Worst Max Contracts in NBA Free Agency History
The NBA's max contract, collectively bargained amid the 1998-99 lockout, seems to please almost no one.
Elite players are capped beneath their actual value. On the flip side, teams are routinely self-sabotaged by the wrong max-money investments.
Our focus lies on the latter.
Given the massive amounts of money these deals are worth, almost all were defensible at the time they were signed. But the wrong injury can turn a seemingly shrewd signing into a colossal mistake.
We'll go as far back as the NBA does with the "max" label, meaning contracts for the most years, largest salaries and biggest raises possible this side of the '99 lockout. We're also ranking them by negative impact, which is ultimately subjective but compares the return on these investments against their costs.
Gilbert Arenas — Six Years, $111 Million
Apparently out to do the Washington Wizards a solid as they were doing him a spectacular favor, Arenas left $16 million on the table, which just spared him from an official spot on this list.
The fact his pact is still worth mentioning shows just how massive an overpay it was.
At one time on a short list of the Association's most explosive scorers, Arenas inked this pact in July 2008. That date is significant because he basically had the 2007-08 campaign erased by a knee injury. He underwent an operation in April 2007 and again that November, made just 13 regular-season appearances and shut himself down in the playoffs.
And still, the Wizards deemed him worthy of a nine-figure investment.
It predictably blew up in their face almost immediately. His knee was never the same, and the Wizards eventually traded him for the equally overpaid Rashard Lewis. Arenas played just 121 games after he signed the deal, which the Orlando Magic escaped via the amnesty clause less than a year after they acquired him.
John Wall — Four Years, $171 Million
Can a max deal be one of history's worst before it even starts?
Though he inked the supermax in July 2017, Wall's mega millions don't officially reach the ledger until next season. Technically, the five-time All-Star still has a chance to eventually earn his keep.
But it's off to a brutal start.
His stock has been sliding for two straight seasons, both in terms of availability (73 combined appearances) and production (18.7 player efficiency rating, his lowest since 2011-12). But now it's falling faster than a cartoon anvil. His 2018-19 campaign closed in December due to heel surgery. His 2019-20 season might've already been erased after he ruptured his Achilles in February.
If the injuries aren't worrisome enough, his 29th birthday looms in September. While that's not necessarily a problematic age on its own, players with his injury history and reliance on athleticism tend to age in dog years around their 30th.
While it's premature to put Wall on the list now, too many warning signs keep us from omitting it entirely.
Andrew Wiggins — Five Years, $148 Million
Like with Wall, the one thing sparing Wiggins is time.
He signed the deal in October 2017, and it just kicked in last season. Given his status as a 24-year-old former No. 1 pick, it seems awfully early to abandon hope.
At the same time, he's played five seasons and finished all of them below replacement level. His 14.5 career PER says he's a hair below the league average.
His physical tools should translate into elite defense. This past season, he landed 450th out of 514 players in defensive real plus-minus, per ESPN. Since entering the NBA, he has the third-worst rebounding rate among qualified players 6'8" or taller, and his career assist rate is seventh-worst for all non-centers in league history with a 25-plus usage percentage (minimum 5,000 minutes).
He has basically established himself as an inside-the-arc volume scorer who contributes little else. In what world will that ever be worth anywhere near the money he's making?
He has four seasons to change the narrative, and maybe his natural gifts can help him do so. Based on everything we've seen so far, though, this is one of the worst max-money investments any team has made.
6. Derrick Rose — Five Years, $94 Million
Derrick Rose's launch into the NBA's celestial collection of superstars was so sudden and so spectacular the league created a special provision in the 2011 CBA to ensure he was properly compensated.
It was dubbed "The Derrick Rose Rule," and it allowed for higher raises to players coming off their rookie contracts if they met certain criteria—like winning the MVP, which Rose miraculously did as a 22-year-old to become the youngest player to take home the Maurice Podoloff Trophy.
"It's unbelievable," Rose told CSNChicago.com of the rule change (via ESPN). "But the rule, I guess, it fits me for what I've achieved at a young age and hopefully there will be a couple more people like me."
Of course, you all know where the story traveled from there.
