Honorable Mentions
Blake Griffin
Detroit Pistons
5 years/$171 Million (exp. 2022)
Blake Griffin is no longer the premier dunker and electrifying superstar he once was with the Lob City Clippers, but a slow transition into a floor spacing 4 might be the career saving move he needs to justify this monster of a contract. Signing this mega-deal with the Clippers in 2017 and then having to pack his bags for Detroit also seems like a pretty good trade off as Griffin is the Pistons' new number one guy as they move away from their overreliance on Andre Drummond.

The main concern with Griffin going forward and his escalating cap number (reaching $39M in 2021/22) lies with the health of his knees and ability to transition his game to today's league. While he has shown the ability and willingness to pull the trigger from deep, his knees look like they may belong to a sixty year old man. The bounciness and high-flying game he once relied on in Los Angeles has come to collect its debts on Griffin, mainly in the joints of his knees. Breaking down and tiring out over the course of last year and into the playoffs, Blake looked as if he needed a cane in order to get around during Detroit's first round series against Milwaukee last year.
#23 has the ability to justify this monster of a contract over the next three years, but it will not be easy by any means.
Gordon Hayward
Boston Celtics
4 years/$127 Million (exp. 2021)

The inclusion of Gordon Hayward on this list could come back to look quite foolish after next season, but for now this contract for the player Hayward is at the moment is downright atrocious. While much of his struggles have been attributed to the devastating leg injury sustained in 2017, there has to be a point where his cap hit to the Celtics and on-floor production for Brad Stevens have to equal one another. For right now, Gordon Hayward is a non-superstar on a SUPERstar deal.
Technically, Hayward only has one year left on this current deal with 2021 becoming a player option, but best believe he will be opting into every bit of that $34M. Once this deal does run its full course over four uneventful and disappointing years, the Celtics will have paid Hayward a grand total of $127,829,970. That investment so far has netted them a total of 73 games through two years with a stat line of 11.5PPG, 3.4AST, 4.2REB, and all on 46% from the field and 33% from three. These numbers would be fine if Hayward was a typical role player on any given NBA roster, but the salary he is on is that of an NBA superstar and he is nowhere even close to that standard at the moment.
Look, injuries such as the one Hayward suffered in 2017 are debilitating and take time to recover from. This is not to question his ability to bounce back from setbacks, but more of his chance of living up to such a huge contract. Hayward may have the potential to return to his previous All-Star form, but as of right now this contract is pretty ugly.
5. Otto Porter Jr.
Chicago Bulls
4 years/$106 Million (exp. 2021)
No, the notorious front office of John Paxson and Gar Forman is not to blame for handing out this terrible contract, nor is it a direct product of their work on the free agent market (quite poor however). While, they are responsible for orchestrating the 2019 trade that sent Bobby Portis, Jabari Parker, and a 2023 second round pick in return for Porter, they cannot be credited for the disgusting amount of money owed to him over the next two years.
Paxson and Forman may not be responsible for handing out the original deal, but they are to be questioned for even trading for Porter in the first place. In their current organizational state, Chicago looks to be rebuilding with key young pieces in place such as: Lauri Markkanen, Wendell Carter, Coby White, Chandler Hutchison, and Daniel Gafford. At 26 years old and such a big salary cap number alongside a multitude of players on rookie scale deals, Porter simply does not line up with what Chicago is seemingly building towards. Snagging up a large portion of the roster's cap and taking away valuable developmental minutes from younger guys, Porter does not have a place on this team now or in years to come.

Outside of his questionable place on this current Chicago roster, Porter has not shown the production value in order to justify such a large cap hit. Last year saw #22 post numbers of 14PPG, 5.6REB, and 2AST in only 56 games. If that type of production is netting $27M going into 2019/2020, there are going to be a lot of guys around the league pushing for some contract re-negotiations.
Porter is not a bad NBA player by any means, but his place on this Chicago team makes no sense and at such a large cap hit, he will be an asset that is hard to move on from going forward if his production does not see a sizable uptick.
4. Andrew Wiggins
Minnesota Timberwolves
5 years/$147 Million (exp. 2023)
Andrew Wiggins might still have some hope to one day become a good basketball player in the NBA as the one thing he still has going for him is his youth. At a mere 24 years old and entering only his sixth season in the league, the Kansas product may still possess some room to grow. As for now however, the once renowned "Maple Jordan", is far from performing at the ability his current contract speaks for.

