The Cleveland Cavaliers can claim one of the greatest free agent signings in NBA history, adding some guy named LeBron James in the summer of 2014. He left the Miami Heat, signed with the Cavs and took them to four straight NBA Finals, including the only NBA championship in franchise history.
LeBron is just one of a number of great decisions in free agency. The reality, especially for such an up-and-down franchise, is that this team has also made a number of poor decisions in free agency. Stretching all the way back to the 1980s, the Cavs have spent a lot of money on players who did not work out.
The Cleveland Cavaliers have made quite a few bad signings in free agency
The question therefore becomes: who have been the worst free agent signings in Cavaliers franchise history? Of the many whiffs, gaffes and blunders, who have been their biggest mistakes? Taking into account contract cost, contract length and any other repercussions, balanced with how poorly the player in question performed for Cleveland, we have compiled a list of the 15 worst free-agent signings.
This list is made up of players who signed a contract in free agency with the Cavaliers coming from another team; these aren’t incumbent players sticking around or rostered players signing extensions. Modern free agency has picked up much more in the last 25 years, but there are a couple of selections from before then.
With our most sincere apologies to Dirk Minniefield, Jelani McCoy and many others who just missed the cut, here are the 15 worst free agent signings in Cavaliers franchise history.
Worst Cavaliers free agent signings No. 15: Henry Sims, 2013
In 2013 the Cleveland Cavaliers were ready to push for a winning record. They had built a youg core up after LeBron James’ departure, headlined by Kyrie Irving, and wanted to add pieces to propel them forward. They focused on the center position particularly, signing Andrew Bynum and Henry Sims to free agent deals.
Bynum was in the midst of an injury-riddled tailspin for his once-promising career, and Sims was entirely inept as his backup. He averaged just 2.2 points and 2.8 rebounds per game, and the Cavs’ offense cratered whenever he was on the court. It was so bad that at the trade deadline the Cavs sent Sims, Earl Clark and a future pick that would become Jerami Grant to the Process Philadelphia 76ers for center Spencer Hawes, just to be respectable at the position.
Worst Cavaliers free agent signings No. 14: Mike Woodson, 1990
All of the other 14 players on this list were signed to full-season contracts, but in 1990 a veteran shooting guard named Mike Woodson — the same one who would go on to – signed a deal in mid-December with the Cavaliers hoping for one last ride in the NBA.
Woodson didn’t last two weeks, giving the Cavs one of the worst runs of any player signed to any team as a free agent. He shot only 21.7 percent from the field, receiving a wild 5.8 shots per game in just 11.5 minutes; his per-36 average would have been 18 shot attempts per game. He generated -0.3 win shares during his tenure, a phenomenal feat for such a short time. Woodson was easily waived, but his status as perhaps the worst pure free agent ever signed is enough to place him on this list.
Worst Cavaliers free agent signings No. 13: Dwyane Wade, 2017
The 2017 offseason was a tumultuous one for the Cavaliers, who responded to a Kyrie Irving trade request by sending him to the Boston Celtics for a top draft pick and a collection of veterans. They filled in the gaps around Irving through other transactions, including signing LeBron’s old wingman in Miami to a deal, Dwyane Wade.
Wade had clearly lost a step from his glory days, or maybe two or three. He had an abysmal season for the struggling Cavaliers team, scoring a career-low 11.2 points per game. His athleticism was abandoning him, and as a result his free-throw attempts dropped and his finishing became inconsistent. The Cavs ended up sending him home to Miami just to clear the roster spot.
Worst Cavaliers free agent signings No. 12: Ed Davis, 2021
After winning just 22 games in the 2020-21 season, the Cavaliers made a number of moves that following summer that propelled them to a winning record the following season. Newcomers like Evan Mobley, Lauri Markkanen and Ricky Rubio played key roles in the Cavs’ success; unfortunately, Ed Davis did not.
Davis was signed to be the third-string center and veteran mentor to the group. Perhaps he accomplished the second, but he was terrible when pressed into service on the court. During a key stretch late in the season when Jarrett Allen was injured Davis was leaned on for a rotation role and he could not deliver, a significant reason why the team faltered in the final section of the season and dropped out of the playoffs entirely. He averaged just 0.9 points for the season and his NBA career appears to have ended with the Cavs.
