7 Yankees trade deals that came to bite them back

Yankees Gleyber Torres, who is rumored to be traded, and Yankees fan Jon is holding a "Fire Cashman" poster outside Yankee Stadium on August 1, 2023.
Sara Molnick
Tuesday August 1, 2023

Table of Contents

Historically, the New York Yankees are buyers not sellers at the trade deadline. However, in 2023, the team is in a precarious position and expected to be different from most of the past Bronx Bombers. They are currently in last place with a record of 55-50 and struggling to stay afloat in tough AL East competition. With the present lineup slumping, the Yankees look to trade to recast their fortune this season.

During the last season, the Yankees made several trades at the deadline. They brought in Harrison Bader, who has an outstanding performance in the postseason. However, the deals for Frankie Montas and Scott Effross ended in disaster.

As the Yankees approach the uncertain trade deadline, it’s a great opportunity for them to think about all the things they should avoid doing. Let’s take a look at some of the trades that only returned to haunt the Yankees.

#1. Yankees sent OF Willie McGee to Cardinals for pitcher Bob Sykes

Back in 1981, during Game 2 of the World Series against the Dodgers, the Yankees made a trade that appeared quite unimportant at the moment. The Yankees traded minor-league outfielder Willie McGee to the Cardinals in exchange for pitcher Bob Sykes, who had already shifted to a reliever role in his career at that time, on October 2.

The trade turned out to be a total disaster. Following the Yankees’ loss in the 1981 Fall Classic, Willie McGee played a key role in leading the Cardinals to the World Series the following season as a rookie. In his first year in the major leagues, he achieved an impressive batting average of.296 and stole 24 bases.

After that, in Game 3 of the 1982 World Series, McGee made a significant impact with two home runs and a crucial catch that saved the game. Thanks to his contributions, the Cardinals won the championship in a thrilling seven-game series.

The right-handed outfielder went on to have an amazing career. He earned the opportunity to play in four All-Star games and achieved a remarkable feat in 1985 when he won the MVP award. In that year, he also won the batting title with an impressive.353 average and stole an incredible 56 bases.

McGee became a four-time All-Star, two-time National League batting champion, three-time Gold Glove winner, National League Most Valuable Player, and World Series champion.

On the other hand, Bob Sykes encountered shoulder problems and was sent to the minor leagues. Unfortunately, he never had the chance to play for the Yankees again.

#2. Yankees traded Fred McGriff to Toronto for Dale Murray, Tom Dodd


Predicting whether young prospects will succeed, especially when they are only 18 years old, is always challenging. The Yankees made a mistake on December 9, 1982, when they made a trade involving a rookie named Fred McGriff, who had finished his second season in rookie ball. In exchange, they acquired reliever Dale Murray and designated hitter Tom Dodd.

At that time, the Yankees couldn’t foresee what Fred McGriff would become, even though he had an amazing .870 OPS in rookie ball. The left-handed first baseman had an incredible career and is now a legend in the Hall of Fame. He played for 19 years and had his most outstanding performances while with the Padres and Braves, hitting 30 home runs in 10 different seasons.

In total, he achieved an impressive 493 home runs and a remarkable 56.3 WAR, according to FanGraphs. His achievements were recognized, and he was honored with induction into the prestigious Cooperstown in 2023.

McGriff went on to become a top MLB player and was an important part of two teams that made it to the World Series. He helped the Braves win the World Series in 1995, and he also helped them get back to the Fall Classic in 1996. At the end of his career, he was chosen for five All-Star teams, won three Silver Slugger Awards, and twice led the league in home runs.

On the other hand, Murray turned out to be an average reliever for the Yankees, and Dodd didn’t even get a chance to bat for the team. He only played one season in the major leagues.

#3. Yankees gave up Doug Drabek to acquire three players from Pirates

Just when it seemed like the trades couldn’t be any more disappointing for the 1980s Yankees, they made another regrettable move. In 1986, they traded 23-year-old Doug Drabek, along with Logan Easley and Brian Fisher, to the Pittsburgh Pirates. In return, the Yankees got Pat Clements, Cecilio Guante, and Rick Rhoden. Unfortunately, this trade turned out to be another mistake that hindered their performance during the 1980s.

After a decent rookie season with the Yankees, where he achieved a league-average 4.10 ERA in 131.2 innings, Drabek’s career took off when he joined the Pittsburgh Pirates. There, he became one of their top pitchers and even won a prestigious Cy Young Award during his six-year tenure with the team.

Drabek continued his successful career, playing for a total of 13 seasons with additional stints in Houston, Chicago, and Baltimore. He accumulated an impressive 29.2 WAR, according to Baseball Reference. Both Easley and Fisher joined the Pirates’ pitching staff after the trade. Easley became a reliever, and Fisher became a starter, playing for a few seasons with the team.

On the other hand, the players the Yankees received in the trade, except for Rhoden, didn’t perform very well for the team. Neither Clements nor Guante found success in the Yankees’ rotation, while Rhoden had two decent years at the end of his career.

#4. Yankees allowed Jay Buhner to leave for Mariners

Back on July 21, 1988, the Yankees made a trade that had a significant impact. They traded 23-year-old outfielder Jay Buhner to another team in exchange for 33-year-old first baseman/designated hitter Ken Phelps.

