When it comes to the greatest free agent signings in the history of the NBA, the Cleveland Cavaliers have got to be mentioned in the conversation when they signed LeBron James in 2014. Not only is this because LeBron is one of the best players this game has ever seen, but more importantly, this brought the Cavs their first title in franchise history. The fact that this prodigal son-type signing came a few years after the whole city turned on LeBron for jumping ship and joining the Miami Heat only makes the deal even sweeter.

It hasn't been all good for the Cavs, though, and they have had some terrible free agent signings in the past. Below are the Top 5 worst free agent signings in Cleveland Cavaliers history.

5. Donyell Marshall

During his heyday, Donyell Marshall was a pretty good player, who served as a double-double threat on any given night. This was not the case when he joined the Cavs in 2005 at 32 years of age. This deal came out to the tune of $22 million for four years.

Marshall was already at the tail end of his career when he signed for the Cavs. At that point, he had transitioned his game as more of a three-point threat, posting a career-best 2.3 triples per contest on a 41.6-percent clip in the season preceding his move to Cleveland. Unfortunately for both parties, the 6-foot-9 forward lost his hot hand with his new team, dropping to just 1.6 3-pointers per game on 32.4 percent shooting in his first season with the Cavs.

After two and a half seasons with the squad, Cleveland decided to trade away Marshall and his expiring deal to the Seattle SuperSonics as part of a complex three-team deal that brought over the likes of Ben Wallace and Delonte West — among others — to the Cavs.

4. Ira Newble

In 2003, the Cavs signed a 29-year-old Ira Newble on a four-year, $15 million deal. That actually does not sound so bad for a role player that averaged 18.3 minutes per contest in his four years in Cleveland. However, things get a bit problematic when you look at his numbers. During this four-season span, Newble put up 4.2 points and 2.5 rebounds per game. That's certainly not the production one would expect from a player earning close to $4 million per year during the early 2000's.

Needless to say, Newble's time with the Cavs did not exactly turn out to be a fruitful one. Cleveland sent him packing in 2008, incidentally, in the same deal as the one described above involving Donyell Marhsall.

3. J.R. Smith

JR Smith

J.R. Smith's contributions to the historic 2016 championship run is undeniable. So much so, that after a bit of a stalemate, the Cavs ultimately re-signed the 6-foot-6 swingman to a hefty $57 million deal for four years a few months after winning the title. This was the biggest deal Smith had signed in his entire career, and as it turns out, this also marked the beginning of the end for him.

Over the next couple of seasons, Smith's production would drop to 8.4 points, 2.9 rebounds, and 2.0 triples per game on a 36.5-percent clip. Let's also not forget about that pivotal mistake he made in the Game 1 of the 2018 Finals, which the Cavs eventually lost in a cleans sweep against the Golden State Warriors. By the time the 2018-19 season kicked in, with LeBron departing for the Los Angeles Lakers, Smith became an afterthought in Cleveland side that was centered around youth development.

The Cavs eventually waived Smith in July of 2019, stretching the remainder of his massive deal over the next few years.

2. Andrew Bynum

Andrew Bynum was once one of the most promising young big men in the league. Unfortunately for him, injuries got in the way. He suffered a major injury in 2012 — a season in which he was named to the All-Star squad for the one and only time in his entire career — which forced him to miss out the entirety of the succeeding campaign.

Once he was ready to make a comeback prior to the start of the 2013-14 season, it was the Cavs who gambled on a 26-year-old Bynum. This required Cleveland to shell out $24.8 million for a two-year deal. The Cavs did not get much of a return on their investment.

Bynum was a shadow of his former self, and was only able to suit up for a grand total of 24 games for the team, averaging 8.4 points (on a miserable 41.9 percent shooting), 5.3 rebounds, and 1.2 blocks. It did not take long for Cleveland to pull the plug on this experiment, sending the 7-foot big man to the Chicago Bulls mid-season. He was waived by the Bulls shortly after, and that pretty much put an end to his NBA career.

1. Larry Hughes

The 2005 signing of Larry Hughes to the sum of $65 million for five years remains to be, without a doubt, the worst free agent signing in Cavs history. The team were desperate to sign a second star to pair alongside a young LeBron James, but after failing to lure Ray Allen and Micheal Redd to Cleveland, the team settled for a 27-year-old Hughes, who was coming off a huge year with the Washington Wizards.

Things did not work well with Hughes in Cleveland, as he averaged just 14.3 points (on 39.6 percent shooting), 3.9 rebounds, 3.3 assists, and 1.4 steals in two and a half rather forgettable seasons with the Cavs. That's actually not so bad looking at the raw numbers, but considering how much they expected (and paid) from (for) Hughes, it is clear that he failed to meet the team's demands.

In 2008, the Cavs offloaded Hughes to the Chicago Bulls as — you guessed it — part of the same blockbuster deal that sent both Marshall and Newble packing. From this perspective, you can clearly see that that was a great player dump move by the Cavs front office, ridding themselves of some of their biggest mistakes from the past few years.