Things aren't great for the New York Yankees right now. A team that once seemed like it might run away with the AL East division now finds itself in a midsummer tailspin, having dropped the first two games of a crucial series against the Toronto Blue Jays to fall to jsut 6-12 in their last 18 games. Something has to change, and this month's trade deadline is Brian Cashman's last, best chance.
If there's a silver lining here, though, it's that this team has a long and storied history of reshaping its roster via trade. Heck, that history might be longer and more storied than any other franchise in professional baseball, if not American professional sports. But just what are the greatest Yankees trades of all-time? We've ranked out a list of our top 20, in hopes that maybe Cashman can use it for inspiration.
For more news and rumors, check out MLB Insider Robert Murray’s work on The Baseball Insiders podcast, subscribe to The Moonshot, our weekly MLB newsletter, and join the discord to get the inside scoop during the MLB season.
1. Yankees acquire Babe Ruth from the Boston Red Sox (1919)
Date: Dec. 26, 1919
Yankees get: Babe Ruth
Red Sox get: $125,000, plus a $300,000 loan
Yankees stats: .349/.484/.711, 659 HR, 1978 RBI, 1923 AL MVP, seven World Series titles
Next season result: 95-59, third place in the AL
It's arguably the most famous transaction in the history of American sports, and for good reason: At the time, nothing was bigger than baseball, and no player was bigger than Babe Ruth, Boston's two-way star who'd just led the team to a World Series title in 1918.
Ironically enough, Red Sox owner Harry Frazee had developed a reputation for being among MLB's biggest spenders, turning his team into a powerhouse in the 1910s by being willing to throw just about any amount of money at just about anyone. But despite Boston's on-field success, Frazee found himself strapped for cash, at least in part due to his side hustle as a theatrical producer. So when Ruth, keenly aware of his own celebrity, demanded that his salary be doubled, Frazee decided to let him be someone else's problem. You know the rest.
Why the Yankees trade for Babe Ruth is one of their greatest trades
Ruth was already the best hitter in baseball, but he found another gear once he got to New York. He averaged 44 dingers a year in pinstripes, leading MLB in home runs 10 times in a 12-year span, and he rewrote basically every line in baseball's offensive record book. Ruth ended his career with 714 homers. Second on the list at the time of his retirement? Old partner in crime Lou Gehrig ... at 378. His slugging percentage stood at .690, a full50 points ahead of Gehrig and Jimmie Foxx.
He also helped turn the Yankees into the behemoth they are today. New York had never reached the World Series when Ruth arrived; heck, they'd only finished higher than fourth four times in 17 years of existence. But with the Sultan of Swat on board, the Yankees found another gear, winning six AL pennants in an eight-year span and entering the financial stratosphere thanks to Ruth's star power. Both on the field and off, arguably no trade in baseball history has mattered more.
2. Yankees acquire Alex Rodriguez from the Texas Rangers (2004)
Date: Feb. 16, 2004
Yankees get: Alex Rodriguez
Rangers get: Alfonso Soriano, Joaquin Arias
Yankees stats: .283/.378/.523, 351 HR, 1096 RBI, 3x AL MVP, one World Series title
Season result: 101-61, lost to the Red Sox in the ALCS
Rodriguez was a nigh-unprecedented player, a former No. 1 overall pick who reached the Majors at 18 and was a superstar by age 20. So of course he signed an unprecedented contract in free agency, landing with the Texas Rangers for a then-unheard of 10-year, $252 million deal — $63 million beyond the next-richest deal in baseball history at the time.
But while A-Rod didn't miss a beat in Texas, the Rangers struggled to put a functional roster around him. And after three years, they decided they'd be better off freeing all that money up, resolving to trade their star shortstop in the winter of 2003. The team originally struck a deal with the Red Sox for Manny Ramirez and a young prospect named Jon Lester. But the MLBPA nixed it, concerned about Rodriguez volunteering to reduce his salary in order to help Boston build a contender.
