The best trade is actually a recent one. On July 24th, 2018 the Yankees traded Josh Rogers, Cody Carroll, and Dillon Tate to the Orioles for Zack Britton. The trade was the most memorable between the two franchises in recent times. Britton had been rumored to be on the market as he was due to hit free agency at seasons end and the Orioles were the perennial cellar-dwellers of the AL East. A complicating factor for Britton was that he began the years on the injured list because he was still recovering from a ruptured Achilles tendon in 2017. After making the move up north to the Bronx, Britton had a decent 25 game showing for the Yankees. In 25 games he pitched to a 2.88 ERA with three saves, a 7.6 K/9 and 4.0 BB/9. Those numbers were fine but also came with a 4.08 FIP so Britton was a bit lucky. After the 2018 season, Britton and the Yankees agreed to a three year, $39 million deal and has since became one of the more reliable arms in the bullpen.
Boston Red Sox – Babe Ruth
Is there really any debate here? Of course the biggest trade between the division rivals would be The Great Bambino. On December 26th, 1920 the Red Sox sold the contract of Babe Ruth to the Yankees for the sum of $125,000. Ruth would go on the cement his legacy of the Mount Rushmore of Baseball by playing in 2084 games for the Bronx Bombers posting a .349/.484/.711 slash line with 659 home runs, 1975 RBIs, and a staggering 149.9 WAR. This will probably remain the biggest, franchise altering trade in the history of sports despite the Red Sox ending the curse in 2004.
Chicago White Sox – Nick Swisher
There was a bit of a back-and-forth when choosing which trade to write about here. There are really two that come to mind. The 2008 offseason trade for Nick Swisher and 2017 mid-season trade of Todd Frazier, David Robertson, and Tommy Kahnle. I decided to go with the Swisher trade because it helped deliver a World Series trophy and main cog in the Yankee Machine from 2009 to 2012. On November 13th, 2008 the Yankees traded Wilson Betemit, Jeffrey Marquez, and Jhonny Nunez for Nick Swisher and Kanekoa Teixeira (no relation to Mark Teixeira). Cashman originally said that the trade was made in order to have Swisher man first base in 2009. That didn’t sit well with fans seeing as Swisher was coming off a season that saw him hit .219 for the White Sox and knowing Mark Teixeira was still available and was seen as the prize offensive free agent in the 2008 offseason. Alas, the Yankees ended up signing Tex and decided to play Swisher in right field for the 2009 season. He more than delivered that year and the following three seasons. Swisher would hit .268/.367/.483 for the Yankees with 105 home runs while helping deliver the franchise’s 27th World Series championship.
Cleveland Indians – David Justice
On June 28th, 2000 Brian Cashman made a move to boost the Yankees mid-season by trading Zach Day, Ricky Ledee, and Jake Westbrook for David Justice. Immediately, Justice went on a hot-streak helping propel the Yankees to another division title. In 78 games with New York, Justice hit .305/.391/.585 with 20 home runs. The Yankees limped to a division title in 2000 and without David Justice it’s pretty clear that they would not have won the AL East. Justice would deliver some big moments in the postseason as well. He won the ALCS MVP that year by doing things this clutch home run in the bottom of the seventh inning in Game 6 against the Seattle Mariners. It’s hard to know for sure what would have happened had Cashman not made the Justice trade however David Justice was a big reason why the Yankees got to the 2000 World Series and won their third World Series in a row and 26th title overall
Detroit Tigers – Curtis Granderson
Coming off a 27th World Series title, the Yankees were looking to make an upgrade in centerfield and try to repeat of champions. What they ended up getting was an MVP candidate and all around good guy named Curtis Granderson. On December 9th, 2009 the Yankees acquired Granderson in a three-team trade with the Arizona Diamondbacks and Detroit Tigers that saw Arizona get pitchers Edwin Jackson and Ian Kennedy and Detroit get Max Scherzer and Daniel Schlereth. Granderson homered in his first at-bat for New York (against the Red Sox) on April 4th, 2010. After that however an injury plagued season lead to Granderson finishing 2010 hitting .247/.324/.468 with 24 home runs and 12 stolen bases. It wasn’t a terrible season by any means but not what the Yankees were hoping for when they made the big trade in the prior offseason.
