The Celtics began trade deadline week by sending Anfernee Simons to the Bulls in exchange for Nikola Vučević in a significant move for the short term and potentially setting up long-term flexibility for the franchise as they attempt to return to contention. The move, or any others that happen ahead of 3 p.m. on Thursday, will all face an uphill battle in stacking up with some of the most significant moves in franchise history.
Boston built its championship teams through trades as much as they did in the draft, and certainly more than in free agency, where they didn’t strike on a star in his prime until Al Horford in 2016. The Celtics build the Bill Russell and Larry Bird dynasties through shrewd moves, and returned to championship status in 2008 through a pair of blockbuster deals for Kevin Garnett and Ray Allen. Jayson Tatum and Jaylen Brown’s arrivals to Boston came through picks acquired in the Paul Pierce and Garnett deal with the Nets.
CLNS Media’s Nick Gelso counted down the top trades in Celtics history ahead of Thursday’s deadline and settled on five that stood apart from any others.
The Bill Russell draft trade
- Celtics receive No. 2 overall pick in the 1956 draft (Bill Russell)
- St. Louis Hawks receive Ed MaCauley and Cliff Hagan
The Celtics used their territorial pick in 1956 to select Tommy Heinsohn, and they originally received the 13th overall selection in the draft. Red Auerbach and Celtics owner Walter A. Brown famously angled to prevent the Rochester Royals from selecting Bill Russell by offering guaranteed performances from the Ice Capades. Rochester balked at paying Russell, took Sihugo Green, and the Celtics drafted Russell, pairing him with Heinsohn and K.C. Jones, who they took at 13 as Russell’s teammate from San Francisco. All three made the Basketball Hall-of-Fame and won eight championships together, Russell securing 11 for the franchise while impacting the style of NBA play, solidifying the Celtics’ franchise identity and paving the way for generations of Black players by challenging institutional racism.
Robert Parish and Kevin McHale draft trades
- Celtics receive Robert Parish and the No. 3 overall pick (Kevin McHale)
- Warriors receive the No. 1 (Joe Barry Carroll) and No. 13 (Rickey Brown) overall picks
The Celtics entered the 1980 draft with the top pick despite going 61-21 in the previous season because they dealt Bob McAdoo to Detroit in September, 1979 for two first round picks. One of them became the top pick, which they traded back to No. 3 from and selected Kevin McHale while acquiring Warriors veteran Robert Parish. Parish joined Larry Bird and Cedric Maxwell in the front court and immediately won the 1981 championship with McHale thriving off the bench immediately as a rookie. That core won again in 1984 before McHale moved into the starting lineup in 1986 as part of arguably the greatest team in franchise history. Bird, McHale and Parish played together through 1992, McHale retired in 1993 and Parish departed for Charlotte after 1994. The original Big Three teams went 690-294, won three championships and lost the Finals in 1985 and 1987.
Ray Allen and Kevin Garnett trades
- Celtics receive Kevin Garnett, Ray Allen and No. 35 overall pick (Glen Davis)
- Supersonics receive Delonte West, Wally Szczerbiak and No. 5 overall pick (Jeff Green)
- Timberwolves receive Al Jefferson, Gerald Green, Sebastian Telfair, Ryan Gomes, Theo Ratliff, 2009 first round pick (Wayne Ellington) and Minnesota’s own first (Jonny Flynn)
The Celtics went 24-58 in 2007 through injuries and with Greg Oden and Kevin Durant looming as two generational prospects atop the draft, Boston received poor lottery luck and fell to the No. 5 overall pick. A relatively new ownership group led by Wyc Grousbeck and Steph Pagliuca alongside Danny Ainge pivoted, and traded the pick for Ray Allen to appease Paul Pierce, with his future with Boston growing tenuous across several uneven seasons. The Celtics and Timberwolves also almost pulled off a blockbuster to bring Kevin Garnett to Boston, and revisited talks one month later to secure one of the best players in the NBA and form a new Big Three. Pierce, Allen and Garnett alongside young guard Rajon Rondo and big man Kendrick Perkins won 66 games, an NBA record 42-win turnaround on their way to the championship. They raced to a 27-2 start in 2009 before Garnett fell with a knee injury, returning to the Finals in 2010 and blowing a 3-2 lead to the Lakers. Boston returned to the East Finals in 2012, losing in seven games, before Allen departed for the rival Heat in controversial fashion. Pierce and Garnett reached the playoffs once more in 2013, losing in six games to the Knicks in the first round.
Paul Pierce and Kevin Garnett trade to the Nets
- Celtics receive Gerald Wallace, Kris Humphries, MarShon Brooks, Keith Bogans, Kris Joseph, 2014 (James Young), 2016 (Jaylen Brown), 2017 (Jayson Tatum) and 2018 first round picks
- Nets receive Paul Pierce, Kevin Garnett and Jason Terry.
The Celtics decided to rebuild following the 2013 season, trading Paul Pierce and Kevin Garnett to Brooklyn to appease a franchise hoping to make a splash after their move from New Jersey to New York City. Boston also allowed Doc Rivers to go to the Clippers that offseason, paving the way for Danny Ainge to hire Brad Stevens as head coach. The Nets’ Billy King added extra draft compensation, including a pick swap that became Jayson Tatum in 2017 and a 2018 first the team later used to acquire Kyrie Irving. Boston also drafted Jaylen Brown with the 2016 Nets pick. Brooklyn lost Pierce in free agency to the Wizards after only one season then traded Garnett to Minnesota in 2014-15, falling into a string of losing seasons that vaulted the Celtics back into contention in the East.
Jayson Tatum draft night trade
- Celtics receive No. 3 overall pick (Jayson Tatum) and a 2019 first round pick (Romeo Langford).
- 76ers receive No. 1 overall pick (Markelle Fultz)
The Nets won the 2017 NBA Draft lottery, allowing the Celtics to move up to the No. 1 pick with their swap from the Pierce and Garnett trade. Many speculated that they’d select consensus top prospect Markelle Fultz from Washington, but Ainge focused on Duke’s Jayson Tatum, feeling comfortable about his chances to still select Tatum third overall if they passed up on Fultz. The Celtics, during the week leading up to the draft, traded back to third overall and while the deal itself didn’t return any substantial assets, Ainge’s decision to take Tatum over Fultz, who’s no longer in the NBA after eight seasons, established the core that’d reach the 2022 NBA Finals and win the franchise’s first championship in 2024. Tatum made six straight All-Star teams, four straight All-NBA First Teams and emerged as one of the best players in the NBA and Celtics history before tearing his Achilles during the 2025 playoffs. He’s signed with Boston through at least the 2028-29 season and is expected to return to the floor sometime in 2026 alongside Jaylen Brown, who’s also signed through 2029.
