All Sales Final: The 10 Worst NBA Free Agent Signings of All Time

Some teams will be looking to spend big this summer. However, they should learn from these cautionary tales of the past. Aidin Ebrahimi looks at the 10 worst NBA free-agent signings in recent memory.

Throughout the history of the NBA, there have been numerous instances of teams making regrettable decisions in free agency, resulting in what can be considered as "horrible" signings.

These signings involve substantial financial commitments to players who fail to live up to expectations, whether due to injury, underperformance, or a mismatch with the team's playing style. From high-profile signings that turned into major disappointments to deals that severely hampered a team's salary cap flexibility, these poor free-agent signings serve as cautionary tales about the risks involved in player acquisitions.

With that in mind, this article will look at the worst free agent signings in recent NBA history, in chronological order. Nine of these signings are from the 2010s, while four of them are from the infamous 2016 offseason.

#10. Ben Wallace to Chicago (2006) (Four-years, $60 million)

BULLS LEGEND BEN WALLACE 😉 pic.twitter.com/pe2d5GSqTH

— CallMeMeech_ (@CallMeMeech_) March 21, 2023

The Chicago Bulls made a statement to the rest of the NBA in 2006 with the signing of All-NBA second team center Ben Wallace. They wanted to show that they were no longer pushovers and wanted to get back to their winning ways after Michael Jordan's retirement. They had made the playoffs for two seasons in a row before signing Wallace, and had aspirations of overtaking Wallace's former team, the Pistons, to win the Central division. The Bulls won 49 games in 2006-07 and had a nice playoff run which included a memorable sweep of the defending NBA champion Miami Heat, before losing to the Pistons in six in the second round.

Despite the team's success, it was clear that Wallace was no longer the force he once was. Things would only get worse for Wallace, as he had one of his worst seasons ever in 2007-08. We all know that Ben Wallace was a poor offensive player, but a true shooting percentage of 39.1% (which is the worst of all time for a player since 1962), combined with his rapidly declining defensive contributions was the nail in the coffin for Wallace's time in Chicago, who traded him to the Cavs. On the bright side, he helped them get Derrick Rose.

#9. Gerald Wallace Resigns with Brooklyn (2012) (Four-years, $40 million)

One of the most beloved players in the history of Charlotte basketball, Wallace was one of the few bright spots on the expansion Bobcats. Wallace was consistently excellent on both sides of the ball, as he is one of three players (the other two being Hakeem Olajuwon and David Robinson) to average over two steals and two blocks in a season, which he accomplished in 2005-06. In 2011, Wallace was traded to Portland and kept up his solid play, which caused the Nets, who were aggressively looking to build a championship contender around that time, to acquire him in exchange for the pick that eventually turned into Damian Lillard.

Wallace was good in his half-season with the Nets, which caused the team to resign him. Wallace had a solid November and December, but once 2013 began, Wallace suddenly lost his scoring ability. He went from 13 points on 46.8% shooting (November to December) to 6.3 points on 37.8% shooting (January to April). Despite a good playoff showing, Wallace was traded to Boston in the infamous Nets/Celtics trade in 2013 and was never the same player again.

#8. Josh Smith to Detroit (2013) (Four-years, $54 million)

As of now, Pistons owe Blake Griffin $56 million. In recent history, the team paid Josh Smith $36 million NOT TO PLAY.

— Darren Rovell (@darrenrovell) March 5, 2021

Josh Smith is one of the most athletically gifted players we have ever seen. The man won the slam dunk contest in his rookie year and has a long list of highlights. He was always ferocious and electrifying, throwing it down with authority every time to ensure his dunks will be remembered forever. Another thing about Josh that will be remembered forever was his god-awful three-point percentage and his constant shot-chucking. According to The Atlanta Journal-Constitution, prior to the start of the 2009-10 season, HC Mike Woodson told Smith: "Don't worry about the 3-point ball." Since they had "so many guys on this team that can make that shot."