After the trade, things seemed to improve for both players throughout the rest of the season. Buhner, now with the Mariners, had a solid .778 OPS, and Phelps, playing for the Yankees, compiled an even better .890 OPS. The trade didn’t look as bad as it did initially.

Unfortunately, the situation took a turn for the worse after that. Buhner had an incredible career with the Mariners, playing for 14 years. During this time, he became a star player, hitting an impressive 307 home runs with a.857 OPS. He received multiple All-Star nods and was even considered for the MVP award.

The trade led to a famous scene in the TV show “Seinfeld,” where Frank Costanza questions George Steinbrenner about why they traded Buhner. It became a very popular and memorable moment in the show.

An agitated Costanza asked the Yankee owner why they had traded Jay Buhner. He pointed out that Buhner had 30 home runs and over 100 RBIs last year and had a strong throwing arm. Costanza further expressed his frustration, saying that the owner didn’t seem to know what he was doing.

In the TV show, the fictional Steinbrenner responds that his baseball team has a high opinion of Phelps. However, despite that, Phelps didn’t have a long-lasting career with the Yankees. He only played for a short time after 1988 and left the league in 1991.

While Phelps failed miserably to last just less than a year, the 23-year-old Buhner played for the Seattle Mariners for 13 seasons, during which he hit 310 home runs, won a Gold Glove, made an All-Star team, and was inducted into the Seattle Mariners Hall of Fame.

#5. Yankees made an error by trading Mike Lowell to Marlins


The Yankees of 1998 are commonly regarded as the greatest team in baseball history. However, they did make one serious error: trading Mike Lowell to the Marlins after the season had finished.

The Yankees in February 1999, made a trade involving Lowell, a promising third base prospect. They traded him for pitchers Ed Yarnall, Todd Noel, and Mark Johnson. The Yankees felt confident about the position’s future due to Scott Brosius’ strong performance during the 1998 season.

However, Brosius was not able to replicate his outstanding performance from 1998, while Lowell turned into a star. Lowell enjoyed a remarkable 13-year career in the major leagues, hitting 223 home runs with an amazing .805 OPS and he was selected for four All-Star teams.

What hurt the Yankees the most was Lowell’s exceptional performance in the postseason. He played a crucial role in the Marlins’ victory over the Yankees in the 2003 World Series. Later, he joined the Red Sox and contributed to their 2007 championship, making it even more painful for the Yankees as their bitter rival benefited from his talent.

Yarnall, Noel, and Johnson didn’t live up to expectations at all. Among them, only Yarnall got a chance to play in the big leagues for the Yankees, but his performance was disappointing, with a high 5.40 ERA in just 20 innings.

Looking back, Brian Cashman, the Yankees’ general manager, admitted that this trade was the one deal he would love to have a second chance at during his 25-year tenure.

#6. Yankees’ mistake over Joey Gallo

Imagine the Yankees getting an outfielder with a powerful left-handed swing, a strong throwing arm, and it seems like a perfect match for the team in the 2020s.

But, when they traded for Joey Gallo in 2021, hoping to boost their offense with another good hitter, it didn’t turn out as they had hoped.

Gallo, who had been a two-time All-Star and Gold Glove winner with the Rangers known for hitting massive home runs, but also striking out and walking a lot (which they call the three true outcomes), didn’t perform well at all with the Yankees. He had a really tough time, and his performance dropped to an all-time low.

The left-handed outfielder didn’t do well with the Yankees. He had a batting average of.159, an on-base percentage of.291, and a slugging percentage of.368 over two years. He hit 23 home runs but also struck out 38% of the time. The fans in the Bronx were not happy with his poor performance and constantly booed him.

On the other hand, the players that the Rangers got in return for the trade have been a big help in improving their team. They acquired Ezequiel Duran, Josh Smith, Glenn Otto, and Trevor Hauver, and these players have played a significant role in the Rangers becoming a strong team competing for success.

Joey Gallo in the Yankees pinstripes and Twins' uniform.

Duran seems to be the shining star of the trade, as the 24-year-old infielder has been outstanding for the Rangers this year. He has an.820 OPS and has hit 13 home runs, while also playing excellent defense all around the infield.

The Yankees were able to get something back for Gallo when they traded him to the Dodgers in 2022. In return, they received minor-league starting pitcher Clayton Beeter, who had an impressive 2.08 ERA in 60 innings of Double-A games this year.

#7. Yankees traded Tyler Clippard to Nationals

Before he was traded to the Washington Nationals in 2007, Tyler Clippard only started six games for the Yankees. In 2008, the Nationals let him start two games. In 2009, they moved him to the bullpen. Clippard did well right away as a relief pitcher. Since then, he has worked as a closer and set-up man. He has also been to the All-Star Game twice and has found a place for himself as a reliever in the late innings.

Pitcher Jonathan Albaladejo was the person the Yankees got in exchange for Clippard. He was a relief pitcher for the Yankees for parts of four seasons. He went 5-2 and had an ERA of 4.70, but he never made a big difference. In 2012, Albaladejo did not pitch in a major league game, while Clippard kept doing well in the MLB and the deal ranked among the Yankees’ biggest trade mistakes.

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