Between the years of 1998 and 2008 NBA teams lost their minds, signing players to huge, long contracts. Many didn’t work out and eventually forced the owners to institute a “harder” salary cap, limits on number of years and amount of “max money” that can be given. Essentially, the owners had to protect themselves, from themselves.
A new television contract was just signed this year and as per the NBA Collective Bargaining Agreement, this will raise the salary cap significantly, giving front offices more money to invest in players. Did this group learn their lesson the first time? Probably not, and we are going to be in for another round of multi-year deals approaching $100 million only to find these contracts that more often hurt than help. Don’t get me wrong, “max money” is okay in certain circumstances, but typically you expect to compete for a championship. Mark Cuban maxed out several players in order to bring a championship to Dallas. My guess is if he believed he could win another championship and had the opportunity to max out the players he wanted he wouldn’t hesitate to do it again.
There are a lot of dishonorable mentions, some you may not even remember. Travis Knight signed a $22 million contract with the Boston Celtics, Austin Croshere inked a deal worth $51 million over seven years with Indiana and Jon Koncak got $13 million from Atlanta. Remember Milwaukee Buck Tim Thomas? You probably remember him more from his one season with Villanova. Anyway, he got a $67 million deal from Milwaukee. We don’t need stats to know he didn’t live up to this deal. Finally, Anfernee “Penny” Hardaway and his $87 million deal for seven years was foolishly given by the Phoenix Suns, Hardaway’s best days were well behind him at this point in his career.
Enough about these deals, we’ve got many more that have given General Managers ulcers (especially ones working for the New York Knicks). Here are the 20 worst NBA contracts of all time.
20 Bobby Simmons - Milwaukee Bucks: 4 years, $47 million
Simmons was the classic case of having a great contract year, getting paid and then underperforming for the duration of his contract. In the 2004-05 season Simmons was named the NBA’s Most Improved Player while playing for the Los Angeles Clippers. It’s important to note that this was the Clippers, a tough team to really know how good a player is given the general dysfunction with the franchise. Milwaukee made a lucrative offer to Simmons to get him to leave Los Angeles for Milwaukee and he took the money. Simmons would average just over 10 points in two seasons with the Bucks before they cut ties with him and their money.
19 Erick Dampier - Dallas Mavericks: 7 years, $70 million
18 Antonio Davis - Toronto Raptors: 5 years, $60 million
There are so many things wrong with this deal. First of all, Davis pulled off a great contract year, sneaking into the All-Star game as a center in the weak Eastern Conference. Davis was always just a one-dimensional player – he could rebound. Dennis Rodman didn’t get this kind of deal (length plus money and he was the greatest rebounding specialist of all time. Here’s the kicker, Davis was 33 years old and clearly was not going to be able to sustain his All-Star year numbers. Davis never averaged over 10 rebounds a game for Toronto. How does this deal make it to contract? A great example of why several NBA teams were losing money (owners claim) during this time.
17 Brian Grant - Miami Heat: 7 years, $86 million
16 Ben Wallace - Chicago Bulls: 4 years, $60 million
15 Gilbert Arenas - Washington Wizards: 6 years, $111 million
During contract years both player agents and front offices can feel a sense of urgency to get a deal done and secure a player. The Arenas contract is lesson to all that sometimes it pays to let things play out before you make major financial commitments to an athlete. Arenas had been Washington’s best player and a rising star in the NBA for a few years by then. In 2008, after only 13 games the previous season the Wizards announced that they had signed Arenas to an extension of $111 million over six years. Arenas would play 55 games over the next three years in Washington.
14 Jerome James - New York Knicks: 5 years, $30 million
Given the way the Knicks flush money down the drain, this one almost doesn’t hit the radar, but that’s only because it was the Knicks. It doesn’t change the fact that this was an awful contract that should not have happened. Here are the quick facts: James' career averages were less than 5 points a game and less than 4 boards a game. James averaged over 10 points and 6 rebounds in the 2005 NBA Playoffs. That was all Isaiah Thomas needed to see, cutting him a check for $30 million. The next season James showed up fat to camp. He played 5 minutes the first year with the Knicks and then 2 games after that. Just the facts folks: brutal.