So Smith attempted only seven threes, 80 less than the previous season while having the best year of his career. Woodson was not brought back after that year, and Smith's shot-chucking tendencies returned under Larry Drew. The Pistons thought that they could fix Smith, but were horribly wrong as Smith had a poor first year in Detroit before having one of the worst shooting seasons ever in 2014-15, causing the Pistons to cut him. The team would end up paying him until 2020.

#7. Andrew Bynum to Cleveland (2013) (Two-years, $25 million)

This is an acquisition that still bothers me 😂. Was anybody else super hype when the Cavs acquired Andrew Bynum? #LetEmKnow pic.twitter.com/Z3f9qAJc6P

— Mack Perry (@DevaronPerry) June 1, 2023

To show you how desperate the Cavs were before the return of LeBron James, they paid Andrew Bynum, a man that hadn't played a basketball game since May 21, 2012, $25 million to save their franchise and get back to the playoffs. Bynum, who holds the record for being the youngest player ever to play in the NBA, had a really good career with the LA Lakers, winning two championships and making the All-NBA second team in his last season in LA. However, the Lakers' mentality is that they don't settle for second-best, they want the very best, so they traded Bynum to land the only center that was better than him that year, Dwight Howard.

Bynum went to Philly, where he never played in a game due to his bowling-related injury, and indirectly helped start "The Process". Bynum had some ups and downs in his short, two-month stint in Cleveland before going crazy. According to Adrian Wojnarowski, Bynum began shooting the ball every time he received it in practice, from whatever remote part of the court he had caught the ball. He was suspended before the beginning of 2014 and never played for the Cavs again. He would only play two more games in his NBA career.

#6. Omer Asik resigns with New Orleans (2015) (Five-years, $60 million)

Omer Asik is a relic of the past. He was a big and slow center that specialized in getting rebounds, and obviously, you don't see many players like that anymore. After a solid career at Fenerbahçe, Asik was drafted by the Bulls in the second round of the 2008 draft. Asik barely saw the court in his two years in Chicago, but after three solid performances as the Bulls' emergency starter in the playoffs when Joakim Noah got hurt, he caught the attention of many NBA teams. The Rockets went out and signed Asik to a pretty sizeable deal, and it worked out pretty well, as he averaged 10.1 points and led the league in total rebounds in his first year in Houston.

He was moved to the bench in year two after the aforementioned Dwight Howard joined the team but had very productive per 36 numbers. After being traded to New Orleans in the deal that brought Trevor Ariza to Houston, Asik looked solid in his first year, which prompted the Pels to give him a massive extension. Asik couldn't re-innovate his game to stay on the floor in the new pace and space era of basketball, as he only averaged 3.2 points and 5.3 boards a night in the 113 games since his extension. He would play the last four games of his career with the Bulls.

#5. Monta Ellis to Indiana (2015) (Four-years, $44 million)

Monta Ellis will always be remembered fondly by Warriors fans. Yes, the team started winning almost immediately after getting rid of him, and yes, he was initially hesitant to mentor Stephen Curry, but he also led the team through a very tough period, and his Most Improved 2006-07 campaign helped the team make the playoffs and create the legend of the "We Believe" Warriors. The team also used to rely on him very heavily, which can be seen by his absurd number of minutes played in his prime. Maybe one of the reasons for his athletic decline was the Dubs' overreliance on him.

By 2015, it was fairly obvious that Ellis was nothing more than a high-volume/low-efficiency scorer, but that somehow didn't stop Larry Bird and the Pacers to give him a big payday in the offseason. He continued to chuck shots in his first year before getting hurt midway through his second year and getting replaced by Glenn Robinson III after he won the dunk contest. Ellis was subsequently waived and never appeared on an NBA court again. Despite that, the Pacers had to pay him until the end of the 2021-22 season.

#4. Evan Turner to Portland (2016) (Four-years, $70 million)

Here we are, the 2016 offseason. After the NBA signed a nine-year, $24-billion television deal, the salary cap went from $70 million to over $94 million. That is a yearly increase of over $24 million, and before this, the cap had never experienced a yearly increase higher than $7 million. This meant that a lot of role players would be getting fringe all-star-level money, especially since the 2016 FA class was pretty weak apart from Kevin Durant. The first guy on this list who signed a big deal was Evan Turner, who was coming in after having a nice end to the previous campaign with Boston.

