Can you think of at least one time you heard about a NBA player signing a contract that was beyond ridiculous to the point you started to question the owner and his front office staff?

Since no one has the ability to see into the future, at least we think no one has any magical powers that allow them to control time, it is not easy to criticize an owner about a move he made when, at the time, that specific player was a good, if not great, fit.

If you do some searching on the internet, you can quickly come across lists of the NBA’s worst free agent signings of all time. These lists talk about deals that turned out to be terrible but no one really knew that at the time of the signing. A lot of the players on these lists were hyped up to be the next big star in the NBA, leading to a team making a decision that could pay-off dividends in the long run.

We are trying to explain that judging something from ten years ago is easy, anyone can do that. So we added another caveat to the idea of the NBA’s worst signings by giving you a name that would have been a much better fit for the team instead. And we found a handful of them to discuss today.

15. Vin Baker (1999), PF/C, SEA (7-Year, $86 Million)

via cnbc.com

Vin Baker is in the 15th spot because his issues were never on the court, rather, it was off-the-court where he struggled with alcohol, sending him down a dark and lonely road that cost him his career. But how does a millionaire NBA star hide his drinking problem while having to play 82 games each year over the course of 8 months. He did it carefully and it was not until he arrived in Boston and started getting into fights with coach Jim O’Brien that people started to notice something was not right with him.

Prior to the realization that he was battling demons that were beyond his control, we should back up to the reason you are here, his massive seven-year contract worth about $86 million. He managed to play three seasons of the contract before being traded to Boston. In those three years he managed 14.3 points, 6.6 rebounds, and 1.5 assists per game. Compared to what was available that offseason, he might have been the best choice at the time, just not for $12 million per year.

Better Option: Vin Baker for Less Money.

14. Raef LaFrentz (2002), PF/C, DAL (7-Yearr, $70 Million)

via wonba.fr

Raef LaFrentz sounded like some kind of European stud that was brought over to help a franchise get over in the postseason. But that was far from the truth. He was born and raised in Hampton, Iowa before attending Kansas for college. There was nothing about him that screamed foreign, except the way he played. He was a tall, powerful center that could score from anywhere on the floor, including behind the arc while also providing some impressive defensive skills.

During the 2001-02 season, he was traded from the Denver Nuggets to the Dallas Mavericks, where he then played out the rest of the season, averaging 10.8 points, 7.4 rebounds, and 2.2 blocks per game, in just under 30 minutes. He then signed a seven-year deal the following summer for $70 million. Mark Cuban must have gotten cold feet and ended up unloading such a long term deal in 2003. They honestly did not need him, that Mavs team was built to win already and ended up 60-22 that season.

Better Option: Anybody Else.

13. DeMarre Carroll (2005), SF, TOR (4-Year, $60 Million)

Tom Szczerbowski-USA TODAY Sports

DeMarre Carroll is an anomaly when it comes to the NBA free agent market today. That is simply because he is one of the guys everyone should root for. He does not get into trouble on or off the court and has a reputation for working hard at practice too. He is considered to be one of the league’s best two-way players and is a very good defender that was coming off a season with Atlanta where he averaged 12.6 points, 5.3 rebounds, and 1.3 steals per game in a breakout season.

Those numbers, combined with his defensive style of play, can result in a team overpaying for him in the free agent market, and that is exactly what the Toronto Raptors did in 2015 when they gave him $60 million over four years. Because of their already successful lineup, DeMarre Carroll was simply added for his defense and his numbers have dropped over the past two years as a result. He only makes the list because of the other players that were available that year, most importantly, Kevin Love. They signed Carroll before they even tried to chase after Love for fear of losing out on him.

Better Option: Kevin Love.

