With the NBA’s salary cap at an all-time high, max contracts usually go for record-breaking amounts nowadays.

Even mediocre players break the bank in this era, while the best of the best are gifted with immense fortune beyond their wildest dreams. Some superstars prove that they are worth every penny, complementing their amazing talents with the ability (and some sheer luck) to stay healthy.

Other franchises, however, are not so lucky when it comes to their multi-million investments. Here, we look at the five worst contracts in league history.

We will be taking into account the amount of money, the length of the deal and how long it came to haunt each franchise.

Juwan Howard, Washington Bullets/Wizards

7-years, $105 million – 1997

With the popularity of the league at an all-time high — thanks in large part to the Chicago Bulls — the NBA experienced a major spike in revenue in 1997.

Howard looked like he was headed to the Heat on a nine-figure contract, until the league vetoed the deal citing Miami’s miscalculation of their cap space.

The Bullets thought Howard was their franchise star for years to come, and they shelled out a lot to keep him in DC. The 6-foot-9 forward certainly earned it, averaging 22.1 points and 8.1 rebounds in his sophomore year. The University of Michigan alum even made it to the All-Star team the following year.

Little did they know that was the first and only time he will be selected for the festivities. Injuries hampered Howard from 1997-99. He managed to play all 82 games in 1999-2000, but it was clear that he was not the same player.

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Howard put up great numbers the following year, but the Wizards brass elected to ship him to Dallas to free up cap space. He became a well-traveled journeyman since and has won two NBA titles with the Heat.

Rashard Lewis, Orlando Magic

6 years, $118.2 million – 2007

To be fair, Lewis justified the first two seasons of the mammoth sign-and-trade agreement from the Sonics to the Magic. The sweet-shooting forward set personal bests from downtown and made his second All-Star team in 2009.

Lewis’ floor-spacing capabilities were the perfect complement to the team’s superstar center Dwight Howard, as the Magic returned to the Finals in 2009. However, with four years still remaining on his deal, Lewis’ age began to show.

His efficiency plummeted the next two seasons and the Magic was stuck paying superstar money for a player past his prime. Making things worse, Lewis’ deal was backloaded, meaning he got more expensive while becoming less valuable.

Orlando had to absorb another horrendous contract from the Wizards in 2010 (more on that later) just to get out of their arrangement with Lewis.

Penny Hardaway, Phoenix Suns

7 Years, $87 Million – 1999

Money-wise, this deal wasn’t as bad as the others on this list. But judging by how poorly — and how seldom — Hardaway suited up for the Suns, his contract was indeed wasted money for Phoenix.

Following a spectacular, yet also injury-riddled tenure with the Magic, the Suns took a gamble with the 6-foot-7 playmaker. Hardaway’s services weren’t cheap, given he was a four-time All-Star and was, at the time, seen as the modern-day Magic Johnson.

Hardaway was a good fit for Phoenix in his first year, tallying 16.9 points, 5.8 boards and 6.3 assists. The injury bug got him the following year, as Hardaway missed 78 games following two microfracture surgeries on his left knee.

He bounced back by playing 80 regular-season games the ensuing year, but it was clear that the surgeries sapped him of his All-Star form. He became a very expensive bench player for the rest of his contract as injuries kept him in and out of the lineup.

To his credit, Hardaway was still at his best in 15 playoff games for the Suns, tallying 17.3 points, 5.3 rebounds, 5.1 assists and 1.8 steals. Still, the Suns expected more out of him and didn’t deliver on that promise.

Allan Houston, New York Knicks

6-years, $100 million – 2001

The Knicks have paid a ton of money to undeserving players, but their massive extension with Houston might just be their worst of all time. There was a time when the 6-foot-6 scorer looked like one of the brightest stars in the league.

Sadly for the Knicks, that time passed by quickly once Houston signed the dotted line. Houston was still the lethal bucket getter he was when healthy, but knee injuries limited him to fulfilling that massive contract. He played all 82 games in 2002-03 before his knee eventually gave out on him.

New York had little to no options surrounding his situation, given that Houston’s $20 million a year salary made him virtually untradeable.

His contract was so bad that the NBA created the “Allan Houston Rule” as part of the next NBA CBA. The clause allowed teams to negate a player’s contract from luxury tax calculations on a one-time basis.

Gilbert Arenas, Washington Wizards

6-years, $111 million – 2008

The Wizards’ obligation with Arenas officially ended years ago, but they probably still feel that sting to this day. Agent Zero was a walking bucket in his heyday with the Wizards. However, he was coming off an MCL injury entering the 2008-09 campaign.

Arenas forced the Wizards’ hand by opting out of his contract that year, as Washington had to write a massive check to retain him. A string of bad luck followed the team soon after, as Arenas’ injury woes worsened in the coming years.

Making things worse was the now infamous locker room gun incident in 2009, where Arenas was suspended for the entire season. He made his return the following year but proved to be a shell of his former self. Washington willingly absorbed Rashard Lewis’ large contract to offload Arenas to Orlando in 2010.

Honorable Mentions: Chris Bosh (5 years, $118 million -2014), Derrick Rose (5 years, $94 million- 2011), Chandler Parsons (4 years, $94.5 million), Grant Hill (7 years, $93 million)