Weeks later, a fluke injury to Aaron Boone in a pickup basketball game left the Yankees in need of a third baseman. So George Steinbrenner did what George Steinbrenner always did: He got his man, sending Alfonso Soriano to Texas in exchange for A-Rod and building arguably the most high-wattage left side of the infield in baseball history with Derek Jeter.
Why the Yankees trade for Alex Rodriguez is one of their greatest trades
Yankees fans might quibble a little with A-Rod landing so high on this list. But while his record in the clutch left much to be desired, and his Yankees tenure ended in steroid scandal, the fact remains that Rodriguez was a spectacular player in New York, winning three AL MVPs and seamlessly picking up a new defensive position on the fly. He was far from the biggest thing that ailed the team in the mid-2000s; if anything, an aging and bloated roster should've been even worse if it weren't for him.
And hey, eventually he did finally make good, delivering time and time again while leading the Yankees to their last World Series title in 2009. He might not be the most beloved Yankee ever (or anywhere close), but New York would've been much worse off with Soriano in his place.
3. Yankees acquire Roger Maris from the Kansas City Athletics (1959)
Date: Dec. 11, 1959
Yankees get: Roger Maris, Joe DeMaestri, Kent Hadley
A's get: Hank Bauer, Don Larsen, Norm Siebern, Marv Throneberry
Yankees stats: .265/.356/.515, 203 HR, 547 RBI, 2x AL MVP, three World Series titles
Next season result: 97-57-1, lost to the Pirates in the World Series
Under skinflint owner Arnold Johnson, Kansas City sent so many promising young players to New York that they began to be known as the Yankees' unofficial farm team. But the most criminal of all was Maris, who at the time was just 24 years old and coming off an All-Star season in 1959.
Rather than build around the outfielder, Johnson did what he always did: He flipped Maris to New York, despite the fact that Maris told anyone who would listen that he wanted to remain with the A's.
Why the Yankees trade for Roger Maris is one of their greatest trades
Maris immediately became a star in New Yor, leading the AL in RBI while winning MVP honors in 1960. He one-upped himself in 1961, taking home the MVP again while breaking Babe Ruth's single-season home run record. Injuries cut short his prime, but for a few years, Maris was as feared a hitter as there was in baseball, making the All-Star team in each of his three full campaigns in New York.
It also helps that the Yankees essentially got him for pennies on the dollar. Bauer was well past his prime, and would retire after the 1961 season. Larsen, while a franchise legend for his perfect game in the 1956 World Series, suffered through the worst season of his career in Kansas City, going 1-10 with a 5.38 ERA. Throneberry bounced around the league for a few more years before retiring after hitting .143 with the Mets in 1963.
4. Yankees acquire Graig Nettles from Cleveland (1972)
Date: Nov. 27, 1972
Yankees get: Graig Nettles, Gerry Moses
Cleveland gets: John Ellis, Charlie Spikes, Rusty Torres, Jerry Kenny
Yankees stats: .253/.329/.433, 250 HR, 834 RBI, 2x Gold Glove winner, two World Series titles
Next season result: 80-82, finished fourth in AL East
Nettles had already blossomed into a star in Cleveland, averaging six WAR per year in the three seasons leading up to this trade. So why would a team be looking to move an impact two-way player smack in his prime? Blame manager Ken Aspromonte: Player and coach feuded throughout the 1972 season, over what Nettles claimed were broken promises about his playing time and his spot in the batting order.
By the end of the year, Nettles was determined to get traded, and the Yankees were all too happy to grant his wish.
Why the Yankees trade for Graig Nettles is one of their greatest trades
Kenny and Torres never amounted to much in Cleveland, and while Spikes and Ellis enjoyed some success, neither of them lasted too long. In return, the Yankees got a perennial All-Star: One of the slickest defensive third basemen in the game, Nettles won Gold Gloves while finishing top-six in AL MVP voting in both 1977 and 1978, helping New York capture back-to-back titles.
