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5 Worst NBA contracts that players should NOT have signed

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We often talk about players that got overpaid by signing ridiculously large contracts and never lived up to it. That happens more than often, as some of the first names that come to mind are Gilbert Arenas, Chandler Parsons, or Nicholas Batum. But what about the players that got underpaid? A handful of stars in this league played for much less money than they deserve due to bad timing and wrong business decisions. It's easy to say that these weren't good deals, but the fact is they could have pushed for more and earned much better salaries. Some of these even led to controversies, as players wanted renegotiating and terminations in order to get paid. Here are the five worst contracts players should not have signed.

5. Lou Williams (24$ million, 3 years) 2018

A few years ago, "Sweet Lou" signed a contract extension with the Los Angeles Clippers, worth 24$ million for 3 years. At the time, that was one of the best bargains in the whole NBA, as Lou came off possibly the best season of his career. Considering this was even before Kawhi and PG came, Lou was fine without chasing a ring because of his love for the Los Angeles lifestyle. That played a huge role in him staying a Clipper rather than earning a more significant amount of money. After the Clippers became the super-team we know today, Lou struggled to fit in and find his touches, as he was traded this season to the Hawks. Even though now it seems all good for him, as the Hawks surprised everybody, at the time, Lou was hurt and considering retirement due to the fact he took less money to stay in LA, only to get traded shortly after. Just another example of how loyalty doesn't fly in the NBA too often.

4. Isaiah Thomas (27$ million, 4 years) 2014

Even though he became a star with the Boston Celtics, Thomas was an outstanding player before that in Sacramento. His height never got in the way, as Thomas was one of the better point guards in the game, averaging 20.3 ppg and 6.3 apg in his final season with the Kings. After he received numerous disappointing and short-term offers, Thomas opted out for a 4-year,27$ million contract with the Phoenix Suns. You can't blame him, as that is a tremendous amount of money for a guy that was the 60th pick. In those 4 years, a lot of things happened, as he became a superstar in Boston, but only to injure his hip and never be the same. It would cost him a lot of money, as nobody believed in him anymore after the injury. Now he is fighting to get the spot back in the league, but he is still on the market. An unlucky scenario, in which Thomas could have gotten a massive amount of money if he signed a shorter contract.

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3. John Starks (4.8$ million, 4 years) 1992

Back in the 1990s, the New York Knicks were a very respectable franchise that always had teams fighting for a championship. One of their most essential pieces throughout those years was John Starks. Starks was never a superstar, but he was vastly underpaid throughout his career even though he played a key role for his team despite the fact he came into the NBA undrafted. In 1992 he would sign a 4 year, 4.8$ million contract to stay with the Knicks. Even though salaries were smaller back in the 90s, this was unbelievably modest. After making the All-Star game in 1994, averaging 19 ppg and helping the Knicks make the Finals, this contract was clearly looked like the worst one in the NBA for Starks and the best one for the Knicks. But this was a common theme back in the day, as longer, non-negotiable contracts were a common sight to see. That is why opt-out clauses, player protections, and other details were introduced to help the players, as you will see another bizarre example later on the list.

2. Ben Wallace (34$ million, 6 years) 2000

In the early 2000s, Ben Wallace was considered one of the premier defenders in the league, making his name known with the Detroit Pistons. When he joined the Pistons on a 34$ million, 6-year contract, some argued it was an overpay for a guy that didn't yet establish himself in the league. He was hard to evaluate because of his unbelievable defensive ability and horrible offensive game. But Ben would prove everybody wrong, becoming the defensive anchor of the Pistons, making a huge effect, and helping his team achieve numerous deep playoff runs, and ultimately the championship in 2004. He was dominating the defensive end of the NBA for quite some time, even though he wasn't nearly as paid as the other stars. That would eventually force him to accept a big amount form money from the Bulls in 2007, even though Pistons fans criticized him for it. But after being underpaid for so long, you had to understand that Ben had to go. 

1. Scottie Pippen (18$ million, 5 years) 1991

Back in 1991, Pippen signed an extension with the Bulls that started in the 1993-1994 season and lasted till 1998, the last championship season of the Chicago Bulls. This would be the result of the immense growth in popularity the NBA had due to Jordan and the Bulls becoming a global phenomenon as the salary cap went up. This would make Pippen the 6th highest player on his team, even though he was the instrumental second-hand to MJ and one of the best players in the whole NBA. When Pippen signed the deal, it was considered okay, especially when you consider he wanted to have some stability and take care of his family. Even though, later on, Pippen wished to renegotiate the deal and get paid, Krause refused to have the luxury of assembling a championship team. That would leave to a lot of bad blood and controversies, as we saw in the "Last Dance" documentary how the relationship between Pippen and Krause went down. By fair, the most underpaid player in NBA history!

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