10 Money Lessons From the Worst Contracts in NBA History

10-money-lessons-from-the-worst-contracts-in-nba-historyNBA owners and general managers give out terrible contracts all the time. And since they’re unlikely to ever stop, we figured SOMEONE should learn from their financial mistakes.

Everybody’s made mistakes with their money. We all have a purchase or investment or two that we would really (really!) like to take back. Maybe it’s a used car that fell apart two weeks after you bought it or a payday loan that, no matter how hard you try, you can just never seem to pay off.

Whatever your mistakes have been, we feel your pain, and we are dedicated to making sure that you avoid money mistakes in the future. But rather than having you think about your past errors, we’re going to do something different. Because while learning from our own mistakes can be valuable, learning from someone else’s mistakes is way more fun.

So, since the NBA is about to kick off its 2018-19 season next week, we figured it’d be nifty to look at some of the worst money mistakes in the league’s history. It’s pretty clear that NBA owners and GMs aren’t going to learn from their previous contract misfires, so we figured someone should.


10. Jermaine O’Neal – Indiana Pacers – 7 years, $126.6 million (2003)

This might be the least-awful contract on the list, but it was nonetheless a massive overpay.

Still, if you had asked Indiana Pacers management whether they were happy with O’Neal’s new contract after the 2003-04 season, they would have given you an emphatic “Yes!”

They could never have anticipated that the following year O’Neal would be suspended for 15 games for his role in the infamous “Malice in the Palace” brawl between the Pacers and the Detroit Pistons.

While the following 2004-05 season would still mark a statistical peak for O’Neal as a scorer (24.3 points per game), it was all downhill from there. Injuries contributed to a decline in performance—not to mention in games played—over the next three seasons.

By the end of the 2007-08 season, during which O’Neal scored only 13.8 points per game and averaged a mere 6.7 rebounds, his $19.73 million annual salary was too much for the team to bear.

Over the summer, the Pacers traded him to Toronto, who then flipped him to Miami midseason. While his stats over those last two campaigns held steady at around 13 points and seven rebounds per game, the amount he was owed each year only continued to rise.

O’Neal made the All-Star game every year during the first four years of this contract—yet another reason why this is only number 10 on the list. Still, when all is said and done, the Indiana Pacers got way less from O’Neal than they paid for.

Lesson: Know when to cut bait on a bad money decision. 

9. Penny Hardaway – Phoenix Suns – 7 Years, $87 Million (1999)

When a player’s game is reliant on their insane athleticism, recurring knee injuries can easily turn a superstar into a bad-to-average player … who still has a superstar’s contract.

While Derrick Rose probably comes to mind nowadays, Penny Hardaway is still one of the best—and therefore the saddest—examples of this trend.

In 1999, after six years with the Orlando Magic—the final three of which saw him play only 59, 19, and 50 games—the incredibly talented and incredibly injury-prone Hardaway signed a seven-year, $87 million deal with the Phoenix Suns.

The first year of that new deal, Hardaway played 60 games. The second year he played four.

From there, Hardaway began shifting to a bench role, with his per-game stats declining every year. Phoenix traded Hardaway to the New York Knicks in early 2004 and soon replaced him with Steve Nash.

During the years Hardaway spent in Orlando playing alongside a young Shaquille O’Neal, he was one of the most exciting players in the game. During the years he spent playing in Phoenix alongside a mid-career Jason Kidd, he was one of the most depressing.

And he was expensive to boot.

Lesson: Warning signs are meant to be heeded. 

8. Allan Houston – New York Knicks – 6 Years, $100 Million Dollars (2001)

Allan Houston was not a bad basketball player. On the contrary, he was a great player and a key part of the 1999 Knicks team that shocked the NBA by beating the top-seeded Miami Heat and making it all the way to the Finals.

And Allan Houston was even very good for the first two years of this contract, which he signed in 2001.

The problems came after that.

A knee injury limited Houston to only 50 games in 2003, and it only got worse from there, eventually forcing Houston to retire in 2005 and leaving the Knicks stuck with the final two years (and nearly $40 million) left on his contract.

It was so bad that the NBA added the “Allan Houston Rule” to the 2005 Collective Bargaining Agreement (CBA), which allowed teams to amnesty one player on their team. The player still got paid, but their salary no longer counted against the luxury tax.

Lesson: When someone names a rule after one of your financial mistakes, you know you’ve screwed up.

7. Chris Bosh – Miami Heat – 5 years, $118 million (2014)

We’re not going to linger on this one. It’s just too sad.

After being one of Miami’s “Big Three” and remaking his game to bring Heat fans four straight Finals appearances and two Larry O’Brien trophies—all while dramatically reshaping his game to fit around Lebron James and Dwyane Wade—Chris Bosh deserved this contract.