12. Ben Gordon (2009), SG, DET (5-Yr, $50 Million)

via zimbio.com

The Chicago Bulls selected Ben Gordon third overall during the 2004 NBA Draft because they saw a player that had the ability to score from all over the court while also finding ways to get to the basket. So for his first five NBA seasons, Ben averaged 18.5 points, 3.0 rebounds, and 3.0 assists per game, which led to him becoming one of the league’s best free agents during the 2009 off-season.

That was when the Detroit Pistons jumped in and signed him for five-years and $50 million. They had hoped he would be that same prolific scorer he was in Chi-Town. But when they reduced his minutes from 31 to 25 per game, the slight difference showed an issue with his game and his numbers began to drop and he averaged 12.4 points per game with the Pistons.

The biggest reason he makes the list of bad signings is because the Pistons should have re-signed Allen Iverson instead but focused on younger players with brighter futures.

Better Option: Re-Sign Allen Iverson.

11. JaVale McGee (2012), C, DEN (4-Year, $40 Million)

Chris Humphreys-USA TODAY Sports

At the height of his popularity, JaVale McGee cashed in and signed a $40 million deal with the Denver Nuggets that was nothing more than a gamble that never paid off for them. It is rare that a 7’0″ player, with hops, could also move and run around like anyone else on the floor. JaVale McGee was so athletic and fun to watch that he was thought to be a good investment because of the chances he breaks out and becomes a superstar like Dwight Howard or DeAndre Jordan.

However, he only averaged 8.0 points, 4.3 rebounds, and 1.7 blocks per game. We can understand the scoring being so low if they plan on using him for his big frame and defensive nature. But from the looks of his numbers, his defense is not that great either.

He ended up only playing three years for Denver before they sent him packing and is now playing for the Golden State Warriors. If the Nuggets could return to that summer and sign someone else, they almost certainly would have taken a shot at Ersan Ilyasova instead.

Better Option: Ersan Ilyasova

10. Ian Mahinmi (2016), C, WAS (4-Year, $64 Million)

Geoff Burke-USA TODAY Sports

Ian Mahinmi’s 2016 contract with the Washington Wizards is a direct result of poor decision-making last summer by the Wizards front office which all started with Kevin Durant. The Wizards expected themselves to be able to attract Kevin Durant to Washington because that is where he grew up, it was his hometown. So they made moves during the season, and even the year before, to free up the space they would need to sign him. However, when KD announced the teams he would meet with last summer, the Wizards did not make the cut.

That was when panic set in and they then started chasing after Al Horford and nearly got him before he landed the largest deal in Boston Celtics history before deciding to go there. That left the Wizards with a need that needed to be filled and Ian Mahinmi was apparently the guy. But a career backup will always be a career backup yet they paid him $64 million for four years of work, or about $50 million more than he is worth.

Beter Option: Kevin Durant or Al Horford (if affordable).

9. Chandler Parsons (2016), SF, Memphis (4-Year, $95 Million)

Sergio Estrada-USA TODAY Sports

Last summer, the NBA free agency pool featured Kevin Durant, Mike Conley, DeMar DeRozan, Al Horford, Dwyane Wade, and Andre Drummond (Restricted). It was pretty weak beyond them and it showed when team’s starting signing players for massive deals that made us all scratch our head. Even Mike Conley, who is one of the best Point Guards in the NBA, but not the best, signed with Memphis for $152 million over five years, the largest contract in NBA history.

So once the top guys landed the deals they were looking for, the second wave of stars began signing deals that went beyond confusing, they were tragedies. Chandler Parsons somehow convinced the front office in Memphis that he was worth $23 million per season and now they are stuck with him for four years. He is making more this year than Kawahi Leonard, Blake Griffin, Kevin Love, Marc Gasol, Jimmy Butler, John Wall, Paul George… should we stop? Because he is the 18th highest paid player this season but is ranked 325th in win shares. There was no reason to sign him for that much money and it still makes us wonder about the decision-making of the Grizzlies front office.

Better Option: Any Big Name Free Agent.

