Worst free agent signings in NBA history

In the summer of 2005, then New York Knicks President of Basketball Operations Isiah Thomas signed center Jerome James to a five-year, $30 million contract. James was coming off a surprisingly solid postseason, but considering that he only averaged 4.9 points and three rebounds per game during the regular season, it was a shocking move by the Knicks — one that turned out to be disastrous. James never averaged more than three points per game for the Knicks in his four seasons with the team and only played a total four games for the Knicks in the final three years of his contract.

To be fair to the Trail Blazers, forward Darius Miles appeared to have found a home in Portland after the team acquired him in 2004. However, the choice to sign Miles to a six-year, $48 million contract that summer was a poor one to say the least. The following season, Miles repeatedly clashed with head coach Maurice Cheeks, reportedly insulting him with racial slurs. His play on the court wasn’t much better, mainly because he couldn’t stay on the floor. A bad right knee caused Miles to miss two straight seasons, after which was suspended for violating the NBA’s substance abuse policy. In total, the Blazers paid Miles $48 million to play 145 games for them.

After receiving a mediocre return on the first three years of the six-year, $60 million contract the Knicks gave center Eddy Curry in 2005, the final three years of the contract proved to be a nightmare. Curry struggled to maintain a reasonable playing weight and was eventually benched by then head coach Mike D’Antoni. In the end, Curry played only 10 games in the final three years of his massive contract.

After making it all the way to the NBA Finals in 1996, the SuperSonics were positioned to be a dominant force in the Western Conference for years to come. Instead of bringing in a quality veteran that offseason, however, the Sonics chose to sign unproven center Jim McIlvaine to a seven-year, $35 million contract. Let’s just say the 23-year-old McIlvaine was unproven for a reason. After scoring 3.5 points per game over two season for the Sonics in which his main responsibility was keeping a seat on the bench warm, McIlvaine was shipped off to the Nets, where he spent the remainder of his career. The Sonics never made it past the first round again during their time in Seattle.

A superstar with the Orlando Magic, Penny Hardaway didn’t come close to living up to the seven-year, $87 million contract the Phoenix Suns signed him to in 1999. After one solid season with the Suns, injuries began to take their toll on Hardaway, and he could hardly manage to play 30 minutes a night for the team. Eventually Hardaway was traded to the Knicks in 2004 after averaging just 8.7 points for the Suns.

After winning the NBA’s Most Improved Player Award with the Clippers in 2005, small forward Bobby Simmons signed a four-year, $47 million contract with the Milwaukee Bucks and proceeded to convince the basketball world that his play the previous year was a fluke. After a subpar first year with the team, Simmons averaged just 7.6 points in 21.7 minutes a night for the Bucks. He was eventually traded to the Nets and was out of the league by the 2011-12 season.

The details surrounding Vin Baker’s failure to live up to the seven-year, $86 million contract he signed with the Seattle Supersonics in 1999 are more sad than anything else. A four-time All-Star when he signed with the Sonics, Baker began to have serious troubles with alcoholism after joining Seattle. In addition to his weight shooting up to around 300 pounds, Baker revealed he would binge drink after poor games with the team. The Sonics eventually suspended Baker from the team before releasing him 2003. He was out of the NBA by 2006.

To be fair to Amar'e Stoudemire, the first two years of the five-year, $100 million contract he signed with Knicks in 2010 were excellent; the three years after, not so much. Stoudemire began experiencing knee problems and soon became a shell of the explosive player he once was. Additionally, paying Stoudemire $20 million a year gave the Knicks little to no financial flexibility to remedy the situation. A player Knicks fans loved to hate, Stoudemire was bought out of the final year of his contract.

While power forward Rashard Lewis was an All-Star in Seattle, he was never worth the $118 million the Magic shelled out to him the summer of 2007. Although Lewis was instrumental in leading the Magic to the NBA Finals in 2009, the following season he was suspended by the NBA for failing a drug test, and his play steadily declined from there. In 2010, Lewis was traded to the Washington Wizards for Gilbert Arenas.

“Agent Zero” managed to revive the Wizards in the mid-2000s, averaging nearly 30 points per game twice for Washington. However, when the Wizards signed Arenas to a six-year, $111 million contract in 2008, his best days were far behind him. In the coming years, Arenas missed long stretches of games due to injury and was suspended for the final half of the 2010 season for brandishing a firearm in the Wizards locker room. Arenas was arrested for the incident and eventually sentenced to 30 days in a halfway house and two years of probation. After being traded to the Magic, “Hibachi” was out of the NBA by 2012.

Six years and $13 million for a player might seem like chump change by today’s standards, but when the Atlanta Hawks signed center Jon Koncak to that contract in 1989, he was immediately making more money than Michael Jordan and Magic Johnson. A career 4.5 points per game scorer, it’s safe to say Koncak never did quite live up to his contract.

After two seasons of being a backup center in Philly, the New Jersey Nets signed center Todd MacCulloch to a six-year, $34 million contract that can be perfectly summed up by MacCulloch's own reaction to the offer: "I was blown away. I thought my agent was pulling my leg a little bit."