Sure, Miami might have given it to him out of post-Lebron desperation when the Houston Rockets offered Bosh a max deal of their own, but still. This should have worked out.

Instead, a very scary series of blood clots in Bosh’s lungs forced him to retire in mid-2016, only one-and-a-half seasons after signing this extension, a period during which he only played in a total of 97 games.

Eventually, the Heat bought out the final two years on Bosh’s deal for $52 million, which provided them some financial relief. But that doesn’t make this inglorious ending to a glorious career any less heartbreaking.

Lesson: Sometimes you do everything right and it all still goes wrong.

6. Joakim Noah / Luol Deng – New York Knicks / Los Angeles Lakers – 4 Years, $72 Million (2016)

Ah, the summer of 2016.

With a massive spike in the NBA salary cap courtesy of a brand-new TV deal, the 2016 offseason saw teams around the league throw caution to the wind and hand out contract after magical contract—all of which turned into pumpkins the second the ink was dry.

While these aren’t the last 2016 contracts on this list, there is a perfect symmetry to them that merits their joint inclusion.

Both Joakim Noah and Luol Deng were aging ex-Bulls frontcourt players in an increasingly perimeter-oriented league who were rewarded with the same freaking contract (four years, $72 million) by two of the league’s starriest big-city franchises.

After years of playing in Tom Thibodeau’s meat-grinder system, Deng and Noah were worn down well beyond their respective ages. While injuries limited both players in the first years with their new teams, their second years saw the bottom fall out entirely.

Noah only played seven games for the Knicks in 2017-18 before injuries took him off the court and a bad attitude left him practically exiled from the team. Meanwhile, Deng played only one game for the Lakers last year before they shut him down entirely. And he wasn’t even injured!

Deng was recently bought out, and Noah looks to be heading that way as well. If you want to understand the NBA’s summer of 2016 spending spree, look no further than these two wildly ill-advised overpays.

Lastly, as a Chicago-based company, all of us here at the OppLoans Financial Sense Blog want to say that we are 1) overjoyed that both these players got massively overpaid, and 2) equally overjoyed that it was not the Bulls who paid them.

Lesson: Just because everyone else is spending money doesn’t mean you have to spend money too. 

5. Rashard Lewis – Orlando Magic – 6 Years, $118 Million (2007)

Before signing with the Magic in 2007, Rashard Lewis was a really good player—not a star, just a really, really good player—for the Seattle Supersonics (RIP). After a particularly “really good” season in 2006-07, the Magic got Lewis for six years and a staggering $118 million via sign-and-trade.

The Magic had a transcendent young Dwight Howard at center; they were ready to go all-in. And while Lewis was, as ever, a good player in Orlando, helping the team make the 2009 Finals, his production declined every year from “really good” to “pretty good” to “uh-oh.”

As it turns out, that 2006-07 season was his statistical peak. Plus, Lewis’ back-loaded deal meant that his annual salary traveled in opposite direction from his stats. Every year, Orlando was playing more money for a worse player.

Lewis’ salary rose from almost $15 million in the first year of his deal to over $21 million in the fifth year. Luckily, the Magic didn’t have to pay him past mid-2010, when they traded him to the Washington Wizards.

Who would trade for such a ridiculous contract you ask? Read the next entry to find out.

Lesson: Whenever possible, avoid putting off the financial pain. Your future self (and your future bank account) will thank you. 

4. Gilbert Arenas – Washington Wizards – 6 Years, $111 million (2008)

Why, exactly, were the 2010 Washington Wizards willing to take on Rashard Lewis and his massive deadweight contract? Well, it’s because they had a massive deadweight contract of their very own, courtesy of a Gilbert “Best-Ever NBA Player Named Gilbert” Arenas!

Lewis’s contract might have been worse due to the backloaded salaries, but Arenas was definitely the more washed player, making this trade one of the most hallowed “my trash for your garbage” transactions in NBA history.

For three seasons, 2004 to 2007, Gilbert Arenas was an electrifying point guard and new-age superstar for the Washington Wizards. He was also a bit of a clown, which will become important later.

Unfortunately, during the 2007-08 season, knee injuries (surprise, surprise) forced him into street clothes for all but 13 games.

After that season, Arenas opted out of the final year of his contract. That might seem like a weird decision, but the Wizards took the bait, offering him six years and $111 million to stay.

On the one hand, that contract was $16 million less than the max, which would be a great deal for a true-blue superstar. On the other hand, Arenas’ superstar days were all in the past.

Over the next two seasons, Arenas played in only 32 games, further limited by his injuries and by the famous incident where he brought firearms into the team’s locker room. (We told you his clownishness would be important.)

