Visit any NBA fan’s Facebook feed or Twitter stream and you’ll inevitably see people pretending to be General Managers, coming up with ideas like “we should trade this guy” or “we should acquire this guy via trade.” In the case of free agency, they’ll think: “we should sign this guy to come play for our team.” Simply put: you might think it’s a great idea for your team to make a trade or a free agent move, but it’s not quite as simple as that.

With all of that being said, there are plenty of times in NBA history where two teams, or a player and a team, came together to make a deal with both parties walking out thinking they’ve made themselves better off for the future. Except in many of those cases it’s quite the opposite. One NBA team ends up getting the much better end of the deal, while the other one may have short-circuited their short-term or long-term success. In the case of free agency, a team might be giddy to sign a player to a particular contract, only to be stuck with a player they’re not nearly as interested in as they were when they first signed him.

While there are numerous examples to choose from, we’ve put together this list of the 20 worst offseason moves ever made by NBA teams. As you’ll see, there are some horrific, history-altering mistakes on this list; that’s why you should always think twice before thinking “my team would be better off if we just make this one deal”. No one knows the future, but hindsight is 20/20, so here are the 20!

20. The Portland Trailblazers Sign Darius Miles

via blazersedge.com

Entering the 2000 NBA Draft, basketball scouts saw Darius Miles and envisioned a hybrid of Kevin Garnett and Tracy McGrady. But when the Los Angeles Clippers decided to trade Miles to the Cleveland Cavaliers, in exchange for point guard Andre Miller, that’s when it all came crashing down for Miles. Miles lasted less than two years in Cleveland, before again being flipped to the Portland Trailblazers. Portland re-signed Miles to a six-year, $48 million deal, and he immediately got caught up in the bad behaviour of the “Portland Jailblazers” era.

Two years after signing that deal, Miles injured his knee, which caused him to miss the next two NBA seasons after undergoing the infamous microfracture surgery to repair it. The Blazers were so ready to get rid of him that they had their team doctor’s declare it a potential career-ending injury, so they could get out from underneath Miles’ contract.

19. The Charlotte Hornets Trade Kobe Bryant In 1996

via si.com

Kobe Bryant’s legendary career with the Los Angeles Lakers might’ve been facilitated by the Bryant family (him and his father Joe “Jellybean” Bryant), Arn Tellem (Bryant’s agent), and Sonny Vaccaro, but it was made possible by a Charlotte Hornets team that thought they’d be just fine without Bryant.

After Bryant’s entourage and Lakers General Manager Jerry West plotted a way for Kobe to get to Los Angeles through the 1996 NBA Draft, Bryant fell to the Hornets, who had the 13th pick in that draft. Bryant later stated that Hornets head coach Dave Cowens told Bryant point blank: “We don’t really need you here.” When the Hornets asked for centre Vlade Divac in return Bryant, the Lakers realized that trading Divac would actually give them enough space under the salary cap to go out and sign centre Shaquille O’Neal. In other words: this one deal built one of the two greatest NBA dynasties in the post-Michael Jordan era.

18. The Knicks Acquire Eddy Curry From The Bulls

via sportsroids.com

Eddy Curry represents just one chapter in Isaiah Thomas’ book of running the New York Knicks into the ground with his horrible personnel decisions. Thomas never bothered to think there was a reason the Chicago Bulls would be so willing to trade away a guy for whom they used a top-3 lottery pick; it’s because they were concerned Curry had a congenital heart condition that could derail his NBA career. But throwing such caution to the wind, not only did Thomas trade for Curry, but he also handed him a six-year, $60 million contract.

Unsurprisingly, after a somewhat promising start in New York, Curry began to have major issues with his conditioning and health, which led to prolonged stints in head coach Mike D’Antoni’s “doghouse.” Towards the end of his career, there were reports that Curry’s weight had ballooned to as much as 350lbs.

17. The Dallas Mavericks Sign Erick Dampier

via hoopshabit.com

When Mark Cuban first took over as owner of the Dallas Mavericks, he was another one of those impetuous owners who thought he could outspend other teams and build a championship contender instantaneously. If we’ve learned anything in professional sports, it’s that this idea almost always ends up in a total disaster.

One of Cuban’s first “splash” moves was to acquire centre Erick Dampier from the Golden State Warriors via trade, and then sign him to a seven-year, $73 million contract. Everyone knew Dampier only played hard in the last year of his previous contract to fool some team into signing him to a massive deal except Cuban. The sentiment that other NBA players had towards Dampier was best summed up by Shaquille O’Neal, who referred to him as “Ericka Dampier.” As a member of the Mavericks, Dampier never averaged more than 10 points or nine rebounds in the six seasons he was there.