Turner was expected to be the team's starting small forward, but lost out on the starting job to the young Maurice Harkless, meaning that the Blazers just paid $17.5 million a year for a backup small forward. The same amount as Kawhi Leonard. Yes, Evan Turner was paid the same amount as a top-five player that season. Turner ended his Blazers tenure with a three-point percentage of 27.8% and would only play in 19 more NBA games after that.

#3. Bismack Biyombo to Orlando (2016) (Four-years, $72 million)

The only player on this list who's still on an NBA roster, Biyombo has found a good role for himself on the Suns as a solid rim protector, and he provides tremendous value with his $1.8 million contract. But for $17 million a year? What were the Magic thinking? Well, apparently they thought Bismack had turned into Bill Russell due to his impressive rebounding performances in the playoffs. Bismack had six games with 13 boards or more, including a monster 26-rebound game against the Cavs.

What they failed to realize was that it was way easier to get a lot of rebounds in slow-paced playoff games, and playing around 40 minutes a night certainly helps, too. Biyombo only lasted two years in Orlando, averaging 5.8 points, 6.3 rebounds, and 1.1 blocks while earning more than prime DeMarcus Cousins in 2016-17. He was swapped with another terrible 2016 offseason contract in Timofey Mozgov and spent three years in Charlotte before finding his niche in Phoenix.

#2. Chandler Parsons to Memphis (2016) (Four-years, $94 million)

This man somehow earned a max contract @ChandlerParsons https://t.co/3dtziL3uup pic.twitter.com/v0WxDaZ6Ag

— Hookah 🤠 (@HookahDoncic_77) June 27, 2023

Most of these deals shouldn't have been done in hindsight, and it's obviously true that Chandler Parsons wasn't worth more than Anthony Davis and Paul George, but this signing could have been so much better if it wasn't for the injuries. Parsons became a sensation with the Rockets which caused Mark Cuban to splash the cash to bring him to Dallas. Parsons wasn't bad in Dallas, but his injury struggles started there. He missed 16 games in his first year and underwent surgery to address a cartilage injury in his right knee.

The next season, he tore his meniscus, causing him to undergo surgery again and miss 21 games in his final season in Dallas. After signing for Memphis and looking disappointing on the court, he tore his meniscus again and had to go under the knife yet again. In his first 20 games of 2017-18, he shot 52.6% from the floor and 47.2% from three-point land, but you guessed it, he got hurt again. He was named the team's starter in 2018-19, but, you've figured it out by now. After playing just 95 games for Memphis, Parsons was traded to Atlanta and played five games before he was hit by a drunk driver, which ended his career.

#1. J.R. Smith Resigns with Cleveland (2016) (Four-years, $57 million)

May 31, 2018:

JR Smith’s infamous blunder in Game 1 of the NBA Finals 😬pic.twitter.com/c9jveK2ZcX

— BetMGM 🦁 (@BetMGM) May 31, 2023

Last, but certainly not least is the one and only J.R. Smith. Smith signed his deal on October 15 of 2016 after a contract holdout, making him the most recent entry on this list. There were a lot of other terrible contracts signed that summer, but come on, would you rather talk about someone like Timofey Mozgov or the legendary J.R.? Anyway, LeBron convinced the Cavs to pay up for Smith, meaning that he'd earn more in 2016-17 than Kyle Lowry, Kemba Walker, Isaiah Thomas, and Steph Curry. Smith was sharp from deep in his first two years as a Cavalier, shooting 39 and 40 percent respectively. He also shot 50% from three during the Cavs' 2016 championship run.

However, ever since signing that extension, Smith struggled to keep up his sharp shooting and simply failed to produce. His advanced stats dipped as he had two seasons with a true shooting percentage below 50%, and he went from averaging 0.15 win shares per 48 to just 0.027 in his last three years in "The Land". He also averaged a PER of 8.3 and a VORP of -0.7. And, of course, how could we forget his blunder in game one of the 2018 Finals which cost his team the game? At least he ended his career on a high note, as he won a championship in his final year with the Lakers.