The Worst Trade Deadline Deals of All-Time
There have been a lot of awful trades over the years, like the St. Louis Hawks trading Bill Russell to the Boston Celtics for Cliff Hagan and Ed Macauley or the Milwaukee Bucks shipping off Kareem Abdul-Jabbar in 1975 for Junior Bridgeman, Dave Meyers, Elmore Smith and Brian Winters. But luckily, the majority of those awful trades haven’t happened at the trade deadline.
That doesn’t mean there haven’t been some egregious swaps that have taken place in February. The following are the deadline deals that proved to be awful decisions for at least one of the teams involved:
2011 – Oklahoma City Thunder trade Jeff Green, Nenad Krstic and a future first-round pick to the Boston Celtics for Kendrick Perkins and Nate Robinson
Not only did this trade dismantle a champion Celtics team, but the two guys Boston got back in the deal—Green and Krstic—didn’t even play in the league last season.
2011 – L.A. Clippers trade Baron Davis and a first-round pick that becomes Kyrie Irving to the Cleveland Cavaliers for Jamario Moon and Mo Williams
This one was brutal for the Clippers, who ended up trading away the No. 1 overall pick in that summer’s draft just so they could get Baron Davis’ salary off the books. The really frustrating part of this deal was that most teams had some idea that an amnesty provision would be included in the next collective bargaining agreement, so L.A. could have gone that route in cutting Davis loose while keeping the pick that would eventually turn into newly christened All-Star Kyrie Irving.
2011 – Charlotte Bobcats trade Gerald Wallace to the Portland Trail Blazers for Joel Przybilla, Dante Cunningham, Sean Marks, and two first-round picks
By the time the Bobcats traded Gerald Wallace, the longest-tenured player on the team at the time, both he and Charlotte were ready for the split. Still, the Bobcats really should have tried to get more in exchange for the best player in franchise history. Przybilla, Cunningham, and Marks is an admittedly pretty weak haul.
2008 – Memphis Grizzlies trade Pau Gasol to the L.A. Lakers for Marc Gasol, Kwame Brown, Javaris Crittenton, Aaron McKie, two first-round picks and a second round pick
“Here, Lakers, have a couple of championships on us. Sincerely, the Grizzlies.” Okay, so Memphis did end up with the better long-term player in Marc Gasol, but at the time nobody knew what he would become. Back in 2008, it looked like one of the most lopsided trades in league history because the Lakers did immediately win two championships without having to give up anywhere near market value for Pau.
2008 – Phoenix Suns trade Shawn Marion and Marcus Banks to the Miami HEAT for Shaquille O’Neal
The Suns made this trade hoping that O’Neal could help Phoenix tackle Tim Duncan and the San Antonio Spurs in the postseason should the two teams meet up, but when the two teams actually did meet up in the first round just a couple of months later, Shaq showed his age and Phoenix lost the series to the Spurs. He had a better 2008-09 season, but the fit was just never quite right, and the Suns had to bid adieu to Marion to make it happen.
2005 – New Orleans trades Baron Davis to Golden State for Speedy Claxton and Dale Davis
While there was a certain measure of risk in acquiring a player with Davis’s injury history, there’s no question that he was far and away the most talented player in this deal. The 2007 playoffs, in which Davis’ Warriors upset the Dallas Mavericks in one of the most exciting postseason series ever, was the exclamation point on the mistake the Hornets made.
2003 – Milwaukee Bucks trade Ray Allen, Kevin Ollie, Flip Murray and a first-round draft pick to the Seattle SuperSonics for Gary Payton and Desmond Mason
The deal made a ton of sense for Seattle, who acquired maybe the best pure shooter in NBA history for an aging Payton that may have left in the offseason when his contract expired anyway, but for Milwaukee, this meant giving up maybe the best pure shooter in NBA history for an aging Payton, who only played 28 games in Milwaukee and left in the offseason when his contract expired. In short, the Bucks dumped their best player to avoid the luxury tax, which made sense at the time but in retrospect looks pretty bone-headed.
1998 – Boston Celtics trade Chauncey Billups to the Toronto Raptors for Kenny Anderson
After using a top three pick to select Billups in the 1997 NBA Draft, the Celtics gave up on him after only 51 games because they couldn’t figure out where to play him. All they got in exchange from Toronto was Anderson, who played reasonably well for Boston, but never came close to living up to what Billups did once he broke out for Detroit later in his career.
What were the worst deadline deals you can remember? Did your team make a huge mistake at the deadline at some point and don’t see it listed above? Hit up the comments section and make sure we hear about it!






