Ranking the All-Time Misfires in NBA Free Agency over Last Decade

As teams land their big-name free agents, fans across the nation revel in unbridled glee. But will any of these signings join the ranks of the worst misfires over the last decade?

It takes some serious overpaying and more serious underplaying to join these ranks, but it’s not impossible that some recent signatories will someday make this not-top-10.

In selecting players there were two criteria that had to be met.

First, they had to be players who switched teams. Technically, free agents—even restricted—are still free agents, but the concern here isn't technicalities. We’re more concerned about the team that landed the big fish.

Second, a minimum of a $50 million contract was necessary to be considered. Yes, there are horrible contracts for less than that (are you reading, Tyrus Thomas?), but they don’t impact a team’s flexibility for years to come, ergo a certain measure of massiveness needed to be considered.

The players are ranked by cost per win share, derived by dividing the contract value by the total accrued win shares. Win shares are an advanced stat tracked at Basketball-Reference which are an estimate of how many "wins" a player adds to the team. 

A Quick Look at Different Contract Values

Perspective is always a good thing because the name that jumps to mind first might not end up being as bad as you think.

For me, the name was Gilbert Arenas. Certainly there are a number of reasons to include him on the list, including little things like getting prosecuted and convicted for bringing a gun into the locker room and threatening a teammate.

He missed a gargantuan number of games, 168, over the seven-year contract due to injuries and suspensions.

To say he was not a positive locker room presence is an understatement.

But he still produced fairly well while he was on the court. He averaged 23 points, 5.4 assists and 4.0 rebounds over the course of it.  He was paid $111 million to get 41.7 WS, a rate of $2.66 million per WS. He wasn’t great. The combination of stupid and criminal behavior certainly doesn’t add anything, but he fell short of the list. There were just even worse contracts out there.

If we played the word-association game in Chicago, if you said “amnesty,” 98.9 percent of Bulls fans would say, "Carlos Boozer." However, he’s on pace to get paid just $910,000 per WS, even less than LeBron James’ $1.34 million. Of course that doesn’t mean it’s a better value, but it does mean that it’s not one of the 10 worst signings in the last decade.  

The point here is that “bad” is a range. There are a lot of bad contracts, but these are the worst contracts. There may be other ways to define what a bad signing is, and if you change the way you define it, then you would change the order of the list. But based on this method, these are the worst I could find.

10. Corey Maggette, Golden State Warriors, $3.65 Million Per Win Share

Corey Maggette was always one of those undervalued players when he signed with the Golden State Warriors. He was coming off the second-best year of his career, averaging 22.1 points, 5.6 rebounds and 2.7 dimes per game.

He had the reputation as being one of those guys with a tremendous work ethic as well. Sure, he was going to be 30 before long, but he worked hard, so that would compensate, right?

Then again, maybe not.

Even in Don Nelson’s ridiculously fast-paced system, Maggette’s scoring dropped below 20 points a contest, and in 2010 he was traded to the Milwaukee Bucks, where he was paid $9.6 million to waste away.

Then he was traded to Charlotte, where he was injured and played just 32 games. Then he spent a year in Detroit, where he only saw the court 18 times and averaged a meager 5.3 points.

The irony is that the Warriors, who gave him the contract, actually got marginal value off of him, paying just over $17 million of the $50 million contract and getting decent years. Last year, the Pistons paid him almost $11 million to do almost nothing.

There may be no “I” in team, but there’s a "Maggette” in “I’Maggette-ng” paid.  Coincidence? I think not. He racked up $3.65 million per Win Share in the services rendered to his varying teams over the years.

9. Peja Stojakovic, New Orleans/OKC Hornets, $3.74 Million Per Win Share

In 2007, the New Orleans/Oklahoma City Hornets (it was that year) inked Peja Stojakovic to a five-year, $64 million contract. It made sense. He was one of the best sharp-shooters in the NBA at the time and was generally regarded as the best European player not named Pau Gasol or Dirk Nowitzki.

He’d been averaging 20.6 points, 5.5 rebounds and 2.1 assists over the previous five years. What could possibly go wrong? (Cue ominous music.)  

Every year after signing, his points per game fell as his paychecks rose. In his first season with the Hornets, he was averaging 17.8 points and making $10.8 million. By the end of his contract, and after he got traded to Toronto, he was getting almost $15 million to average 8.5 points a contest.

Over the course of the contract, he got paid $3.74 million per win.

8. Kenyon Martin, $3.89 Per Win Share

There was a time that Kenyon Martin had real value. Some even thought he could be a franchise player. The New Jersey Nets thought so when they drafted him No. 1 overall. Certainly the Denver Nuggets did when they offered him a seven-year, $93 million contract.