16. The Chicago Bulls Trade Jimmy Butler

via chicagonow.com

Nobody should argue with the fact that the Chicago Bulls were better off trading All-Star forward Jimmy Butler. The dimwitted duo of Vice President of Basketball Operations John Paxson and GM Gar Forman couldn’t decide whether to build a team that would perennially fight for one of the final playoff spots in the Eastern Conference, or rebuild the team to be a contender in the future.

In the process of trading Butler, they ensured the Bulls wouldn’t be anything close to a good team. How else could you explain the fact that the Bulls traded Butler AND a first-round pick in the 2017 NBA Draft in exchange for a worse return. The fact that the Bulls traded Butler for two guys who will never play in the All-Star game is bad enough, but why in the world did they throw in a first round pick in the process, especially if their intentions really were to rebuild them team?

15. The Seattle Supersonics Sign Jim McIlvane

via nothinbutnets.com

Jim McIlvane is a living testament to the old basketball adage that if you’re seven-feet tall and can chew gum without hurting yourself, some NBA team in the 1990’s or 2000’s was going to pay you way more than you were worth. Despite the fact that he couldn’t crack the starting rotation of the then-Washington Bullets, and that he averaged fewer than 15 minutes a game during his “breakout” second year, the Seattle Supersonics signed McIlvane to a seven-year, $33.6 million contract. That immediately sent one of the most promising young teams in the NBA into an immediate funk. Sonics superstar Shawn Kemp was beyond irate at the team’s decision, and went from one of the most exciting young players in the NBA to a jealous diva who eventually demanded a trade out of town.

14. The New York Knicks Sign Allan Houston

via nbcnewyork.com

You know a contract is terrible when your league institutes a rule named after you which bails out teams who have given horrible contracts to its players. After arriving via free agency from the Detroit Pistons, the sharpshooting Allan Houston took over the shooting guard spot for the New York Knicks. He was a key cog in the Knicks team that went from the #8 seed in the East all the way to the NBA Finals in 1999.

The following summer, the Knicks signed Houston to a six-year, $100.4 million contract that crippled their salary cap for years to come. Even worse, during his last two seasons in New York, he missed over 90 games due to injuries. After he retired, the NBA adopted a rule that allowed teams to effectively release a player from their roster, giving them a reprieve from any disastrous contract; while it’s officially known as the amnesty clause, it’s colloquially known by everyone else as “The Allan Houston rule.”

13. The Dallas Mavericks Select Sam Perkins

via trendingtoplists.com

Ironically enough, while this selection will go down as one of the biggest draft day oversights in NBA history, it wasn’t even the worst one to take place in the 1984 NBA Draft (but we’ll get to that one in a second). Between 1982 and 1985, Cleveland Cavaliers owner Ted Stepien traded away five consecutive first-round picks; it was such egregious mismanagement that the NBA eventually instituted the “Stepien Rule,” which states that a team cannot trade its first-round pick in consecutive years.

Cleveland sent that pick to the Dallas Mavericks, who used what turned out to be the 4th overall selection in the 1984 NBA Draft to take forward Sam Perkins from the University of North Carolina. The player that Dallas passed on, who was taken with the fifth overall pick (right after Perkins) would be future Hall of Fame player and Dream Team member Charles Barkley, one of the 50 greatest players in NBA history.

12. The Atlanta Hawks Select Marvin Williams

via cbslocal.com

During the early 2000’s, the Atlanta Hawks were known for making breathtakingly terrible decisions in the NBA Draft. Atlanta passed on J.J. Redick to instead take Sheldon Richardson in 2006. Passing over Andre Iguodala and Luol Deng in 2004, to instead take Josh Childress, was even worse. But all of those terrible decisions pale in comparison to what they did in the 2005 NBA Draft: selecting forward Marvin Williams.

You know who would’ve been a great solution for that need? Chris Paul or Deron Williams, both of whom Atlanta passed over to take Marvin. Deron Williams had just come off a season where he led his team to the championship game in the NCAA Tournament, and Chris Paul was a consensus first-team All-American. Paul now looks like he’ll be a future Hall of Famer. Deron Williams was a three-time All-Star. Marvin Williams ended up leaving Atlanta after disappointing seasons, where he never averaged more than 15 points, seven rebounds, or two assists per game.

11. OKC Trades James Harden To The Houston Rockets

via thunderousintentions.com

The Oklahoma City Thunder trading James Harden illuminated one of the dirty secrets of the NBA’s competitive landscape: even with a salary cap in place, the small market teams simply don’t have the resources to compete with the big market teams because of all the extra revenue the big market teams make, allowing them to pay the NBA’s luxury tax when they exceed the salary cap.

