It’s hard moving on from players, especially if they have meant something to a franchise. There are relationships and emotions tied into these situations, and callously sending away a beloved player – star or role player – is harder than it seems. Just ask the Portland Trail Blazers and Damian Lillard.
The Cleveland Cavaliers are no exception to this situation either, especially with the violent oscillation between basement and contention based largely on whether or not LeBron James was on the roster. That caused them to hold on to some players for far too long, missing out on value in a trade or short-circuiting the best path forward for the franchise.
In no particular order, then, here are seven players that the Cavs held onto for way too long.
No. 7: Antawn Jamison
Antawn Jamison is a test case for the Hall of Fame, a consistently high-scoring forward who scored over 20,000 points (generally a HOF lock) but made just two All-Star Games and never made a postseason impact. In 2010 a Cleveland Cavaliers team heading for the top seed in the Eastern Conference traded for Jamison to give their offense a boost.
Whether or not he accomplished that, the Cavs lost in the second round to the Boston Celtics; a few weeks later, LeBron James was taking his talents to South Beach. At that point, the Cavs had absolutely no use for a shoot-first, second and third 34-year-old forward.
That was the time to trade Jamison, when it was clear that the Cavs were going to be rebuilding. Owner Dan Gilbert stubbornly tried to win games, however, and while the team was bad that kept the Cavaliers from trading Jamison for two entire seasons, at which point he left for nothing in free agency.
No. 6: Damon Jones
The Cleveland Cavaliers invested heavily in free agency in the summer of 2005, trying to build a contender around a young LeBron James. One such player they signed was Damon Jones, a guard who had a career year in Miami the season before.
That spike in efficiency stayed in Miami, however, as Jones’ shooting came back to earth and he failed to provide anything else to the team. Yet despite this lack of an impact, the Cavaliers kept him around for three entire seasons. He never averaged more than 6.7 points per game, shot under 40 percent from the field and and was a wreck on defense, but he maintained a rotation role for three entire seasons. The time to pull the ripcord was after season one.
No. 5: Ira Newble
A common issue for the Cavaliers during LeBron James’ first tenure was the lack of offensive firepower around him. The Cavs largely fielded elite defensive units but couldn’t surround LeBron with shooting, secondary scoring or playmaking. That was triply the case with Ira Newble.
The Cavs signed the 6’7″ wing in the summer of 2003 and he provided above-average defense during his tenure. On offense, however, he was a non-entity, essentially forcing Cleveland to play 4-on-5. He couldn’t shoot, score, handle or pass. Yet the Cavs held onto Newble for a whopping 4.5 seasons, playing him in 230 games and even starting him 111 times. They should have moved on from Newble years before they did.
No. 4: Collin Sexton
Now we come to a more complicated case, that of one Collin Sexton. The Cleveland Cavaliers used the draft pick acquired in the Kyrie Irving trade to draft Sexton eighth overall just a week before LeBron James packed up and heading to the Los Angeles Lakers.
Sexton, a relentless point guard out of Alabama, had a very up-and-down career with the Cavaliers. He built himself into a prolific volume scorer, including averaging a whopping 24.3 points per game in 2020-21. The problem with his fit in Cleveland was two-fold: he was too small to play shooting guard but too poor of a playmaker to play point guard.
With Darius Garland outpacing him and boasting those true point guard chops, it seemed fait accompli that the Cavs would move on from Sexton. To their credit, they didn’t err so much that they signed him to a lucrative contract extension, but they also held onto him all the way to restricted free agency, eventually using him as salary ballast in the Donovan Mitchell trade.
There was a point the offseason before that the Cavs could have traded Sexton for real value. Coming off that high-scoring year, Sexton could have brought back a real wing to add to the Cavs’ core, but instead, his value was reduced to a salary number. The Cavaliers should have seen the writing on the wall and moved Sexton a year earlier.
No. 3: Larry Hughes
It’s possible that you may notice a trend emerging with the players on this list. Larry Hughes is the fourth such player that fits a very specific mold: the Cavaliers overspent in free agency or the trade market, added a one-way contributor who failed to live up to expectations, and then Cleveland compounded the issue by holding on to him for far too long.
Hughes signed a massive $65 million contract in free agency, joining the Cavaliers in the summer of 2005 after one of the least-efficient 20-points-per-game seasons in modern NBA history. Unsurprisingly, high-volume and low-efficiency scoring isn’t the best fit with LeBron James, and he failed to make much of an impact.
Imagine if the Cavaliers had moved on from Larry Hughes after his first mediocre season in Cleveland; they could have added a player or two who could have helped them in their run to the NBA Finals. Instead, Hughes averaged 11.3 points per game on 34.7 percent shooting in those playoffs, filling up a whopping 35.5 minutes per game. BPM estimates that he had such a negative impact offensively that he was 1.9 points per 100 possessions worse than a league-average player.
Hughes would play 2.5 seasons with the Cavs before they moved on, including Hughes in a three-team deal that completely reshaped their rotation. LeBron James was so dominant during those seasons that he willed his team to the NBA Finals, and Hughes was a wholly unqualified running mate for him.
No. 2: Tristan Thompson
Speaking of themes, there will be one with the last two players on this list. Similarly to Antawn Jamison earlier, the Cavaliers transitioned into a post-LeBron era but refused to move on from their veterans. J.R. Smith essentially forced his way out, and Ty Lue did the same, but Tristan Thompson stuck around for a bit.
Thompson was a key member of the Cavaliers’ run to the NBA Finals for four consecutive years, serving as a versatile big both in the starting lineup and coming off of the bench. It’s no surprise that the team was reluctant to move on from him when LeBron left for the Lakers. Thompson was also clearly not convinced the team was rebuilding, famously boasting prior to the 2018-19 NBA season that “We’re still four-time Eastern Conference champions, so until you take us down from that, teams ain’t got much to say.”
The problem, of course, was that no team needed to “take them down” because the Cavs won just 19 games that season, and wouldn’t win more than 22 for another pair of years. Thompson’s brand of rebounding and defense wasn’t needed on a team playing for lottery balls, which is what the Cavs became that year.
Thompson had real trade value heading into that season, in large part because of his role on those Eastern Conference goliaths. The Cavs kept Thompson around for two seasons in the wilderness, however, and got nothing for him as he signed with the Boston Celtics in free agency. If they had moved much more quickly, they likely get real assets back for Thompson as they started their rebuild.
No. 1: Kevin Love
The first name that likely popped into the heads of many Cavaliers fans upon clicking on this list was that of Kevin Love. The former Minnesota Timberwolves big man (and current member of the Miami Heat) joined the Cavs via trade the same summer that LeBron James returned to bring a title to The Land.
Love may have struggled with untimely injuries during a couple of the Cavaliers’ postseason runs, but he was a valuable regular-season player and only increased his role in 2018 after Kyrie Irving left. A player once defined by his on-ball offense and rebounding was asked to spot up in the corner, and to his immense credit, he transformed his game and helped the Cavs win a title and make it to the NBA Finals a whopping four-straight times.
The problem came in the summer of 2018. Dan Gilbert was once again eager to show that his team was not going to fold upon the departure of LeBron James, and to that end he offered Kevin Love a lucrative contract extension to stick around. Then, instead of moving Love while he still had value, they kept him around on their losing team and watched injuries and malaise set in, nearly derailing Love’s career and providing the Cavs a whole lot of nothing when they ultimately bought him out five years later.
Love could have returned a hefty package of players and/or picks if traded early in the process, but instead, the Cavaliers held onto him through some combination of pride and stubbornness. It ultimately provided them very little and is a prime example of holding onto a player for too long.