8. Jared Jeffries (2006), SF/PF, NYK (5-Year, $30 Million)

via alchetron.com

NBA teams will overpay for defense and that is the only justification for the New York Knicks signing of Jared Jeffries in 2006 for five-years and $30 million. That amount might not sound like a lot when compared to some of the deals we are seeing today but it was back in 2006, especially for a defensive minded player like Jared Jeffries, who came in averaging 26 minutes per game. He was not a big scorer but was a decent rebounder. The rest of his game focused on guarding the other teams best players, which he was good at doing.

If the New York Knicks wanted a defensive stud, they should have reached out to Ben Wallace that summer because he was also a free agent looking for a new home. They settled for Jeffries and were left with buyer’s remorse as he would only average 4.6 points and 3.9 rebounds per game while in New York. He was traded in 2010 to the Houston Rockets.

Better Option: Ben Wallace

7. Darius Miles (2004), SF, POR (6-Year, $48 Million)

via nba.nbcsports.com

The 2004 NBA free agent market was loaded with talent from just about every position, starting with the most coveted of them all, Kobe Bryant. He hit the market like he was the hottest Christmas toy that year, everyone wanted him and tried offering him a contract. Some other notable free agents that summer were Steve Nash, Travis Best, Rod Strickland, Robert Horry, Bruce Bowen, Steve Smith, Derek Fisher, Stromile Swift, Rafer Alston, and Marcus Camby. Oh, and one more name we forgot to include…Darius Miles, who the Trail Blazers believed to be their best option that year.

Portland decided to give him a six-year contract worth a total of $48 million that they probably regret to this day. All he did was play in 104 games over the first two seasons under the contract, battling suspensions and injuries, before going down for the third and fourth years of his deal with a knee injury that the Trail Blazers considered to be career-ending. It ended up not being and it cost Portland $18 million, to pay the remainder of his deal, in 2009.

Better Option: Anybody Listed Above.

6. Hedo Turkoglu (2009), SF/PF, TOR (5-Year, $52.8 Million)

via sportsnet.ca

In July of 2009, Hedo Turkoglu was was coming fresh off a five year stint with the Orlando Magic where he turned into a very hot free agent Small Forward. So he started shopping around and testing the market when the Portland Trail Blazers stepped in, Hedo was ready to make a decision. He even, according to many of the reports published back then, gave a verbal to the Trail Blazers to let them know he was ready.

Between the day he told Portland he was coming and the next morning, something had changed and Hedo decided to remain with the Toronto Raptors instead. It ended up simply being a change of heart. He only played one season of his contract with Toronto before being traded the following summer. During the 74 games he played with the Raptors, he averaged 11.3 points, 4.6 rebounds, and 4.1 assists. Although those numbers are not that bad, it was all lower than the previous five seasons for Hedo. Not to mention they traded him after just one year. That alone makes this a bad signing.

Better Option: Anybody Who Could Fill the Small forward Position.

5. Bobby Simmons (2005), SF, MIL (5-Year, $47 Million)

via yardbarker.com

The summer of ’05 was a great one for the Milwaukee Bucks, who drafted Andrew Bogut with the number one overall pick in the draft. They then went on to re-sign one of the league’s best scorers, Michael Redd, to a long term contract. But then they surprised a lot of people by landing Bobby Simmons, who was quickly becoming a top-five Small Forward in the NBA.

He  had his break out season the year prior, with the Clippers, in Los Angeles and averaged 16.4 points, 5.9 rebounds, 2.7 assists, and 1.4 steals per game while shooting 46.6% from the field. The idea that a future star on the cusp of an All-Star season would come to Milwaukee over anywhere else remains one of the biggest question marks about this man. It was actually not a bad signing, at first. But when he got injured during his second season, and missed the entire year, he never recovered from that much time off. He only played two seasons of his five year, $47 million deal.

Better Option: Somebody Who Could Have Complimented Michael Redd.