Martin had been a key figure in the Nets' two trips to the finals. He’d averaged 15.1 points and 7.6 rebounds per game with them. Hitting the prime of his career, the 26-year-old seemed like a player the Nuggets could combine with sophomore Carmelo Anthony to build a contender around.

The first year was smooth enough. He averaged 15.5 points and 7.3 boards, and the Nuggets made it to the postseason. Martin missed a dozen games but played decently.

Then the knee problems happened. He missed 26 games in 2006 with knee tendonitis. He ended the season by being suspended for conduct detrimental to the team during the playoffs.

The next year tendonitis turned into a microfracture which required surgery.  After mending from that, he needed microfracture surgery on his other knee.

He missed at least 10 games every year of the contract and played only 371 total games in seven years. He amassed a mere 23.9 WS, meaning he was paid $3.89 million for every game he helped Denver win. He evolved into a solid defensive player, but not $93 million worth.

7. Rashard Lewis, Orlando Magic, $3.89 Million Per Win Share

Rashard Lewis was on the top of everyone’s underrated list when he got inked by the Orlando Magic in 2007. That’s always a danger, because when someone gets that underrated, they tend to get overrated, and then they end up getting overpaid.

From 2001 to 2007, Lewis was 20th league-wide in win shares. He was 18th in points. The only player in the NBA that had more points, rebounds and threes over that span was Antoine Walker. Being the next Antoine Walker should have been the warning.

Orlando gave Lewis one of the most lucrative contracts in the history of the league though, offering him a deal of six years for $118 million—that’s $28 million more than Michael Jordan made in his entire career.

Then they converted him to power forward, where he steadily declined. He dropped from 22.4 points in 2007 to 18.2 his first year in Orlando, then 17.7 in 2009, 14.1 in ’10, and 11.7 in ‘11.

During that final season, he was traded to Washington, and continued to push the envelope of sucking. Finally he hit rock bottom and got paid a remarkable $21 million to rack up just 364 total points in 2012.

No wonder the New Orleans Hornets eventually penned him a $13 million amnesty check to not play for them.

When all was said and done, Lewis provided just 30.3 Win Shares for all that money he raked in, a sum of $3.89 million per win share.

6. Amar’e Stoudemire, New York Knicks, 4.05 Million Per Win Share

Amar’e Stoudemire is a tricky one on our list because he still has two years left on his contract, and last year brought his averages down considerably. He’s had up-and-down experiences with the Knicks, though more down of late.

His first year was commendable. He scored 25.3 points per game and averaged 8.2 rebounds. Then things started getting worse. In 2012 he averaged 17.5 points and 7.8 boards, missing 19 games. Last year he averaged 14.2 points and 5.0 rebounds while missing 53 games.

The question is whether this is an anomaly or a trend. Considering that Stoudemire’s knees are so bad that he has the most massive uninsured contract in league history (or at least I can’t fathom a larger one), it’s probably more likely the former than the latter.

There’s also the fact that he and Anthony have yet to establish they can be productive on the court together. In fact, calculating the last two years of data from Basketball-Reference, the tandem are a combined minus-4.0 points per 100 possessions when they both play.

But let’s give him the benefit of the doubt and assume that he’ll have flashes of all three years, and the truth is somewhere in the middle. If we project his previous three-year pace over the length of his contract, he still lands sixth on our list of worst contracts, as he makes $4.05 million per win share.  That could be even worse if his production continues at its present level or falls even lower.

5. Ben Wallace, Chicago Bulls, $4.35 Million Per Win Share

July 13, 2006, is a day that will live in infamy with the Windy City. That is the day the Chicago Bulls forked over a ridiculous four-year, $60 million contract to Ben Wallace so they could have veteran toughness and inside defensive presence.

During his first year, it seemed to be a decent contract. The Bulls led the NBA in defensive rating, and Wallace, the defensive leader of the team, was a large part of the reason why. He was second team on the All-Defense team, had the second-best defensive rating in the league and was second in defensive win shares as well.   

Then the next year he fell off a cliff. His rebounding dropped from 10.7 per game to 8.8. His defensive rating spiked upwards nine points. His contract was suddenly an albatross.

So Chicago did what every reasonable team does in those situations, they turned to Cleveland and made him their problem. After finishing the following season with the Cavaliers, Wallace was traded to the Phoenix Suns, who spent $10 million to waive him.

By the time the smoke had cleared, Wallace had been paid $57 million to contribute 13 WS.

The WS in this case can stand for a host of things, “Wallace Sucked,” “Wallace Stole” or, if you’re thinking of the time he was coming off the bench, “Wallace Sat.”

Of course, if you want to think of him cashing his check, it’s “Wallace Smiled.”

4. Hedo Turkoglu, $4.49 Million Per Win Share

Hedo Turkoglu has been more “he don’t” since he inked his newest deal—well, unless we’re talking about taking performance-enhancing drugs that is.

