Ranking the Worst Max Contracts in NBA History

Grant Hughes@@gt_hughesNational NBA Featured ColumnistJuly 12, 2017

Ranking the Worst Max Contracts in NBA History

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    Collectively bargained into existence during the 1998-99 lockout, the max contract has long been a source of controversy.

    Oh, and also regret.

    In addition to there being several types of max agreements—variances depend on years of service, annual raise rates, and who's offering the deal in the first place—there's rarely a consensus that the player receiving one of these designated deals deserves it.

    Why? Because it just seems wrong when two-time MVP Stephen Curry and a player coming off his rookie deal with zero career postseason appearances are both eligible for the max. And that's before you even get to the super max extensions available to guys like James Harden.

    Confusion aside, some maximum deals are objectively bad. They can cripple a team, particularly when injury arises or sudden ineffectiveness turns a cornerstone into an anchor.

    For our purposes, we'll confine the term "max" to mean the most years possible (either four or five under today's rules but longer in the past) with the largest annual salary and raises permitted by the CBA. Most importantly, we're only considering contracts agreed to after the max label showed up following the '99 lockout.

    We won't employ some catch-all metric to order these bad max deals. The league's economy has changed several times over since 1999, so a dollar-per-win-added stat would skew things. Instead, we'll simply judge the level of financial commitment against the franchise's return on investment.

Near Max, Big Miss

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    Before we get to the official list, two players who signed for just less than the full maximum warrant mention.

    Gilbert Arenas — Six Years, $111 million

    Arenas left $16 million on the table when he inked a six-year, $111 million contract with the Washington Wizards in 2008.

    So, um...this could have been worse?

    It's remarkable that the Wizards agreed to such a commitment following a season in which Arenas played just 13 games because of knee injuries. He logged only two contests in the first year of his new deal, missed 50 more games the following season and was then traded for Rashard Lewis and his own albatross salary.

    Arenas agreed that his contract might have been the worst in NBA history, but it wasn't a true max. So he gets off on a technicality.

    Hibachi!

    Carmelo Anthony — Five Years, $124 million

    It's a good thing Anthony agreed to forego $5 million on the contract he signed with the New York Knicks in 2014. Otherwise, it might have hamstrung the franchise and made it nearly impossible to get fair value for him in a trade.

    Wait.

10. Jermaine O'Neal — 7 Years, $127 Million

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    Jermaine O'Neal made four straight All-Star games after signing his massive extension with the Indiana Pacers in 2003, but the volume of his production and the statistical decline in the latter portion of his deal mark his max contract as the best of the worst on our list.

    Faint praise.

    O'Neal was suspended for 15 games following the Malice in the Palace in November 2004, then missed 31 more games due to injury in 2005-06. He recovered to play 69 games in 2006-07, the fourth year of his contract, but was already showing signs of slippage.

    He shot just 43.6 percent from the field that season, and then missed another 40 games the following year.

    A trade sent O'Neal to the Toronto Raptors in 2009 before another landed him in Miami. His averages hovered around 13 points and seven rebounds in those two stops, far cries from what he was producing early on with Indiana—though, to O'Neal's credit, he remained an intelligent defender and stayed relatively healthy toward the end of his huge deal.

    The Pacers paid for a no-questions-asked superstar cornerstone and got something far less: a once-suspended, chronically injured big man who missed 126 games in five years with the team and eventually had to be unloaded at a discount.

    It's important to note something that'll apply to most of the contracts here. It's the team's responsibility to consider player health when paying max money. Injury makes for a bad deal, but it doesn't make the injured party a bad guy.

    O'Neal and the rest of these players (with limited exceptions) aren't to blame for landing on this list.

9. Steve Francis — 6 Years, $84 Million

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    Signed in August 2002 and taking effect at the start of the 2003-04 season, Steve Francis' mega extension went bad almost immediately and clogged the books of four different teams before all was said and done.

