently had the Thunder held onto Harden. Things worked out well for the Rockets, but this was a terrible trade for the Thunder.
3. Nets Give Up Draft Pick for Gerald Wallace
The Nets made some bad moves out of desperation during their New Jersey days, but this was one of the worst. When the Nets realized they weren’t getting Dwight Howard, they had to resort to Plans B, C, and D to get Deron Williams to re-sign with them. The brilliant idea they came up with was to trade for Portland’s Gerald Wallace, giving up Mehmet Okur, Shawne Williams and a first-round pick in that year’s draft.
The other shoe dropped when Portland received the no. 6 overall pick as part of the trade and used it to take Damian Lillard, who has become a perennial all-star and one of the best players in Trail Blazers history. For what it’s worth, the Nets were able to keep Williams, although they eventually waived him and had to buy out the last two years of his max deal after his performance declined. Re-signing Wallace the following summer didn’t help matters either. He might as well have fallen off a cliff with the way his numbers dropped the following season in what was the beginning of the end of his career. Within a year or so of this trade, the Nets had virtually nothing to show for it while the Trail Blazers used New Jersey’s old draft pick to add a bonafide star.
2. Nets Trade for Kevin Garnett, Jason Terry, and Paul Pierce
Moving to Brooklyn didn’t create enough buzz for the Nets, so they decided to get desperate and trade for aging stars Kevin Durant, Paul Pierce, and Jason Terry in the summer of 2013. At the time, all three were close to 40 than they were to 30, yet the Nets believed that they had somehow put together a super team that overnight would make them a serious contender in the Eastern Conference. We know now that the trade backfired in a big way. The Nets pulled off an upset of the Raptors in the first round of the 2014 playoffs, but that was the peak of what Brooklyn accomplished in the aftermath of the trade.
For what it’s worth, the Celtics didn’t exactly come out of that trade as massive winners. However, they ultimately turned the draft picks from the trade into players like Jaylen Brown and Jayson Tatum, who have become key contributors. Meanwhile, once the likes of Garnett, Pierce, and Terry were completely washed up, the Nets became one of the worst teams in the NBA for multiple seasons and are still in the process of digging themselves out of such a deep hole.
1. Knicks Acquire Andrea Bargnani
Some trades look terrible at the time while others seem to look worse over time. This is one of those rare trades that falls into both categories. Bargnani had peaked during the 2010-11 season, seeing his production (not to mention health) drop-off considerably. Yet, the Knicks insisted on giving up three draft picks, including a first-rounder, as well as Marcus Camby, Steve Novak, and Quentin Richardson to trade for Bargnani. At the time, the trade made no sense for the Knicks, and it got worse when Bargnani continued to miss time due to injury and be a disappointment on the court when he was healthy enough to play.
If it matters, the Raptors didn’t get much out of the deal other than getting rid of the injury-prone Bargnani and the satisfaction that the Knicks ended up the laughing stock of the NBA because of it. Plus, in an unusual twist, the Knicks later backed out of trade talks for Kyle Lowry because the trade with Toronto for Bargnani backfired so much. Of course, Lowry went on to play an important role in the Raptors winning the NBA title in 2019, something that may not have happened if the Knicks weren’t so gun-shy about another trade with Toronto.