A cascade of injuries prevented Rose from ever reaching that level again. He signed the deal in December 2011 and tore his ACL the following April. He never suited up in 2012-13, which was the first year of his max extension.
He played just 10 games the ensuing season, and while he made 117 appearances over the next two years, his MVP form never resurfaced. The Bulls finally cut bait in June 2016, shipping out Rose and others to the New York Knicks for Jose Calderon, Jerian Grant and Robin Lopez.
Rose played in just 191 of a possible 410 games over the life of his extension while posting an almost perfectly average 15.1 PER.
5. Chris Bosh — Five Years, $118 Million
Spurned by LeBron James, the Miami Heat reached a crossroads during the 2014 offseason. One direction offered a path to relative recovery by re-signing their other stars and supplementing them with whatever the budget allowed. The other offered a total split from the Big Three era and a head-first dive into uncertainty.
It wasn't surprising that hyper-competitive team president Pat Riley selected the former. It was a bit surprising, though, that Miami made Chris Bosh—not Dwyane Wade—the face of that plan. While Bosh cashed in for a cool $118 million, Wade settled for a two-year, $31 million deal with a player option on the second.
Given Bosh's two-way versatility and Wade's nagging knee problems, Bosh seemed the safer investment. And when he made it inside the lines, he lived up to that assessment. He was selected to both the 2015 and 2016 All-Star Games, averaging 20.0 points and 7.2 rebounds across the two campaigns.
But each was cut short by recurring blood clots that prevented him from playing after February 2016.
Given the severity of the situation, it feels crass to focus on the basketball side of things. But this is a basketball discussion, so we can't avoid how little Miami received on its basketball investment.
The five-year pact could've featured as many as 410 games. Bosh played just 97. The Heat waived him in July 2017 after an NBA doctor ruled in their favor and agreed with their belief his condition was career-ending.
Bosh, who didn't retire until this year, has made peace with a career that was taken away from him.
"I'm very happy with where I'm at, with how I feel," he said at his Heat jersey retirement, per Tim Reynolds of the Associated Press. "That's what is most important. I couldn't even imagine trying to play basketball again. So I had a pretty solid run. And yeah, it's over. But it was a pretty solid run."
4. Anfernee Hardaway — Seven Years, $87 Million
The longest contract on our list originated with an intriguing idea that briefly breathed life into the Phoenix Suns.
They already had one dynamic playmaker in Jason Kidd, who finished the 1998-99 season with an NBA-best 10.8 assists per game. But with four-time All-Star Anfernee Hardaway ready for a fresh start away from the Orlando Magic, the Suns swooped in with a seven-year, $87 million deal to assemble a backcourt that had rocket-powered potential.
"[This] ranks right up there with any acquisition we've ever made," then-Suns owner Jerry Colangelo said at the time. "He's a marquee guy."
Hardaway looked the part the first season, averaging 16.9 points, 5.8 rebounds and 5.3 assists while helping the Suns reel off 53 wins. But knee injuries that bothered him in Orlando resurfaced in Phoenix, and they forced him to undergo microfracture surgery that served as the beginning of the end of his NBA career.
"I was one of the first guys to get microfracture surgery," Hardaway told SLAM Magazine's Khalid Salaam in 2012. "And I didn't handle the recovery well. It wasn't even heard of in the NBA yet. It took away my legs, my athleticism."
Hardaway would go on to play seven more seasons in the league, but his days as a transcendent talent were far behind him. In five of those campaigns, he averaged single-digit points and fewer than four assists. Over the other two, he topped out at 12.0 points and 4.1 helpers per game.
The Suns transitioned him to a reserve role and then later traded him to the New York Knicks, who eventually salary-dumped him back in Orlando. Once his body betrayed him, his game never recovered.
3. Chandler Parsons — Four Years, $94 Million
While injuries played a role in souring each of these contracts, Chandler Parsons' deal looked troublesome from the start.
The Memphis Grizzlies maxed him out in 2016, now known as the summer of NBA regrets. At the time, he held career averages of 14.3 points, 5.1 rebounds and 3.0 assists. Those aren't max-contract stats from any angle. Even buying them as the foundation for future growth was tricky, as he turned 28 years old before playing a game on the new deal.
Plus, the Grizzlies were already his third different franchise.
