The Boston Celtics have a long history of success in the NBA. Along with their long history of team success is a myriad of hall of famers that have passed through the organization. On the other hand, there have also been some players the team has either whiffed on or decided to cling on for a bit too long (for several reasons).
We explore a few of those recent players that the Celtics probably should’ve cut ties with earlier but because for one reason or another decided to keep them around for way too long.
9 players the Boston Celtics kept around too long
Romeo Langford (2019-22)
Almost from the onset, it was pretty clear that the Boston Celtics had “missed” on Romeo Langford, who was selected in the lottery (14th overall) of the 2019 NBA Draft. During his rookie season with the Celtics (which, in fairness, was impacted by injury), Langford appeared sparingly for Boston and averaged 2.5 points on 35 percent shooting from the field.
Boston continued to invest in Langford for (roughly) two more seasons after that and tried to force the issue with him being a contributor for the team. However, the more he played the more it became clear that he simply didn’t fit on a team that was trying to make the shift to legitimate contender status.
Eventually, the Celtics traded Langford (and Josh Richardson) to the San Antonio Spurs as part of the deal for Derrick White. It was clear that the Celtics missed on Langford and held on a year too long after it became clear it wasn’t working.
After a season and a half with the Spurs, Langford is currently a free agent.
Tony Allen (2004-10)
As a late first-round pick during the 2004 NBA Draft, Tony Allen became a contributing part of the Boston Celtics’ success during the 2000s. He also played a role for the team during the C’s Big 3 championship in 2008. Allen statistically had his best season in 2006-07. He only played 33 games that year but would go on to average 12 points and four rebounds on 51 percent shooting from the field.
However, after that 2007 season, Allen would continue to struggle with consistency and injuries with the Celtics. Still a strong defender, he’s probably a player that the Celtics could’ve decided to move on from sooner. After winning the championship in 2008, the Celtics re-signed Allen to a two-year deal. Though, he would miss roughly 30 games in each of the next two seasons.
Boston would go on to lose in the second round of the playoffs to the Orlando Magic in 2009 and then in the NBA Finals to the Los Angeles Lakers in 2010.
Looking back, you could make the argument that the Celtics and Allen should’ve parted ways after winning the championship. Allen would play out the next two seasons with the Celtics and then signed with the Memphis Grizzlies via free agency during the summer of 2010.
Enes Freedom (2019-20; 21-22)
As one of the most polarizing players in the NBA in recent history, Enes Freedom, formerly known as Enes Kanter, is a player that the Boston Celtics could’ve probably done without giving two separate stints. Freedom originally signed a two-year deal with the Celtics during the summer of 2019. During that first season in Boston, Freedom would go on to average eight points and seven rebounds per game on 57 percent shooting from the field.
A few weeks into the 2020-21 season, the Celtics traded Freedom to the Portland Trail Blazers. Less than a year later, during the 2021 offseason, the Celtics decided it was a good idea to sign Freedom in free agency. Bringing Freedom back to Boston, his second stint with the Celtics was not nearly as successful (if that’s what you would categorize his first season with the team) as the first. In 35 games played for the Celtics, he averaged just four points and four rebounds with the team during the 2021-22 season.
On Valentine’s Day in 2022, Freedom was traded to the Houston Rockets and soon after waived. He would not play another game in the NBA. The fact that Freedom got two stints with the Celtics leads me to say that he was a player they held out hope for too long.
Tacko Fall (2019-21)
You have to give the Boston Celtics a little credit for trying to make Tacko Fall happen. After Fall went undrafted in the 2019 NBA Draft, Boston took a flier on the 7-foot-6 big man out of the University of Central Florida. Playing with the Celtics’ summer league, while it was clear to understand the team’s intrigue, Fall wasn’t exactly all that impressive overall. Still, Boston decided to sign Fall to a two-way contract with the team. He would only go on to appear in seven games for the Celtics during the 2019-20 season.
But that wasn’t the end of Fall in Boston, even though it probably should’ve been. During the 2020 offseason, Fall was re-signed by the Celtics to another two-way contract. However, because of the canceled G-League season, Fall was limited to the time he saw on the floor with the Celtics.
In his second season with the Celtics, Fall appeared in 19 games and only averaged seven minutes in each of his appearances. The Fall experiment fizzled out quickly for the Celtics and he would go on to leave the franchise in free agency the next season.
The fact that Fall got two years with the Celtics, however, is a good enough accomplishment. That said, it was all head-scratching at the moment.
Semi Ojeleye (2017-21)
During the 2017 NBA Draft, the Boston Celtics took a flier on Semi Ojeleye, an intriguing wing prospect out of SMU. But at least at the beginning, it was a struggle to see how Ojeleye was going to break into Boston’s rotation. And it just never seemed to click for him.