    In the first year of Francis' big contract, worth around $84 million with the Houston Rockets, he averaged 16.6 points, 6.2 assists and 5.5 rebounds while hitting only 40.3 percent of his shots from the field and 29.2 percent from long range. Thanks in large part to the presence of teammate Yao Ming, who helped many Rockets earn votes from China over the years, Francis got into the All-Star Game with those shoddy numbers.

    After clashing with head coach Jeff Van Gundy, Francis wound up with the Orlando Magic via offseason trade. His numbers picked up there, but weren't compelling enough to avoid yet another trade, this time in the middle of the 2005-06 season, to the New York Knicks.

    Francis was never an All-Star again after leaving Houston, and he broke down physically during his final season with the Knicks in 2006-07, missing 38 games and averaging just 11.3 points.

    The Portland Trail Blazers traded for Francis on draft night in 2007, and then bought out the final two years and $34 million let on his contract.

    From max-level star to being paid not to play.

    Life after basketball has been rough for Francis, which makes his presence on this list somewhat trivial. It also feels like piling on.

    Again, though, the poor quality of this contract is on the Rockets. Not him. And even if Francis never lived up to the deal he signed, the Rockets managed to get Tracy McGrady (who also broke down, but that's another story) for him in that 2004 trade with the Magic.

8. Stephon Marbury — 4 Years, $74 Million

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    Stephon Marbury signed his four-year, $74 million extension with the Phoenix Suns in 2003, but ended up on the New York Knicks before it kicked in for the 2005-06 season. Good work by the Suns to get off that money before it started to hurt.

    And hurt the Knicks it did, as Marbury repeatedly clashed with head coaches—from Lenny Wilkens to Larry Brown to Isiah Thomas to Mike D'Antoni—while suffering steady statistical decline. Marbury's All-Star days were done by 2003, and his rocky tenure with the Knicks culminated in an indefinite suspension in December 2008. He and top executive Donnie Walsh couldn't reach an agreement on a buyout figure until February 2009.

    The Knicks paid Marbury roughly $88 million in his five years with the team and never won a playoff game.

    Also, fun fact: One of the first-rounders New York surrendered in the trade to get Marbury, a 2010 lottery selection, turned into Gordon Hayward.

    Marbury checks in above Francis because the Knicks could never find a trade partner and were stuck on the hook for all of Marbury's contract until the buyout. Plus, the Francis situation never got as ugly as this one, which you can gauge from Marbury's comments to Frank Isola of the New York Daily News in 2008:

    I didn't hear one of my teammates say, 'Why isn't Stephon Marbury playing? This is a good system for him, even to play with the second unit and bring more firepower.' When things got bad and then worse, guys like Quentin Richardson say, 'I don't consider him a teammate. He let his teammates out to dry.' He didn't care I was his teammate when I was banished. They left me out for dead.

7. Chandler Parsons — 4 Years, $94 Million

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    It's too soon to include the max contracts of Marc Gasol, Al Horford, Mike Conley, DeMar DeRozan, Blake Griffin and Andre Drummond on this list.

    Some look fine so far, and even the ones that appear questionable in hindsight (Drummond, Griffin) have time to turn out well.

    That leniency doesn't apply to Chandler Parsons' four-year, $94 million deal with the Memphis Grizzlies.

    It was signed in 2016, and Memphis is already assured of at least one of the four seasons being a total bust. Parsons, limited by multiple knee surgeries before joining the Grizzlies, logged just 34 games in his debut season and rated as one of the league's worst players when on the floor.

    He averaged just 6.2 points in 19.9 minutes with a true shooting percentage of 43.6—all career worsts by a significant margin. His PER of 7.7 was the fourth-worst in the league among players who started at least 30 games.

    At this point, even if Parsons returns to his absolute peak (which we'll call something like 16 points, five rebounds and four assists with passable defense) the deal for Memphis would still turn out to be a bad one.

    But with so many surgeries, and after seeing how athletically diminished Parsons was in his truncated 2016-17 campaign, it's impossible to imagine him regaining anything close to his previous top form.

    Worse still, Memphis is also locked into max contracts with both Gasol and Conley. Those contracts are off to great starts, but the real burden of Parsons' deal lies in the way it prevents the Grizzlies from adding wing talent around its two best players.