13 Amar’e Stoudemire - New York Knicks: 5 years, $99 million
Yeah! More Knicks! Do you remember what happened? The reason the Knicks signed Stoudemire was because they missed out on LeBron James who took his talents to South Beach instead of ruining his career in a Knicks uniform. The Knicks ensured they got Stoudemire by throwing a lot of money at him, never mind that he was already damaged goods and there were red flags flying from Phoenix to New York with this deal. His first season was decent, averaging over 25 points and 8 rebounds a game, but his defense was already failing him and over the next 5 seasons Stoudemire was hit hard by injuries, limiting his playing time to less than half the games. His numbers dropped off and his defensive went from bad to non-existent. The Knicks finally amnestied him in 2015 and set him free from Knick purgatory.
12 Jermaine O’Neal - Indiana Pacers: 7 years, $126 million
It’s hard to say O’Neal deserved $126 million, but if there was a player and time, maybe this was it. As a center hitting his prime, O’Neal was a force both on the offensive and defensive side of the ball. He had already played a couple seasons with Indiana so they knew what they were getting. After signing the contract O’Neal put up another great year and then it happened. The following year the infamous Pacers and Pistons brawl that went into the stands changed the Indiana franchise. They sent away many of their veterans, leaving them with a high priced center they didn’t really need. To make matters worst, O’Neal started to break down and suffered injuries that cause him to miss over 100 games the remainder of his contract.
11 Elton Brand - Philadelphia 76ers: 5 years, $80 million
If the Philadelphia 76ers had not lucked out with Allen Iverson this franchise could be going on over 30 years of futility. The contract given to Brand is one example of the bad moves the 76ers have made since the days of Julius Erving and Moses Malone. Brand was already on the downside of his career (peaking with Los Angeles Clippers) and had already ruptured his Achilles tendon. Let me repeat that. Brand had already ruptured his Achilles tendon; using 76ers logic that equates to giving someone $80 million over 5 years. A despicable contract that would have corporate or political officials treated as criminals and put in jail.
10 Bryant Reeves - Vancouver Grizzlies: 6 years, $65 million
Remember “Big Country?” He was a mammoth center that clogged up the middle with a soft touch around the hoop, a white (poor man's version of) Moses Malone. After two seasons the Vancouver Grizzlies gave Reeves $65 million. Unfortunately he began having weight problems. He was always big, over 7 feet tall and weighing close to 300 lbs so when he exceeded that it caused a lot of problems and injuries. Reeves never produced the numbers expected of him and didn’t come close to earning his contract. He may have been responsible for Vancouver not having an NBA team today. Too harsh?
9 Rashard Lewis - Orlando Magic: 6 years, $118 million
The Magic really wanted to sign Lewis. After receiving in a trade from Seattle, Orlando overpaid to keep Lewis happy. Lewis was a productive wing that played above average offense and good defense, but was not a superstar. He made two All-Star games in his career. The reason this is one of the worst contracts of all time is because he was never worth $118 million. Sure enough, he signed with the Magic, put up one “good” year and then declined each year after. Everyone could see this one coming; even Isaiah Thomas wouldn’t do this deal. Okay, that’s not true; Thomas would have done this deal as well.
8 Vin Baker - Seattle SuperSonics: 7 years, $86.7 million
Baker was a beast for Milwaukee his first few seasons, averaging over 20 points and 10 rebounds a game. After Glenn Robinson and Ray Allen joined Baker it appeared they had a “Big 3” in place before they were called such things. That’s why it was surprising when Milwaukee traded Baker to Seattle. Seattle gave him a new contract worth over $86 million and after initially producing as he did in Milwaukee the wheels came off. Baker never came close to producing the numbers he had for the Bucks and for the remainder of his career fought a battle with alcoholism that never allowed him to consistently stay on the court.
