As the winningest franchise in the history of the NBA along with the Lakers, the Boston Celtics are not often associated with mistakes in the draft, the trade market, or free agency like some of their Atlantic Division luminaries are.
The Nets have become synonymous with taking big swings on aging superstars only to have it all fall apart within a few years. Danny Ainge famously fleeced Brooklyn in 2013 with the Paul Pierce/Kevin Garnett trade, while Kyrie Irving and Kevin Durant played for the Nets for less than the duration of the original contracts they signed to be in Kings County. Across the East River, the Knicks are no better. New York is synonymous with some of the most head-scratching free-agent agreements (Jerome James, Eddy Curry, Amar’e Stoudemire) in the history of the league for any team. Even the 76ers could be burned by James Harden if/when he leaves Philadelphia this upcoming summer less than two years after giving up multiple draft picks to land him.
Throw in the Lakers’ endless free agent gaffes — Timofey Mozgov and Luol Deng spring to mind immediately — and you have a league that has seen numerous big market front offices spend recklessly and make fools of themselves in the process.
The Celtics haven’t made such famous mistakes, but their history isn’t flawless either. In honor of Boston’s 17 championships, Hardwood Houdini takes a look at the 17 worst free-agent signings in franchise history:
Worst Boston Celtics free agent signing No. 17: Gordon Hayward
While it’s difficult to blame Gordon Hayward too much for how his Celtics tenure went — he had a season-ending injury within his first few minutes of his debut in green — his max contract signing was supposed to provide the final piece of a core that also included Kyrie Irving, Al Horford, Jayson Tatum, and Jaylen Brown that would bring Banner 18 to Beantown.
Instead, he was the clear sore spot and someone who was out of place his entire time in a Celtics uniform.
Worst Boston Celtics free agent signing No. 16: Enes Kanter
Enes Kanter’s first stint with the Celtics cost more, but it was during his second stint in 2021-22 that saw the center’s impact skew mostly negative. Kanter was always an efficient scoring big, and he provided that during the 2019-20 season, but by the time he re-signed last season, even that part of his game had disappeared.
Kanter’s defense was always a question mark, and his inability to stay in front of defenders only grew worse as he aged. What makes his signing a negative was the locker room drama with Ime Udoka that came to light after the coach’s suspension — drama that may have impacted the team’s chemistry during the first half of the 2021-22 season.
Worst Boston Celtics free agent signing No. 15: Jason Collins
Jason Collins’ career was already on the decline by the time the Celtics signed the seven-footer, but after being a starter for much of his career and even a spot-starter in Boston, it was clear Collins didn’t have much left in the tank.
Collins was not the Greg Stiemsma replacement the Cs thought they were bargaining for.
Worst Boston Celtics free agent signing No. 14: Troy Murphy
Troy Murphy only played 17 games in Boston, but during that time, the career 39% 3-point shooting big man shot a nearly single-digit percentage from beyond the arc during the 2010-11 season.
Murphy was able to get back on track with the Lakers the following season, driving home how disastrous his Celtics tenure was.
Worst Boston Celtics free agent signing No. 13: Stephon Marbury
Stephon Marbury was a star on the Suns before he was traded to the Knicks. In New York, Marbury took his brand to a new level but his game suffered significantly and arguments with then-Knicks coach Mike D’Antoni led to his buyout in 2009.
Marbury didn’t help the defending champion Celtics get any closer to Banner 18 upon his arrival. The guard had a 34/24/46 shooting split before becoming a legend in China and leaving the NBA altogether the following offseason.
Worst Boston Celtics free agent signing No. 12: Wayne Turner
If you blinked at the start of the 1999-2000 season, you may have missed Wayne Turner’s Celtics stint, which lasted three games and turned out to be the only three games the local product played in during his short-lived NBA career.
Turner was a star heading into his freshman year at Kentucky, but he left Lexington with a resume that didn’t get him drafted. Boston took a chance on him, but got four points on 1/6 shooting during his brief run in Celtics green.
Worst Boston Celtics free agent signing No. 11: Dwayne Schintzius
Dwayne Schintzius was out of the league when he was signed to a deal ahead of the 1998-1999 season, and he looked like someone with significant rust without his famed hockey-style mullet hairdo.
Schintzius played in 16 games and shot 25% at the rim as a seven-footer. Needless to say, the Florida product was out of the league for good after the experiment from the darkness that was the 1990s Celtics.
