Free agency is in full swing and we’re expecting some of the big names to sign soon. But not all the teams are going to land the superstars they want, yet they will be left with a bunch of cap room and money to spend. You can already see where this is going, teams are going to spend stupidly and pay for contracts that seem great now, but will turn up to be huge problems later.
But it’s not like general managers in this league ever learn. The mistakes they’ve made before, they’ll make it again. There’s always so much hope in free agency, and so much disappointment after the players actually step on the court for their new teams. We opted out of including Gilbert Arenas’ still-horrendous $111 million deal with the Wizards because even he admits it’s too obvious.
Here’s a run-down of the 14 worst free agent signings since 2000.
Bobby Simmons -- Milwaukee Bucks: four years, $47 million
In the 2004-05 season, his fourth year in the league, Bobby Simmons had a breakout season, averaging 16.4 points, 5.9 rebounds and 2.7 assists with the Los Angeles Clippers. After making just six three-pointers in his first three seasons, Simmons made 50 during the ‘04-05 season, shooting 43.5 percent.
After being named Most improved Player, Simmons hit the open market and received a four year, $47 million deal from the Milwaukee Bucks. Along with Andrew Bogut and Michael Redd, the Bucks thought they had a core of contenders. Instead, Simmons regressed. In his first season as a Buck, he played in 75 games and saw his average fall to 13.4 points. He missed the entire 2006-07 due to an ankle injury, and played just one more season in Milwaukee (averaging 7.6 points) before being waived.
Simmons would play three seasons with the New Jersey Nets and San Antonio Spurs before returning to the Clippers for his last season in the NBA at age 31. He never averaged double digits again.2 of 15
Erick Dampier -- Dallas Mavericks: seven years, $70 million
The Mavericks had a decision to make after the 2003-04 season. Their starting point guard Steve Nash was a free agent at the height of his powers, but Mark Cuban had concerns about his durability and the risk of handing a long-term contract to a guard with a history of back injuries.
So, instead of tossing a ridiculous amount of money to retain Nash, the team let him go to Phoenix. All the money that should have gone to Nash was given to Erick Dampier, who was coming off a career season with the Golden State Warriors in which he averaged career highs of 12.3 points, 12.0 rebounds and 53.5 percent shooting from the field.
The Mavs were a capable offensive team and felt like Dampier would provide them with the rim protector they needed to be stronger on the defensive end. In six seasons with the Mavericks, Dampier never averaged double digits in points or rebounds. He also never averaged more than 30 minutes a game, becoming a serviceable big man, but not someone worthy of the contract he was given.
To make matters worse, Nash went to Phoenix, started the Seven Seconds or Less era, and won two Most Valuable Player awards.
Larry Hughes -- Cleveland Cavaliers: five years, $70 million
Heading into the summer of 2005, the Cleveland Cavaliers were desperate to find a running mate for LeBron James, who was starting to come into his own. The big push that summer was to sign Michael Redd away from the Milwaukee Bucks. But when he returned to Milwaukee, the Cavs turned their attention to Larry Hughes.
Hughes was coming off a monster season with the Washington Wizards, averaging 22.0 points, 6.3 rebounds, 4.7 assists and led the league with 2.9 steals per game. The Cavs were getting a 27 year-old swingman heading into his prime, except there was one problem: Hughes struggled to stay healthy, and when he did get on the floor, he couldn’t make shots on a consistent basis, which is kind of important when you’re playing next to LeBron.
Hughes played just 36 games in his first season in Cleveland, and in the three years he spent with the Cavs, he saw his season to season field goal percentage fall from 40.9% to 40.0% to an atrocious 37.7% in 2007-08 before he was shipped off to the Chicago Bulls.
Hughes was not the reason why LeBron ended up leaving Cleveland, but he definitely reflected the poor player personnel decisions that were common during the LeBron era.4 of 15
Hedo Turkoglu -- Toronto Raptors: five years, $53 million
The Toronto Raptors were desperate prior to the 2009-10 season. Chris Bosh was entering the final year of his contract, and general manager Bryan Colangelo had one last shot to prove to Bosh he was capable of building a contender around him.
So, as general managers do to appease their superstar, Colangelo swooped in on the one of the biggest free agents on the market and signed Hedo Turkoglu away from the Orlando Magic.
