The New York Knicks have made plenty of unquestionable and even disastrous moves since James Dolan took over as owner. Before he arrived, the Knicks were one of the most successful franchises, but they have since been better known for their dysfunction than their dominance.
They are one of the founding members of the NBA, and the Knicks have played in the finals eight times and won two championships. All of that happened before 2000 when Dolan began running the show.
There have been some downright awful moves since their NBA Finals run in 1999. The Knicks have made the playoffs just eight times since 2000, and only three times in the last decade. Their lack of success has been the result of poor front office management, including multiple blunders with their roster. Here are the ten biggest offseason mistakes in Knicks’ history.
New York Knicks’ 10 biggest offseason blunders
10. Giving big money to declining Joakim
The Knicks were determined to make some win-now moves in the 2016 offseason after three straight years of missing the playoffs. Team President Phil Jackson traded for Derrick Rose and his big free agent splash was signing Joakim Noah.
Noah was a two-time All-Star, who won the Defensive Player of the Year in 2014. This is not a knock on the 6’11 big man, who was fantastic during his time in Chicago, but injuries were starting to catch up to him. Noah missed 15 games in 2014-15 before being limited to just 29 games total in his final season with the Bulls. Despite the injuries and missed time, the Knicks did not even get him on a discount as he inked a four-year, $72 million contract.
Noah played 53 games in New York over the next two seasons before being waived in 2018. The two-time All-Star played just 100 games over the next four years total, and he retired in 2020 after just five games with the Clippers.
The Knicks paid $72 million for just over 53 games, which was disastrous and part of the reason why New York failed to make the playoffs in each of those four years.
9. Drafting Jordan Hill over DeRozan and Holiday in 2009
Dissecting the Knicks’ draft blunders is a whole article of it is own, but some of their misses seemed massive and franchise-altering. New York had just missed the playoffs for the fifth straight year in 2009 when the organization selected eighth overall. The Knicks had David Lee, Al Harrington, Wilson Chandler, and Danilo Gallinari, but they desperately needed guard help.
Instead, New York selected Jordan Hill, a 6’10 big man that lasted just 24 games with the Knicks. New York acquired Tracy McGrady and Sergio Rodriguez in the deal in Feb. 2010, but T-Mac was on the decline. He too lasted just 24 games with the Knicks. Hill spent eight years in the NBA as primarily a backup center.
There were a ton of talented guards in the 2009 draft class, including DeMar DeRozan. The six-time All-Star has scored over 20 points per game for a decade straight, and he will go down as one of the best scorers of his generation.
Jrue Holiday, one of the NBA’s best perimeter defenders was picked 17th in 2009. Brandon Jennings, Ty Lawson, Jeff Teague, and Darren Collison were all quality starting point guards for stretches that the Knicks could have drafted over Jordan Hill.
The Knicks made a massive blunder drafting Jordan Hill over the talented guards in this class, but it was not their biggest draft mistake.
8. Failing to land a star in 2019
The Knicks had enough cap space to sign two max contract players in the summer of 2019 with a bit of maneuver, and New York believed it was serious in a loaded class that featured Kevin Durant, Kawhi Leonard, Kyrie Irving, Jimmy Butler, and Kemba Walker. Their front office thought the changed culture and top-three draft pick would help sway a big name to the Big Apple.
Instead, Durant and Kyrie teamed up in Brooklyn where they selected a young Nets roster that just reached the playoffs without a superstar over the Knicks. Kawhi went home to LA to team up with Paul George on the Clippers. Jimmy Buckets was sent to Miami in a sign-and-trade, and Kemba Walker replaced Irving as the Celtics’ starting point guard.
It left the Knicks shopping in the second tier of free agents, and their massive cap space turned into Julius Randle and overpaying for role players. New York signed Bobby Portis, Taj Gibson, Wayne Ellington, Elfrid Payton, Marcus Morris, and Reggie Bullock to round out their roster, and the ultimate result was the Knicks missing the playoffs for the seventh consecutive year.
The New York Knicks again had a prime opportunity to remake their franchise, and they walked away with a slew of role players on short-term deals and Julius Randle, who has transformed into a two-time All-Star in the Big Apple. It was not the worst haul but did not result in postseason success either.