He was one of the primary catalysts in New York's surge back into relevance toward the end of the decade, and while things eventually devolved toward the end of his time with the team (really, everything devolved for this franchise in the 1980s), his legacy endured. "If he never plays another game for me," Steinbrenner once said, "he has earned more than what I have paid him."
5. Yankees acquire Red Ruffing from the Red Sox (1930)
Date: May 6, 1930
Yankees get: Red Ruffing
Red Sox get: Cedric Durst, $50,000
Yankees stats: 231-134, 3.47 ERA, 1.282 WHIP, 6x All-Star, six World Series titles
Season result: 86-68, finished third in AL
With Ruth long gone, the Red Sox had become a mess by the end of the 1920s. The team hadn't seen a winning season in more than a decade, and owner Bob Quinn was staring down foreclosure thanks to a mountain of debt. So, amid another miserable year in 1930, he shipped Ruffing to the Yankees for reserve outfielder Cedric Durst, $50,000 in cash and another $50,000 loan from New York owner Jacob Ruppert.
At the time, it seemed painless enough. Ruffing had won around a third of his games with a 4.61 ERA over five years in Boston.
Why the Yankees trade for Red Ruffing is one of their greatest trades
Unfortunately for Quinn, Ruffing just needed a change of scenery. New Yankees manager Bob Shawkey, himself a former pitcher, identified a tweak in the righty's delivery that he thought could help unlock Ruffing's game. It worked almost immediately: He went 15-5 down the stretch in 1930, and from there he'd grow into one of the better pitchers in the league, making six All-Star teams in the Bronx.
He was also one heck of a big-game pitcher: He appeared in seven Fall Classics with the Yankees, and New York won six of them, with Ruffing posting a 7-2 record and a 2.63 ERA. Durst, meanwhile, never played in the Majors again after 102 miserable games in Boston in 1930.
6. Yankees acquire Sparky Lyle from the Red Sox (1972)
Date: March 22, 1972
Yankees get: Sparky Lyle
Red Sox get: Danny Cater, Mario Guerrero
Yankees stats: 141 saves, 2.41 ERA, 1.207 WHIP, 1977 AL Cy Young, two World Series titles
Next season result: 80-82, finished fourth in AL East
We promise, Red Sox fans, the misery is (almost) over.
With a slider he learned from Ted Williams, Lyle blossomed into an all-world reliever in Boston, finishing near the top of the AL saves leaderboard in each of his four full seasons with the team. The Red Sox, however, thought they needed a jolt of offense ahead of the 1972 season, and they viewed Lyle as a luxury, flipping him to New York for Cater and a player to be named later.
Why the Yankees trade for Sparky Lyle is one of their greatest trades
Cater was never much more than a league-average bat over his three seasons in Boston. Lyle, meanwhile, took off: Over the next six seasons, he racked up 48 wins and 132 saves, while making three All-Star teams and taking home the 1977 AL Cy Young Award. To twist the knife even more, the Yankees finished just 2.5 games ahead of the Red Sox in the AL East in '77.
Injuries and the arrival of flamethrower Goose Gossage brought Lyle's time in New York to an abrupt end. But he was a game-changing player, on the forefront of innovations in bullpen usage, and he helped carry the Yankees' staff to consecutive titles.
7. Yankees acquire Paul O'Neill from the Cincinnati Reds (1992)
Date: Nov. 3, 1992
Yankees get: Paul O'Neill
Reds get: Roberto Kelly, Joe DeBerry
Yankees stats: .303/.377/.492, 185 HR, 858 RBI, 1994 batting title, four World Series titles
Next season result: 88-74, finished second in AL East
O'Neill was Ohio through and through, a Columbus native who was taken by the Reds in the fourth round of the 1981 draft. He grew into a very good player with Cincinnati, but he had a down season in 1992, and with his free agency looming, then-GM Jim Bowden decided to make a pivot toward the future, flipping him to New York for promising young outfielder Roberto Kelly
Why the Yankees trade for Paul O'Neill is one of their greatest trades
This wasn't exactly a fleecing; Kelly made the All-Star team in 1993 amid a long and successful MLB career. But O'Neill found another level in New York, where his swing and his scrappy (sometimes bordering on ornery) attitude was tailor-made for Yankee Stadium.