It seems to crazy to think of Turkoglu as a premier free agent now, but at the time, he was coming off a Finals appearance with the Magic in which he averaged 15.8 points, 4.5 rebounds and 4.8 assists and ran a deadly pick-and-roll with Dwight Howard.
Colangelo envisioned the same type of partnership with Bosh, but Turkoglu showed up to training camp out of shape, was spotted out partying in Toronto during the season while he was recovering from an illness, and did nothing to endear himself to the team or the city. Turkoglu averaged just 11.3 points on 40.9 percent shooting with the Raptors. They missed the playoffs and Bosh left for Miami in the offseason. Turkoglu spent just one season with the Raptors, and was traded to Phoenix the year after.
Ben Wallace -- Chicago Bulls: four years, $60 million
Ben Wallace was the defensive anchor in Detroit, where he won DPOY four times (in 2002, 2003, 2005 and 2006.) At the prime of his career, he averaged a league-leading 15.4 rebounds per game during the 2002-03 season and won a title in 2004.
Despite all that, when the Chicago Bulls swooped in to sign Wallace to a four-year deal in the summer of 2006, many observers had their doubts right away. Wallace was turning 32 years-old, and was leaving a great fit in Detroit where he played alongside Rasheed Wallace, Chauncey Billups, Richard Hamilton and Tayshaun Prince.
Wallace still averaged 10.7 rebounds and 2.0 blocks in his first season in Chicago, but he started to shown significant decline in his athleticism and ability to anchor the defense. He also clashed with head coach Scott Skiles and failed to dominate on defense. In the middle of his second season in Chicago, the Bulls were more than thrilled to offload his contract to the Cavaliers.6 of 15
Jerome James -- New York Knicks: five years, $30 million
When Jerome James hit free agency after the 2004-05 season as a 29 year-old center, he had never averaged more than 5.4 points or 4.2 rebounds per game, only shot over 50 percent from the field in just one of his first five NBA seasons, and was, as the numbers show, merely a serviceable big man off the bench. But what James did do was average 17.2 points and 9.4 rebounds in a first round win over the Sacramento Kings in 2005. That was enough of an impression for Isiah thomas to splurge on the big man from Seattle.
James didn’t regress in New York as much as he just kept being the player he always was. In four seasons with New York, he played in just a total of 90 games, starting 20 of them, and never averaged more than 3.0 points per game or 10.0 minutes per game.7 of 15
Elton Brand -- Philadelphia 76ers: five years, $80 million
In his prime, Elton Brand was one of the most reliable big men in the game, providing 20 points and 10 rebounds every single season. But he missed all but eight games in the 2007-08 season with the Clippers because of a ruptured left Achilles’ tendon, returning at the end of the season as an audition before he hit the open market.
When Brand opted out, many expected his intention to be helping the Clippers to open up cap room to pursue other stars, which happened when his close buddy Baron Davis chose the Clippers over staying in Golden State. But Brand had a change of heart and signed with the Sixers, instead, leaving Davis in the lurch. He averaged 13.8 points in his first season in Philadelphia and played just 29 games because of a shoulder injury. By 2012, the Sixers were ready to part ways with Brand and used the amnesty exception to say goodbye.
Baron Davis -- Los Angeles Clippers: five years, $65 million
Baron Davis was coming off a superb season with the Golden State Warriors in the summer of 2008, averaging 21.8 points, 4.7 rebounds, 7.6 assists and 2.3 steals while appearing in all 82 games. But his signing with the Clippers was a disaster in so many ways.
First, Davis was often out of shape in Los Angeles and it showed in his play. He later confessed that then-Clipper owner Donald Sterling routinely heckled him and caused him anxiety. He saw his averages dip to 14.9 points, 3.7 rebounds and 7.7 assists in his first season in Los Angeles. The Clippers finished 19-63 that season. The next few years didn’t get any better, and by the middle of his third season in Los Angeles, he was traded to the Cleveland Cavaliers in a salary dumping move. To get the Cavs to take his contract, the Clippers tacked on a first round pick.
How did that pick turn out? The Cavs won the lottery with it that summer and drafted Kyrie Irving.9 of 15
Rashard Lewis -- Orlando Magic: six years, $118 million
Once in awhile, you’ll have a summer when there are no clear cut superstars available via free agency. The danger is that teams still have cap space and a willingness to spend anyways so a lot of money is thrown at above average players whose long-term contracts become very problematic by the end of the term.