That’s why the Thunder ended up trading James Harden when they couldn’t re-sign him to a contract that both sides were happy with. There are several layers to why this was a terrible trade. For one, it’s because the Thunder decided to choose handing a larger contract to forward Serge Ibaka over Harden. And then there’s the fact that what the Thunder got in return wasn’t quite as magical as Harden. Imagine how good this team could’ve been with a nucleus of Kevin Durant, Russell Westbrook and James Harden all in their prime?

10. The Supersonics Trade Scottie Pippen For Olden Polynice

via nba.com

Former Seattle Supersonics General Manager Bob Whitsitt was nicknamed “Trader Bob,” thanks to his penchant for making blockbuster deals. While he’s remembered as the architect of the great Supersonics teams of the 1990’s he could also be considered the a chief architect for another legendary dynasty: the Chicago Bulls of the early 1990’s.

During the 1987 NBA Draft, Whitsitt selected a Swiss army knife-type forward named Scottie Pippen with the 5th overall pick. But thanks to the obsession by NBA teams with big men, Whitsitt traded Pippen plus a first and second round pick in the 1988 NBA Draft for centre Olden Polynice. Here’s where it gets better: that 1988 first round pick Whitsitt sent to Chicago turned into point guard B.J. Armstrong, a key cog in the Bulls’ first “three-peat” of NBA Championships between 1990 and 1992. Not to mention Pippen turned into a Hall of Famer.

9. Warriors Give Away Robert Parish And Kevin McHale In 1980

via bostonglobe.com

One of the biggest reasons that the Boston Celtics were historically so good for so long was because of the shrewd dealings made by legendary team president Red Auerbach. Among the franchise-changing moves he made is trading the first and 13th picks in the 1980 NBA Draft to the Golden State Warriors, in exchange for the third pick in that same draft, as well as fourth-year centre Robert Parish.

The Warriors were struggling after winning the NBA Championship in 1975, and eager to select centre Joe Barry Carroll, an All-American from Purdue University. Golden State selected Carroll with the #1 pick, and the Celtics ended up selecting Kevin McHale with the #3 pick they got from Golden State. So if you’re keeping score: Auerbach managed to acquire two major building blocks of the great Celtics teams of the 1980’s in that trade, while the Warriors selected a player whose nicknamed ended up becoming “Joe Barely Cares.”

8. The Bucks Trade Dirk Nowitzki To The Dallas Mavericks

via espn.com

In the 1998 NBA Draft, the Dallas Mavericks selected oversized forward Robert “Tractor” Traylor with the sixth overall pick. The Milwaukee Bucks saw Traylor as an undersized version of Shaquille O’Neal. So the Bucks traded forward Pat Garrity and a mysterious German prospect named Dirk Nowitzki for him. Nowitzki ended up changing the fortures of the entire Dallas Mavericks franchise, leading them to 15 NBA Playoffs appearances from 2001 through 2012, and then 2014 through 2016. He was the league MVP in 2007 — the season after he led the Mavericks to their first NBA Finals appearance — and finally won a league championship in 2011. He’s a 13-time All-Star, a 12-time All-NBA Team member, and the first European player to start in an All-Star Game. Meanwhile, Traylor struggled with his adjustment to the NBA game, and battled weight issues throughout his career. He lasted only three seasons in Milwaukee.

7. The Detroit Pistons Select Darko Miličić In 2003 NBA Draft

via cbslocal.com

The Memphis Grizzlies, who were one of the two teams left with a chance at the #1 pick in 2003 (along with the Cleveland Cavaliers) as the Draft Lottery unfolded, would have to surrender their pick to the Detroit Pistons if they didn’t get the #1 overall pick as part of a 1997 deal that brought them forward Otis Thorpe. As we all know, the Cavaliers secured the #1 pick, and the right to take high school phenom LeBron James, while the Grizzlies then had to give the Pistons their pick at #2.

But instead of taking Carmelo Anthony, NCAA Tournament breakout star Dwyane Wade, or the super-talented and athletic big man Chris Bosh, the Pistons famously selected Darko Miličić, the seven-foot Serbian centre who had just turned 18 years old days before the draft. Miličić is almost single-handedly responsible for killing the infatuation of NBA Teams with selecting raw-but-talented players from Europe.

6. The Brooklyn Nets Acquire Kevin Garnett And Paul Pierce

via masslive.com

The sad part of this deal is that the Nets were the team most eager to push it through, no matter the cost. New Brookyln Nets owner Mikhail Prokhorov and team liaison Dmitry Razumov were obsessed with adding “big name” players to the Nets in order to generate buzz, sell tickets, and win an NBA championship (in that order of priority).