It’s easy to see the intrigue that surrounded Ojeleye as a prospect. Just looking at his measurables and natural ability, he’s a player that any team would want to invest time and effort into. He’s 6-foot-6 with a nearly 7-foot-wing span. He was considered one of the more NBA-ready players coming out of college and was viewed as a versatile forward with much promise and upside.
It simply didn’t work out for Ojeleye with the Celtics. Ojeleye got his opportunities with the Celtics but simply never developed into the player that the team hoped he would. However, the Celtics kept trying to make it happen with Ojeleye. After two seasons, it was pretty clear what Ojeleye was and what he wasn’t. Nevertheless, Boston gave him two more seasons after that.
During his final season with the Celtics, Ojeleye appeared in less than 60 games and averaged less than five points per contest. Boston moved on from Ojeleye after the 2020-21 NBA season.
Brian Scalabrine (2005-10)
The White Mamba, or Brian Scalabrine, is a player that is going to live forever in the minds of those that followed the late-2000s Boston Celtics closely. Not a huge contributor by any means, but he was the consummate professional and exact role player that every team wants at the end of the bench. And he somehow managed to catapult that to a few extra years with the team that he probably, from an objective point of view, never should’ve gotten.
During the 2005 offseason, Scalabrine signed a five-year deal with the Celtics. He would go on to play out the entire length of his contract in Boston. But after his second season with the team, his production, minutes, and role quickly diminished. During his final season with the team, Scalabrine appeared in just 52 games and was averaging less than 10 minutes per appearance.
While he may have been the example of a true professional in that locker room and was probably a welcomed veteran presence for the big 3, it’s a true riddle how he managed to hang around in Boston without playing a huge role on the team after the first two years of his five-year deal. Especially with how much the team was shuffling the roster around the big 3.
James Young (2014-17)
After the 2013-14 season, now in the post-big 3 era, the Boston Celtics needed a player and a foundation to rally around as a new build was beginning. With the sixth overall pick in the 2014 NBA Draft, the Celtics took Marcus Smart. But it was largely their selection with the 17th overall pick that many were fawning over. The selection was James Young, a highly-touted guard prospect out of Kentucky that many believed had star potential coming out of college.
Young never simply developed as many predicted he would. During his first season with the Celtics, Young appeared in just 31 games for the Celtics and averaged under 11 minutes per game. By his second season with the Celtics, it was clear he was never going to be the player they hoped he could be. He played in even fewer games and fewer minutes per contest. The writing was on the wall as nearly every other guard on the team was getting minutes over him.
Still, the Celtics brought him back for a third season in hopes that something would click for him in his development. It never came. He was let go by the Celtics, finally, after the 2016-17 season. He only appeared in six more NBA games (with the Philadelphia 76ers) after leaving the Celtics.
Payton Pritchard (2020-present)
Being a late first-round pick in the 2020 NBA Draft, there was hope that the extremely experienced and NBA-ready Payton Pritchard could play a contributing role for a Boston Celtics team that was trying to break through in the Eastern Conference. And during his rookie season with the Celtics, that’s exactly what Pritchard was able to do. During the 2020-21 season, Pritchard appeared in 66 games for the Celtics while averaging eight points per game on 41 percent shooting from 3-point range. The key stat is he averaged 19 minutes per game.
After an encouraging rookie season, however, Pritchard’s role changed during his sophomore season. He managed to play in five more games but played fewer minutes across the board. In his third season, his role was reduced even further. With a logjam in the backcourt, it wasn’t surprising. However, it has gotten to the point where it’s been reported that Pritchard wants a trade.
You can make the argument that Pritchard should’ve been moved after his sophomore season. Really, there’s no argument that he shouldn’t be moved now. Even after trading Marcus Smart, there’s no guarantee that Pritchard will play a huge role with the team this upcoming season.
Rajon Rondo (2006-15)
You can’t tell the complete story of the modern Boston Celtics without mentioning Rajon Rondo. He was an undervalued and underrated part of the team’s success with the big 3 and emerged as his own star during his time in Boston. At the same time, you can also make the argument that the Celtics held on to Rondo a couple of years too long. Part of that was due to injury, in fairness, but they missed a window to capitalize on his value nonetheless.
During his final season with the Celtics (2013-14), Rondo played 22 games for the team before he was traded. In that stint, he was still averaging eight points, eight rebounds, and 11 assists per game. However, it was pretty clear that his magic was almost all but gone. As the team moved further into a rebuild, it was clear Rondo no longer fit with the team’s timeline.
Rondo’s career with the Celtics came to an end in 2014 when he was traded to the Dallas Mavericks. Rondo would go on to play seven more years in the NBA, with eight different teams. He’ll forever be remembered as a Celtic, even if they did hold on to him a couple of years too long.