7. Drafting Frank Ntilikina over Donovan Mitchell in 2017
Kristaps Porzingis was fresh off a breakout second season with the Knicks, but New York missed the playoffs for the fourth straight year. With Derrick Rose set to depart in free agency and the Knicks looking to trade Carmelo Anthony, New York desperately needed a guard that could make plays and create shots. They had the eighth overall pick in a draft that featured five point guards that were projected to go in the top ten.
Markelle Fultz and Lonzo Ball were the top two selections over Jayson Tatum. The Kings took De’Aaron Fox fifth, which left the Knicks choosing between Frank Ntilikina and Dennis Smith Jr., who ended up in New York by 2019, but neither was the correct choice. Donovan Mitchell was the superstar guard of this class, and he slipped to 13th on draft night.
After six seasons, Mitchell is a four-time All-Star who has helped his team reach the playoffs six times. Ntilikina never averaged more than 21.9 minutes per game in his four years with the Knicks, and New York let him walk in free agency in 2021, despite being able to restrict him.
To make matters worse, Mitchell is a New York kid, who would have been coming home to play for the Knicks. He has talked about his desire to play (subscription required) for the franchise, and they again had a chance to acquire him in 2022 but passed on the opportunity.
6. Making Phil Jackson president
The Knicks technically made Phil Jackson their team president in March of 2014 while the regular season was still going on, but that is how the executive offseason works in some ways. Teams have to be preparing for the draft, free agency, and trade discussions with almost no way to improve their current rosters until the season wraps.
Jackson’s five-year deal worth $60 million to run the franchise was a disaster and his tenure only lasted three years. Nearly every move made during that span blew up in the executive’s face.
From hiring Derek Fisher as head coach with zero experience to trading away most of the roster from their 54-win team in 2013, not much worked for Jackson. He wanted his team to run the triangle offense, but coaches and players were not on board. Jackson kept bringing in former players from his days with the Lakers, but none of them worked out. It was poor decision after poor decision by one of the greatest coaches in NBA history.
The Knicks won just 80 games in Jackson’s three years as team president, and there was dysfunction everywhere. The legend did draft Kristaps Porzingis, but he was also responsible for taking Frank Ntilikina over Donovan Mitchell in his final move in charge of the franchise.
Phil Jackson’s Knicks were one of the worst franchises in the league, but he was not the worst lead executive in New York’s history.
5. Isiah Thomas signs Jerome James to a 5-year deal worth $30 million
Isiah Thomas was a Hall of Fame point guard and one of the 75 greatest players in NBA history, but during his tenure running the Knicks, he was known for his terrible basketball decisions (subscription required) and an awful harassment lawsuit that found Thomas liable for being part of the toxic environment. New York had the league’s highest payroll during his five years in charge but made the playoffs just once and won just 151 games.
Thomas is responsible for some of the biggest blunders in franchise history, and his hiring as president of basketball operations may have landed him number one on this list if it was done during the offseason. The Knicks were 28 games into the regular season in 2003-04 when Zeke was brought on board.
Thomas was 18 months into his tenure when he signed Jerome James to a five-year deal for the mid-level exception. The problem was the seven-foot big man had averaged 4.9 points, 3.5 rebounds, and 1.3 blocks in 15.2 minutes per game to that point in his career. James had a monster playoff series to help the Sonics defeat the Kings in 2005, and that was enough for Thomas to hand out a massive contract.
James was already 30 years old, and he played a total of 90 games over the five-year deal. The seven-footer averaged 7.7 minutes per game over those contests in what turned out to be one of the worst free-agent signings in franchise history.
4. Larry Brown’s disastrous season with the Knicks
After Zeke’s first season in charge of the team, the Knicks hired Larry Brown to be their head coach. The 65-year-old had won the Eastern Conference in three of the last five years, including leading the Pistons to the championship in 2004 when they upset Kobe and Shaq’s Lakers in the finals. Brown was flirting with other jobs after 2005, so the Pistons let him walk.
He signed a massive deal to be the head coach of the Knicks that was set to pay him over $50 million over the next five years. New York was coming off a 33-win season, but they believed Brown could help them return to the playoffs and make a run.
