The New York Knicks haven’t been on the “winning” side of too many trades (or basketball games, for that matter) in the franchise’s history. However, displays of organizational ineptitude have been more frequent in the James Dolan era (beginning in 1997), and particularly in the 21st century.

Now, with a revamped front office led by Leon Rose — whose only major move thus far has been hiring Tom Thibodeau— and a cabinet of assets with debatable degrees of value, the Knicks will be looking to deal in the months ahead.

Hopefully, for Rose and Knicks fans, any major transactions will end up on an updated version of this list. For now, though here are the five best trades in Knicks history.

5) 2011: Knicks Acquire Carmelo Anthony 

February 21st, 2011, marks the last time the Knicks acquired a superstar in his prime. New York had built an intriguing young roster around recently signed $100-million man Amare Stoudemire, but injury concerns threatened his long-term reliability as a franchise centerpiece. Plus, as it turns out, those young players didn’t exactly take over the league.

Anthony, ready to depart the Denver Nuggets, brokered a trade to New York months before he was set to hit free agency—costing the Knicks a package of Wilson Chandler, Danilo Gallinari, Raymond Felton, Timofey Mozgov, a 2014 first-round pick, and 2016 pick swap rights. (Chauncey Billups also went to New York; he was amnestied before 2011-12.)

Anthony’s insistence on being traded rather than signing outright (the Knicks had cap space)—and the acrimonious ending to Carmelo’s tenure—detracts from the trade. But, anecdotally, I’m confident that the vast majority of Knicks fans (myself included) would happily make the deal again, rather than (retroactively) see Anthony go elsewhere.

Anthony quarterbacked the most exciting Knicks team of the century in 2012-13, winning the scoring title (28.7 PPG) and powering an entertaining bunch to a 54-28 record—finishing third in the MVP voting. The Knicks made the playoffs each of his first three seasons in town—an era that is now profoundly cherished by New Yorkers.

Overall, Anthony averaged 24.7 points per game and made seven All-Star games in orange-and-blue. His #7 will hang in the Madison Square Garden rafters one day.

4) 1999: Knicks Acquire Latrell Sprewell

Just before the strike-shortened ’99 season began in January, the Knicks surprised the NBA by acquiring the talented but controversial Sprewell from the Golden State Warriors. 36-year-old Terry Cummings, solid bench guy Chris Mills and the beloved yet declining John Starks headed West.

Sprewell had made an All-NBA First Team in Golden State in 1994 but hadn’t played in a game since being suspended for 68-games in 1997 for choking Warriors head coach P.J. Carlesimo.

But, he provided the exact injection of energy Jeff Van Gundy’s plodding team needed. Sprewell quickly became a fan-favorite and, more importantly, a crucial spark on both ends of the floor. He would lead the Knicks in scoring during their Cinderella run to the ’99 Finals, primarily as a sixth man.

Sprewell played four more seasons in New York, averaging 17.9 points per game, including a selection to the 2001 All-Star Game.

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3) 1988: Knicks Acquire Charles Oakley

After the 1987-88 season, New York traded quality center Bill Cartwright to the Chicago Bulls for a 24-year old Charles Oakley. Oakley was three seasons into his career but had already established himself as one of the game’s premier rebounders. Cartwright had given the Knicks nearly a decade of productive basketball (16.8 PPG) after being drafted 3rd overall in 1979, but he became expendable after the 1985 draft lottery.

Oakley, of course, would become the face, heart, and soul of the bruising Knicks teams of the 1990s. He averaged 10.4 points and 10.0 rebounds per game in New York, and the team made the playoffs each of his 10 seasons. Oakley made his lone All-Star team in 1994 on his way to helping the Knicks reach the NBA Finals.

Cartwright won three rings in Chicago, but this trade began the souring of the relationship between Oakley’s good friend, Michael Jordan, and Bulls GM Jerry Krause.

New York Knicks best trades in Knicks franchise history


2) 1968: Knicks Acquire Dave DeBusschere

The Knicks were ascending into contenders during the late 1960s, and DeBusschere was the final piece of the puzzle. Midway through the 1967-68 season, the Knicks traded prolific center Walt Bellamy (18.9 PPG, 13.3 RPG as a Knick) and Howard Komives to the Detroit Pistons for DeBusschere—a high-character, high IQ forward with elite defensive and rebounding skills.

DeBusschere—a member of the NBA’s 50 Greatest Players—played in five All-Star games in New York and helped deliver titles in 1969-70 and 1972-1973. He averaged 16 points and 10.7 rebounds in his Knicks tenure. 

1) 1971: Knicks Acquire Earl Monroe

The Knicks already had a Hall of Fame guard who was just as smooth and stylish off the court as he was on it in Walt “Clyde” Frazier. Nevertheless, they traded for playground legend and Baltimore Bullets All-Star Earl “The Pearl” Monroe in November of ’71. Miraculously, they only had to surrender bit players Mike Riordan and Dave Stallworth to satisfy Baltimore (therefore earning the top spot on these rankings.)

Frazier and Monroe formed the “Rolls Royce Backcourt”, driving the Knicks to consecutive Finals appearances, culminating in the 1973 championship. In nine New York seasons, The Pearl averaged 16.2 points per game and made two All-Star teams.