This was the case with Rashard Lewis, who got close to $120 million from the Orlando Magic. Lewis averaged 18.2 and 17.7 points, respectively, in his first two seasons in Orlando, and was a key part to their run to the NBA Finals in 2009. But by the 2011 season, his play was in decline and his contract had clearly become an albatross. The Magic traded Lewis to Orlando for Gilbert Arenas, and well, let’s just say that didn’t pan out too well either.10 of 15
Jared Jeffries -- New York Knicks: five years, $30 million
Overpaying for role players is never a good idea, but that didn’t stop Isiah Thomas from throwing a five-year, $30 million offer sheet at restricted free agent Jared Jeffries in the summer of 2007. In four seasons in the league, all with the Washington Wizards, Jeffries had never averaged more than 6.8 points or 5.2 rebounds up to that point.
He was just 25 years-old, and at 6’11″, had the potential to be a decent two-way player, but no one on the market was rushing to give that kind of money to Jeffries. When the Knicks made the offer sheet, the Wizards happily said goodbye to Jeffries. Jeffries lasted for parts of four seasons in New York, and never averaged more than 23.8 minutes, 5.3 points and 4.3 rebounds while he was with the Knicks.
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Eddy Curry -- New York Knicks: six years, $60 million
On a list with this many ridiculous decisions, the Eddy Curry signing is actually one of the more defensible ones, at least at the time. At the age of 22, Curry was coming off a season with the Chicago Bulls in which he averaged 16.1 points and shot 53.8 percent from the field. His rebounding rate was a bit concerning, as he averaged just 5.4 rebounds from the center position. But he showed enough potential for Isiah Thomas and the Knicks to think he could blossom into an elite big man. Didn’t happen.
Curry had a heart condition which made his contract uninsurable. The condition was deemed life-threatening and scared off many teams, including the Bulls. Thomas swooped in on this opportunity and gave a huge contract to Curry. In his first few seasons in New York, Curry could score with the best of them, once averaging 19.5 points per game. But he never even came close to double-digits in rebounding, was a liability on defense and became a sieve on offense once the ball went into the low post.
In the last three seasons of his contract, he appeared in just 69 games, total.12 of 15
Darius Miles -- Portland Trail Blazers: six years, $48 million
This was a perfect example of when betting on potential can go awry. When the Blazers gave Darius Miles his contract, he was just 22 and had averaged 12.6 points and shot 52.6 percent from the field in 28.4 minutes of play with the Blazers after a mid-season trade from Cleveland during the 2003-04 season.
Miles appeared in 103 games over two seasons during the duration of his contract, as a knee injury derailed his career. The Blazers released him thereafter. The team saved $18 million on Miles’ contract, however, after they had an independent doctor determine that his injury was career-ending. But in the last twist of this saga, Miles was determined to play again. The Blazers sent out a memo to all 29 other teams threatening legal action if teams did pursue him. The Memphis Grizzlies signed Miles in 2008, which meant Portland lost their $18 million in savings. That amount was placed back on their payroll.13 of 15
Peja Stojakovic -- New Orleans Hornets: five years, $64 million
In his prime, Peja Stojakovic was one of the five best pure scorers in the league, and a huge part of the Sacramento King’s run in the West. In his best individual season in 2003-04, he averaged 24.2 points, 6.3 rebounds, shot 43.3 percent from three, and 92.7% from the free throw line.
But he was already regressing by the time he hit the free agent market in 2006 when the Hornets decided he would be the piece to add next to Chris Paul to vault them to contender status. Stojakovic was a strong shooter in New Orleans, making over 37 percent of threes in each of his four seasons there. But the scoring average and ability to create his own shot dipped as the years went on. In 2011, the team parted ways with Stojakovic after just 6 games in which he averaged 7.5 points in 14.8 minutes of play.
Raef LaFrentz -- Dallas Mavericks: seven years, $70 million
Back in the era when big men like Shaquille O’Neal dominated the league, teams were obsessed with acquiring centers to combat dominant bigs. Mark Cuban was a huge proponent of going big. Erick Dampier was not the only time he splurged.
After acquiring LaFrentz in a mid-season trade in 2001-02, the team watched as he became the first player in league history to record 200 blocked shots and 150 three-pointers in a season. For that, Cuban awarded him with a huge contract, and watched in the next season as LaFrentz average 9.3 points and 4.8 rebounds in 23.3 minutes. After just one season, he was traded to the Boston Celtics.15 of 15