Top 15 Worst Trades in New York Yankees History

Whatever the New York Yankees want the New York Yankees usually get. As rich of a history and bank account as any sports franchise on the planet, the Yankees haven’t always made the best decisions. De

Whatever the New York Yankees want the New York Yankees usually get. As rich of a history and bank account as any sports franchise on the planet, the Yankees haven’t always made the best decisions. Deep pockets have allowed them to make their share of bad free agent signings and poor scouting has led them to making bad trades.

In spite of winning enough championships to wear a ring on every finger and toe, the Yankees have had failed transactions. Whether it was sending minor leaguer away who turned into an All-Star or acquiring a star pitcher that went bust once he put on a Yankees’ uniform, this successful franchise has erred.

Qualifying a trade as one of the worst in a team’s history takes some time. We need to know how the players turn out and weigh everyone involved as well as the money the team, the Yankees in this instance, took on. Because they are typically so daring and willing to pay whatever it takes to win, the Yankees have historically not been shy about taking a chance. Usually they have done it with starting pitchers with many of them failing.

Whether these players who came to New York failed because of the pressures of the New York spotlight or for another reason cannot quite be determined. Whatever the case was, there are plenty of other players who the Yankees traded that played well in other cities, sometimes wearing a major rival’s uniform. It’s hard to imagine a team like the Yankees could ever make a mistake, however they have made these 15 terrible trades they probably wish they could take back.

15 Trading Tyler Clippard for Jonathan Albaladejo 

Jerry Lai-USA TODAY Sports

Who remembers Tyler Clippard as a member of the Yankees? Few probably do as he only started six games for them in 2007 before he was traded to the Washington Nationals. The Nationals allowed him to start a pair of games in 2008 before moving him to the bullpen in 2009. Clippard immediately excelled as a relief pitcher and has worked as a closer and setup man ever since. He has also been to the All-Star Game twice and has found a niche as a late inning reliever. The guy the Yankees traded Clippard for was pitcher Jonathan Albaladejo. He spent parts of four seasons with the Yankees as a relief pitcher going 5-2 with a 4.70 ERA without ever making a significant impact. Currently, Albaladejo has not pitched a big league game since 2012 while Clippard continues to succeed in the MLB.

14 Trading Bob Tewksbury for Steve Trout


The Yankees acquired starting pitcher Steve Trout in July of 1987 from the Chicago Cubs for a package of players. Rich Scheid, Bob Tewksbury, and Dean Wilkins were all sent to the Yankees for Trout who at the time was 6-3 with a 3.00 ERA with Chicago. Trout barely made it through the season with the Yankees as he went 0-4 with a 6.60 ERA in nine starts and five relief appearances. It was the clear end of his career as he suffered through two more poor seasons in 1988 and 1989 with the Seattle Mariners thereafter. Tewksbury was the most notable player traded as he went on to have a long and very successful career, primarily with the St. Louis Cardinals. The Yankees would have been much better keeping him.

13 Acquiring Kevin Brown 


Starting pitcher Kevin Brown was regularly a Cy Young Award candidate and All-Star throughout the 1990s. In 2003, he was an All-Star at 38-years-old with the Los Angeles Dodgers in a really good year that saw him go 14-9 with a 2.39 ERA. The Yankees wanted the veteran, but struck too late in his career. Brown was only 14-13 with a 4.95 ERA in two seasons with the Yankees. He retired after the 2005 campaign on a down note from an otherwise successful career. This trade wasn’t an absolute failure in regards to what the Yankees gave up, as it did help them get rid of Jeff Weaver.

12 Trading Mark Melancon and Jimmy Paredes for Lance Berkman 

Ron Chenoy-USA TODAY Sports

At the time of this trade, nobody saw it landing on a list of the worst trades made by the Yankees. Now, with Mark Melancon as one of baseball’s top closers, it looks a little worse. At the trade deadline in 2010, the Yankees sent Melancon and Jimmy Paredes, who is currently with the Baltimore Orioles, to the Houston Astros for Lance Berkman. Berkman only ended up spending the remainder of the season with the Yankees in 2010, contributing 1 home run in 123 plate appearances. Along with the lack of power, Berkman hit only .255.

11 Acquiring Jeff Weaver 


Yet another pitcher the Yankees acquired that turned into a bust, Jeff Weaver came to the Bronx in early July of 2002 in a three-team deal with the Detroit Tigers and Oakland Athletics. Most notably, the Yankees sent a very serviceable pitcher in Ted Lilly to the Athletics. In return, the big haul was Weaver, who at the time was 6-8 with a 3.18 ERA along with 3 shutouts for the Tigers. Weaver ended up going 5-3 with a 4.04 ERA for the Yankees and landed in the bullpen by the season’s end. The following year he was 7-9 with a 5.99 ERA leading to his departure to the Los Angeles Dodgers in the Kevin Brown trade.

10 Trading Armando Benitez for Jeff Nelson 


One of the more interesting trades the Yankees made on this list was the one involving Armando Benitez in 2003. They acquired him midseason from the New York Mets for a couple of guys who never did much. After only nine games with a 1.93 ERA to boast about, the Yankees traded him to the Seattle Mariners for Jeff Nelson. Nelson struggled with the Yankees, leaving many fans wondering why they moved on from Benitez when he was pitching so well. The insult was added in 2004 when he saved a league leading 47 games with the Florida Marlins while posting a 1.29 ERA. He would have been a great option as a setup man to Mariano Rivera had he stayed in New York.

