The 2020 trade deadline is rapidly approaching. And as the scuttlebutt around the NBA reaches a fever pitch, there is a possibility that the Knicks will be involved in a trade at the deadline.

The Knicks have made 15 deadline deals total, dating back to 1989. Here are the five biggest trade deadline deals in the franchise's history.

1) 2001: Chris Childs and a 2002 first round draft pick (Kareem Rush) to the Toronto Raptors for Mark Jackson and Muggsy Bogues

A mini soap opera developed in Madison Square Garden after the Knicks reunited with point guard Mark Jackson. A 2001 trade deadline deal saw the Knicks add Jackson and Muggsy Bogues from Toronto for backup point guard Chris Childs and a future first round pick.

In his first game against his former team, Childs stared at the Knicks bench every time he scored in a Raptors win on national television. The incident and some additional trash talk led to raucous boos for Childs in his first game back at MSG.

Childs would have the last laugh. The Knicks and Raptors met in the first round of the 2001 playoffs. Despite having home court advantage in the fifth and final game of the series, the Knicks fell short, losing at MSG, 93-89. Looking for payback, Childs came alive in the final two games of the series, scoring 35 points and knocking down six threes.

Since 2001, the team has qualified for the postseason just four out of the past 18 seasons. 35 years old at the time of the trade, Jackson was near the end of his career. He lasted one more season as the team's starting point guard before the Knicks dealt him, Marcus Camby and the draft rights to Nenê to the Denver Nuggets for Antonio McDyess.

2) 2010: In a three-team trade, Jordan Hill, Jared Jeffries and a 2012 first round draft pick (Royce White) were traded to the Houston Rockets for Tracy McGrady; the Rockets traded Joey Dorsey and Carl Landry to the Sacramento Kings; the Knicks traded Larry Hughes to the Kings; the Kings traded Hilton Armstrong and Kevin Martin to the Rockets; and the Kings traded Sergio Rodríguez to the Knicks.

Nate Robinson and Marcus Landry were traded to the Boston Celtics for J.R. Giddens, Eddie House, Henry Walker and a 2014 top-55 protected second round draft pick

When Donnie Walsh took over as president of basketball operations for the Knicks in 2008, he endured a massive rebuild. Keeping an eye on the summer of LeBron James in 2010, Walsh made several trades to clear long-term salary ,including deals to move Jamal Crawford and Zach Randolph in 2008. The final pieces to the free agency puzzle came at the 2010 trade deadline.

First, New York dealt Jared Jeffries' onerous contract, a future first round pick and 2009 lottery pick Jordan Hill to the Houston Rockets in a three-team deal for Tracy McGrady and Sergio Rodriguez. Next, they offloaded Nate Robinson's deal to the Boston Celtics for three expiring contracts.

A former scoring champion and All-Star, McGrady lost most of his luster after microfracture surgery. He averaged 9.4 points in 24 games. The only player acquired at the deadline to play beyond the 2009-10 season for the Knicks was Henry Walker. Walker was with the club until 2012.

The Knicks put themselves in a position to make a run at the famed 2010 free agent class headlined by LeBron James, Dwyane Wade and Chris Bosh. New York struck out on all three players in free agency. After also losing the free agent race for All-Star Joe Johnson, the Knicks settled on Phoenix Suns injury prone All-Star Amar'e Stoudemire with a five-year, $100 million deal. You know how that story goes.

3) 1989: Knicks trade 1989 first round draft pick (Byron Irvin) to the Portland Trail Blazers for Kiki VanDeWeghe

The Knicks were rumored to acquire former All-Star Kiki VanDeWeghe from the Portland Trail Blazers as early as the 1987-88 season. The Blazers had balked at all of New York's offers. The Blazers finally accepted a deal to acquire VanDeWeghe with around four hours left before the deadline.

VanDeWeghe joined a successful Knicks team in the 1988-89 season. Under coach Rick Pitino, the Knicks embraced shooting three-pointers and finished with their best record (52-30) in 17 years. VanDeWeghe had a bench role, averaging 9.2 points in 27 games. The Knicks won their first round series against the Philadelphia 76ers before succumbing to Michael Jordan and the Chicago Bulls in a six-game second round matchup. VanDeWeghe spent three more seasons with the Knicks, averaging double figures in two of those years.

4) 2005: Jamison Brewer and Nazr Mohammed to the San Antonio Spurs for Malik Rose a 2005 first round draft pick (David Lee) and a 2006 first round draft pick (Mardy Collins)

Vin Baker, Moochie Norris and a 2006 second round draft pick (Steve Novak) to the Houston Rockets for Maurice Taylor

Isiah Thomas' run as the president of basketball operations in New York was inventive to say the least. He became the first executive to build his team through trades that followed a consistent pattern. Thomas traded expiring contracts for exorbitant-salaried players for reasons unknown.

Thomas famously spearheaded the Phoenix Suns' rebuild by sending a compilation of expiring deals to the Suns for guards Stephon Marbury and Anfernee "Penny" Hardaway. The move gave the Knicks a minor boost for a first round appearance that saw them get swept by the New Jersey Nets in 2004. Meanwhile, Phoenix used the cap space gained from the trade to sign future MVP Steve Nash and guarantee the Suns 50 wins five of the next six seasons.

During the 2005 trade deadline, the Knicks made two separate deals as they faded out of the playoff race. They traded Vin Baker, Moochie Norris and a second round pick to the Houston Rockets for Maurice Taylor. The other deal saw them acquire Malik Rose and two first round picks for the expiring contracts of Nazr Mohammed and Jamison Brewer.

Explaining the moves, Thomas highlighted New York's acquisition of two first-round picks. When asked about New York's growing payroll, he replied "the dollars are the dollars." Taylor and Rose were owed a combined $45 million in future salaries. Neither player made much of an impact off the bench.

Taylor spent one and a half seasons with the Knicks while Rose lasted four years with the club. One bright spot from the deal was the 2005 draft pick from San Antonio. Originally owned by Phoenix, David Lee was taken 30th overall in the 2005 draft and despite years of losing during his time in New York, he did make the All-Star team in 2010 as a Knick.

5) 2018: In a three-team trade, Doug McDermott to the Dallas Mavericks; the Mavericks traded Devin Harris to the Denver Nuggets; the Nuggets traded a 2018 second round draft pick (Shake Milton) to the Mavericks; the Nuggets traded Emmanuel Mudiay to the Knicks; and the Knicks traded a 2018 second round draft pick (Justin Jackson) to the Nuggets

Looking for a young player to develop at the 2018 trade deadline, the Knicks moved three-point ace Doug McDermott to the Dallas Mavericks in a three-team deal that netted them former lottery pick Emmanuel Mudiay from the Denver Nuggets. In the trade, the Knicks sent a second-round pick to Denver.

A disappointment in Denver, Mudiay went on to share the starting point guard spot over the next year and a half with Trey Burke, Frank Ntilikina, Jarrett Jack and Dennis Smith, Jr. in a crowded Knicks backcourt. He put together the best season of his young career on last year's 17-win Knicks team, averaging 14.8 points, 3.3 rebounds and 3.9 assists in 59 games. Mudiay left in the offseason, signing a free agent deal with the Utah Jazz.

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