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Biggest trades in New York Yankees history

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The trade deadline for the 2021 Major League Baseball season will officially arrive on Friday, July 30, as rumors across the league continue to circulate about potential game-changing moves.

Over the years, the New York Yankees have been active participants in the trade marketplace, benefitting from a number of moves that helped boost the roster down the stretch.

Following the Yankees’ recent acquisition of hard-throwing righty reliever Clay Holmes from the Pirates and the departure of relievers Luis Cessa and Justin Wilson, there’s no telling what other deals might be in the works as the Bombers gear up for a tightly contested finish in 2021.

Here now, in chronological order, let’s take a look at some of the most notable trades that played a role in shaping Yankees history through the decades.

January 3, 1920: Yankees acquire Babe Ruth from Boston in exchange for $125,000 and a $300,000 loan

The “Curse of the Bambino” was born when these two rival clubs came together to orchestrate the most fateful trade in all of baseball history. Ruth was both a stellar pitcher and hitter in his first six MLB seasons with Boston, but thanks in part to Red Sox owner Harry Frazee’s off-the-field pursuits and financial foibles, Ruth was ultimately shipped off to New York where he soon became an American cultural icon while establishing the Yankees as the most beloved team in all of baseball.

May 6, 1930: Yankees acquire Red Ruffing from Boston in exchange for Cedric Durst and $50,000

While Ruth’s landscape-shifting move from the Red Sox to the Yankees will never be forgotten, another pivotal trade between the two clubs took place just over a decade later as Red Ruffing, a future Hall of Famer and six-time World Series champion, was dealt to the Yankees for outfielder Cedric Durst and $50,000 back on May 6, 1930. Ruffing remains the Yankees’ all-time leader in complete games with 261 and ranks top-five in franchise history in wins (231 – 2nd), strikeouts (1,529 – 5th), starts (391 – 3rd), innings pitched (3,168 – 2nd) and shutouts (40 – T/2nd).

December 11, 1959: Yankees acquire Roger Maris, Joe DeMaestri and Kent Hadley from Kansas City in exchange for Hank Bauer, Don Larsen, Norm Siebern and Marv Throneberry

You’d be hard-pressed to find another player that provided the kind of instant impact Roger Maris gave the Yankees after being traded from the Kansas City Athletics. In his first season in the Bronx, Maris earned a Gold Glove and an MVP Award and made a trip to the World Series. His second season ended with a second straight MVP Award, a new MLB single-season home run record and a World Series title. His third season ended with yet another World Series title and a third straight year playing in both All-Star Games (more on that here). Playing alongside fellow “M&M Boy” Mickey Mantle, Maris was a bona fide Yankees superstar in the 1960s.

March 22, 1972: Yankees acquire Sparky Lyle from Boston in exchange for Danny Carter and Mario Guerrero

Surprising as it may seem to find yet another Red Sox-Yankees trade on this list, it was Boston that gave Sparky Lyle his start in the Majors before he went on to become a key member of the Yankees bullpen for seven seasons from 1972-1978. Lyle earned three All-Star nods over that span as well as the Cy Young Award in 1977 – the same year the Bombers captured their 21st championship. Lyle ranks eighth all-time in Yankees history with 420 career games pitched, and fourth all-time with 141 saves in pinstripes.

December 11, 1975: Yankees acquire Willie Randolph, Ken Brett and Dock Ellis from Pittsburgh in exchange for Doc Medich

Willie Randolph, one of the greatest Yankees infielders of all time, was originally a seventh-round selection by the Pirates out of Brooklyn’s Tilden High School in 1972 before establishing himself as a perennial All-Star with the Bombers. Over 13 seasons in the Bronx, Randolph was a prolific hitter, run scorer and base stealer for the Yankees, ranking 13th all-time in franchise history with 1,731 hits, ninth all-time with 1,027 career runs and fourth all-time with 251 stolen bases. Later in his Yankees career, Randolph was named a captain of the team in 1986, a role he served until the end of the 1988 season.

December 5, 1984: Yankees acquire Rickey Henderson and Bert Bradley from Oakland in exchange for Tim Birtsas, Jay Howell, Stan Javier, Eric Plunk and Jose Rijo

Though Rickey Henderson – the “Man of Steal” – is largely remembered for his time in Oakland, he was a four-time All-Star during his five-year stint in the Bronx from 1985 to 1989. Over that span Henderson led the American League in steals four times and led the Majors in runs three times, all while earning four All-Star nods and a Silver Slugger in 1985.

November 3, 1992: Yankees acquire Paul O'Neill and Joe De Berry from Cincinnati in exchange for Roberto Kelly

Chances are if the Reds could turn back time and never make this move, they would do just that. Paul O’Neill brought a fiery brand of leadership and intensity to the Bronx, where he would stay for nine sensational years. “The Warrior” earned four All-Star selections as a Yankee and batted .303 over 1,254 career games in pinstripes and was an integral part of the unforgettable Yankees teams that captured four championships during their remarkable late-90s dynasty years.

