The Yankees are the most successful team in the Big Four North American sports in terms of winning trophies. Over the years, many great players have worn the Yankees’ pinstripes proving their recruitment right. However, the team too had its share of bad business and there are many instances of the Yankees’ biggest trade mistakes.

The Yankees have never been afraid to take a chance because they are usually so brave and willing to do whatever it takes to win. Most of the time, they have done it with starting pitchers. While this had allowed them to have multiple superstars, many of those acquisitions have failed ending in the Yankees’ biggest trade mistakes.

It is hard to imagine a well-oiled team like the Yankees making trade mistakes. But the reality is that they have made some player trades that proved to be disastrous. In their long history, the Yankees have had some great players and made some strange trades. Let’s look at the player acquisitions that led many to name them the Yankees’ biggest trade mistakes.

Esteban Loaiza

Two-time All-Star pitcher Esteban Loaiza played in Major League Baseball for eight different teams. In 2004, he was traded to the Yankees just before the deadline day from the White Sox. Jose Contreras went in the opposite direction to the Southside of Chicago. He was an All-Star twice for Chicago, but he couldn’t keep up his good play in New York City. He left New York with a record of 1–2 and an earned run average of 8.50 ranking his acquisition among the Yankees’ biggest trade mistakes.

Jay Buhner

The Yankees acquired veteran Ken Phelps from Seattle in 1988. Jay Buhner and Rich Balabon went to the Mariners as part of the deal. At that time, no one had ever thought of it going down the history as one of the Yankees’ biggest trade mistakes. 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.

This led Frank Costanza of “Seinfeld” fame to ask on TV, “What the hell did you trade Jay Buhner for?” The comment soon became one of the most famous lines in TV history.

Javier Vazquez

Javier Vazquez was on the New York Yankees team twice and both proved to become the Yankees’ biggest trade mistakes. They first acquired him from the Montreal Expos after the 2003 season. Despite an Aal-Star performance in the first half, he was a pale shadow of himself in the second half. The Yankees traded him to the Diamondbacks.

In 2009, the Yankees had him again from the Atlanta Braves. He was “one of the top starters in all of baseball” then. But he went with a record of 10-10 and an earned run average of 5.32. He was demoted and the Yankees didn’t renew his contract after the season.

Willie McGee

On October 21, 1981, the New York Yankees exchanged outfielder Willie McGee for pitcher Bob Sykes. He would never again play for the Yankees or in the major leagues proving it to be one of the Yankees’ biggest trade mistakes.

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. There has been enough talk about how crazy this trade was. Skyes ended up playing for minor league teams.

Fred McGriff

In 1982, the New York Yankees traded Fred McGriff and two others to acquire Dale Murray and Tom Dodd from the Toronto Blue Jays. For a few years, Murray was a reliever in the bullpen, and Dodd barely played any games in the major leagues. But 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.

Jeff Weaver

In 2002, the Yankees got Jeff Weaver in a three-way deal with the Oakland Athletics and the Detroit Tigers. Ted Lilly moved in the opposite direction to Oakland. But the enthusiasm surrounding the deal proved to be short-lived and it ranks among the Yankees’ biggest trade mistakes.

Weaver pitched for the Yankees for the second half of 2002 and all of 2003 but was often benched following disastrous performances. He played 47 games for the Yankees, 32 of which were starts. He went 12-12 and had a 5.35 earned run average. In the playoffs, he only pitched three and two-thirds innings in relief and allowed three runs. By the time Cashman got rid of Weaver, he could only trade him for Kevin Brown, which was another bad trade.

On the other hand, Ted Lilly had a very good career for the A’s, the Blue Jays, the Cubs, and the Dodgers since he was with the Yankees. He ended his career with a 130-111 record and a 4.13 ERA. The Yankees could have used his arm for the last 10 years.

Mike Lowell

In 1999, the Yankees sent Mike Lowell to the Florida Marlins for Mark Johnson, Ed Yarnell, and Todd Noel. They gave up one promising player for three less important ones and committed one of the Yankees’ biggest trade mistakes. They didn’t know that the prospect they traded away would go on to win Most Valuable Player of the World Series for their biggest rival.

Mike Lowell was a good third-baseman and first-baseman for the Marlins and the Boston Red Sox. In his 13-year career, he hit 223 home runs and had an OPS of .805. When the Red Sox beat the Colorado Rockies in the 2007 World Series, he was named the Most Valuable Player. In the series, he hit .400 and had a home run in four of the games.

Ed Yarnell pitched 20 below-average innings for the Yankees, and neither Mark Johnson nor Todd Noel ever played for them.

Tyler Clippard

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.

Steve Trout

In July 1987, the Yankees got starting pitcher Steve Trout. The deal also involved Bob Tewksbury and two other players going in the opposite direction to the Chicago Cubs. Trout, who was 6-3 with a 3.00 ERA with Chicago at the time. Trout barely survived his first season with the Yankees, going 0-4 with a 6.60 ERA in nine starts and five relief appearances, and becoming part of the Yankees’ biggest trade mistakes.

Tewksbury went on to have a long and successful career, largely with the St. Louis Cardinals. The Yankees would have been much better off retaining him.

Kevin Brown

Throughout the 1990s, starter Kevin Brown was among the player regularly nominated the Cy Young Award and All-Star games. At 38 years old, he was an All-Star with the Los Angeles Dodgers in 2003, when he went 14-9 with a 2.39 ERA. The Yankees wanted the veteran, but they waited too long. In two seasons with the Yankees, Brown went 14-13 with a 4.95 ERA ranking himself among the Yankees’ biggest trade mistakes. In terms of what the Yankees gave up, this transaction wasn’t a complete flop since it helped them get rid of Jeff Weaver.

Larry Gura for Fran Healy

In early 1976, the Yankees and the Kansas City Royals traded these two players. At the time of the trade, Healy was only a part-time player for the Royals who was hitting .125. Over the next three years, he only played 74 games for the Yankees. In his last at-bat, which was in 1978, he struck out. Gura, on the other hand, finished in the top 10 for the Cy Young Award three times in four seasons for the Royals. He had two seasons with 18 wins. This deal ranks among the Yankees’ biggest trade mistakes.

Do you have any other Yankees’ biggest trade mistakes to add to the list? Let’s know in your comment.

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