9 Trading Larry Gura for Fran Healy 


Two of the less familiar names you will see on this list are Larry Gura and Fran Healy. These two were involved in a trade between the Yankees and Kansas City Royals back in early 1976. It was a strange trade as Healy was just a part-time player, one hitting .125 for the Royals at the time of the trade. He only ever played 74 games for the Yankees over the next three seasons, finishing his career with 1 at-bat in 1978 where he struck out. Meanwhile, Gura was a top 10 Cy Young Award finisher three times in four seasons for the Royals, including two seasons of 18 wins.

8 Trading Jose Contreras for Esteban Loaiza


Esteban Loaiza was never a very good starting pitcher, but coming off of a 2003 season where he won 21 games for the Chicago White Sox, the Yankees had some faith he could turn into a great trade deadline pickup in 2004. Loaiza began the year with the White Sox going 9-5 with a 4.86 ERA. Not very good numbers, but he was much worse with the Yankees. Loaiza was dealt to New York on July 31st straight-up for Jose Contreras. He went on to pitch very poorly, going 1-2 with an 8.50 ERA in six starts and four relief appearances before becoming a free agent at the end of the year. As for Contreras, he won 15 games for the 2005 White Sox who also ended up winning the World Series.

7 Trading Tommy Holmes 


Outfielder Tommy Holmes was an amateur free agent signed by the Yankees in the 1930s. He never ended up playing a game for them as he was traded before making his MLB debut. Holmes spent almost his entire big league career with his new team, the Boston Braves, where he played very well. After an impressive rookie season in 1942, Holmes really began to become a star. He led the league in hits with 224 in 1945 and again in 1947 with 191. From 1943-1946 he received MVP consideration including a second place finish in 1945. Had the Yankees kept Holmes they could have had a few more championships in the 1940s; as if they needed any more.

6 Trading for Javier Vazquez Twice 


‘The Who’ might not get fooled again, but the Yankees were when it came to pitcher Javier Vazquez. Twice they traded for him and neither time were they really able to get much out of the starting pitcher. The first trade was with the Montreal Expos, which cost the Yankees Randy Choate, Nick Johnson, and Juan Rivera. He lasted just one year and was actually an All-Star, but was only 14-10 with a 4.91 ERA. The Yankees were able to use him to acquire Randy Johnson from the Arizona Diamondbacks the following year to at least turn him into something, although Johnson wasn’t particularly phenomenal with the Yankees. Half a decade later, the Yankees traded for Vazquez again, this time from the Atlanta Braves. The most notable player they surrendered this time was outfielder Melky Cabrera. In his second trip through the Yankees Vazquez was 10-10 with a 5.32 ERA. If they could do it again, another starting pitcher would have been the way to go.

5 Trading for Vernon Wells and His Big Salary 


Vernon Wells was a superstar with the Toronto Blue Jays in the early part of his career and was able to load up on a giant contract that eventually ended up getting paid out by the Yankees. After two bad years with the Los Angeles Angels of Anaheim making big bucks, the Yankees acquired the falling star, even though he had $42 million left on his contract over the next two seasons. Wells spend only one year with the Yankees, slashing .233/.282/.349 with 11 home runs. They released him with a year left on his contract, putting him out of his misery and ending a partnership nobody really understands why the Yankees were willing to take on.

4 Trading Mike Lowell Away 


Third baseman Mike Lowell only had 15 at-bats with the Yankees in 1998 before he was traded to the Florida Marlins. The Yankees didn’t get anything good in return and Lowell embarked on a very successful career. He hit over 200 home runs with a career .279/.342/.464 slash line. Perhaps the worst part for the Yankees is Lowell was a big part of the 2003 Marlins that defeated the Yankees in the World Series. He was later a member of the 2007 Boston Red Sox Championship team as well, while also facing the Yankees plenty during the five seasons he spent there. Lowell was a major part of the Red Sox glory days as the Yankees consistently were eliminated early in the postseason.

3 Trading Willie McGee for Bob Sykes 


One of the best leadoff hitters in the 1980s was Willie McGee. The 1985 National League MVP was actually traded by the Yankees for Bob Sykes, a pitcher who never played a game for New York. Few would have guessed McGee would have been a St. Louis Cardinals’ legend, but he was and the Yankees surely regret this trade as they got nothing in return. McGee had an 18-year career which included 2,254 hits, 352 stolen bases, and a .295 batting average. The 1980s and early 1990s were bleak for the Yankees and bad trades like this were a big reason.

2 Trading Jay Buhner for Ken Phelps 


With over 300 career home runs, including three straight seasons of over 40, Jay Buhner was another guy the Yankees traded way too early in his career. Dealt in mid-1988 to the Seattle Mariners with a few players for Ken Phelps, the Yankees made a huge blunder with this transaction. Phelps only hit .240 with the Yankees in parts of two seasons and was traded a year later for a minor leaguer. Meanwhile, Buhner thrived with the Mariners for the remainder of his career as a top power hitter in the league.

1 Trading Fred McGriff 


First baseman Fred McGriff hit 493 career home runs. Even though he was originally drafted by the Yankees, none came while wearing their uniform. New York traded McGriff along with a few other players to the Toronto Blue Jays in December of 1982 for Tom Dodd and Dale Murray. McGriff would become a power hitting first baseman, twice leading the league in this category. From 1988-1993 he received MVP consideration as a member of the Blue Jays and San Diego Padres. Ultimately, McGriff may not have had a role with the Yankees because they went on to employ Don Mattingly at first base. Considering they never won a World Series with Mattingly, we can still question their decision to go with him over McGriff.

Give TheSportster a Thumbs up!

Looking for an AD FREE EXPERIENCE on TheSportster?

Get Your Free Access Now!

More in MLB

Top 15 Worst Trades in New York Yankees History