Finally, in late 2010, the Wizards cut bait and traded him to the Orlando Magic, who waived Arenas via the amnesty clause after that season.

Arenas lasted only one more season in the NBA before retiring, but Orlando still owed him all the money left on that contract. In 2014, Arenas reported that the Magic wouldn’t be done sending him checks until 2016.

Lesson: Don’t base financial transactions on what happened in the past. Base them on what you think will happen in the future. 

3. Shawn Kemp – Cleveland Cavaliers – 7 Years, $107 Million Dollars (1997)

If the Rashard Lewis contract seems mystifying to you, then you can at least say this about the Shawn Kemp contract: It made sense at the time. When the Cleveland Cavaliers traded for Shawn Kemp in 1997 and signed him to a seven-year, $107 million dollar extension, they were paying a superstar like a superstar.

And for the first year of that contract, Kemp even played like a superstar too!

But then came the 1998-99 NBA lockout, after which Kemp came back to work completely out of shape. And while he managed to average a career high 20.5 points per game over the following (abbreviated) season, things only deteriorated from there.

After one more disappointing season in Cleveland, Kemp was traded to the Portland Trail Blazers, where his play fell off a cliff. His first season in Portland ended with him in rehab for abusing cocaine; his second season ended with him being waived.

But first, the Trail Blazers restructured that massive contract, with ESPN reporting deferred payments being made to Kemp over the next 10 years.

This is one of those bad contracts that somehow ended up being worse for the team that traded for the player than the one who signed him initially.

Lesson: If a deal seems too good to be true—like getting Kemp must have seemed for Portland—then it probably isn’t true. Or good. 

2. Chandler Parsons – Grizzlies – 4 Years, $94 Million (2016)

This might be recency bias talking, but when it comes to paying a whole lot to get almost nothing in return, Chandler Parson’s contract with the Memphis Grizzlies is verrrry close to taking the bad contract cake.

Signed during—when else—the summer of 2016, Parsons was seen as the final piece of the puzzle that would push Marc Gasol and Mike Conley-led Memphis over the top.

Instead, his contract has been the albatross that’s weighed them down.

When he played for the Dallas Mavericks, Parsons was very good. He was never an All-Star (literally, he never made an All-Star team), but he was the kind of player that an owner could talk themselves into being the third-best guy on a championship contender.

This contract was always going to be an overpay, but it still could have worked out okay.

Except it didn’t. Parsons’ knee injuries, an extremely known problem from his Dallas days, have limited him to only 70 games over the past two years. And in those games he has played, he’s been … quite bad.

In the salary cap era of the NBA, overpays like this one can completely doom an otherwise promising team. Memphis went all in when they made a big bet on Parsons, but they should have taken a look around the table and simply folded instead.

Lesson: Sometimes, the best money you spend is the money you don’t spend.

1. Jim McIlvaine – Seattle Supersonics – 7 Years, $34 Million (1996)

Jim McIlwho? Exactly.

One of the reasons this contract stands out as so egregiously bad is that Jim McIlvaine was a completely anonymous player.

While keeping in mind that contracts in the 1990’s were much lower than they are today (before the 1996-97 season, Michael Freaking Jordan never made more than $4 million a year), McIlvaine’s seemingly reasonable salary was still a monumental overpay.

In his second year in the league playing for the Washington Bullets, Center Jim McIlvaine started a grand total of six games and averaged 2.3 points, 2.9 rebounds, and 2.1 blocks per game.

So, of course, the 1996 Seattle Supersonics decided to sign him to a seven-year deal that paid him $3 million dollars in his first season—almost as much as Seattle star Shawn Kemp, who you might remember from spot number three.

In fact, McIlvaine’s deal was one of the reasons that Kemp soured on the Sonics and forced a trade to Cleveland. This deal was so bad that is begat other historically awful deals!

If the Sonics were expecting some kind of massive leap from their new acquisition (and they had to be, right?), it was a dream that never became reality.

McIlvaine’s best year with the team was his first, wherein he started 79 games and contributed a whopping … 3.8 points, 4.0 rebounds, 2.0 blocks per game—plus 1.0 furious superstars.

After two seasons, McIlvaine was traded to the New Jersey Nets, where he played for three more seasons before being cut. In 2000-01, McIlvaine’s final NBA season, he brought home $6 million.

Oh, and when the Nets cut him, they still owed him an extra $4 million for the final year on his terrible, awful, no good, historically bad contract.

Lesson: This contract is so bad there is no lesson. Just don’t … don’t do this. Whatever “this” is.  

To learn more about the financial side of sports and pop culture, check out these related posts from OppLoans:

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