4. Timofey Mozgov (2016), C, LAL (4-Year, $64 Million)

Jayne Kamin-Oncea-USA TODAY Sports

What in the world is going on in Los Angeles these days? Before their embarrassing 2013-14 season, the Lakers had only missed the postseason five times in their team’s history, dating back to 1948. They have won 16 NBA titles in 31 Championship game appearances and have a multitude of Hall of Famers that have once worn the purple and gold.

But then Phil Jackson retired and things started to get desperate in LA with Kobe Bryant basically owning the team the last few years, preventing them from being able to progress anyone else on the roster. This has turned them into a place that no one wants to play anymore and it became evident last summer when the biggest name they could attract was Timofey Mozgov, a 30-year old worker that averages 7.0 points and 5.0 rebounds per game, for his career.

They must have been worried that he would not sign and overpaid him just to make sure he could not turn the offer down. They went after DeMar DeRozan and Al Horford last summer and were left hanging out to dry. All of this panic led to a contract that will be studied for many years to come, because of how absurd it is.

Better Option: DeMar DeRozan or Al Horford.

3. Omer Asik (2015), C, NOP (5-Year, $60 Million)

Benny Sieu-USA TODAY Sports

If there is one team in the NBA today that is just plain frustrating to watch, it is the New Orleans Pelicans. Their head coach, Alvin Gentry, should have stayed in Oakland because he is not the answer for the Pelicans, he has proven that in his first 130 games. How can a team that has Jrue Holiday, Tyreke Evans and Anthony Davis, easily one of the top-three players in the NBA, win only 30 games in 2015 and find themselves falling again in 2016? It has to be coaching.

It could also be poor chemistry or simply just bad front office moves, like when the Pelicans signed Omer Asik to a $60 million deal in 2015. He has become a benchwarmer and has only played in 30 games this season with his minutes on a downfall, playing only 15 minutes per game, which is about $40,000 per minute that they are simply getting nothing in return for. They could have saved the money for this upcoming offseason or really pushed after LaMarcus Aldridge or another superstar.

Better Option: LaMarcus Aldridge

2. Jerome James (2005), C, NYK (5-Year, $30 Million)

via alchetron.com

Nope, Jerome James was definitely not the answer to the New York Knicks problem at Center heading into the 2005-06 NBA season. He has become a legend for one reason, his terrible contract. That alone is the only reason anyone even remembers this man today. Without this tragedy of a contract, Jerome James would be just another veteran in the NBA, nothing more.

So what did the Knicks see in him that no one else did? After analyzing the data, the only thing we found was his playoff performance the previous season, specifically in the first round series against the Sacramento Kings when he averaged 17.2 points, 9.4 rebounds, and 2.2 blocks per game, helping to propel the Sonics to the next round.

Looking back, that is not enough justification to give him $6 million per season. He probably should have received whatever the league minimum was at the time, or less.

Better Option: Jerome James for Less Money.

1. Jim McIlvaine (1996), C, SEA (7-Year, $33.6 Million)

via bulletsforever.com

During the summer of 1996, the Seattle Supersonics were still trying to recover from the previous year’s NBA Finals loss even after finishing the regular season with 64 wins, a franchise record. They were starting to click as an organization but they had a problem, Shawn Kemp was not very happy about his current, well-underpaid, contract. He even sat out the first three weeks of training camp, protesting the fact that he was heading into the 1996-97 season averaging 15.9 points, 9.5 rebounds, 1.2 steals, and 1.6 blocks per game and was easily the star of the Sonics roster but was only making $3 million per year in 1995 and 1996.

Imagine you were the star of any NBA team and also considered as one of the league’s best players but an unproven young prospect named Jim McIlvaine gets signed for $33.6 million and is making $3 million in his first year with the team. Although he never blamed Jim for leaving Seattle, this contract is horrible because it broke up a team that potentially could have become a NBA Champion within the next few seasons.

Better Option: Appease Shawn Kemp.

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