    The Grizzlies, lacking a team option, are stuck for three more years, or until a buyout relieves them of the worst max deal signed in the last few seasons.

6. Rashard Lewis — 6 Years, $118 Million

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    If it's any consolation to the Orlando Magic, Rashard Lewis would probably command a max salary in today's NBA.

    If you're 6'10" and can shoot the rock, which Lewis was and could, you're in line for huge cash.

    Lewis got six years and $118 million from the Magic in 2007—parlaying a 2006-07 season with the Sonics that included 22.4 points, 6.6 rebounds and 39.0 percent shooting from long range—into a sign-and-trade that sent him across the continent.

    Lewis never came close to matching his 2006-07 volume, but he actually had his two best seasons after arriving in Orlando, as measured by VORP.

    The physical breakdowns started in 2009-10, though, as Lewis' true shooting pecentage dipped and his player efficiency rating fell below the league average for the first time since his rookie year. He missed at least 25 games per season over the remaining three years of the deal, during which he split time with the Magic, Wizards and Heat.

    Orlando had to get off Lewis' money halfway through the contract, and even if he was solid early in the deal, Lewis wasn't the type of star that justified that kind of investment. He stays out of the top five because he was still a useful piece on the Orlando team that fell to the Lakers in the 2009 Finals and met the Celtics in the conference finals the following year.

5. Derrick Rose — 5 Years, $94 Million

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    Derrick Rose's extension, signed in December 2011, earned him 30 percent of the cap with 7.5 percent annual raises. Having won MVP while still on his rookie-scale deal, he got an entire rule named after him—one designed to reward players who ascended that high so quickly.

    He was a hometown darling, a team leader and a superstar who averaged 25.0 points, 7.7 assists and 4.1 rebounds while taking his team to the conference finals as a 22-year-old.

    You know how the rest goes.

    Rose played just 39 games in the first year of his max extension, then tore his ACL in the opening round of the playoffs. That cost him all of the 2012-13 campaign and set off a cascade of injuries thereafter.

    He logged only 10 games in 2013-14 and then managed 51 in 2014-15 while never coming close to his MVP form.

    On balance, Rose has played below replacement level since his initial injury, as measured by box plus-minus and value over replacement player. Unavailability due to injury is the main reason this contract wound up looking so bad, but the fact that Rose was unproductive and inefficient when he was healthy enough to play made it worse.

    After spending the final year of his deal with the Knicks in 2016-17, Rose is a free agent looking to prove he can help a winning team.

4. Chris Bosh — 5 Years, $118 Million

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    The Miami Heat paid more to and got less from Chris Bosh than the Bulls did with Rose.

    Bosh was an All-Star in two abbreviated seasons (44 and 53 games played, respectively) after signing his max deal in the summer of 2014, but that solid start wasn't enough to save the rest of the contract.

    Recurring bouts with blood clots rendered Bosh unable to play after the 2016 All-Star break, which ended his career with the Heat (and likely the NBA) with three-and-a-half seasons left on his contract. With a condition as serious as Bosh's, focusing on the value he generated relative to his contract feels crass.

    But there's no denying the deal didn't work out for the Heat, who eventually agreed with Bosh on a buyout for the remaining final two years and $52 million.

    The Heat may have gotten off the hook for some portion of that $118 million, but they had to have been hoping for more than 97 games when agreeing to the deal initially.

    All class, Bosh dropped a line to his fans after parting ways with the franchise. He wrote on his personal website: "We went through life together, Miami. You showed me how to stay strong and push through in the toughest moments. And although I didn’t like it at the time, it made all the difference in the long run. It made me a better man, the person I am today. Thank you."

3. Anfernee Hardaway — 7 Years, $87 Million

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    The longest contract in our top 10, Anfernee Hardaway's huge post-lockout agreement didn't go south right away.

