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Data Dimes: The five worst $100 million contracts in NBA history

After an NBA free agency period that included a record eight $100 million contracts, we reflect on the worst nine-figure deals in league history.

Although it’s been happening for more than a decade now, it’s still pretty jarring to see athletes command nine-figure contracts. That trend reached a new level during the 2016 NBA free agency period.

Consider this: A whopping eight $100 million contracts were consummated this summer. Only eight total nine-figure contracts had been signed prior to 2001.

With $100 million deals becoming the new norm for basketball superstars, it seems like a good time to review what can happen when a lucrative deal goes wrong. Using win shares as a measuring stick and PointAfter visualizations to illustrate player performance, we will count down the five worst $100 million contracts in NBA history.

The list is solely determined by the win shares a player averaged during the seasons their contracts were originally projected to cover. No buyouts were taken into account—we’re simply calculating which guys were least valuable over the period of time they committed to play for the signing team.

Only contracts with at least three years completed were considered, which left 21 contracts eligible. Here are the five mega-millionaires who provided the least bang for their buck.

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5. Jermaine O’Neal, Indiana Pacers

Contract: 7 years, $126.6 million (2003–10)

Win shares per season: 4.5 WS

Things were going swimmingly for O’Neal and the Pacers one year into this extension. Indiana had logged a league-best 6121 record in 200304 with O’Neal averaging a double double and receiving All-NBA honors for the second straight season. The ascendant squad was fresh off an Eastern Conference finals berth, and seemed poised to overcome the rival Pistons as the East’s premier team.

No one knew that battle would extend to the stands, though. The Malice at the Palace resulted in lengthy suspensions for O’Neal (15 games), Ron Artest (73 games), Stephen Jackson (30 games) and Anthony Johnson (5 games). To compound matters, O’Neal injured his shoulder soon after returning, the beginning of a string of injuries that coincided with a dip in his numbers down low as a rebounder and defender.

Jermaine O'Neal Career PPG, RPG, BPG | PointAfter

O’Neal missed an average of 30 games over his final four years in Indiana. With two seasons left on his contract, the Pacers traded him to Toronto. There, O’Neal suffered yet another injury and lost his starting job to Andrea Bargnani. This wasn’t as disgraceful back then as it sounds now, as the 200809 season was easily Bargnani’s best in the NBA.

After the Italian Stallion’s brief resurgence, the Raptors shipped O’Neal to Miami, where the seven-footer enjoyed a brief resurgence. But it wasn’t enough to negate the injury-plagued years that ultimately defined O’Neal’s “what-if” tenure with the Pacers.

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4. Chris Webber, Sacramento Kings

Contract: 7 years, $122.7 million (2001–08)

Win shares per season: 4.0 WS

The first season of Webber’s contract was virtually a mirror image of how O’Neal’s first extension year played out in Indiana.

The Kings recorded a league-best 6121 record in 200102 as Webber garnered All-NBA honors before they fell in the Western Conference finals to the hated L.A. Lakers. Though the bitter, controversial defeat left a bad taste in the mouths of Kings fans, the team’s future appeared bright with the core of Webber, Peja Stojakovic, Mike Bibby and Vlade Divac.

Unfortunately, things similarly unraveled from there. Well, minus the surreal fan-player brawl.

Webber sprained his ankle and missed the 2003 All-Star Game before suffering a torn ACL during the playoffs, wiping out nearly a year of play. His final postseason run with Sacramento resulted in a wide-open look that could have sent a Game 7 contest against Kevin Garnett’s top-seeded Timberwolves to overtime. It rimmed out.

The first portion of C-Webb’s nine-figure contract resulted in memorable moments. But it was ultimately a disappointment. And as Kings fans will tell you, most of those memories stick out because they’re so disheartening.

Chris Webber Career PPG, RPG, APG | PointAfter

The latter stages of Webber’s contract were equally sad, though not as easily recalled as his years in Sac Town.

Webber was traded to Philadelphia in the middle of the 200405 season, where his production immediately cratered. He never quite fit alongside Allen Iverson, as he totaled just 4.6 win shares in 114 games across parts of three seasons with the 76ers. He briefly found new life as a starter in Detroit after the Sixers bought him out of his contract in 2007, but the Pistons were upset by LeBron James and the Cavaliers in the Eastern Conference finals.

With that, as the first notable playoff run of one NBA star forward pressed on, the final chance for Webber to find redemption ended.