After 2010, Granderson and hitting coach Kevin Long revamped his approach and swing against left-handed pitchers and the results were stellar. In 2011, Granderson would finish the season hitting .262/.364/.552 with 41 home runs and 25 stolen bases while leading the league in runs scored and RBIs. He finished fourth in MVP voting that year as well. He would follow up his career best season with a decent season in 2012 before having injury problems in 2013 and leaving the Yankees for the crosstown rival New York Mets prior to the 2014 season.
Houston Astros – Lance Berkman
There weren’t a lot of great options to choose from here. We decided to go with the Lance Berkman trade that was made on July 31st, 2010. Prior to 2010, the Yankees had decided to move on from Hideki Matsui as the Designated Hitter and signed former Yankee prospect Nick Johnson as the everyday DH. As was the story for most of Nick Johnson’s career, injuries killed that plan and by mid-season the Yankees were looking for another DH. On the day of the trade deadline, the Yankees sent Mark Melancon and Jimmy Paredes to Houston for Berkman. Berkman would have a disappointing 37 game showing for the Yankees hitting only .255/.358/.349 with just one home run. Berkman did have a minor moment in the ALDS that year so I suppose we will always have this home run.
Kansas City Royals – Lou Piniella
We go back almost fifty years for this retrospective. Prior to the 1974 season, the Yankees traded for leftfielder Lou Piniella who would go on to play 10 years with the Yankees before retiring and entering the world of coaching. All told, Piniella would hit .295/.338/.413 with 57 home runs in route to helping the Yankees win two World Series titles in 1977 and 1978. After retiring, he would join the Yankee’s coaching staff as the hitting coach before going on to manage the team in 1986 and 1987 and even becoming the team’s General Manager in 1988 before departing to manage the Cincinnati Reds in 1990.
Los Angeles Angels of Anaheim — Jim Abbott
Here is a trade that I love only because I’m big a fan of Jim Abbott in retrospect despite never seeing him pitch. I just love the idea of an underdog and with all due respect to Jim Abbott, being born without a right hand making it all the way to highest professional level of baseball is about as underdog as you can get. Prior to the 1993 season, the Yankees took advantage of a situation that saw me the Angels needing to cut payroll, and they swung a trade for Jim Abbott sending three players back to the Angels including the Yankees top minor league hitter, J.T. Snow.
Abbott would pitch two seasons for the Yankees before signing with the Chicago White Sox prior to the 1995 season. His numbers with the Yankees were decent for the era in which he pitched, finishing his Yankee tenure with a 20 and 22 win/lose record and a 4.45 ERA and 3.6 WAR over 56 starts. His crowning achievement in pinstripes will always be this start on September 4th, 1993.
Minnesota Twins – Chuck Knoblauch
Chuck Knoblauch was one my favorite players to watch just as I was discovering baseball and Yankee fandom. On February 6th, 1998 the Minnesota Twins cemented a 4-for-1 trade with the Yankees where they received traded Brian Buchanan, Cristian Guzman, Eric Milton, Danny Mota.
Knoblauch was coming off two straight All-Star seasons and a Gold Glove award in 1997. There was a lot of excitement at the idea of having a double-play tandem of Knoblauch and Derek Jeter. Knoblauch was known for being an on-base machine and brought that skillset to New York. In four seasons with New York from 1998 to 2001, Knoblauch would have a .366 OBP to go along with a sub-10% strikeout rate, 112 stolen bases and 7.0 WAR. He had a couple of rough moments in pinstripes, like this, but also a couple of really big game-tying home runs in the 1998 World Series and 1999 World Series. All in all, Knoblauch’s tenure with the Yankees was very fruitful and that’s all any fan truly remembers.
Oakland Athletics – Scott Brosius
Coming off a disappointing loss in 1997 ALDS, the Yankees traded struggling starting pitcher Kenny Rogers and cash to the Oakland Athletics for a player to be named later. That player turned out to be Scott Brosius and might be the greatest player to be named later in recent Yankee history. Brosius’s first year with the Yankees would turn out to be his best. He finished the 1998 season hitting .300/.371/.472 with 19 home runs and 11 stolen bases in 152 games.
The regular season was good enough but Brosius really made some noise in the 1998 World Series with these plays on both sides of the ball. Brosius wouldn’t produce the same way he did in the following three seasons as he did in his first season with New York, but he did provide one final Yankee Moment in his last season.
Seattle Mariners – Tino Martinez
There is a detailed history of trades between the New York Yankees and the Seattle Mariners. A few years ago, it seemed as though a Yankees/Mariners swap was an annual event. There is one trade that holds a special place in the hearts of Yankees fans however.