O'Neill's .869 OPS with the Yankees was more than 100 points higher than his mark in Cincinnati, and he'd go on to make four All-Star teams. But it was his role in New York's four titles in five years from 1996 to 2000 that made him a true Yankees legend; there was never anyone who cared more about winning a baseball game, even if that passion sometimes boiled over into outburst.
8. Yankees acquire Willie Randolph from the Pittsburgh Pirates (1975)
Date: Dec. 11, 1975
Yankees get: Willie Randolph, Ken Brett, Dock Ellis
Pirates get: Doc Medich
Yankees stats: .275/.374/.357, 251 steals, 6x All-Star, one World Series title
Next season result: 97-62, lost in World Series to Reds
It was a risk at the time. Randolph was just 21 years old, coming off a bumpy 30-game debut with the Pirates in 1975. Medich was by no means an ace, but he was a perfectly acceptable big-league starter, one who could churn out innings and keep his team in the game. But New York wanted to get younger and more athletic after a series of down seasons, so president Gabe Paul took a leap of faith.
Why the Yankees trade for Willie Randolph is one of their greatest trades
Yankees fans everywhere are thrilled he did. Randolph became the Yankees' heartbeat; between 1976 and 1989, they wouldn't have another Opening Day second baseman, and he made five All-Star teams over that span. He was the prototypical leadoff man: He played just about every single day, he got on base at a consistently high clip (he led the league in walks in 1980) and he wreaked havoc once he was out there.
The fact that he went on to spend more than a decade as a key part of Joe Torre's coaching staff before managing the Mets in the 2000s is just the cherry on top.
9. Yankees acquire Tino Martinez from the Seattle Mariners (1995)
Date: Dec. 7, 1995
Yankees get: Tino Martinez, Jeff Nelson, Jim Mecir
Mariners get: Sterling Hitchcock, Russ Davis
Yankees stats: .276/.347/.484, 192 HR, 739 RBI, 2x All-Star, four World Series titles
Next season result: 92-70, won World Series
In 1995, Martinez was a Yankees villain, an All-Star first baseman who'd helped the Mariners knock off New York in a thrilling five-game ALDS. That just happened to be the final season of Don Mattingly's legendary career, opening up a hole at first base that New York needed to fill over the winter. By 1996, Martinez would be on his way to becoming a Yankees legend.
Why the Yankees trade for Tino Martinez is one of their greatest trades
New York paid what at the time seemed like an exorbitant price, giving up two of their top prospects in Hitchcock and Davis. But the former was nothing more than a journeyman, while Davis' bat never materialized at third base like scouts expected. Martinez, on the other hand, just kept on doing what had been doing in Seattle, churning out consistently quality at-bats and raising his game when it mattered most.
Martinez was a crucial part of the Yankees' late-90s dynasty, hitting .292/.376/.429 in the postseason from 1998 to 2000 while authoring several clutch homers. The fact that New York also landed a quality reliever in Jeff Nelson in this trade is just the cherry on top.
10. Yankees acquire Eddie Lopat from the Chicago White Sox (1948)
Date: Feb. 24, 1948
Yankees get: Eddie Lopat
White Sox get: Aaron Robinson, Fred Bradley, Bill Wight
Yankees stats: 166-112, 3.21 ERA, 1.277 WHIP, 1953 ERA title, five World Series titles
Next season result: 94-60, finished third in the AL
The Yankees have made a habit of pouncing on good players mired in bad situations. Lopat established himself as a rock-solid pitcher over his first four years on the South Side, but the White Sox never had a winning season over that span and decided to use the lefty to try and kickstart a rebuild.
