The 25 Worst Free Agent Signings in NBA History

Image via Complex Original

Year: 2007
Contract: $30 million/5 years
Team: Knicks
What they got for the money: $27,985/point with New York

A warning to all of the Knicks fans out there: You are going to see a lot of former Knicks on this list. So if you don't want to take a trip down memory lane, we'd advise you to head elsewhere right now. Jeffries wasn't the worst signing that the Knicks ever made. But it was a little bit strange to see them give so much money to a guy who was basically a role player both before and after the Knicks signed him.

Even more puzzling: they agreed to re-sign Jeffries in 2011 after trading him away in 2010. It was like they wanted all of their fans to hate them.

Year: 2009
Contract: $53 million/5 years
Team: Raptors
What they got for the money: $490,741/three-point field goal made with Toronto

During the 2009 NBA Finals, Turkoglu averaged 15.8 points, 4.5 rebounds, and 4.8 assists per game. So Toronto general manager Bryan Colangelo signed him to a large contract during the summer of 2009 in an effort to convince Chris Bosh to re-sign with the Raptors the following year. Only one problem: Turkoglu looked like a shell of himself during the 2009-10 NBA season and didn't prove that he was worth anywhere near $53 million over five years.

So Bosh left in the summer of 2010, the Raptors got stuck with a guy that they didn't really want anymore, and Toronto shipped Turkoglu off to the Suns a short time later.

Year: 2006
Contract: $64 million/5 years
Team: Hornets (via sign-and-trade with Pacers)
What they got for the money: $104,159/three-point field goal made with New Orleans

If it weren't for all of the injuries, Stojackovic would probably not be on this list. But after signing his lucrative deal, he suffered an injury that sidelined him in his first season with the Hornets for 69 games. The following year, he was back to his original form. But in the season after that, Stojakovic had another setback that forced him to miss 21 games. So he wasn't worth what the Hornets were paying him.

Year: 2008
Contract: $80 million/5 years
Team: 76ers
What they got for the money: $24,457/point with Philadelphia

The former Clippers forward missed almost the entire 2007-08 NBA season after suffering a ruptured left Achilles' tendon. So he did not seem like the kind of player who warranted an $80 million deal. But the Sixers rolled the dice on him anyway in the summer of 2008 and planned to build their team around him. That plan didn't pan out, though, as Brand was forced to miss most of his first season with the team due to a shoulder injury.

He never really returned to being the player he was before his Achilles injury, either, and while he put up relatively decent numbers for the Sixers, he was eventually cut loose via the amnesty exception in 2012.

Year: 2000
Contract: $67 million/6 years
Team: Bucks
What they got for the money: $11,227/point with Milwaukee

Tim Thomas was never the type of player that you would associate with elite. So there was no plausible reason for him to receive such a huge amount of money from the Bucks in 2000. Thomas would never live up to his contract but he would travel a lot. And yes, we're talking about his journeyman status.

Year: 1997
Contract: $65 million/6 years
Team: Grizzlies
What they got for the money: $361,111/block in Vancouver

Big men are hardly a dime a dozen in the NBA. In fact, if you want to sign a center to a deal, you usually have to shell out quite a bit of money. And that's exactly what the Grizzlies did when they gave Reeves a large contract back in 1997. But back injuries derailed his career a short time later and Reeves was never able to transform himself into one of the league's elite centers. The Grizzlies were sstuck paying him like one for more than half a decade.

Year: 1997
Contract: $86.7 million/7 years
Team: Supersonics
What they got for the money: $12,253/point with Seattle

After making one bad decision in keeping an overpaid Jim McIlvaine and trading away Shawn Kemp, the Sonics followed that up by acquiring Vin Baker in a deal and signing him to max contract. While it wasn't numbers or injuries that forced a decline in Baker's career, it was the off-the-court issues that homie just couldn't shake that put a stop to his time in the NBA.

Year: 2000
Contract: $51 million/7 years
Team: Pacers
What they got for the money: $14,417/point scored with Indiana

One good postseason can make a world of a difference in a player's income. Croshere averaged 6.8 points per game in his entire NBA career, but during the Pacers' 2000 playoff run, Croshere put up good enough numbers to hit a huge payday in the offseason with Indiana. The following year, Croshere went back to his crappy playing days and the Pacers were stuck with a $51 million problem.

