While there have been plenty of lopsided deals made throughout the NBA over the years, every once in awhile a mutually beneficial trade takes place where front offices of different organizations can claim what is referred to as a "win-win."
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3.) Charles Oakley to the Knicks / Bill Cartwright to the Bulls (1988)
In 1988, the Bulls and Knicks made a blockbuster trade that sent center Charles Oakley to New York and Bill Cartwright to Chicago. Notably, this trade was made in order to fit specific team needs, as Oakley's toughness and Cartwright's offensive versatility contributed to success for each organization.
- Chicago Bulls: Cartwright playing alongside Michael Jordan and Scottie Pippen led to three straight championships for the Bulls (1991-1993).
- New York Knicks: Oakley's rebounding prowess and no-nonsense attitude fit right into the Knicks' identity in the 90s, as he was a key player in helping New York become perennial playoff contenders each season, while reaching the NBA Finals in 1994.
2.) Shaquille O'Neal to the Heat / Lamar Odom, Caron Butler, and Picks to the Lakers (2004)
The LA Lakers dynasty was broken up in 2004 as Shaquille O'Neal left Kobe in Los Angeles after being traded to the Miami Heat in exchange for Lamar Odom, Caron Butler, Brian Grant, and draft picks. In view of how this turned out for both franchises, it's safe to say each team found success with their new players.
- Miami Heat: In 2006, Shaq along with Dwyane Wade led the Heat to their first NBA championship, which was the Big Diesel's fourth championship of his career.
- Los Angeles Lakers: Odom played a key role in the Lakers frontcourt, as he later was paired with Pau Gasol and Andrew Bynum. The Lakers utilized the assets from the trade to build a championship squad around Kobe, who won back-to-back Finals in 2009 and 2010.
1.) Karl-Anthony Towns to the Knicks / Julius Randle and Donte DiVincenzo to the Timberwolves (2024)
During the summer of 2024, the New York Knicks shocked the NBA world when they traded for All-Star center Karl-Anthony Towns, while sending Julius Randle and Donte DiVincenzo to the Minnesota Timberwolves. And now with both teams reaching the 2025 Conference Finals, it's safe to say this turned out to be advantageous for each franchise.
- New York Knicks: Towns averaged 24.4 points and 12.8 rebounds per game this season. Being paired with Jalen Brunson and Josh Hart has led to a new-look Knicks squad that defeated the defending champion Boston Celtics, now reaching the Eastern Conference Finals for the first time in 25 years. That is, New York is vying for their first NBA Finals win since 1973.
- Minnesota Timberwolves: After giving up Towns, their No. 1 overall pick from the 2015 NBA Draft, the Timberwolves gained cap space ($220 million) and draft stock. Overall, Randle and DiVincenzo have fit well with their new team, helping Minnesota reach the Western Conference Finals for the second year in a row.
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