Over the next four years, the Minnesota Timberwolves are on the hook for a grand total of more than $120M, a rather large price to pay for a player who's ceiling in today's league looks to be no more than a dollar store D-grade version of Tracy McGrady (& that's a compliment to Wiggins). So far throughout his career, Wiggins has displayed an inability to do just about anything productive on a basketball court: a total non-factor on defense, rebounding numbers comparative to that of a PG, unwillingness to pass the ball, and shooting numbers that would make anyone run away in disgust. Sure, he can put the ball in the basket on a few occasions, but even that does not come without some serious issues of high rate of turnovers when handling the ball and solidified tunnel vision.
Canada's once dubbed "Mr. Fantastic" and former number one overall draft pick (2014), looks to be a far cry away from ever reaching his once highly touted potential. Now being discussed in salary dumping trades and a number of different rumors, the future of Wiggins on the Timberwolves and in today's game is far from guaranteed. While the youth of his career is still on his side, the entirety of his game seems to be turning away from him along with the rest of the league.
3. Russell Westbrook
Oklahoma City Thunder
5 years/$206 Million (exp. 2023)
Over the past couple seasons the debate has raged on over Westbrook's place in the league hierarchy in comparison to fellow superstars, his style of play and its effect on team chemistry, statistical accomplishments and their meaning, and many other hot button issues that we can only briefly get into. Point being, anytime someone chooses to discuss "Brodie", it usually comes with a flurry of argument and debate one way or the other. With that being said, let's do it.
Positives about Russ: Averages a triple double. MVP award(s). Playoff berths. Signature shoes. Top tier athleticism and bounce (for now). Unbridled energy with the dance moves to match.
Negatives about Russ: Monster salary that pays an average of $41M, eating almost 40% of the Thunder's cap space per season for the next five years. An inability and unwillingness to play alongside a fellow superstar (see Kevin Durant & Paul George). Gigantic usage rates to go along with poor 3PT%'s and high turnover %'s. First round playoff exits. Style of play that does not age well with increasing years played (entering his 12thseason).

At the end of the day, Russell Westbrook will be entering his twelfth NBA season in 2020 at 31 years old. Those twelve years of experience have taken quite a toll on his body already as Westbrook has dealt with multiple injuries to both knees as well as others, resulting in a number of surgeries and procedures that are too many to even keep track. Going forward, Westbrook will not be able to rely on his speed and bounce like he has for so long as his body continues to break down with such a high usage rate and physically demanding style of play.
If Russell Westbrook wishes to remain relevant and continue raking in that monster yearly salary until 2023, he has quite a bit of work to do. First, he must demonstrate a willingness and determination to make things work with a fellow superstar. The NBA is powered by its stars and in order to succeed, an organization is usually in need of more than just one lone wolf. Westbrook must also continue to develop his stroke from behind the arc, percentages such as 29% over the past two years is not going to cut it in a league where the trend is revolving around three-point shooting. Developing an outside game will also allow Russ to maintain his health as he will not have to exert himself as much as he currently does on the offensive end of the floor. Being able to shoot from 23 feet away is a lot less exhaustive than making runs to the basket each and every possession. Outside of those two main concerns, Westbrook must demonstrate the ability to work within a team-centric offense, not in a system that revolves around only one player. If the Thunder are able to change their offensive style and Westbrook shows the willingness to change, they may have the ability to begin to attract other superstars back to Oklahoma City…one day…far down the road.
2. Chris Paul
Houston Rockets
4 years/$159 Million (exp. 2022)
There is no better way to summarize Chris Paul's current contractual situation with the Houston Rockets other than that he will be receiving $44M in 2022 at the age of THIRTY-SIX. While Paul is arguably one of the five best point guards in league history, he is on a fast track of decline all the while having his position alongside James Harden on the Rockets put into question. Paul's game at the top of offense has the potential to age just fine, but his physical health and relationship with Harden and GM Daryl Morey are more of the pressing concerns here.
Yes, handing Chris Paul this monster contract in 2018 was probably a show of good faith on the Rockets part after their trade with the Clippers in 2017 came with a virtual assurance to Paul that they would be handing him a max contract the following summer. Well, that show of good faith has come back to bite the Rockets in a big way as their cap is all but maxed out in only three players: Harden, Paul, and Clint Capela. Tying up their money in three guys was a bet on beating Golden State, winning an NBA Championship, and enjoying all the spoils of a Larry O'Brien Trophy, but that window is now seemingly closed even as the Warriors are in decline. Ongoing bad blood between Harden and Paul, Capela's inability to stay on the floor late into games, and a rocky organizational relationship with head coach Mike D'Antoni has all but doomed Houston from ever making good on that bet.