Things ... did not work out that way.
Why the Yankees trade for Eddie Lopat is one of their greatest trades
Lopat, as we've seen before on this list, went from good to great the moment he got to the Bronx. It wasn't just his 3.19 ERA over eight seasons; he was an absolute workhorse, firing 91 complete games in 202 starts with New York. The original command and control lefty, he hardly walked anybody, allowing him to keep runners off the bases and work deep into games.
He also saved his best for the biggest moments. The Yankees won five straight World Series between 1949 and 1953, and Lopat was a huge reason why, going 4-1 with a 2.70 ERA in seven starts.
11. Yankees acquire David Cone from the Toronto Blue Jays (1995)
Date: July 28, 1995
Yankees get: David Cone
Blue Jays get: Marty Janzen, Jason Jarvis, Mike Gordon
Yankees stats: 64-40, 3.91 ERA, 1.331 WHIP, 2x All-Star, four World Series titles
Season result: 79-65-1, lost to the Seattle Mariners in the ALDS
The Blue Jays acquired Cone, fresh off winning the AL Cy Young Award in 1994, hoping that he could help the team keep its budding dynasty rolling. But the '95 season didn't go as planned, and so, sitting 12 games below .500 just ahead of the trade deadline, Toronto decided to ship the righty to New York, where the resurgent Yankees had their sights set on their first playoff appearance in more than a decade.
Cone wasn't quite as effective with his new team as he had been with the Jays, and the Yankees would fall to Seattle in an instant-classic ALDS that fall. But as they say, it's not how you start; it's how you finish.
Why the Yankees trade for David Cone is one of their greatest trades
Cone missed most of the 1996 season with an aneurysm in his arm. But when he came back that September, he was dynamite, firing seven no-hit innings against the Athletics in his return to the mound. And he was great in October, too, delivering six innings of one-run ball in a must-win Game 3 of the World Series against the Atlanta Braves.
Cone excelled in each of the next three seasons, notching two All-Star nods, two top-six Cy Young finishes and even a perfect game in 1999. Age and injuries took their toll from there, but with four World Series rings in tow, his Yankees legacy was secure. Plus, the players New York gave up to get him never amounted to much; only Janzen appeared in the Majors, and he only lasted two seasons.
12. Yankees acquire Allie Reynolds from Cleveland (1946)
Date: Oct. 11, 1946
Yankees get: Allie Reynolds
Cleveland gets: Joe Gordon, Eddie Bockman
Yankees stats: 131-60, 3.30 ERA, 1.364 WHIP, 1952 ERA title, five World Series titles
Next season result: 97-57-1, won the World Series
Cleveland had a pitching staff anchored by Bob Feller, but a gaping hole at second base. The Yankees, by contrast, were in desperate need of rotation help. The story goes that Cleveland offered New York any pitcher on its staff not named Feller in exchange for former AL MVP Joe Gordon. Head executive Larry MacPhail initially wanted Red Embree, but Joe DiMaggio begged to differ, pleading with him to ask for Reynolds instead.
As it turns out, listening to Joe DiMaggio is usually a pretty good idea.
Why the Yankees trade for Allie Reynolds is one of their greatest trades
What knocks this trade down the list a little bit is that Gordon remained a very solid player, earning two All-Star nods in Cleveland. But he retired after the 1950 season at the age of 35, just as Reynolds was blossoming into one of the best pitchers in the league.
The man they called Superchief ripped off five All-Star appearances in six seasons, including two top-three finishes in AL MVP voting in 1951-52. In the former he threw not one but two no-hitters, while in the latter he led the league in ERA, all while helping the Yankees to a run of six titles in a seven-year span. Oh, and he went 7-2 for his career in the Fall Classic, too.
