The Yankees and Pirates have aligned for several notable trades (and non-trades) over the last decade. New York memorably balked at Pittsburgh’s asking price for Gerrit Cole, only to sign him to a record free agent contract two years later. The Yankees have also acquired Clay Holmes and Jameson Taillon via the Pittsburgh connection in recent years; however, all these swaps pale in comparison to a 1975 trade that landed one of the most beloved Bombers of all time in the Bronx.
December 11, 1975: The Pirates trade Willie Randolph, Dock Ellis, and Ken Brett to the Yankees for Doc Medich.
Entering the second half of the ‘70s, the Yankees and Pirates were two teams on differing paths. Pittsburgh was in the midst of a decade of dominance but needed starting pitching to extend their window while New York was, emerging from a decade of darkness, under new ownership and with the beginnings of dynastic core. And so, during the Winter Meetings, Gabe Paul sent the up-and-coming starter Doc Medich to the Pirates for a package centered around a young fielding phenom by the name of Willie Randolph.
Randolph burst onto the scene in his first season in the Bronx, leading all rookies with 4.6 fWAR as the Yankees returned to the playoffs for the first time in 12 years. The Bombers may have gotten swept by the Reds in the World Series, but the 1976 campaign proved New York was back and ready to compete on the biggest stage. It would also launch the career of one of the best middle infielders of his generation.
A year later, the Yankees returned to the postseason, where Randolph would play the hero on more than one occasion. Though his overall statline for the playoffs was far from spectacular, key plays by the second baseman scored or drove in the tying or winning run in three separate games, allowing the Yankees to capture their first title in 15 years.
At the time, Medich was a decent price to pay for the trio of player, the righty pitcher finishing third in the 1973 AL Rookie of the Year race and compiling a four year career with the Yankees in which he went 49-40 with a 3.40 ERA in 787 innings, however looking back this swap turned out to be one of the steals of the century. Medich would pitch just one season for the Pirates before getting dealt to the A’s the next winter, while Ellis and Brett would also pitch one unremarkable season apiece in the Bronx before bouncing around an assortment of teams to finish their careers.
Malachi penned a fabulous biography of Randolph in our Top 100 Yankees series, and I strongly recommend giving it a read for the full account of Randolph’s career. Willie finished with five All-Star appearances across his 13-year Yankee career, slashing .275/.374/.357 with a 110 wRC+ while finishing comfortably among the top-ten most valuable players by fWAR over that span. His contributions earned him the co-captaincy in his final years with the club, and his job as coach during the Core Four dynasty years cemented his place in the hearts of multiple generations of Yankees fans.
November 26, 1986: The Yankees trade Doug Drabek, Logan Easley, and Brian Fisher to the Pirates for Pat Clements, Cecilio Guante, and Rick Rhoden.
When the Yankees trade for a young Doug Drabek in 1983, it appeared they were getting an up-and-coming future star, the righty coming off a 12-5 season at Double-A with a 2.24 ERA. He continued to impress in the upper-minors of the Yankees system, eventually earning his MLB debut in relief of Joe Niekro on May 30, 1986. However, after just one partial season in which Drabek finished 7-8 with a 4.10 ERA in 131.2 innings, New York decided to cash in on the graduated prospect, dealing him alongside Logan Easley and Brian Fisher for starter Rick Rhoden and relievers Pat Clements and Cecilio Guante.
The trade made sense at the time — Rhoden was a two-time All-Star coming off a 15-12 season with a 2.84 ERA in 253.2 innings that earned him a fifth-place finish in NL Cy Young voting while Clements and Guante were able relievers, with ERAs in the low-threes during their time in Pittsburgh. Little did the Yankees know what sort of pitcher Drabek would turn into. While Rhoden, Clements, and Guante would all be pitching for different teams by 1989, Drabek immediately became one of the better starters in the NL.
Across his first three seasons in Pittsburgh, Drabek made 94 starts, going 40-31 with a 3.19 ERA in 640 innings. 1990 saw him reach the pinnacle of the pitching world, his 22 wins tops in the NL en route to comfortably capturing the Cy Young as the Pirates won the first of three consecutive NL East crowns. 1992 would see a fifth-place Cy Young finish before signing with the Astros, with whom he would enjoy another four successful seasons including his lone All-Star nod in 1994 — a year that would culminate in a fourth-place Cy Young finish. In the ten years between 1987 and 1996, only Greg Maddux, John Smoltz, José Rijo, and Tom Glavine would produce more fWAR than Drabek among NL pitchers.