Year: 2008
Contract: $72 million/6 years
Team: Bobcats
What they got for the money: $14,510/rebound with Charlotte

In one of the most public cases of buyer's remorse ever, the Bobcats signed Okafor to a lucrative contract—and then proceeded to include him in every trade discussion they ever had ("You have a Nolan Ryan rookie card? We'll take it—for Okafor!"). Charlotte was actually able to deal him for Tyson Chandler in 2009 (how the hell did that happen?). But his contract with the Bobcats is still one of the worst of all time.

Year: 1996
Contract: $33.6 million/7 years
Team: Supersonics
What they got for the money: $16,298/rebound with Seattle

Initially, Jim McIlvaine was anointed the role of "Shaq Stopper." It overshadowed his lack of offensive skills (i.e. a slim 2.3 points, 2.9 rebounds per game for the Washington Bullets). But that former title must have blurred the senses of the Sonics, who offered him $33.6 million and traded away Shawn Kemp. And you wonder why there's no team in Seattle these days.

Year: 2000
Contract: $86 million/7 years
Team: Heat
What they got for the money: $18,516/rebound with Miami

In 2000, the Heat gave Grant—a guy who averaged less than 10 points and 10 rebounds per game—a deal worth $86 million. The following year, Grant posted his best career numbers, but it was a seven-year deal and every year after that was a forgettable one. When Grant signed, Miami boss Pat Riley called the forward the missing piece to the team's championship puzzle.

Sadly for Grant, though, he was traded to the Lakers in 2004, a year before the Heat got the real missing piece to their championship puzzle—Dwyane Wade.

Year: 2008
Contract: $111 million/6 years
Team: Wizards
What they got for the moneyy: $412,946/three-pointer made with Washington

Did Arenas have pull in the Wizards organization or what? After getting the team to re-sign his friend Antawn Jamison to a nice $50 million deal, Arenas followed that work of magic by getting the Washington front office to offer him a ridiculous $111 million contract. Now, we don't wanna believe that Agent Zero had to resort to using firearms and making threats to get his way, but we already know that dude has a track record...

Year: 2005
Contract: $70 million/5 years
Team: Cavaliers
What they got for the money: $33,429/point with Cleveland

In fairness to the Cavaliers, they thought that they were getting a guy who could drop 20 a night and serve as the perfect running mate for a young LeBron James when they inked Hughes to this deal. He had, after all, averaged 22.0 points, 6.3 rebounds,  4.7 assists, and 2.9 steals with the Wizards the season before Cleveland signed him. But Hughes forgot how to shoot when he got to Cleveland (his field goal percentage dipped to just 37.7 percent during the 2007-08 NBA season) and he also struggled to stay healthy.

So he never turned into LeBron's version of Scottie Pippen like the Cavs hoped he would and he was traded away to the Bulls in 2008.

Year: 2004
Contract: $92.5 million/7 years
Team: Nuggets
What they got for the money: $5,115/rebound with Denver

Do you know what posting 16 points and snatching eight rebounds per game will get you? Apparently, a maximum contract worth $92.5 million! Of course, Martin was never a player to score his points in the conventional post-up or jump shot way, so we can't help but wonder what the Nuggets were thinking when they offered K-Mart this contract.

But they gave it to him and he responded by…well, by posting lower averages in each season after he signed the deal with Denver. D'oh!

Year: 2004
Contract: $70 million/7 years
Team: Mavericks
What they got for the money: $18,315/block with Dallas

In another case of Mark Cuban trying to fill a void with a big-name, high-contract player, the Mavericks signed Dampier for an unreal $70 million. Dampier had a long, mediocre stay with the Mavs before bolting to the Heat in an attempt to capture that elusive 'chip. How'd that turn out for ya, big fella?

Year: 1999
Contract: $87.7 million/7 years
Team: Suns
What they got for the money: $19,281/point with Phoenix

Back in the day, Hardaway was a great player. But when his career was on the decline, the Suns offered him a contract that he would never be able to return in value. Eventually, Penny landed in the stomping ground where many players go when their career is almost done for—with the Knicks. And it's a known fact that when you're in your 30s and playing for New York, you're as good as retired.