Worst Cavaliers free agent signings No. 11: Earl Clark, 2013
We wrote earlier about the spending spree the Cavs went on in the summer of 2013, adding veteran players to supplement their talented youngsters. Earl Clark was signed to bolster the forward corps, handed a very strong $4.25 million contract for his services.
Those services were, unfortunately for both the Cavaliers and Clark’s career, quite lacking. Clark shot just 37.5 percent from the field and 34.5 percent from 3-point range, averaging 4.8 points and 2.6 rebounds. The Cavs ended up using his salary to trade for Spencer Hawes, and he would play just 19 games the rest of his career as he fizzled out as an NBA player.
Worst Cavaliers free agent signings No. 10: Mike Miller, 2014
LeBron James loves to play with other players he can trust, and there were few players in his career he trusted more than Mike Miller. The wing shooter won two titles with LeBron on the Miami Heat, and in 2014 he followed James to Cleveland and signed with the Cavaliers to make a run at another title.
Unfortunately for the Cavs, Miller just didn’t have it anymore by the time he was in Cleveland. He played in 52 games but his 3-point shooting plummeted to 32.7 percent and he averaged just 2.1 points per game. His defense vanished, his minutes dissipated and he became a fringe rotation player on a good team that succeeded despite him, not because of him.
Worst Cavaliers free agent signings No. 9: Scooter McCray, 1986
There is a rhythm to most free-agent signings. Players that have a good season often parlay that into a solid contract by a team that buys into that player’s “growth” instead of their hot season. Another group are those players with a track record of success who are coming off of an injury or bad season, the classic “buy-low” candidates. Either of these groups could result in successful signings, or they could result in disappointments. Some of both fill this list.
What is so unusual about the saga of Scooter McCray is that he doesn’t fall into either category. The 6’9″ power forward was drafted 36th overall in the 1983 NBA Draft, and he played 53 nondescript games for the Seattle SuperSonics. He averaged 2.7 points per game, shot just 40.5 percent from the field, and had nearly as many turnovers (44) as he did assists (51).
The following season McCrary couldn’t even find an NBA team willing to sign him, instead going to play in France. Yet inexplicably, the Cavs decided to sign him that next offseason, in 1986, to bolster the bench for a team on the rise.
What happened when the Cavs handed a contract to a player who had been terrible in the NBA? He was terrible in Cleveland! He played in 24 games, including two inexplicable starts, averaging 3.3 points per game. He was waived by February and never again saw another NBA minute.
Worst Cavaliers free agent signings No. 8: Kevin Pangos, 2021
Sometimes an offseason win turns into a loss once the ball is tipped and the games actually begin. That’s what happened to the Cleveland Cavaliers in the 2021-22 season, when offseason acquisition Kevin Pangos was not quite the slam-dunk signing he appeared to be.
Kevin Pangos is a 6’1″ point guard who played college basketball at Gonzaga, following in the footsteps of John Stockton (also a Gonzaga alum). He went undrafted coming out of college but became one of the best players in Europe in 2020 and 2021, leading to a two-year contract from the Cavs in the summer of 2021.
With Darius Garland the expected starter and Ricky Rubio a high-level backup, Pangos didn’t need to be a starting-level point guard. Even so, his success in Europe built the expectation that the Cavs had a steal on their hands.
That was certainly not the case, as Pangos was bad whenever he was pressed into duty. He shot just 23.1 percent from 3-point range, played just 166 total minutes, and didn’t provide value on either end of the court. When Rubio tore his ACL and Darius Garland missed time, Pangos was absolutely atrocious in relief and led to drastic scrambling to find other options at the point. Pangos was signed to be an emergency option, and when the Cavs had an emergency he was an abject failure.
Worst Cavaliers free agent signings No. 7: Jarrett Jack, 2013
We come to our third member of the 2013 Cleveland free agency class, and we aren’t even done yet. That summer the Cavaliers spent a whole lot of money and got relatively nothing out of it. One year after winning 24 games, they went all in and ended up winning…33 games. Any success they had was mostly because of the growth of young players like Kyrie Irving and Tristan Thompson, not their free agent class.