The “no matter the cost” element allowed Celtics General Manager Danny Ainge to absolutely fleece the Nets, acquiring Gerald Wallace, Kris Humphries, MarShon Brooks, Kris Joseph, Keith Bogans, three first-round picks (2014, 2016 and 2018), plus the right to swap first-rounders in 2017. Obviously, the deal was more about the draft picks than it was the players the Celtics acquired. Those picks netted the Celtics forward James Young, wingman Jaylen Brown, forward Jayson Tatum, and the 2018 pick they used to acquire All-Star Kyrie Irving.

5. The Portland Trailblazers Select Greg Oden Over Kevin Durant

via foxsports.com

In fairness to the Portland Trailblazers, the vast majority of NBA teams would have made the same mistake if they were placed in the same position. Greg Oden, the #1 player in the nation coming out of high school was higher on nearly everyone’s draft board than forward Kevin Durant, a skinny seven-foot wing player with scoring skills the NBA had never seen in a guy with his height.

Even though there were considerable red flags about Oden’s medical makeup (there was a rumor that one of his legs was shorter than the other), and the fact that Oden barely played his only season at Ohio State University because of risk of injury, Portland took Oden, and the Seattle Supersonics (who became the Oklahoma City Thunder) took Durant. By 2016, Oden was out of the NBA.

4. The Atlanta Hawks Give Up Bill Russell

via si.com

This could be the greatest move that Red Auerbach ever made among all his great personnel moves for the Boston Celtics. Despite the fact that most teams scouted centres based on their offensive potential (while Auerbach was fascinated by Bill Russell’s defensive and rebounding skills), Auerbach traded two players coveted by the then-St. Louis Hawks — Ed Macauley and Cliff Hagan — in exchange for Russell.

Auerbach and Russell combined to win 11 NBA championships in 13 years, including three against the Hawks. Russell is considered one of the five best players in the history of the NBA, especially given the fact that he has twice as many championship rings as Michael Jordan. This move truly changed the course of history in the NBA.

3. The Milwaukee Bucks Trade Kareem Abdul-Jabbar

via fadeawayworld.com

In complete fairness to the Milwaukee Bucks, it’s not like they actually wanted to trade away Kareem Abdul-Jabbar, the man who would go on to become the NBA’s all-time scoring leader (and remains so to this day). For one, Milwaukee outbid the then-New Jersey Nets of the American Basketball Association to secure his rights when he came out of UCLA in 1969. The Bucks went on to win the 1971 NBA championship, and Abdul-Jabbar won three MVP awards while playing for the Bucks.

But Abdul-Jabbar felt that Milwaukee was too culturally homogenous for someone who chose the faith he did, and too far away from his loved ones back in Southern California. That’s why he forced a trade to Los Angeles. The Bucks received centre Elmore Smith, guard Brian Winters, and rookies Dave Meyers and Junior Bridgeman in return. Obviously, history does not look back on those guys anywhere close to how we all look back on Kareem.

2. The Washington Wizards Re-sign Gilbert Arenas

via defendernetwork.com

It’s not that Gilbert Arenas was a bad player or anything; after the 2006-2007 season, he was named to the All-NBA Second Team. But later that season, he tore the MCL, which caused him to miss almost the entire next season, playing in only 13 games in during the 2007-2008. When Arenas opted out of his deal to test the free agent waters, instead of letting the market dictate what he should be paid (coming off said knee injury), Grunfeld and the Wizards rushed out and signed Arenas to a six-year deal worth $111 million. As basketball fans are well aware, not only did Arenas play in only two games the season after signing that massive extension, but during the season after that (the 2009-2010 season), the NBA suspended Arenas indefinitely without pay after confirming that Arenas was storing firearms in his locker at Verizon Center.

1. The Trailblazers Select Sam Bowie Over Michael Jordan

via si.com

The Portland Trailblazers passing on Michael Jordan and instead selecting centre Sam Bowie is unquestionably the worst player personnel move in the history of professional basketball, if not the history of all of professional sports. Jordan’s transcednent talent was apparent to everyone.

He was a two-time All-American and the Naismith and the Wooden College Player of the Year as a Junior. After coaching Jordan in the 1984 summer Olympics, Hall of Fame coach Bobby Knight was so impressed that he implored Portland Trailblazers General Manager Stu Inman to select Jordan. When Inman responded that Portland needed a centre, Knight told Inman to draft Jordan and play him at centre.

Not heeding Knight’s advice, Inman instead selected Bowie with the second overall pick (after the Houston Rockets took centre Hakeem Olajuwon with the #1 overall pick), despite the fact that Bowie struggled with numerous injuries in college. Unsurprisingly, Bowie suffered an injury at the end of his rookie year, and then again at the start of his second year. He only played in 63 games out of a possible 328 during his last four seasons in Portland. Meanwhile, we all know that Jordan went on to become the greatest player in NBA history.

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