Worst Boston Celtics free agent signing No. 10: Sly Williams
Sly Williams could’ve had a much more destructive tenure on the dynastic mid-1980s Celtics had he stayed longer than 38 days. As someone who was rarely accountable during his brief stint in Boston, Williams left the team for periods of time without letting his employer know where he went.
Williams was coming off a successful season in Atlanta in 1984-85, so his behavior cost him a spot in the league — as he ended up playing his last NBA games in a Celtics uniform for just six appearances.
Worst Boston Celtics free agent signing No. 9: Tom Gugliotta
Anytime a player averages less than one basket (two points) per game, it’s fair to label that team-player union a failure. Tom Gugliotta was a serviceable second option for much of his career, but by the time he was a Celtic, he had lost many steps.
While he would recover with a more respectable run on the Hawks to end his career, his Boston tenure will go down in infamy.
Worst Boston Celtics free agent signing No. 8: Vincent Poirier
“Mr. Sexy Pants” Vincent Poirier was a great locker room signing, but he did nothing to help the Celtics cure their big man woes during the 2019-20 season. While he was signed at just $2.5 million, the fact that Danny Ainge gave him a multi-year deal will always be a head-scratcher.
Poirier only lasted one more season after leaving the Cs in 2020, and he now plays overseas. While Ainge hit on Daniel Theis two years prior, his 2019 signing of a European big man didn’t pan out as well.
Worst Boston Celtics free agent signing No. 7: Mark Blount
Mark Blount had a great run with the Celtics up until the 2004-05 season, when his game looked less refined and his contributions were less geared towards winning. Some blame the presence of Gary Payton, who had just come out of a toxic situation with the final season of the Kobe Bryant-Shaquille O’Neal tandem.
Whatever it was, Blount didn’t make good on a six-year, $41 million contract that soon became an albatross.
Worst Boston Celtics free agent signing No. 6: Jermaine O’Neal
Before Jermaine O’Neal became a member of the Celtics, he was one of the best big men in the NBA. From his fourth season in the league until his year in Miami in 2009-10, O’Neal was a nightly double-double threat. Even after his time in Boston, O’Neal was a serviceable backup big man.
His two years in a Celtics uniform were by far his worst in his career, though. O’Neal was never a fit with the “big 3” Cs.
Worst Boston Celtics free agent signing No. 5: Stojko Vrankovic
Stojko Vrankovic was the prelude to other European big men like Dirk Nowitzki and Kristaps Porzingis, or rather, could’ve been the first in a long line of successful power forwards and pivots from across the pond.
Instead, he was one one of the reasons many scouts doubted players from Europe until the 2000s and 2010s and opted for established collegiate players instead.
Worst Boston Celtics free agent signing No. 4: Rasheed Wallace
The man they call ‘Sheed’ was a perfect complementary piece to the mid-2000s Pistons, helping Detroit win the 2003-04 championship over Kobe and Shaq’s Lakers after being traded to the Motor City at the 2004 trade deadline.
The Celtics were hoping Wallace would do the same in 2009 when the front office signed him to a three-year deal, but while they played Bryant’s Lakers again, Boston fell in seven games — before Wallace would confront the refs after Game 7 and was kicked off the team.
Worst Boston Celtics free agent signing No. 3: Tristan Thompson
Tristan Thompson was a completely unnecessary signing by Ainge during his final offseason in charge in 2020, and what made bringing on the one-dimensional offensive big man even worse was the insistence by Brad Stevens, in his final season coaching, forcing him into the starting lineup.
Thompson’s well-documented Khloe Kardashian drama doesn’t belong in Boston, as the quick dismissal of Ime Udoka for similar issues showed us all.
Worst Boston Celtics free agent signing No. 2: Pervis Ellison
Pervis Ellison signed a six-year deal in 1994 with the Celtics and missed the entirety of the 1998-99 season and all but six games of the 1996-97 season. Even when Ellison did play, though, he underwhelmed.
Ellison once averaged over 50% shooting from the field, which is a low bar for a big man who primarily got his shot attempts at the rim. All the star power he flashed in Washington D.C. was gone by the time he suited up in Celtics green.
Worst Boston Celtics free agent signing No. 1: Travis Knight
The Rick Pitino era in Boston started off with a major oversight with the signing of one-year veteran Travis Knight to a seven-year contract. In a move that was indicative of the failures of the pre-Danny Ainge years, Knight lasted one season in a Celtics uniform before moving on elsewhere.
Had Knight played well elsewhere and thrived, the deal would’ve looked somewhat explainable. But that he peaked in 1997-98 with 6.5 points per game on 44% shooting made it the most notable misstep in the history of the Celtics franchise.