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Home > NBA Trade Rumors > Toronto Raptors Trade Rumors > 10 Most Heartbreaking Trades In NBA History

10 Most Heartbreaking Trades In NBA History

The NBA has seen some heartbreaking trades, including the departures of Derrick Rose from the Chicago Bulls, Russell Westbrook from the Oklahoma City Thunder, and Kevin Garnett from the Minnesota Timberwolves.

Fran Leiva
Apr 6, 2024
21 Min Read
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Credit: Fadeaway World

In the NBA, trades are often the catalysts for both excitement and heartbreak, shaping the fortunes of players and franchises alike. From iconic stars bidding farewell to their longtime teams to franchises making tough decisions for their future, each trade tells a story of its own. 

Contents
  • 1. The Derrick Rose Trade Away From Chicago
  • 2. Russell Westbrook’s Goodbye To The Thunder
  • 3. Kevin Garnett’s Sad Move To Boston
  • 4. Toronto Trading DeMar DeRozan To San Antonio
  • 5. Hakeem Olajuwon Sign-And-Trade To The Raptors
  • 6. An Abrupt End For Vince Carter In Toronto
  • 7. The Pau Gasol Trade To Chicago By The Lakers
  • 8. Isaiah Thomas’ End For The Boston Celtics
  • 9. Jrue Holiday Moved For Damian Lillard
  • 10. Memphis’ Farewell To Marc Gasol

Join us as we explore some of the NBA’s most emotional trades, diving into the highs and lows of player movements that have left lasting impressions on the league’s history and the hearts of fans.


1. The Derrick Rose Trade Away From Chicago

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The Derrick Rose trade away from the Chicago Bulls sent shockwaves through the NBA community, marking the end of an era for the Bulls and a significant shift in the league landscape. Rose, a former NBA MVP, had been the cornerstone of the Bulls franchise and a beloved figure in Chicago.

On June 22, 2016, the Bulls traded Rose, along with Justin Holiday and a 2017 second-round draft pick, to the New York Knicks. In exchange, the Bulls received Robin Lopez, Jerian Grant, and José Calderón.

Rose’s departure from the Bulls was primarily due to his ongoing struggles with injuries, particularly knee injuries, which had hampered his performance in recent years. Despite these challenges, Rose had left an indelible mark on the Bulls franchise.

During his time in Chicago, Rose posted impressive statistics, including averaging 19.7 points per game, 6.2 assists per game, and 3.7 rebounds per game. He earned the NBA MVP award in 2011, becoming the youngest player in league history to receive the honor at the age of 22. Additionally, Rose was named to multiple All-Star teams and garnered All-NBA honors.

The trade away from Chicago was devastating for Bulls fans, as it signaled the end of an era and the departure of a player who had brought hope and excitement to the franchise. Despite the disappointment, Rose’s legacy in Chicago remains intact, defined by his electrifying playing style, remarkable talent, and resilience in the face of adversity.

In New York, Rose continued to showcase flashes of his brilliance, but injuries continued to plague his career trajectory. Nevertheless, his impact on the Bulls and the NBA as a whole is undeniable, and he will always be remembered as one of the most dynamic players to ever don a Bulls jersey.


2. Russell Westbrook’s Goodbye To The Thunder

Russell Westbrook Oklahoma City Thunder 2018

Russell Westbrook’s departure from the Oklahoma City Thunder marked the end of an era for both the franchise and its fans. Westbrook, known for his electrifying playing style and unwavering competitiveness, had become synonymous with the Thunder and was beloved by fans across the league.

Westbrook was traded from the Thunder to the Houston Rockets on July 11, 2019, in exchange for Chris Paul, two future first-round draft picks, and the rights to swap draft picks in two additional years. This move came shortly after the Thunder traded Paul George to the Los Angeles Clippers, signaling a significant shift in the team’s direction.

During his time with the Thunder, Westbrook posted impressive statistics and earned numerous accolades. He averaged a triple-double for three consecutive seasons, becoming the first player in NBA history to achieve such a feat. Westbrook’s unparalleled athleticism, relentless drive, and passion for the game made him a force to be reckoned with on the court.

Westbrook’s departure from the Thunder marked the end of an era of competitiveness for the franchise. He had been the cornerstone of the team since the departure of Kevin Durant in 2016 and had led the Thunder to multiple playoff appearances during his tenure.