Center Ben Wallace was as dominant a presence in the paint a coach could ever ask for on defense during his tenure with the Detroit Pistons. However, when the Bulls chose to sign the four-time Defensive Player of the Year in 2006, they were signing a player whose prime years were about to end at the age of 32. Wallace played a year and a half in Chicago before being traded to the Cavaliers. Simply put, he just wasn’t the player he was after leaving Pistons, and it cost the Bulls a lot of money to find that out.

When Mark Cuban and the Dallas Mavericks signed big man Raef LaFrentz to a seven-year, $70 million contract in 2002, they were surely expecting to have an All-Star caliber player to be on their roster for years to come. It didn’t happen. After averaging 9.3 points and 4.8 rebounds for the Mavs in the first year of his contract, LaFrentz was shipped off to the Boston Celtics, where he didn’t do much better. In his five remaining years in the NBA, the center only averaged better than 10 points once and never shot better than 49.6 percent from the field.

When the Cleveland Cavaliers signed shooting guard Larry Hughes to a five-year, $70 contract in 2005, it looked as if LeBron James had found his running mate. Looks, however, can be deceiving. Hughes never really clicked with the Cavs, as he struggled to shoot above 40 percent from the field during his tenure with the team. Realizing the signing was a failure, the Cavs traded Hughes to the Bulls halfway through the 2008 season. Two years later, they lost James himself to the Miami Heat.

For as much as Mark Cuban is praised by the basketball community, he has made more than his share of poor free agent acquisitions. Signing center Erick Dampier to a seven-year, $70 million contract in 2004 counts as one. In his six years with the Mavs, Dampier failed to average more than 9.2 points or 27.3 minutes in any season and was a mediocre defender and rebounder at best.

After averaging 6.4 points and 4.9 rebound in the 2005-06 season, the New York Knicks naturally chose to sign small forward Jared Jeffries to a five-year, $30 million contract. As you may have guessed by now, it was a wasteful way for the Knicks to spend their money. Jeffries never averaged even more than those 6.4 points per game for the Knicks and was ultimately traded to the Rockets in 2010, where he was soon bought out of his contract. The following season, Jeffries was signed by (guess who!) the Knicks — this time however to a minimum salary.

Shooting guard Allan Houston was an excellent basketball player in his prime, but by the time the Knicks signed him to a six-year, $100 million contract in 2001, they were destined not to see a return on their investment. Houston averaged over 20 points for the next two seasons, but by the time the 2004 season rolled around, it was clear Houston was far past his prime. Houston's contract was so egregious that an unofficially titled "Allan Houston Rule" was incorporated into the 2005 NBA CBA that let teams receive some financial relief from disastrous contracts.

A former No. 1 overall pick, Martin was an integral piece of a surprising New Jersey Nets squad that made it to back-to-back NBA Finals. The Nuggets brought in Martin in a sign-and-trade in 2004, and while Martin wasn't a bust in Denver, he never did live up to the $93 million price tag that the Nuggets paid him for his services. 

After being named an All-Star and helping the Clippers reach the second round of the NBA playoffs, the Philadelphia 76ers signed power forward Elton Brand to a five-year, $82 million contract in 2008. From that point on, Brand struggled to stay injury-free and never averaged better than 15 points per game for the Sixers. After four seasons with the team, the Sixers would waive Brand in 2012.

A key role player on a Portland Trail Blazers team that nearly went to the NBA Finals in 2000, the Miami Heat signed power forward Brian Grant to a seven-year, $86 million contract. Considering Grant was at best the sixth man with the Blazers, it was an acquisition doomed from the get-go. Although Grant did an average 15.2 points and 8.8 rebounds per game in his first year with the Heat, he simply didn’t have the talent to live up to contract of that size. Signing Grant wasn’t a disaster for the Heat, but it was a tremendous reach to do so.

When the Indiana Pacers locked up rising star center Jermaine O’Neal for seven years at a total of $126 million in 2003, it appeared they would have an All-Star center leading their team for years to come. Then, Ron Artest and the “Malice at the Palace” happened. O’Neal was suspended 25 games for punching a fan that night, and slowly over the next few years his offensive output dropped. By the time the 2007 season rolled around, the Pacers were looking to trade O’Neal and eventually found a partner in the Heat.

During his time with the Sacramento Kings, small forward Peja Stojakovic was a deadly sharpshooter. During his time for the New Orleans Hornets, not so much. The Hornets signed Stojakovic to a five-year, $64 million contract in 2006, but Stojakovic failed to recapture the magic he had in previous years. By the time of the 2009 season, Stojakovic was a shell of his old self — but at the very least a well-paid one.

When the Raptors acquired Hedo Turkoglu on a five-year, $53 million sign-and-trade deal in 2009, they thought they were getting the player they just saw have a breakout performance in the 2009 NBA Finals. Instead, they seemed to acquire an out-of-shape malcontent who only ended up spending one year up north before being shipped to Phoenix the following offseason. 

In 2008, the Bobcats gave their former No. 1 overall pick a six-year, $72 million deal to keep him in Charlotte, a deal they would come to regret almost instantly. He spent only one more season in Charlotte before being dealt away to New Orleans.