3. Shawn Kemp, Cleveland Cavaliers

Contract: 7 years, $107 million (1997–2004)

Win shares per season: 3.1 WS

A pattern is emerging here. After Kemp’s contract negotiations with Seattle sparked a trade and $107 million deal with Cleveland, the first year of the Cavaliers-Kemp marriage yielded positive results—just like the previous two entries on this list, all things considered.

But Kemp’s peak during his mega-contract wasn’t quite as high as O’Neal’s or Webber’s, and his lows were lower.

After the 199798 campaign resulted in an All-Star bid for Kemp and a first-round playoff exit for the Cavs, the Reign Man showed up to camp drastically overweight for the lockout-delayed 199899 season. Kemp somehow tallied a career-high 20.5 points per game, but the Cavs went just 2228 and missed the playoffs. Another sub-.500 season resulted in widespread changes, and Kemp was jettisoned to Portland, where things really fell apart.

Shawn Kemp Career PPG, RPG, BPG | PointAfter

Kemp’s first season with the Trail Blazers ended early when he went to rehab for cocaine abuse. He was waived after a wholly unsuccessful two-year tenure in Portland, with the contract buyout reportedly structured as a 10-year deferred payment system.

Portland took a chance on Kemp and his expanded waistline, but ended up just eating a bunch of money to get rid of him.

2. Allan Houston, New York Knicks

Contract: 6 years, $100 million (2001–07)

Win shares per season: 2.6 WS

When news broke that Houston had netted the first nine-figure deal in Knicks franchise history, onlookers were stunned. The New York Daily News tabbed the agreement as “more productive than [Houston] could have ever imagined.”

At the time, Houston was a 30-year-old two-time All-Star. Perhaps more importantly, he was two years removed from sinking one of the most clutch shots in franchise history, a runner that helped the No. 8 seed Knicks knock off the top-seeded Heat on their way to the 1999 NBA Finals.

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No matter the reasoning for the contract, it haunted New York for years. The Knicks made the playoffs just once over the next nine seasons, and didn’t win a postseason series until 2013.

As for Houston, he maintained his excellent shooting for two years before a chronic knee injury effectively curtailed his career. Houston refused to go under the knife in the summer of 2004 after an initial surgery the previous year, but the injury proved to be far more serious than anticipated, and eventually forced him into retirement in 2005.

Meanwhile, his onerous contract made him the second highest-paid player in the NBA until 2007. The ordeal sparked a new rule designed to free teams from falling prey to the same fate as the Knicks.

In a cruel twist of irony, one of the NBA’s most durable players through his first decade in the league is now best remembered as a cautionary medical tale for superstars.

Allan Houston Games Played and Missed By Season | PointAfter

1. Gilbert Arenas, Washington Wizards

Contract: 6 years, $111 million (2008–13)

Win shares per season: 0.5 WS

Yep, another player with his own salary-related rule in the books. Amazingly, the Gilbert Arenas provision doesn’t even refer to his disastrous contract with Washington.

Looking back, the Wizards surely wish they’d have been prevented from extending Arenas. The three-time All-Star had played just 13 games in 200708 due to a knee injury, and would appear in just two more during the season following his $111 million windfall.

But it wasn’t Arenas’s injuries that caused this contract to go down in the dishonorable annals of NBA history. It was the shooting guard’s stunning habit of keeping unloaded guns in the team locker room, a violation of NBA and city rules that was uncovered during the 200910 season. Arenas and teammate Javaris Crittenton allegedly brandished guns during an argument over gambling debts.

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To make matters worse, Arenas made light of the situation by wielding finger guns during pregame introductions and in-game shooting celebrations while the league was investigating the incident. Commissioner David Stern didn’t share Arenas’s sense of humor toward the matter, and suspended him for the rest of the season. 

Arenas would only play 21 more games in D.C., which only proved the 28-year-old was past his prime. His 36.6% shooting in 201011 would have ranked him dead last in the NBA if he had enough shots to qualify, and his PER would never again eclipse the league average of 15.

Gilbert Arenas Career PER | PointAfter

Agent Zero was traded to Orlando during his awful 201011 campaign, who waived him via the amnesty clause before the following season. That was far from the monetary conclusion of the contract, however.

According to a 2014 Arenas interview, he was still due to collect deferred paychecks from the infamous deal in 2016. As a result, even Arenas himself wasn’t too surprised to learn that some analysts consider his contract to be the worst in NBA history.