The Houston Rockets might have had their financial reasons to let him walk in 2014, but they still allowed him leave as a restricted free agent. Two years later, the Dallas Mavericks, whose owner, Mark Cuban, had become close friends with Parsons, opted against giving him big money after he had two knee surgeries in two years.
Memphis apparently held no hesitations, although it was, at the time, still attempting to extend the grit-and-grind core's window. While big-ticket free agents never picked the Grizzlies, here was one who was not only interested, but also addressed a years-long vacancy on the wing.
So, the Grizzlies took the $94 million plunge, and they've been paying for it ever since.
Knee problems continue to plague Parsons, who's made just 95 appearances (only 45 of them starts) over three seasons in Bluff City. When he has played, he's been unrecognizable, averaging only 7.2 points, 2.6 rebounds and 1.8 assists while shooting 39.3 percent overall and 34.1 percent outside. His PER with the Grizzlies is a minuscule 10.1.
Parsons and the team agreed to part ways in January. But without an official separation, the two remain bonded by the massively oversized contract.
2. Brandon Roy — Five Years, $82 Million
Brandon Roy didn't just hit the NBA hardwood running; he was shot out of a cannon. The sixth overall pick in 2006 scored 20 points in his debut and never looked back. By year's end, he'd garnered 127 of the 128 first-place votes for Rookie of the Year.
He made his All-Star debut as a sophomore, and he was a nightly 22-point scorer by his third season. That's all the Portland Trail Blazers needed to see, as they inked him to a five-year, $82 million max in August 2009.
As quickly as he ascended, though, his fall was even faster.
He had knee issues dating back to his high school days and was always racing against time to compile whatever career he could before the balky joints got the best of him. Portland wagered he had many good years left.
His knees had other plans.
Roy's extension kicked in for the 2010-11 season, during which he was limited to 47 outings and appeared a shadow of himself (12.2 points per game on 40.0 percent shooting). He retired before the lockout-delayed 2011-12 campaign even tipped off.
"This is a very difficult and painful day," Roy said in a statement released by the team (via ESPN). "I love the game, I love the Portland Trail Blazers and I love our fans, but after consulting with my doctors, I will seek a determination that I've suffered a career ending injury, pursuant to the rules of the collective bargaining agreement."
The Blazers later used the amnesty clause to get his contract off the books. Insurance would have covered $17 million of the money owed to him, but only if he was permanently unable to play. He came out of retirement to play five games with the Minnesota Timberwolves in 2012-13, costing the Blazers the money they thought they'd saved.
Roy later revealed his arthritic knees were one step from necessitating replacement. Whatever Portland thought could be his worst-case scenario, this proved 82 million times worse. Those 47 uncharacteristic contests in 2010-11 were all he provided the Blazers while playing at the max.
1. Allan Houston — Six Years, $100 Million
Allan Houston rolled into the 2001 offseason as a 30-year-old with a career scoring average of 16.4 points.
Naturally, the New York Knicks determined they had to lock him up on a six-year, $100 million pact. Skepticism was evident at his press conference, and he tried to address it as best he could.
"I promise that New York has not seen the best of me yet," Houston told the assembled media.
Reading between the lines, he more or less acknowledged he wasn't a $100 million player. But he promised he could develop into one—as a 30-year-old who'd already completed eight NBA seasons.
To his credit, he'd go on to set a new career high in scoring each of the next two go-rounds. But New York literally banked on getting six good-to-great campaigns, and he couldn't deliver half that.
Chronic knee pain limited him to 70 games over the next two years, and he retired in 2005. By that point, the then-recently adopted amnesty clause had been labeled the "Allan Houston Rule." In classic Knicks fashion, they didn't use it to escape their overpay on Houston, but rather to get out of overpaying Jerome Williams.
Houston was a great shooter and a good complementary scorer. That's not a $100 million skill set to anyone other than the Blue and Orange.
The production was never going to justify the pay. The subsequent injury issues exacerbated the miscalculation. While you perhaps can't blame the 'Bockers for not seeing the future with Houston's knees, you can question the logic behind making a six-year commitment to a pseudo-star on the wrong side of 30.
Zach Buckley covers the NBA for Bleacher Report. Follow him on Twitter: @ZachBuckleyNBA.