Despite Westbrook’s departure, his impact on the Thunder and its fans will not be forgotten. He was not only a superstar on the court but also a beloved figure in the community, known for his charitable work and dedication to the city of Oklahoma City.

The trade of Westbrook to the Rockets marked the end of a chapter in Thunder history but also signaled a new beginning for both Westbrook and the franchise. While his departure was bittersweet for fans, Westbrook’s legacy as one of the greatest players in Thunder history will endure for years to come.


3. Kevin Garnett’s Sad Move To Boston

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The trade of Kevin Garnett from Minnesota to Boston took place in July, 2007. In this exchange, the Boston Celtics acquired Garnett, while the Minnesota Timberwolves received Al Jefferson, Ryan Gomes, Sebastian Telfair, Gerald Green, Theo Ratliff, and two future draft picks.

This trade significantly impacted the Timberwolves as they lost their star player and team leader. With Garnett’s departure, the Timberwolves lost their competitiveness and struggled to find a new on-court leader. The franchise found itself in an extended rebuilding period, fighting to return to the NBA playoffs.

The surprise of this trade lay in its sudden timing, as Garnett had been with the Timberwolves for 12 seasons and had been the face of the franchise. His departure left fans feeling shocked and saddened.

During his time in Minnesota, Garnett accumulated numerous achievements and impressive statistics. He was selected to the All-Star Game multiple times, won the NBA Most Valuable Player Award in the 2003-2004 season, and led the Timberwolves to eight consecutive playoff appearances, including an appearance in the Western Conference Finals in 2004. Additionally, Garnett was named to the All-NBA First Team several times and won the Defensive Player of the Year Award in 2008 with the Celtics. His legacy in Minnesota remains prominent, but his departure left a void that the franchise has struggled to fill ever since.


4. Toronto Trading DeMar DeRozan To San Antonio

DeMar DeRozan

In a move that caught many NBA fans off guard, DeMar DeRozan was traded from the Toronto Raptors to the San Antonio Spurs, marking the end of an era for both DeRozan and the Raptors organization. The trade, which took place on July 18, 2018, was part of a larger deal that involved Kawhi Leonard joining the Raptors.

During his tenure with the Raptors, DeRozan compiled impressive statistics and earned numerous accolades. He averaged 19.7 points, 4.1 rebounds, and 3.1 assists per game. DeRozan’s scoring prowess and ability to create offense made him a key player for the Raptors, and he became the team’s all-time leading scorer.

The trade saw DeRozan, along with Jakob Poeltl, and a protected 2019 first-round draft pick, being sent to the Spurs in exchange for Leonard and Danny Green. This move came as a surprise to many, as DeRozan had become synonymous with the Raptors franchise and had repeatedly expressed his desire to remain in Toronto.

DeRozan’s departure from the Raptors left fans feeling blindsided and disappointed, given his deep ties to the organization and his contributions to the team’s success. His loyalty and dedication to the Raptors endeared him to fans and solidified his place in franchise history.

Despite the unexpected nature of the trade, DeRozan’s impact on the Raptors franchise will not be forgotten. He played a pivotal role in elevating the team to new heights and helped lay the foundation for future success. While his time in Toronto may have come to an end, DeRozan’s legacy as one of the greatest players in Raptors history will endure.


5. Hakeem Olajuwon Sign-And-Trade To The Raptors

Kyrie Irving Calls For Hakeem Olajuwon To Be Recognized And Respected: "Giving People 40 While Fasting"

Hakeem Olajuwon’s significance in Houston was monumental, shaping the Rockets into a championship-winning franchise during his tenure. His statistics reflect his dominance, averaging 22.5 points, 11.4 rebounds, and 3.2 blocks per game throughout his illustrious career.

Olajuwon’s impact extended beyond numbers, earning him numerous accolades, including multiple All-Star selections, All-NBA Team honors, and NBA Defensive Player of the Year awards. He led the Rockets to back-to-back NBA championships in 1994 and 1995, earning NBA Finals MVP honors both times.

The sign-and-trade deal that sent Hakeem Olajuwon to the Toronto Raptors occurred in August 2001. Olajuwon opted to join the Raptors after they offered him a more lucrative contract worth $18 million, compared to the $13 million offered by the Rockets.