    He teamed with Jason Kidd in the Phoenix Suns' big-name backcourt for a solid full season in 1999-2000, playing 60 games with averages of 16.9 points, 5.8 rebounds and 5.3 assists. His 17.9 PER and 54.9 true shooting percentage were higher than they were in either of his final two seasons with the Magic.

    But then microfracture surgery reduced Penny, already a notch below his peak days with Orlando, to a shell of his former self.

    He missed all but four games of the 2000-01 season before gradually transitioning to a bench role. His scoring average fell every year, dropping from 10.6 to 9.2 to 7.3...all the way down to 2.5 in his final year with the Knicks following a trade in 2003.

    The quickness and fluidity of Hardaway's game, the combination of loping strides and explosive bursts, were nearly gone before he signed with the Suns. As his post-Orlando career progressed, Hardaway's body simply wasn't capable of the feats it once was.

    The Suns thought they were getting something spectacular when they signed Penny, with GM Danny Ainge calling him "the most skilled all-around player in the game," and saying, "all of a sudden I really believe this puts us as one of the elite teams in the NBA," per CBS News.

    Neither turned out to be true. The Suns got an injured former star whose game deteriorated in every year of his contract.

2. Brandon Roy — 5 Years, $82 Million

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    The best defense of Portland's five-year, $82 million extension for Brandon Roy, a player whose knees the team knew were questionable enough to warrant medical insurance as part of the deal, is that the former Rookie of the Year and two-time All-Star dramatically outproduced his salaries before signing it.

    Roy had a fantastic 2009-10 season and earned All-NBA Second Team honors after averaging 21.5 points, 4.7 assists and 4.4 rebounds on 47.3 percent shooting. At the time, there may not have been a half-dozen more promising young talents in the league.

    He earned $3.9 million in that banner season.

    The extension kicked in during a 2010-11 campaign that saw Roy average only 12.2 points while missing 35 games. His knees were already shot.

    Roy missed all of 2011-12 and retired at its conclusion.

    The Blazers used the amnesty clause to remove his contract from the cap, and were in line to have insurance cover $17 million of the money still owed to Roy—so long as his injury resulted in "permanent disability."

    When Roy came out of retirement to play five games with the Minnesota Timberwolves in 2012-13, the Blazers had to pay the $17 million they thought they'd saved. 

    A five-year commitment for the max got Portland 35 sub-par games.

    At least Roy delivered a memorable farewell.

1. Allan Houston — 6 Years, $100 Million

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    Penny's contract was longer.

    Roy and Bosh gave their teams fewer games.

    Lewis and O'Neal cost more.

    But Allan Houston's six-year, $100 million contract will always be the standard against which other bad deals are judged.

    Part of it is the perfectly round number. There's just something about that $100 million that sticks with you.

    There's also the New York factor, and the way this deal stands out as a symbol of the chronic mismanagement that has crippled a marquee franchise. Houston is the fourth player on this list to have spent time with the Knicks.

    Note, too, that Houston's deal was a major reason the league added the amnesty provision to the 2005 CBA.

    Oddly, the Knicks didn't use the Allan Houston Rule to relieve themselves of his contract. They employed it to get rid of Jerome Williams' salary, yet another indicator of how badly run the organization has been for years.

    They couldn't even use a provision eventually referred to by Houston's name on Houston because they had other bad contracts to escape.

    Are there any conclusions to be drawn from the fact that the Knicks simultaneously possessed the ninth, eighth, third and worst overall max contracts in league history at the same time, which happened in 2005-06 when they were paying Francis, Marbury, Hardaway and Houston?

    Like, maybe that the current disorder and underachievement is just a symptom of a decades-old disease?

    Yes. Yes is the answer we're looking for on this one.

    Houston gave New York two good seasons on the contract he signed in 2001, slipped in his third year and played just 20 games in his fourth. He retired and collected checks for the final two seasons of the agreement—and is still employed in the front office today.

    There's something poetic about one of the league's greatest examples of misspent money serving as an assistant GM for the same franchise that paid him as a player.

    Only in New York.

    Follow Grant on Twitter and Facebook.

    Stats courtesy of Basketball Reference or NBA.com.

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