7 Stephon Marbury - New York Knicks: 4 years, $76 million
Marbury, Isaiah Thomas and the Knicks were a match made in hell. When Marbury first joined he showed the flash that made him a star in Minnesota and then Phoenix. Acquired in a trade, Marbury played with the Knicks for one season, was eliminated the first round of the playoffs and given a brand new four-year deal worth more than $75 million. Marbury would not lead the Knicks to the playoffs again; instead, both Marbury and Thomas would set the Knicks back many years. Once the finger pointing started it just got plain silly. They were a good match if you like playing with fire.
6 Raef LaFrentz - Dallas Mavericks: 7 years, $70 million
Another Cuban deal before he figured out what he was doing. The length of the contract, seven years, is a real killer here. LaFrentz was one of the first “stretch” forward players. “Stretch” really means power forward that can shoot a three, but often gives up points on the defensive end. For whatever reason this hasn’t changed too much, a more recent example is Ersan Ilyasova getting a deal worth over $40 million from Milwaukee. Not exactly LaFrentz money, but not bad for a “stretch” forward. Bonus: After this contract ran out he got a one-year deal worth over $12 million from Portland. Greatest. Agent. Ever.
5 Larry Hughes - Cleveland Cavaliers: 5 years, $70 million
So, Cleveland thought Hughes could be LeBron James' Scottie Pippen. Apparently a lot of other names were not available. Hughes had his most success playing along side Allen Iverson, but even then he wasn’t that “second banana” that could help Philadelphia win an NBA Championship. Signing Hughes to such a large deal was too much of a commitment and tied Cleveland’s hands, unable to afford other free agents to pair with James. Hughes would average just over 15 points a game, hardly enough to justify such a large contract. The Hughes contact may have been the reason James bolted to Miami. Too harsh?
4 Juwan Howard - Washington Wizards: 7 years, $101 million
Howard had a long NBA career, but suffered a lot of injuries along the way, causing him to miss a lot of time. When on the court, Howard was a consistent post player, but never worth a contract in excess of $100 million or even close to it. This contract was straight up a bad value. During this time Washington threw around a lot of money, but this one was the worst. Jaws dropped when it was offered because it sounded absurd for a player that was never a top-ten superstar expected to deliver a title. A $100 million player needs to be All-NBA and Howard was never on that level.
3 Eddy Curry - New York Knicks: 6 years, $60 million
Sorry Knicks, here’s another one. They just keep coming! Curry never came close to producing anything on the court for New York. This is not a surprise, in fact, everyone already knew this. In Chicago Curry never lived up to the hype or supposed talent so why would he all of a sudden play well in New York? He didn’t; in fact, he played worse, much worse. Actually that’s not fair because he was hardly on the court at all. Curry was out of shape and often injured. He played only 10 games for his final two seasons in a Knicks uniform.
2 Jim McIlvaine - Seattle SuperSonics: 7 years, $33 million
The McIlvaine signing is a classic “what just happened” moment in NBA contracts. Somehow Seattle thought that this was their center of the future. McIlvaine was going to be the big man who could stop Shaquille O’Neal and lead them back to the NBA Finals. Of course, that never happened and his defense was never “that good” to make up for his awful numbers (under 5 points and rebounds per game). He wouldn’t last long and only played seven seasons in the NBA. Signing McIlvaine to a seven-year deal was a major miscalculation by the Seattle front office to say the least.
1 Allan Houston - New York Knicks: 6 years, $100 million
I’m guessing Larry Bird feels pretty good every time he hears the phrase “Larry Bird Rights” which is a rule that states a restricted free agent can be matched or signed for more by his own team. So, how does Allan Houston feel when he hears “Allan Houston Rule?” A rule that states you can waive one player because essentially “you really messed up.” I’m guessing it can’t feel that great. Houston was given this contract after a few clutch shots in a playoff series because that’s just how the Knicks have operated for many years. After all, it’s only money. The fans? Knick fans wouldn’t know what to do if they weren’t being tortured by their front office.