When it comes to the world of professional sports, hindsight is 20/20. If you’re running an NBA front office, you never know with absolute certainty that a player you draft is going to work out, or if a trade deadline deal you put together will wind up making you look like a goat in the long run. Anyone who’s played fantasy sports knows this very well, albeit on a drastically smaller scale. Still, sometimes you have to take risks to try to improve your team, and those risks don’t always pan out exactly the way you’d envision them.

In a lot of cases, “spectacular failure” is a pretty dramatic understatement when it comes to trades in particular. Not only are you talking about straight up player swapping, in which one side completely fleeces the other, but you’re also talking about deals made to move draft picks in hopes of winning right now, instead of saving potential franchise pieces that will be coming along in future drafts down the road. It’s easy to second guess a general manager for making a bad deal, and in most cases you can just kind of shrug it off and realize that, at the time, it was plausible that the deal made sense.

But sometimes you look at the aftermath of a truly disastrous trade, and immediately know that it was the kind of deal that could, and probably should, get someone fired.

10. The Sixers Trade Wilt Chamberlain

via en.wikipedia.org

via en.wikipedia.org

You may have heard of Wilt Chamberlain, a freakish athlete known for his ability to score both with a basketball and the ladies. During the first few years of his career, Chamberlain had set various scoring records and was pretty much the most unstoppable force in basketball. That’s why Philadelphia’s decision to trade him made very little sense to people on the outside looking in.

According to the late Dr. Jack Ramsay, the trade came about because Wilt demanded it, plain and simple. Basically, Chamberlain gave the Sixers an ultimatum saying that if they didn’t trade him to the Lakers, he would leave the NBA altogether and sign with an ABA team. With their hand forced, the Sixers desperately tried to acquire any assets they could so that they wouldn’t be left empty handed when they lost their superstar. Of course, since the pieces they picked up were Darrall Imhoff, Archie Clark, and Jerry Chambers – better known as “three guys you’ve never heard of” – it’s almost as if they let him walk for nothing anyway. The only reason this trade isn’t higher on this list is because the Sixers hand was forced, so we’ll show a little sympathy.

9. The Cavs Trade James Worthy

via kentuckysportsradio.com

via kentuckysportsradio.com

It can be a little hard to call a front office out for trading away a complete unknown, which is what happened when the Cleveland Cavs lost out on acquiring Hall of Famer James Worthy. However, sometimes you have to look back at a deal in hindsight and determine that it was still a hilariously bad move on the part of one team or the other. That’s really the case here, as the Cavs limped to a record of 28-54 in 1980, and decided to trade their first round pick to the Lakers for a guy named Don Ford.

If you’re wondering who Don Ford is, he was a 6-foot-9 forward who scored a whopping 3,016 points for his career, and who was averaging just 3.0 points for the Lakers when the Cavs made the trade. That first round pick that the Lakers acquired for Don Ford wound up being the number one pick in the 1982 draft, and they’d use it to draft the former North Carolina star. Worthy went on to average 17.6 points-per-game and helped the Lakers win three titles over the course of his career.

8. The Bucks Trade Dirk Nowitzki

Jerome Miron-USA TODAY Sports

Jerome Miron-USA TODAY Sports

European imports have always been a little bit hit and miss in the NBA, with far fewer hits than misses. It’s always tricky to draft an international player for a number of reasons, as you may never really know just how good they are due to the drastically lower level of competition until you seem them in North America or the fact that even after you draft them, they could still choose to remain in Europe indefinitely, making your pick a complete waste. With all that said, the Milwaukee Bucks made one of the most disastrous draft day trades in NBA history when they dealt Dirk Nowitzki for Robert Traylor in 1998.