July 28, 1995: Yankees acquire David Cone from Toronto in exchange for Mike Gordon, Jason Jarvis and Marty Janzen

Another key member of the Yankees’ five-year, four-championship run from 1996-2000, David Cone brought a wealth of savvy and experience to the rotation after landing in the Bronx from Toronto before the 1995 deadline. Cone was an All-Star in 1997 and 1999, and a 20-game winner the year in between, but more importantly, he went 6-1 with a 3.86 ERA while holding opponents to a .220 batting average over 14 career postseason appearances in pinstripes. Plus, he gave Yankees fans a perfect memory to hold onto forever.

December 7, 1995: Yankees acquire Tino Martinez, Jim Mecir and Jeff Nelson from Seattle in exchange for Russ Davis and Sterling Hitchcock

Shortly after Don Mattingly’s retirement following the 1995 season, Tino Martinez was tasked with filling the shoes of a franchise legend in his Yankees debut season in 1996. What followed was one of the most successful dynasties in sports history, with Martinez playing a central role in the lineup from 1996-2001. During that six-year span, Martinez slashed .279/.348/.488 while averaging 29 homers and 115 RBI per year. He finished his MLB career in 2005 with the Yankees following brief stints with the Cardinals and Rays, but Tino’s outstanding resume and four World Series rings have cemented him in Yankees franchise lore forever.

November 18, 1997: Yankees acquire Scott Brosius from Oakland in exchange for Kenny Rogers

Though he spent just four years with the Yankees before calling it a career, Scott Brosius was a highly dependable and consistent third baseman anchoring the infield from 1998-2001. Brosius delivered some of his finest moments when the pressure was at its highest, earning 1998 World Series MVP honors and authoring one of the most thrilling playoff moments ever when he took Byung-Hyun Kim deep with two outs in the bottom of the ninth in Game 5 of the 2001 World Series to keep hope alive against the Diamondbacks.

February 18, 1999: Yankees acquire Roger Clemens from Toronto in exchange for Homer Bush, Graeme Lloyd and David Wells

How does a team that won 114 games find a way to get even better the next season? They add Roger Clemens. The ’98 Yankees – widely considered the greatest team ever assembled – acquired a five-time Cy Young winner in Clemens for the 1999 campaign, and before his time in pinstripes were through “The Rocket” would add one more Cy Young in 2001. In the Yankees postseason record books, Clemens ranks tied for third with 18 starts, fifth in innings pitched with 102 1/3 and fourth in strikeouts with 99.

June 29, 2000: Yankees acquire David Justice from Cleveland in exchange for Zach Day, Ricky Ledee and Jake Westbrook

Another midseason move that paid huge dividends for the Yankees was the acquisition of veteran outfielder David Justice in 2000. From June 30 to the end of the regular season, Justice hit .305/.391/.585 with 20 home runs and 60 RBI in just 78 games, serving as a huge producer in the deep Yankees lineup. He would go on to be named MVP of the 2000 ALCS against Seattle en route to a Yankees World Series victory over the Mets.

February 16, 2004: Yankees acquire Alex Rodriguez from Texas in exchange for Alfonso Soriano and Joaquin Arias

One of the most eye-popping trades of the 21st century saw Alex Rodriguez, arguably the biggest superstar in the game, swap a Rangers uniform for Yankees pinstripes prior to the 2004 season. Coming off an MVP season in 2003, Rodriguez had already collected a gaudy number of awards and accolades before joining the Bombers, but he marked his early years in the Bronx with two more MVP Awards in 2005 and 2007. In the 2009 playoffs, Rodriguez was a major force in the Yankees lineup as they went on to defeat the Phillies for their 27th World Series title, slashing .365/.500/.808 with five doubles, six homers and 18 RBI.

July 25, 2016: Yankees acquire Gleyber Torres, Adam Warren, Billy McKinney and Rashad Crawford from Chicago in exchange for Aroldis Chapman

The Yankees’ 2016 season helped usher in a new era and a new talent core thanks in part to the trade of Aroldis Chapman to the Cubs. In return, Chicago sent future All-Star infielder Gleyber Torres to the Bronx while relying heavily on Chapman’s flame-throwing arm on their way to a historic drought-ending World Series title. Chapman returned to the Yankees that following offseason as a free agent, but his brief foray on the North Side paved the way for one of Brian Cashman’s finest trade maneuvers in his outstanding career as Yankees general manager.

December 11, 2017: Yankees acquire Giancarlo Stanton from Miami in exchange for Starlin Castro, Jose Devers and Jorge Guzman

Thousands of trades have taken place over the years, but only a select few carry enough significance to be considered "blockbusters." This one certainly qualifies. The reigning National League MVP Giancarlo Stanton was dealt to the Yankees in an eye-opening move in December 2017, providing 38 home runs and 100 RBI in his Yankees debut season in 2018. Despite injury setbacks in 2019 and 2020, Stanton provided unparalleled power for the Yankees throughout the 2020 postseason and a 129 OPS+ through his first 278 games with the club.