13. Yankees acquire Waite Hoyt from the Red Sox (1920)
Date: Dec. 15, 1920
Yankees get: Waite Hoyt, Mike McNally, Wally Schang, Harry Harper
Red Sox get: Del Pratt, Sam Vick, Muddy Ruel, Herb Thormahlen
Yankees stats: 157-98, 3.48 ERA, 1.336 WHIP, three World Series titles
Next season result: 98-55, lost World Series to the New York Giants
OK, we promise this is the last time the Red Sox will show up on this list. Once again, Boston couldn't turn down a payday in return for a promising young player; Hoyt broke through with the Sox in 1919, just as Frazee was taking any cash he could find to keep his theatrical productions afloat. And while his numbers in Boston didn't jump off the page, they were enough to catch the attention of the Yankees, who acquired him in an eight-player deal in the winter of 1920.
Why the Yankees trade for Waite Hoyt is one of their greatest trades
The Murderer's Row Yankees were of course known for their lineup, but Hoyt was the unquestioned ace, leading the AL in wins in 1927 while pitching to a 2.63 ERA over 256.1 innings of work. He posted a 3.38 ERA overall from 1921-28, helping the team capture six AL pennants over that span. He was never a superstar (he never earned a single Cy Young vote, despite eventually being inducted into the Baseball Hall of Fame in 1969), but he was ever-reliable, and none of the players the Yankees gave up to acquire him spent more than two seasons in Boston.
14. Yankees acquire Roger Clemens from the Blue Jays (1999)
Date: Feb. 18, 1999
Yankees get: Roger Clemens
Blue Jays get: Homer Bush, Graeme Lloyd, David Wells
Yankees stats: 83-42, 4.01 ERA, 1.307 WHIP, 2001 AL Cy Young, two World Series titles
Season result: 98-64, won World Series
The Blue Jays pulled an all-time free agency shocker in the winter of 1996, poaching Clemens from the Red Sox on a four-year, $40 million deal. But while the Rocket lived up to his billing in 1997 and 1998, winning consecutive Cy Young Awards and delivering one of the coldest revenge games in baseball history, the team couldn't back him up, leading Clemens to ask for a trade that winter.
Why the Yankees trade for Roger Clemens is one of their greatest trades
Toronto finally obliged in February of 1999, sending Clemens to New York for three players. Clemens wasn't quite the world-beater he had been to that point in his MLB career, pitching to a 4.01 ERA during his time with the Yankees. But he was a huge reason why New York finished off the threepeat in 2000, striking out 15 batters in the ALCS against the Mariners and firing eight scoreless innings in the Subway Series against the Mets. He won his sixth of a whopping seven Cy Young Awards the next season before tailing off a bit in 2002 and 2003.
Overall, it felt like a bit of a let down relative to the hype that followed Clemens to New York. But he was still a very good pitcher for the majority of his time with the team, and the Yankees didn't give up all that much to get him: Lloyd pitched only one season in Toronto, Bush never panned out after a promising rookie season and Wells was back in the Bronx just two years later.
15. Yankees acquire Scott Brosius from the Athletics (1997)
Date: Nov. 18, 1997
Yankees get: Scott Brosius
Athletics get: Kenny Rogers, cash
Yankees stats: .267/.331/.428, 65 HR, 282 RBI, 1x Gold Glove winner, 1998 World Series MVP, one World Series title
Season result: 114-48, won World Series
Talk about a bounce-back. Brosius was quite possibly the worst regular in the league in 1997, posting a .576 OPS for Oakland over 129 games. That dismal season lowered his value enough that the A's were just happy to get anything for him in return, flipping him to New York in exchange for disappointing lefty Kenny Rogers.
Rogers returned to form in 1998, but it's safe to say the Yankees didn't have any regrets.
Why the Yankees trade for Scott Brosius is one of their greatest trades
Brosius embodied so much about what made the 1998 Yankees special, from his ability to grind out at-bats toward the bottom of the order to his sensational defense at third base. He hit .300/.371/.472 during the regular season, making his first and only All-Star appearance, and then he one-upped himself in the playoffs, posting a 1.060 OPS and hitting a dagger of a go-ahead homer off Trevor Hoffman in Game 3 of the World Series.
