Best Yankees Trades in Franchise History

BEST YANKEES TRADESEvery single team in the history of Major League Baseball has their hits and their misses. The New York Yankees are no different. There have been some horrible trades in the organizations history but on the flipside, there have been some incredible deals as well. Each and every MLB Hot Stove season or trade deadline move brings with it an inherent risk. Sometimes it is giving up a bunch of prospects for a rental when you believe the time is now, other times it is just when a player sounds a lot better in December at the Winter Meetings and totally different when they arrive in Florida in February. Can you think of the best Yankees trades all-time off the top of your head?

Here at NY Yankees Digest, Adam Solowiei and Rich Stowe, have tried to figure out just which deals should be considered the best Yankees trades of all-time and they settled on determining the Top-5. The countdown will be from the fifth best down to the absolute best Yankees trades.  At the end, you will be able to vote for your choice of the best deal. Grab a seat and some popcorn, because we now begin down the path of best Yankees trade in franchise history.


Adam – Paul O’Neill from Reds for Roberto Kelly and Joe DeBerry

At the time of the trade, it seemed at face value as a good deal for both sides. In his first year, Kelly was an All-Star but then became a traveler for years while asset two never made the majors. Meanwhile, O’Neill went from a .270 hitter to a cornerstone of one of the greatest baseball runs in modern history. He became a lockdown outfielder who perennially hit .300+ and drove in over 100 who had four All-Star appearances and four World Series titles. His veteran presence on a team with a young corner was a key to why the Yankees were able to never let the moment get to big and win ring after ring. His commitment, performance, and weight of the deal bring O’Neill in at number four on the best Yankees trades list.

Rich – Paul O’Neill for Roberto Kelly

This trade worked out in two ways for the Yankees.  In Paul O’Neill, the Yankees got the sparkplug for the dynasty of the late 1990s – he was the fire while Jeter was the heart.  No water coolers or bat racks were safe if he struck out or failed in a key situation.  O’Neill also won a batting title and anchored the middle of the Yankees lineup.  By getting rid of Roberto Kelly, it allowed Bernie Williams to have a shot in center field and we all know how that went.


Rich – David Cone for Nothing (Basically)

David Cone was used to being a player that would get traded to a team in contention – and he reveled in it.  Cone was part of four World Series winners on the Yankees, and he threw a perfect game on July 18, 1999 (which just happens to be my birthday so it means even more to me!).  To get Cone, the Yankees gave up, basically, nothing.  So, for a trade within the division (which does not really happen anymore), the Blue Jays got robbed, and the Yankees came out on top for many years because of Cone.

Adam – David Cone from Blue Jays For Jason Jarvis, Mike Gordon, and Marty Janzen

Much like O’Neill, David Cone was a veteran brought to the Yankees for three players that would never see the highest level of baseball. To make matters worse, this was a trade within the division. Cone had previously been a major part of the Blue Jays 1992 World Series title. During his time in New York, Cone was part of four more World Series titles and even those do not compare to one epic night on July 18, 1999. Against the Expos, Cone threw the third perfect game in Yankees team history. Cone falls in at number four on the list of best Yankees trades in franchise history due to his performance and sheer fact that no other player in the deal even played in a MLB game.



Adam – Red Ruffing From Red Sox for Cedric Durst and $50K

Ruffing was a middling pitcher on a perennial cellar Red Sox team for his first few years in Boston before the deal. After the trade, and one can only assume sense of want and excitement to be on a winner, Ruffing found his potential. He pitched in New York for 15 years while Durst, the player the Red Sox got never saw the majors. Ruffing was a six-time All-Star who pitched in seven World Series for the Yankees. He won 20 games on multiple occasions and racked up seven World Series wins. Not lost in this is that Ruffing could flat hit. As a pitcher, he was a career .269 hitter with multiple .300 seasons. Ruffing is on the short list of greatest Yankees pitchers of all-time. The combination of longevity, dominance, and robbery in this deal puts Ruffing squarely at number three on the list of best Yankees trades in franchise history.

Rich – Rickey Henderson for Stan Javier, Eric Plunk, and Others

The Yankees gave up five players to get the best leadoff hitter in baseball history.  Rickey was only on the Yankees for five seasons (second longest stay on a team in his career) but during that time he finished third in MVP voting in 1985, and led the league several times in stolen bases.  Unfortunately, the Yankees teams of the 1980s (Don Mattingly, Dave Winfield, and Henderson) scored a ton of runs, but due to a lack of pitching, never saw the playoffs.  Rickey ended up being traded back to the Oakland Athletics.


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[…] NY Yankees Digest runs down the best trades in franchise history, while Bronx Bomber Ball ranks the Yanks’ all-time best players at each position. […]


[…] NY Yankees Digest runs down the best trades in franchise history, while Bronx Bomber Ball ranks the Yanks’ all-time best players at each position. […]


[…] NY Yankees Digest runs down the best trades in franchise history, while Bronx Bomber Ball ranks the Yanks’ all-time best players at each position. […]


[…] NY Yankees Digest runs down the best trades in franchise history, while Bronx Bomber Ball ranks the Yanks’ all-time best players at each position. […]

Andrew Farelli

It would be interesting to see what the worst Red Sox deals were (partially so Yankees fans could laugh very hard). I’d have the Arroyo deal to the reds on that list for sure along many made with the Yankees,


Willie Randolph, Doc Ellis and Ken Brett for , Doc Medich. – Mickey Rivers and Ed Figueroa for Barry Bonds, both in the same week. – Chris Chambliss for a lot of usless scraps.


Sorry Yanks lost to Pirates in crazy scoring ’60 Series

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