There are some contracts that seemed good at the time they were signed, but then players were injured or just declined.

Turkoglu's was a head-scratcher from the beginning. It was just an odd signing by the Toronto Raptors. Even more bizarre is that first the Phoenix Suns, and then the Orlando Magic, were willing to absorb that colossal stupidity.

Since that contract dried, he’s barely even qualified as a “role player,” much less as a $10 million player. He’s averaged 10.6 points, 4.2 boards and 4.2 assists per game. Last season he played just 11 games and scored just 32 points.

Now the Magic are negotiating to buy out the $12 million remaining. Depending on how that pans out, Turkoglu will have somewhere in the neighborhood of $4.49 million for every win he helped his teams accrue over the course of his less-than-performance-enhancing contract.

Why?

3. Eddy Curry, New York Knicks, $6.02 Million Per Win Share

There are certain names that typify a generation of teams' ineptitude in the NBA.

With the Los Angeles Lakers, nothing screams failure like the “Smush Parker” years, and for the New York Knicks, the ineptitude of Isiah Thomas will always be encapsulated in two simple words: Eddy Curry.

Curry started getting so out of shape that he was in a round shape. He looked like he ate Oliver Miller and then had a doughnut for dessert. Obviously, when you’re pushing 400 pounds, you’re not going to fit very smoothly into Mike D’Antoni’s run-and-gun system.

When you stop running, but you don’t stop moving, it’s a sign you might have a weight problem. When Nate Robinson keeps getting pulled into your orbit, it’s a sign you need to lose weight. And when you can’t see the tips of your skis anymore, it’s really a sign you need to drop some pounds.

But jokes aside, when you can’t run without ruining your knees, or when you have heart problems, it’s much more serious than basketball.

Curry’s contract was ridiculous on many fronts, but perhaps the most ridiculous of all was the marriage of Curry and D’Antoni. Needless to say, it didn’t work, and the Knicks were carrying one of the worst contracts in history.

Durring his five-year Knick career, Curry averaged just 15.2 points and 5.8 rebounds. He played just 222 of the Knicks' 410 games over the span.  

He only cost the Knicks $6.02 million per win share over the course of his contract.  But wait, as they say, there's more!

That is only part of the misery of the sign-and-trade deal worked out with the Chicago Bulls. The other part is that they gave up two first-round picks in the process, which were used on LaMarcus Aldridge and Joakim Noah, meaning the Knicks gave not one but two All-Star centers for the price of one broken down master of obesity. 

I suspect if you walked into a bar in the Bronx and yelled the name Eddy Curry, you would be beaten within an inch of your life. I wouldn’t try it though.

2. Larry Hughes, Cleveland Cavaliers, $6.80 Million Per Win Share

Larry Hughes was given a five-year, $70 million contract in 2006 by the Cleveland Cavaliers. To date, no one understands why. 

Prior to getting inked to the deal, he had been a career 15.2 point-per-game scorer who shot a sad .415 from the field. Sure, he averaged 20.4 points per game the two years prior, but they were inefficient points, as he shot just .414.

Somehow Cleveland saw that 20 points per game and thought $14 million bucks a year though, and gave him a five-year, $70 million deal.

The most fun thing about Hughes' contract was the veritable hot potato the NBA played with it. Hughes played his first year in Cleveland, was dealt to Chicago for his second, to the Knicks midway through his third and finally finished it out in Sacramento, where he was waived.

Over the course of the entire contract, he accrued just 10.9 win shares, less than what 10 players had this season alone. Over the course of the contract, he was paid $6.8 million per win.

I, for one, count it as one of LeBron James' greatest achievements that he made it to the finals with this overpaid mistake as his sidekick. 

1. Ben Gordon, Detroit Pistons, $9.83 Million Per Win Share

It might surprise some to see Ben Gordon topping this list, but my question is simple. How could he not top this list? He. Has. Been. Awful.

His contract is so bad that the other nine people on this list shake their heads every time they see him “play.”

In 2009 he was given a five-year, $58 million deal by the Detroit Pistons. He’s racked up 4.9 win shares in the four years since. Last season alone, 98 players topped that total.

It gets even more obnoxious. Last year, on arguably the worst team in the league, he was the worst player, with -0.6 WS. Yes, he had a negative win share. He was so bad he cost the Charlotte Bobcats wins. He made the Bobcats worse! How do you do that?

He was also their highest-paid player, making $12.4 million.

Perusing the worst season performances of the last 23 years, I could not find a player that did worse and was paid more than Gordon in a single season. Considering how salaries have escalated, excluding amnestied players, you can argue that last year Gordon was the most overpaid player ever.

He has been paid almost $10 million for every game he’s “helped” his team to win over the course of his contract. That’s criminal. If Jim Gordon is any relation, he’s very ashamed.