Brosius never again reached those heights, as his bat regressed over the next few years before he retired following the 2001 campaign. But Yankees fans will always have 1998.
16. Yankees acquire Mickey Rivers and Ed Figueroa from the California Angels (1975)
Date: Dec. 11, 1975
Yankees get: Mickey Rivers, Ed Figueroa
Angels get: Bobby Bonds
Yankees stats: .299/.324/.422, 34 HR, 209 RBI, 93 steals, two World Series titles
Next season result: 97-62, lost the World Series to the Reds
This one certainly didn't land on any greatest trades lists at the time. Bonds was one of the most dynamic hitters in baseball, coming off a 30/30 campaign in his first season in the Bronx in 1975, and the baseball world was shocked when the Yankees decided to ship him to Southern California.
But for as good as Bonds was, New York was stuck in a rut in the mid-70s, and an injury-prone outfielder entering his 30s didn't seem like the best fit for a team looking to get younger. So the Yankees took a gamble, trading Bonds to the Angels for righty Ed Figueroa and a young outfielder by the name of Mickey Rivers.
Why the Yankees trade for Mickey Rivers and Ed Figueroa is one of their greatest trades
It didn't take long for that gamble to pay off. Figueroa kept pitching like he had in California, earning Cy Young votes in 1976 and 1978 and posting a 3.30 ERA over four full seasons in pinstripes. Rivers, meanwhile, emerged as one of the most dynamic outfielders in the sport, a man so fast he became simply known as "Mick the Quick". That speed paid off in center field and on the bases, where he'd swipe an average of 30 bags a season from 1976-78, and he wasn't too shabby at the plate either. He earned MVP votes in all three of his full seasons with the team before being dealt to Texas in the summer of 1979.
As for Bonds? He had a couple more great seasons in him, but eventually age and injury took their toll, and he was done as an impact player by the 1980s.
17. Yankees acquire Chris Chambliss from Cleveland (1974)
Date: April 27, 1974
Yankees get: Chris Chambliss, Dick Tidrow, Cecil Upshaw
Cleveland gets: Fritz Peterson, Steve Kline, Fred Beene, Tom Busky
Yankees stats: .282/.323/.417, 79 HR, 454 RBI, 1978 Gold Glove, two World Series titles
Season result: 89-73, second in AL East
“I can't believe this trade," center fielder Bobby Murcer complained to the New York Times at the time. “It just means they don't think we have a winning ball club.”
It's not hard to understand where Murcer was coming from. Chambliss was a fine player, a former No. 1 overall pick and AL Rookie of the Year who brought a steady bat to first base. But New York didn't need a first baseman; it needed a second baseman, and many were left wondering why they gave up four pitchers to bring Chambliss to the Bronx. They'd get their answer soon enough.
Why the Yankees trade for Chris Chambliss is one of their greatest trades
Chambliss continued to provide reliably above-average offense at the cold corner, with a 108 OPS+ over seven seasons with the team. But it was in October that he etched his name into Yankees history. Chambliss was downright unconscious in the 1976 ALCS, hitting a then-record .524 for the series and capping it off with a walk-off homer in the do-or-die Game 5 to send New York to its first World Series in over a decade.
He helped the team win it all in 1977, and again in 1978. And those four pitchers New York gave up to get him? Only one of them, reliever Tom Buskey, was worth positive bWAR after the trade.
18. Yankees acquire Lou Piniella from the Kansas City Royals (1973)
Date: Dec. 7, 1973
Yankees get: Lou Piniella, Ken Wright
Royals get: Lindy McDaniel
Yankees stats: .295/.338/.413, 57 HR, 417 RBI, two World Series titles
Next season result: 89-73, second in AL East
In the early 70s, McDaniel had established himself as a rock in the Yankees' bullpen. But after six years in New York, the Oklahoma native began to get a bit restless about pitching so far away from home. So, at the 1973 Winter Meetings, the Yankees obliged him by sending him to the Royals — and were rewarded with an all-time figure in baseball history for their troubles.