Year: 2002
Contract: $70 million/7 years
Team: Mavericks
What they got for the money: $30,303/rebound with Dallas

From his deal with the Mavericks worth $70 million to the one-year contract he signed with the Trail Blazers for $12.7 million, LaFrentz has suckered the NBA into believing that his talent is worth the high price-tag time and time again. How's that saying go again? "Fool me once, shame on you, fool me twice, let's lock the players out so we can save ourselves from ourselves..." Yeah, that's it.

Year: 1989
Contract: $13 million/6 years
Team: Hawks
What they got for the money: $7,072/rebound with Atlanta

The Hawks paid Koncak just over $2 million per season starting back in '89. That's chump change these days, but back then it was more than Michael Jordan, Magic Johnson, or Larry Bird made. Those three guys are top 5, dead or alive. Koncak? Yeah, he juuuuuussssst missed the cut.

Year: 2005
Contract: $47 million/5 years
Team: Bucks
What they got for the money: $12,263/point with Milwaukee

After being named the NBA's Most Improved Player for the 2004-05 NBA season, Simmons entered free agency at the right moment. Eventually, the forward signed with the Bucks after they offered him a ridiculous $47 million contract that the Clippers weren't going to match. While in a Bucks jersey, Simmons scored a pedestrian 10.6 points per game and never returned to the old form that Milwaukee invested so much in.

Year: 2006
Contract: $60 million/4 years
Team: Bulls
What they got for the money: $17,828/rebound with Chicago

We all know that defense wins championships, but did you know that it also nets certain players outlandish contracts as well? Just ask Wallace, who is known strictly for picking up boards and blocking shots. He received an uncalled-for $60 million offer from the Bulls in 2006. Wallace quickly signed on the dotted line and went into autopilot for the rest of his career.

Honestly, that's the only way to describe his less-than-spectacular rebounding and shot-blocking numbers during his time with Chicago.

Year: 2001
Contract: $100 million/6 years
Team: Knicks
What they got for the money: $40,526/field goal made with New York

There are many mysteries in life that will probably never be answered. One of those questions has to be "Why in the world did the Knicks offer Allan Houston a $100 million contract over the course of 6 years?" At the age of 30, Houston didn't have the type of standout season that would warrant getting anywhere near $20 million per year. But Knicks GM Scott Layden blew every dime that New York had on a player who would be forced to retire five years after signing the deal.

After a few failed comeback attempts, Houston finally called it quits for good, but dude left a lasting imprint on the Knicks organization—for all the wrong reasons.

Year: 2007
Contract: $118 million/6 years
Team: Magic
What they got for the money: $28,135/point with Orlando

In the summer of 2007, NBA teams didn't have many options with regards to free agency. Just to put things into perspective, Luke Walton—yes, Luke Walton!—was one of the top free agents that year. So there were quite a few teams that went after Lewis, which forced the Magic to offer him a huge contract in order to sign him. It was a huge mistake. Over the next three seasons, Lewis' points and rebounds per game declined dramatically and, while the Magic enjoyed some success thanks to Dwight Howard, Lewis never lived up to his contract.

He was traded to the Wizards in 2010 but his yearly averages never picked up again after he scored his big deal.

Year: 2005
Contract: $60 million/6 years
Team: Knicks
What they got for the money: $7,722/rebound with New York

When it was all said and done, Eddy Curry was known more for his bloated contract and bloated waistline than his actual skills on the court. And even with all that money, dude ended up owing millions in debt payments. But Eddy, look on the bright side...uh, nevermind, there's really no bright side.

Year: 2004
Contract: $48 million/6 years
Team: Trail Blazers
What they got for the money: $11,695/point with Portland

The Blazers felt that they had something special in Miles when they signed him to a six-year deal worth $48 million when he was only 22. What they got was "special" all right. From getting into verbal altercations with former coach Maurice Cheeks to making Portland pay him $18 million without playing a single game, Miles made a whole lot of money for being an sitting on his ass. He lived Homer Simpson's version of the American Dream.

Year: 2005
Contract: $30 million/5 years
Team: Knicks
What They Got For The Money: $147,239/rebound with New York

It only took ten days of 2005 NBA Playoffs competency to convince then-Knicks general manager Isiah Thomas that James and his career averages of 4.9 points and 3.5 rebounds a game were worth $30 million. To no one's surprise, James showed up to camp out of shape and ended up playing a total of just five minutes in his first season with New York. The following year, he played two games before suffering a season-ending injury. In some strange way, the Knicks actually got what they paid for.