After getting knocked out of the playoffs in 1995 by Martinez and the Mariners, the Bronx Bombers decided to bring Martinez for their own championship aspirations by trading Russ Davis and Sterling Hitchcock to Seattle while also acquiring Jeff Nelson as part of the deal.
Martinez signaled a change in the Yankees mindset over the next several seasons. After acquiring Martinez, the Yankees would go on to appear in five of the next six World Series while winning four of them. I’m not saying Martinez was the causation of the Yankees’ winning ways but there is definitely a correlation. For his part, Martinez would hit .279/.348/.488 during his first stint with New York and provided numerous Yankee moments like these. Like many Yankees fans that came of age during the dynasty years, Martinez is one of my favorite players. After leaving the Yankees prior to the 2002 season, he returned to New York for 131 games in 2005 hitting 17 home runs in what would be his final season in the majors.
Tampa Bay Rays – Nick Green
This one was tough and not for a good reason like I mentioned above with the Nick Swisher trade. A combination of the Rays being a relatively new franchise and the fact that they are division rivals with the Yankees means there aren’t a lot of deals that have been made between the two franchises. In fact, there have been three total in the entire history of Rays franchise.
Having said that, I decided to go with the 2006 trade of Nick Green because it had the most relevant (but not major) impact for the Yankees. In May of 2006, the Yankees acquired Green for cash consideration from Tampa Bay before assigning him to one of their minor league teams. Eventually, Green made his debut for the Yankees on July 2nd of that same year and actually had a pretty good game hitting a home run and throwing a runner out at home plate. Green finished his first, and last, season with the Yankees hitting .240/.296/.387 before departing in free agency.
Texas Rangers – Alex Rodriguez
Just like the Babe Ruth trade, there isn’t much speculation as to which trade between these two franchises was the most impactful. After losing to the Marlins in the 2003 World Series and seeing Yankees third basemen Aaron Boone tear his knee up playing pick-up basketball, the Yankees swooped in stealing a deal for MVP third basemen Alex Rodriguez from right under the nose of the Boston Red Sox.
The deal wasn’t all sunshine though as the Yankees were forced to include Alfonso Soriano in the trade, who was coming off a 30/30, All-Star season. Interestingly enough, the Rangers actually had the opportunity to select Robinson Cano as a player to be named later in the deal but ultimately chose Joaquin Arias instead, and we are all glad that happened.
Despite A-Rod’s playoff troubles prior to 2009, the man was everything you could ask for on the field for the Yankees. He won two MVPs, three Silver Slugger Awards, seven All-Star appearances, and of course one World Series. Over his twelve year Yankee career, Rodriguez hit .283 with 351 home runs while producing 51.7 WAR. If it were not for all the trouble he had with PEDs, A-Rod would easily be a first ballot Hall of Famer. A lot of people, both Yankees fans and the rest of baseball, have problems with Alex Rodriguez. He was by no means a perfect player or person. I, however, choose to remember the good things he did on the field like his 2009 postseason run.
Toronto Blue Jays – Roger Clemens
Here we have another controversial player that holds a special place in my heart. Roger Clemens was my favorite pitcher growing up. Everything I did on the mound playing little league baseball was to imitate Roger Clemens.
Just like A-Rod, there was a lot of noise with steroid allegations but we are only going to remember the good and understand that there was also some bad. Coming off a World Series victory and probably the greatest season by a team in baseball history, the Yankees made a move to bring in the reigning AL Cy Young award winner, Roger Clemens. They had to trade fan-favorite David Wells along with Graeme Lloyd and Homer Bush to get the deal done, but on paper the Yankees had just bolstered their pitching rotation for the 1999 season.
Clemens first couple of seasons pinstripes didn’t light the world of fire but he did help the team to two more World Series wins and provided us with this gem in the 2000 ALCS. His best season with the Yankees came in 2001 when he went 20-3 with a 3.51 ERA in route to winning the AL Cy Young award. Clemens would finish his first run with the Yankees in 2003 with a 77-36 win/lose record, a 3.99 ERA and 21.3 WAR. Clemens would depart in free agency prior to 2004 signing with the Houston Astros alongside teammate Andy Pettite. Similar to Pettite, Clemens would return to the Yankees in 2007, but while Pettite would go on to play several more season with New York, Clemens hung up his spikes for good after 2007.