Nowitzki was taken by the Bucks with the ninth overall selection, while “Tractor” Traylor, an out of shape, undersized power forward from Michigan, went sixth overall to the Dallas Mavericks. To make matters even worse, the Bucks actually threw in another player – Pat Garrity – to acquire Traylor, who started only 73 games in his entire NBA career. Heck, even a Garrity for Traylor trade would have been bad considering Garrity scored nearly two times as many career points as Traylor. Then you factor in one of the 25 greatest players in NBA history with Dirk, and it pretty much solidifies this as one of the absolute worst trades ever made.

Of course to soften the blow for the Bucks, at least they can take solace knowing that the 1998 draft will still forever be known as the time the Clippers selected Michael Olowokandi with the top pick.

7. The Hornets Trade Kobe Bryant

Jayne Kamin-Oncea-USA TODAY Sports

Jayne Kamin-Oncea-USA TODAY Sports

Just like International players, drafting high school phenoms was always a bit of a crapshoot back when that was a thing the NBA actually allowed. For every Kevin Garnett, there were half a dozen other high school kids who fizzled out or never even made a team. Of course, that probably should never have been considered a possibility with Kobe Bryant. First of all, he had been raised in an NBA setting, considering his dad played for the Sixers, and it should have been pretty clear early on he was mentally prepared to play in the league, even as an 17 year  old.

Yet that didn’t stop the Charlotte Hornets from drafting Kobe with the 13th overall pick in the 1996 draft, only to turn around and trade his draft rights to the Los Angeles Lakers, who have history had a knack for fleecing teams when it comes to trades, as a few more trades on this list will only continue to confirm. The Hornets picked up Vlade Divac in the deal, and while Divac was always a solid big man with above average skills, it’s pretty obvious that the Hornets would have probably preferred the young superstar over the aging European, particularly since Divac wound up signing a free agent deal with Sacramento two years later.

6. The Bucks Trade Kareem Abdul-Jabbar

via patheos.com

via patheos.com

Before he was an “Airplane!” co-pilot, and even before he was Kareem Abdul-Jabbar, he was Lew Alcindor and he played for the Milwaukee Bucks. The man with the single most devastating offensive move in basketball history had spent six seasons with Milwaukee after an historic college career at UCLA. He had actually helped the Bucks win the championship in 1971, just before he changed his name to Kareem, and five years later he would find himself dealt to Los Angeles.

Apparently, much like Wilt Chamberlain, Abdul-Jabbar simply wanted to be traded. Unlike Wilt, however, he wasn’t trying to blackmail his way into a deal, but at the end of the day, Milwaukee general manager Wayne Embry decided to give his star what he wanted and shipped him off to the Lakers in 1975. In return for Kareem (along with a guy named Walt Wesley), the Bucks received Elmore Smith, Brian Winters, David Meyers, and Junior Bridgeman. The Lakers would go on to win five titles with Kareem. The Bucks would go on to become the Bucks.

5. The Sonics Trade Scottie Pippen

via en.wikipedia.org

via en.wikipedia.org

Scottie Pippen clearly never played for the Seattle Supersonics, but it’s all because of yet another draft day debacle that wound up supplying Michael Jordan with the Robin to his Batman. Arguably the greatest NBA sidekick of all-time, and one of the most versatile, athletic small forwards to ever play the game, Scottie Pippen was drafted fifth overall in the 1987 draft, but was quickly dealt away to Chicago in exchange for Olden Polynice and future draft considerations.

Polynice, a center who played 15 seasons in the NBA, only managed to start seven games during his first stint in Seattle, while Pippen began forming one of the best young forward combinations in the league alongside Horace Grant. Pippen would also go on to play with the Dream Team, and helped the Bulls win six NBA titles. As an interesting side note, the Sonics were also responsible for another key part of the Chicago dynasty of the 1990’s, as the pick the Bulls used in 1989 to select B.J. Armstrong initially belonged to Seattle.