While his time in Toronto was relatively short-lived, Olajuwon’s impact on the franchise and the city was significant. He provided veteran leadership and mentorship to younger players, leaving a lasting legacy both on and off the court. His decision to leave Houston for Toronto marked the end of an era for the Rockets and represented a pivotal moment in NBA history.


6. An Abrupt End For Vince Carter In Toronto

Raptors Planning To Retire Vince Carter's Jersey On April 9th

The trade of Vince Carter from the Toronto Raptors to the New Jersey Nets was a pivotal moment in both the Raptors’ franchise history and Carter’s career. The move occurred on December 17, 2004, after Carter had spent six seasons with the Raptors.

Carter’s trade to the Nets stemmed from various factors, including tensions between Carter and the Raptors’ management, as well as Carter’s desire for a fresh start elsewhere. In the trade, the Raptors sent Carter and cash considerations to the Nets in exchange for Alonzo Mourning, Eric Williams, Aaron Williams, and two first-round draft picks.

During his time with the Raptors, Vince Carter left an indelible mark on the franchise and the NBA as a whole. Known for his electrifying athleticism and highlight-reel dunks, Carter became one of the most thrilling players to watch in the league. He averaged 23.4 points, 5.2 rebounds, and 3.9 assists per game during his tenure with the Raptors.

Carter’s departure left a void in the hearts of Raptors fans, who had seen him as a superstar embodying the hope and future of the team. While his exit disappointed many fans, it also marked the beginning of a new era for the Raptors, who subsequently rebuilt the team and found success in later seasons.

Vince Carter’s career continued after leaving the Raptors, but his time in Toronto remains a significant part of his legacy in the NBA and in Raptors history. His influence on basketball culture in Canada and his impact on the Raptors franchise endure to this day.


7. The Pau Gasol Trade To Chicago By The Lakers

Pau Gasol

The trade of Pau Gasol from the Los Angeles Lakers to the Chicago Bulls on July 14, 2014, marked a significant moment in NBA history and in the careers of all players involved. Gasol’s tenure with the Lakers was illustrious, characterized by his exceptional skillset and contributions to the team’s success.

Gasol’s statistics with the Lakers included averaging 17.7 points, 9.9 rebounds, and 3.5 assists per game. He earned multiple All-Star selections and played a pivotal role in helping the Lakers win back-to-back NBA championships in 2009 and 2010.

The decision to trade Gasol away from the Lakers was multifaceted, influenced by both basketball and financial considerations. Gasol’s departure signaled the end of an era for the Lakers, as they embarked on a rebuilding phase. The trade to the Bulls represented a strategic move for both teams, with the Lakers seeking to acquire assets for their rebuild and the Bulls aiming to bolster their roster with Gasol’s veteran presence and skillset.

The details of the trade saw Gasol being traded to the Bulls in exchange for multiple players and draft picks. The Lakers received the draft rights to Andrew Bynum, as well as future draft considerations. Gasol’s departure from the Lakers marked a significant change for the franchise, leading to a period of rebuilding and transition.

Gasol’s move to Chicago represented a new chapter in his career, as he joined a talented Bulls team with aspirations of contending in the Eastern Conference. While his time with the Bulls did not yield a championship, Gasol’s contributions were invaluable to the team’s success on the court, and his impact was felt both on and off the court.


8. Isaiah Thomas’ End For The Boston Celtics

Isaiah Thomas

The trade of Isaiah Thomas away from the Boston Celtics was surprising due to his impact on the team and his remarkable statistics during his time in Boston. Thomas, a dynamic point guard, quickly became a fan favorite and a key leader for the Celtics. Despite his shorter stature, Thomas consistently delivered clutch performances and earned the respect of both his teammates and fans.

During his tenure in Boston, Thomas posted impressive statistics, including averaging 24.7 points per game, 6.0 assists per game, and boasting a three-point shooting percentage of 37.5%. Additionally, he had a remarkable free throw shooting percentage of 89.3%. Thomas was also selected to the NBA All-Star Game twice and earned All-NBA honors, including being named to the All-NBA Second Team for the 2016-2017 season.

The trade involving Isaiah Thomas occurred on August 22, 2017, when the Celtics traded him, along with Jae Crowder, Ante Žižić, and a future draft pick, to the Cleveland Cavaliers in exchange for Kyrie Irving. This move surprised many Celtics fans, as Thomas had become a beloved figure in Boston and had played a crucial role in the team’s success.