Jarrett Jack was arguably the best of the bunch, playing 2,252 total minutes in 80 total games. If the best ability is availability, Jack at least brought that to the team as a veteran point guard. The problem is that he didn’t bring a whole lot else, shooting just 41 percent from the field and 34.1 percent from 3-point range. On a team of terrible defenders he was at least competent, but he was far from a disruptor on that end.
Mediocre defense and ice-cold offense weren’t what the Cavs were expecting when they signed him to a four-year, $25.2 million contract. Making a mistake, even an expensive one, is manageable for a single season. The long contract forced the Cavs to pay to offload Jack’s salary the following summer to clear cap space for a certain Akron native in free agency.
Worst Cavaliers free agent signings No. 6: Damon Jones, 2005
The Cavaliers signed another four-year contract in the summer of 2005, inking combo guard Damon Jones to a four-year, $16.1 million contract. The eighth-year guard out of Houston was coming off of a career year for the Miami Heat, playing in all 82 games and leading the league in effective field goal percentage.
That efficiency proved to be a mirage, however, as Jones was a horrible shooter for the entirety of his tenure in Cleveland. He shot 38.7 percent from the field in his first season and just 39.5 percent across all three seasons. He became purely a 3-point shooter, which was both unusual in his era and a problem when he couldn’t shoot at an above-average accuracy.
Jones averaged just 6.6 points per game during his tenure in Cleveland. He wasn’t much of a playmaker, either, slinging just 1.9 assists per game. Damon Jones was an offensive specialist who crippled the Cleveland Cavaliers on offense, not exactly a slam dunk of a signing.
In the end, the Cavs jettisoned Jones in a multi-team deal that brought Mo Williams to the squad. Jones played a handful of games for the Milwaukee Bucks before his NBA career was over that very next season.
Worst Cavaliers free agent signings No. 5: Mo Williams, 2016
Mo Williams spent two different stints with the Cleveland Cavaliers. The first saw him arrive by trade in 2008, and while he was largely overrated playing next to LeBron James (he was not a deserving All-Star at any point in his career, but made it in 2009) he was an above-average starter for the Cavs during those final few years of LeBron James’ time in Cleveland (part one).
Williams was routed to the LA Clippers after James left in the deal that landed Cleveland the Kyrie Irving draft pick, and he played in Utah, Portland, Minnesota and Charlotte over the next three seasons. Then, in the summer of 2015, he rejoined the Cavaliers in free agency by signing a two-year, $4.29 million deal to back up Irving.
Narratively the signing worked out; the Cavaliers won the NBA Championship that season, coming back to beat the Golden State Warriors in the NBA Finals, and Williams won the first championship of his career in the wine and gold.
As a value proposition, however, it was a fairly big mistake. Williams did not have much left in the tank at that point in his career, averaging 8.2 points per game in just 41 contests during the regular season. Come the playoffs Williams was borderline unplayable, shooting just 28.6 percent from the field and averaging just 1.5 points per game in 13 brief appearances.
Worst Cavaliers free agent signings No. 4: Ira Newble, 2003
The 2003 offseason was a pivotal one for the Cleveland Cavaliers, as they took a high school student named LeBron James with the first overall pick of the 2003 NBA Draft. The story of those early LeBron years, however, was how the franchise failed entirely in placing other talented offensive players around him.
The poster child for that ineptitude was Ira Newble. The Cavs signed him in that same 2003 offseason, giving him a four-year, $15 million contract. Newble was fine on defense, playing physically in an era where that was rewarded, and the 6’7″ wing had a full rotation role for the next few seasons.
The problem was on offense, where Newble was basically forcing the Cavs to play 4-on-5. He played 4.5 seasons in total in Cleveland and averaged 4.2 points per game. Lest you think that was weighed down by lesser roles, the most he ever averaged was 5.9 points per game in 2004-05.
Newble was a terrible shooter, an incapable ball-handler and generally just couldn’t score. He managed to hang on in Cleveland because his tough brand of defense was a “coach’s favorite” but the Cavs would have provided a much better ecosystem for James if they had signed someone else to a four-year deal back in 2003.