4. The Sixers Trade Charles Barkley

David Richard-USA TODAY Sports

David Richard-USA TODAY Sports

As was the case with most superstars who get dealt away during the primes of their careers, when the Sixers traded Charles Barkley to Phoenix, it wasn’t really by their own choice. Barkley wanted out of Philadelphia – badly – and wasn’t shy about making his opinion known. So, in 1992 the Sixers honored Barkley’s wishes and gave him up to the Suns, where he promptly won an NBA Most Valuable Player award and guided Phoenix to a finals appearance, where they lost to the Bulls.

What makes the trade so bad is the fact that the Sixers got back virtually nothing in return for Sir Charles. Jeff Hornacek was a solid NBA shooting guard and the best piece that Philly received in return for Barkley, but Andrew Lang and Tim Perry, the other players involved in the trade, were so forgettable that, frankly, you’ve probably already forgotten their names by now. Making matters even worse, the Sixers turned around and dealt the one decent part of the trade, Hornacek, to Utah – where he’d go on to partner with John Stockton and Karl Malone on some very good Jazz teams – two years later.

3. The Warriors Trade Robert Parish and Kevin McHale

via digausted33.blogspot.com

via digausted33.blogspot.com

The reason this trade wound up ahead of some of the bigger superstars on this list is the simple fact that with one quick deal, the Boston Celtics got two of the most important pieces of their great 1980’s teams, pairing Kevin McHale and Robert Parish with their young superstar, Larry Bird. Parish was already in the league and playing for the Golden State Warriors, and Red Auerbach used the first and 13th overall picks in the 1980 draft to acquire Parish and the third overall selection. That third selection turned into McHale.

On paper, it looked like a potentially strong move, so it’s hard to fault their front office at the time. After all, in today’s NBA, it’s completely feasible to see a trade like this one take place. What makes it such a bad trade is the fact that the Warriors turned those two high draft picks into – well, not much of anything. Golden State took Joe Barry Carroll with the first overall pick, and Rickey Brown with the 13th selection. If those two had panned out, it would have looked like a great trade all around. Carroll actually had a solid career from a stats perspective, averaging 17.7 points and 7.7 rebounds per game, but Brown was basically a disaster, scoring just 1,482 points in his career and finding himself out of the league after five seasons.

2. The Jazz Trade Magic Johnson

Kirby Lee-USA TODAY Sports

Kirby Lee-USA TODAY Sports

Once again, the gift of hindsight makes this one look unfathomable, not just that anyone would trade away Magic Johnson, but that we could have been looking at a decade of Magic running the point for the Jazz rather than, eventually, John Stockton. Basically, this one trade completely altered the course of history for two franchises. And, naturally, this was a trade of a draft pick rather than a trade of already known asset. The way this one shook out is that, back when they were still in New Orleans and their nickname made sense, the Jazz signed free agent Gail Goodrich. As compensation they had to make a deal with the Lakers as per league rukes and the Jazz also got some other, lesser known players you’ve probably never heard of.

All they had to give up in return was Kenny Carr, Freeman Williams, and Sam Worthen. Oh, and their next first round pick. You can see where this one is going. Naturally, that pick wound up being the first selection in the 1979 draft and the resulting pick was Magic, a guy who didn’t do much other than transform the game and helping shape the new version of the NBA, sculpting the Showtime Lakers in the process.

1. The Hawks Trade Bill Russell

via boston.com

via boston.com

Bill Russell is, without question, one of the greatest winners of all-time. The man simply won championships wherever he went, and for the city of St. Louis, that could have meant delivering titles to them as well, as a member of the St. Louis Hawks. The word is, even though the Hawks drafted Russell with the second pick of the 1956 draft they didn’t actually want him, but they wanted Ed Macauley, Boston’s six-time All Star. Macauley was a St.Louis native and wanted to go home with to be with his son. So the ever savvy Red Auerbach swept in and plucked Russell from them for Ed Macauley and Cliff Hagan. Funnily enough, this was considered a huge price for Russell’s rights.

Both were very productive players, with Hagan scoring more than 14,000 points and Macauley better than 11,000 in their careers, but obviously neither player could come close to matching the dominance that Russell soon brought to Boston.

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