As for Paul, this super-deal might go on to haunt him if he looks to move on from Houston as such a big cap hit makes him almost untradeable in the climate of the current league. Carrying such a large salary would mean that whatever team is looking to acquire Paul would have to give up a substantial amount of assets in order to match the cap hit or even have to give up one of their own team's superstars (see OKC's Westbrook as a possibility). Swapping max contracts is hard to do however when one of the superstars is entering the swan song of his long-tenured career (entering his 15th year in 2019). A possible trade for Paul is hard to conjure up right now, but so is the thought of him remaining alongside James Harden in Houston.
For right now, Chris Paul is a member of the Houston Rockets, a team who looks to be in a position for one of the higher seeds in the Western Conference if they can keep the band together heading into 2020. Over the long term however, Houston or whatever team may look to acquire the once known "Point God", will be on the hook for one of the more atrocious looking salaries around the league.
One more time...Chris Paul will be receiving $44M in 2022 at the age of 36. Read it again. And again...
1. John Wall
Washington Wizards
4 years/$171 Million (exp. 2023)

First things first, it is not completely guaranteed if John Wall still possesses the ability to walk on his own two feet.
Over the past two seasons, Wall has played in a grand total of 73 games for the Washington Wizards as he has dealt with a series of injuries with his left Achilles and both knees. As things stand right now, Wall is not even a sure thing to be suiting up in 2019 or 2020 as Wizards team doctors referred to his rehabilitation process as a "long journey." (via HoopsHype) While Wall may be one of the ten or fifteen best point guards in the league when healthy, for right now the Wizards are paying him a whole lot of money to play not a lot of basketball.
Basketball aside, contractually Wall has the potential to earn over $75M through three seasons (18-20) without playing any actual meaningful basketball or really contributing anything to the Wizards organization. Although it is impossible to prevent injuries and they are extremely unfortunate to any player's career, for Washington to be on the hook for this much money and see little to no return is more than disappointing. Things even get worse towards the back end of this deal as the final year in 2022-2023 is a player option worth a whopping $47M. To pile on the bad news with this deal, Wall will be an aged out 32 years old in that final year, well past the prime of whatever career he may have left.
Washington is currently without a proper full-term GM. Their organization is stuck in perpetual mediocrity amongst the rest of the Eastern Conference. A long-storied rift between stars Bradley Beal and John Wall is at a consistent boil. And they have little to no trade assets in order to offload Wall or other ugly deals such as Ian Mahinmi. Things are not very bright for the Wizards and do not look to be getting better anytime soon.
For Wall, if he wants to make good on this MONSTER contract the answer is simple, get healthy and stay healthy. Until we have confirmation that he has the ability to actually walk, nothing can be assured with John Wall.
At least he is still raking in that average salary of $42M over the next four years.
written and edited by Jack Kurtz