Following his departure from the Celtics, Thomas struggled to replicate his previous success due to persistent hip injuries that affected his performance. He moved to several teams in the following years, never quite regaining the form he displayed during his time in Boston.

Despite leaving the team, Thomas remains a fan favorite in Boston, fondly remembered for his memorable performances and his role in helping to bring the Celtics back to prominence.


9. Jrue Holiday Moved For Damian Lillard

Jrue Holiday

In the 2023-24 offseason, the Milwaukee Bucks stunned fans by trading away one of their most beloved players, Jrue Holiday, for Damian Lillard from the Portland Trail Blazers without warning. This move devastated Bucks fans and even Giannis Antetokounmpo himself, as Holiday had been a key component of the team’s NBA championship run in the 2020-21 season.

During his time with the Bucks, Jrue Holiday left an indelible mark on the franchise. He proved to be a leader on both ends of the court, showcasing his ability to score, distribute the ball, and defend the toughest opponents. His statistics with the Bucks included averaging 19.6 points, 6.1 assists, and 4.6 rebounds per game, highlighting his versatility and contributions across multiple facets of the game.

In addition to his impressive stats, Holiday was instrumental in the Bucks’ championship victory in 2021, playing a pivotal role in the playoff series with standout performances at crucial moments.

The trade of Holiday for Lillard left a void in the hearts of Bucks fans, but it also represented a new beginning with the arrival of a talent like Lillard. While fans mourned the loss of Holiday, they looked to the future with optimism, hoping that Lillard could lead the team to new heights in the seasons to come.


10. Memphis’ Farewell To Marc Gasol

Marc Gasol

The departure of Marc Gasol from the Memphis Grizzlies marked a significant moment in the franchise’s history and in Gasol’s esteemed career. Gasol’s tenure in Memphis was defined by his exceptional skillset, leadership, and contributions both on and off the court.

During his time with the Grizzlies, Gasol showcased his versatility and impact, averaging 14.9 points, 7.6 rebounds, and 3.4 assists per game

. His statistical prowess, coupled with his defensive prowess and basketball IQ, solidified his status as one of the premier centers in the league.

On February 7, 2019, Gasol bid farewell to Memphis as he was traded to the Toronto Raptors. The trade marked the end of an era for the Grizzlies and signaled a new chapter in Gasol’s career. Despite leaving Memphis, Gasol’s legacy as a Grizzlies legend remained intact, with his impact on the franchise and the city transcending his on-court achievements.

Gasol’s move to Toronto proved to be a pivotal one, as he played a vital role in helping the Raptors capture their first NBA championship in 2019. His veteran leadership, defensive prowess, and basketball IQ were instrumental in the team’s playoff success, further solidifying his status as a beloved figure in Toronto.

While Gasol’s departure came before the Grizzlies’ acquisition of Ja Morant and their subsequent rebuilding efforts, his influence on the team’s culture and identity was profound. Gasol’s contributions to the Grizzlies will always be remembered fondly by fans, and he will forever hold a special place in the history of the franchise.

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TAGGED:Chicago Bulls ArchiveDeMar DerozanDerrick RoseKevin GarnettMinnesota Timberwolves ArchiveOklahoma City Thunder ArchiveRussell WestbrookToronto Raptors Archive
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ByFran Leiva
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Francisco Leiva is a staff writer for Fadeaway World from Buenos Aires, Argentina. He is a recent graduate of the University of Buenos Aires and in 2023 joined the Fadeaway World team. Previously a writer for Basquetplus, Fran has dedicated years to covering Argentina's local basketball leagues and the larger South American basketball scene, focusing on international tournaments.Fran's deep connection to basketball began in the early 2000s, inspired by the prowess of the San Antonio Spurs' big three: Tim Duncan, Tony Parker, and fellow Argentinian, Manu Ginóbili. His years spent obsessing over the Spurs have led to deep insights that make his articles stand out amongst others in the industry. Fran has a profound respect for the Spurs' fanbase, praising their class and patience, especially during tougher times for the team. He finds them less toxic compared to other fanbases of great franchises like the Warriors or Lakers, who can be quite annoying on social media.An avid fan of Luka Doncic since his debut with Real Madrid, Fran dreams of interviewing the star player. He believes Luka has the potential to become the greatest of all time (GOAT) with the right supporting cast. Fran's experience and drive to provide detailed reporting give Fadeaway World a unique perspective, offering expert knowledge and regional insights to our content.
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