Most Overlooked Trade
August 30, 1996. The Pirates trade Charlie Hayes to the Yankees for a player to be named later. The Yankees send Chris Corn on August 31, 1996, to the Pirates to complete the trade.
At the 1996 deadline, the Yankees had some magic cooking with their nascent core of homegrown starts but needed veteran depth to bolster the infield, in particular to give the aging Wade Boggs extra days off at third. So, four years after they lost him to the Rockies in the 1992 MLB Expansion Draft, New York re-acquired Charlie Hayes for a player to be named later. He batted .248 in 20 games during the regular season, but it was in the postseason when he would shine.
Hayes scored the only run in Game 5 on a Cecil Fielder RBI double in the fourth. However, he became immortalized in Yankees history by catching a Mark Lemke foul pop up for the final out to deliver the Bombers’ first title in 18 seasons. Now, his son mans third in Pittsburgh.
December 20, 1984: The Yankees trade Tim Foli, Steve Kemp, and cash to the Pirates for Dale Berra, Jay Buhner, and Alfonso Pulido.
Under the direction of team legend Yogi Berra in his first season at the helm, the Yankees missed the playoffs, finishing 17 games behind the first-place Tigers. Whether to improve the team or in a display of nepotism, the Yankees traded for the manager’s son, sending infielder Tim Foli, left fielder Steve Kemp, and cash to the Pirates for infielder Dale Berra, outfield prospect Jay Buhner, and pitcher Alfonso Pulido.
Berra was forced to witness George Steinbrenner fire his father just 16 games into his debut season in the Bronx. He would play just two years in the Bronx, slashing .230/.285/.336 with a 73 wRC+ in 90 games as a backup before being released in 1986 and picked up by the Astros where the elder Berra was a coach. Buhner meanwhile would infamously be traded to the Mariners in 1988 for Ken Phelps, for whom he would have wonderful career. He finished a 13-year span with 40 home runs in three consecutive seasons and became the 87th player in history to slug 300 home runs, eventually getting elected into the Mariners Hall of Fame.
Other Trades of Note
August 7, 2000: The Yankees trade Chris Spurling to the Pirates for Luis Sojo.
Good thing they brought Sojo back into the fold in 2000, eh?
June 13, 2001: The Pirates trade Enrique Wilson to the Yankees for Damaso Marte.
Wilson wasn’t a very good Yankee, but he somewhat weirdly became a secret weapon against Pedro Martinez, and ...
July 26, 2008: The Pirates trade Damaso Marte and Xavier Nady to the Yankees for Jeff Karstens, Daniel McCutchen, Ross Ohlendorf and Jose Tabata.
... Marte ultimately came back around to the Yankees, helping them win the 2009 World Series with dynamite work in bullpen that postseason, even if he never had much regular-season success.
February 19, 2012: The Yankees trade A.J. Burnett and cash to the Pirates for Exicardo Cayones and Diego Moreno.
November 12, 2014: The Yankees trade Francisco Cervelli to the Pirates for Justin Wilson.
August 1, 2016: The Yankees trade Iván Nova to the Pirates for players to be named later. The Pirates send Tito Polo and Stephen Tarpley on August 30, 2016, to the Yankees to complete the trade.
The Yankees sure did like trading with the mid-2010s Buccos, didn’t they? Burnett, Cervelli, and Nova at least went on to better fates in Pittsburgh than they likely would’ve had in New York. (And Wilson eventually turned into Chad Green.)
January 24, 2021: The Yankees trade Maikol Escotto, Roansy Contreras, Canaan Smith-Njigba, and Miguel Yajure to the Pirates for Jameson Taillon.
Taillon was a serviceable starter for a couple years in New York, though they never got past the ALCS. But while the prospect prize Contreras has flashed promise here and there, he’s still trying to prove himself after a shaky 2023.
July 26, 2021: The Yankees trade Diego Castillo and Hoy Park to the Pirates for Clay Holmes.
It didn’t take long for this trade for a reliever who had a 5.57 career ERA at the time to look brilliant.