Why the Yankees trade for Lou Piniella is one of their greatest trades
A former AL Rookie of the Year, Piniella had established himself as a dangerous big-league bat. And with the DH coming just in time for the 1974 season, New York now had just the place to put him in its lineup. Piniella thrived with the Yankees, hitting .296 over his first five seasons with the team while serving as a key part of the back-to-back titles in 1977-78. Injuries took their toll as he entered his late-30s, but he seamlessly pivoted into a coaching role, first as hitting coach and then as New York's manager in the 1980s. McDaniel, meanwhile, retired from baseball after the 1975 season.
19. Yankees acquire Nick Swisher from the White Sox (1973)
Date: Nov. 13, 2008
Yankees get: Nick Swisher, Kanekoa Texeira
White Sox get: Wilson Betemit, Jeff Marquez, Jhonny Nunez
Yankees stats: .268/.367/.483, 105 HR, 349 RBI, 2010 All-Star, one World Series title
Next season result: 89-73, second in AL East
Of all the moves Brian Cashman made in the winter of 2008 — CC Sabathia, Mark Teixeira, AJ Burnett — hardly any attention was paid to Nick Swisher, whom the team acquired in a deal with the White Sox just after the season ended in November. You can understand why: Swisher was coming off an awful year at the plate in which he'd hit just .219 and earned the ire of the entire South Side of Chicago.
The White Sox figured they were wiping their hands of a first-round bust. The Yankees, meanwhile, were about to find a diamond in the rough.
Why the Yankees trade for Nick Swisher is one of their greatest trades
Swisher became a quiet rock in the Yankees' lineup, good for 25 homers a year to go with an excellent on-base percentage. He put up an .869 OPS to go with 29 dingers while helping New York win the World Series in 2009, then earned his first All-Star appearance in 2010. He wasn't anywhere near the most important part of that '09 title, but he was a fan favorite nonetheless, bringing some much-needed wackiness and levity to what had become an all-too-stuffy Yankees clubhouse toward the end of the 2000s. Of course, it helps that Betemit was awful in Chicago in 2009, and that neither Marquez nor Nunez made much of an impact in the Majors.
20. Yankees acquire Rickey Henderson from the Athletics
Date: Dec. 5, 1984
Yankees get: Rickey Henderson, Bert Bradley
Athletics get: Tim Birtsas, Jay Howell, Stan Javier, Eric Plunk, José Rijo
Yankees stats: .288/.395/.455, 78 HR, 255 RBI, 326 steals, 3x All-Star
Next season result: 97-64, finished second in AL East
What George Steinbrenner wanted, George Steinbrenner usually got. And what George Steinbrenner wanted to get his team back to the top of the mountain was Rickey Henderson, who'd emerged like a supernova in Oakland in the early 1980s. Despite the fact that he was a hometown hero, New York made the A's an offer they couldn't refuse, especially as they struggled to put a winning team around Rickey.
Why the Yankees trade for Rickey Henderson is one of their greatest trades
Objectively speaking, this trade didn't work out too well for the Yankees. Not that it's Henderson's fault: Rickey was his typical Hall of Fame self, posting an .863 OPS and averaging 20 homers and 75 steals a season over his four-plus years in New York. But Henderson never even played in a single playoff game, as the team around him slowly devolved into chaos by the late 1980s. Plus, the players New York gave up, especially future Reds ace Jose Rijo, turned out to be pretty good.
Still, come on: It's Rickey freaking Henderson. Any time you have a chance to say that one of the greatest players in baseball history suited up for your team, smack in his prime, that's pretty cool. It may not have worked out exactly how the Yankees hoped, but hey: That's baseball, Suzyn.