Worst Cavaliers free agent signings No. 3: Andrew Bynum, 2013
At one point in his career, Andrew Bynum looked like the next great NBA center. He played big minutes early on for the Los Angeles Lakers, starting 53 games as a 19-year old sophomore before breaking out in his third season alongside Kobe Bryant and Pau Gasol, averaging a double-double on a team that went to the NBA Finals. He battled injuries over the next few seasons but made an All-Star team in 2011-12 before he was traded to the Philadelphia 76ers in the Dwight Howard deal.
That was where he hurt his knee in a bowling accident, aggravating a preexisting injury and setting his career into a tailspin. He did not play for the 2012-13 season, becoming an unrestricted free agent in the summer of 2013.
We’ve discussed that offseason multiple times in that piece; the Cavs were tired of losing and spent wildly in free agency. Their worst contract of the summer was handed to Bynum; despite his health record they decided to take a shot on him, signing Bynum to a two-year, $24.79 million contract.
The deal itself wasn’t overly damaging, as there were injury protections and the second year was a team option. It couldn’t have gone much worse, however, as Bynum played in only 24 games. He was not good when he did play, shooting just 41.9 percent from the field on a diet of only paint touches. He had a high usage, low efficiency and zero versatility to his game.
The Cavs shipped him out to the Chicago Bulls just a few months into the year as part of a deal for Luol Deng, and the Bulls waived Bynum immediately. He caught on for two games with the Indiana Pacers before his career was over.
Worst Cavaliers free agent signings No. 2: Donyell Marshall, 2005
Two players remain on this list, and they both share something in common: they were signed in the summer of 2005. At that point, two seasons of LeBron James had convinced the Cavaliers (correctly) that he was ready to compete at a high level, and they handed out big money (for the time) to upgrade around him. The problem was that they chose the wrong players.
The Cavs had a strong one-two punch with LeBron and Zydrunas Ilgauskas and a bunch of defense-first players like the aforementioned Ira Newble. What they desperately needed was shooting, and they handed a four-year, $22 million contract to 32-year-old forward Donyell Marshall.
The prior season Marshall had flashed a 3-point shot, hitting 41.6 percent from long-range. That accuracy did not carry over to the Cavs, as he hit only 32.4 percent in the 2005-06 season. When over half of his shots came from deep, that lack of accuracy constricted the Cavs’ offense and plummeted Marshall’s personal efficiency.
His lack of contributions in any areas other than rebounding and missing shots led to fewer and fewer minutes, and after 2.5 seasons the Cavs finally gave up and shipped him to Seattle at the 2008 Trade Deadline. In 173 games he shot 33.5 percent from deep, 40.3 percent overall from the field, and averaged only 7.8 points. He was not the weapon the Cavs needed…and neither was the final player on our list.
Worst Cavaliers free agent signings No. 1: Larry Hughes, 2005
In the summer of 2005, the largest contract that the franchise had ever given out was signed. Ready to put a winning team around LeBron James, the Cavs made overtures to elite free agents like Ray Allen and Michael Redd. When they signed elsewhere, the Cavaliers pivoted and signed Washington Wizards wing Larry Hughes to a five-year, $65 million contract.
Larry Hughes averaged 22 points per game the prior season in Washington, which sounds like an impressive number, especially for that era of basketball. That was just inside the top 20 that year. What the basic stat fails to illuminate is that Hughes reached that total while shooting just 43 percent from the field and 28.2 percent from 3-point range; a healthy diet of free-throws (hit at only 77.7 percent) propped him up too.
Joining the Cavs in 2005 Hughes immediately dealt with the injuries that had plagued him earlier in his career, and partially as a result and partially because of how his game was in the first place, he was highly inefficient. Hughes played 2.5 seasons with the Cavaliers and shot just 39.6 percent from the field on a robust 13 shots per game. His free-throws dropped off, his turnovers spiked, his defense was below average, and overall his time in Cleveland on teams that were supposed to be contenders was disastrous. His awful shot diet inspired a clever website title, but any success the team found was in spite of Hughes’ contributions.
The Cavaliers have a history of finding solid talent in the draft and via trade, but their track record in free agency is much more spotty. These 15 players illustrate the lowest points of Cleveland front offices, and Larry Hughes leads the way as the very worst free agent signing in the history of the Cleveland Cavaliers.