The result was utter turmoil. The Knicks finished with just 23 wins and the second-worst record in the NBA. Brown feuded with players, including Knicks starting point guard Stephon Marbury, and the team was a disaster. The veteran head coach was fired after just one season in New York, and things got so bad that the Knicks tried to withhold the remaining money left on his contract.
Ultimately, Larry Brown got an $18.5 million settlement on top of the $10 million he received for his disastrous season in the Big Apple. He has the second-worst winning percentage of a head coach in Knicks history, and the entire situation turned into a disaster.
3. Trade for Antonio McDyess
The Knicks had a streak of 14 straight years in the playoffs snapped in 2002 after head coach Jeff Van Gundy resigned midseason. The second-winningest coach in franchise history was gone and the team quickly slipped into turmoil. They won just 20 of their final 63 games to finish with the seventh-worst record in the NBA.
On draft night, the Knicks tried to stay in contention by trading the seventh overall pick Marcus Camby and Mark Jackson for Antonio McDyess, Frank Williams, and a 2003 second-round pick. It was a massive gamble as McDyess was recovering from a ruptured patellar tendon that limited him to just ten games in the 2001-02 season. He was an All-Star in 2001, but it was not like the Knicks were buying him at a discount, despite the injury.
McDyess played in the preseason where he re-injured his knee and the subsequent surgery forced him to miss the entire 2002-03 season. He played just 18 games the following season but was not the same player before being traded to the Suns in a deal that brought back Stephon Marbury.
The New York Knicks gave up a prime center that won Defensive Player of the Year in Denver, the seventh overall draft pick, and a veteran point guard for 18 games of McDyess, Williams (who played just 77 games with the Knicks), and one second-round pick. It was a disastrous trade that will go down as one of the worst in team history.
2. Missing out on LeBron, D-Wade, and Bosh in 2010
This blunder could be far and away number one on this list or not even in the top ten, depending on what you believe the Knicks’ actual chances of landing LeBron James, Dwyane Wade, and Chris Bosh were in the summer of 2010.
The facts were the Knicks had about $34 million in cap space that summer, and could have cleared enough to sign two max free agents. They had a meeting with LeBron, who ultimately decided to team with D-Wade in Miami with Chris Bosh on the Heat. Miami made the NBA Finals four straight years, including winning two championships.
Bill Simmons made it clear on his podcast that the Knicks were LeBron’s top choice in free agency that summer, but his meeting with the team was an absolute disaster. For fans that do not want to listen to the podcast, Bleacher Report’s Tyler Conway covered excerpts from it here.
New York could have acquired all three players in 2010. A sign-and-trade would have been required to land the third, but the franchise had some young and intriguing assets to deal away at the time.
The Knicks would have been favored to win the Eastern Conference had they landed LeBron and company with King James likely delivering at least one if not multiple championships to New York. Blame James Dolan if you wish, but this is a massive blunder if LeBron truly had the Knicks as his top destination.
1. Trading for Eddy Curry
The worst move by president of basketball operations Isiah Thomas and one of the worst in NBA history was acquiring Eddy Curry via a sign-and-trade in October of 2005. New York gave up a first-round pick, a first-round pick swap, two second-round picks, and three veterans to land Curry and Antonio Davis. It was the picks and the massive six-year contract worth $60 that the seven-footer signed that made this trade an absolute disaster.
Curry had three productive statistical seasons in New York, but the team won just 79 games over that stretch.
They gave up the number two pick in 2006 because of the trade, and LaMarcus Aldridge was selected. The Knicks would have loved to have LMA in New York over Curry, who was so bad over the final three years of the deal that he played a total of ten games. Personal life issues got in the way, but the trade impacted the franchise for years after Curry was gone.
The Bulls also got Joakim Noah out of the pick swap in 2007, who was quickly better than Curry. This trade was an absolute disaster that caused the Knicks to miss the playoffs for five straight years.
The New York Knicks have done well acquiring assets and they are primed to acquire the next star that hits the market, and it could come as soon as this offseason. Will it go down as another front-office blunder or a franchise-altering move that gets the franchise back into contention? Stay tuned to find out.
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