10 worst trades in New York Yankees franchise history

The New York Yankees are high rollers in the free agent and trade markets. But not everything works out. Here are 10 trades that fell flat. 

When, or if, the current labor negotiations ever get resolved, the New York Yankees will have a lot of roster moves to make. Holes need to be filled.

The Yankees have had a successful history on the trade market. Over the years, the Yankees have traded for players such as Alex Rodriguez, Giancarlo Stanton and they even bought Babe Ruth.

So, there is reason to believe Yankees general manager Brian Cashman will make the right moves if he’s inspired by his franchise’s past.

Cashman has identified several positions where the Yankees need to improve. In particular, he identified shortstop, first base, center field and catcher. Should the free agent market fail to pan out, there are plenty of prospects ready to break out that could be used as trade bait.

But not every trade works out. Some fall flat, making the organization look silly. The Yankees have a long sordid history of failed trades.

In rare cases, the trade is so bad it becomes a joke on national television shows.

So, as we look to pass the time while billionaires argue about money with millionaires, let’s take a look at some of the worst trades in Yankees history.

But be warned: this is not a trip down depression drive. Instead, it is a self-deprecating cruise down the river of revelry.

10. Roger Maris Traded to St. Louis Cardinals for Charley Smith, 1966

What is the value of a declining star? Most trades are evaluated in terms of the value received versus the value given up. With the advent of advanced metrics, determining that value has become easier, and more controversial, than ever.

In 1966, the Yankees traded Roger Maris to the St. Louis Cardinals. Maris was the American League MVP in 1960 and in 1961 when he broke the single season home run record. Sadly, his record was given an asterisk that marred its accomplishment.

However, from 1965 through 1966, he battled through a wrist injury he claimed was real … but the Yankees claimed it was not. The ongoing dispute with the Yankees over the injury hurt Maris’ standing with the team. Unfortunately, breaking the single home run record did not exactly endear him with the team, either.

The organization was frustrated with Maris. It began to portray him as lazy and malcontented to the press, easing the path toward a trade. In 1966, the Yankees found their deal.

The wrist injury sapped Maris’ power, turning him into an average hitter. When team trust and press mistrust combines with a steep decline in play to the mean, the result is a change of scenery. The Yankees shipped Maris off for Charley Smith. Smith was a journeyman player who had already been traded five times.

But this trade is not about value. It is about how teams treat their stars. Trading Maris for an average Joe speaks more about the team than Maris. The Yankees should have rallied around Maris, treated his injury, upheld his image and let him leave on his own terms. This was a bad trade because the team handled the situation poorly. Thankfully, the Yankees learned their lesson and allowed players in later generations to leave on their own terms.

Maris’ trade was a particularly bad one for the team. But this next trade hurt the team by shipping out a player who became what they wanted the incoming player to be.

9. Jeff Weaver Arrives in Three-Team Trade, 2002

Ever wish for something so bad that you fail to realize you already had something better all along? If so, then you can appreciate just how badly the Yankees messed up the Jeff Weaver situation.

Looking for an effective pitcher in early July 2002, the Yankees shipped out pitcher Ted Lilly and others to the Oakland Athletics as a part of a three-team trade that landed Weaver in New York.

Lilly had been acquired in a previously in a 2000 trade that sent Hideki Irabu to the Montreal Expos, but the lefty will always be remembered for the long home run he gave up to Barry Bonds.

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Lilly was already an effective pitcher with the Yankees in 2002. But standard pitching statistics had him at 3-6 win-loss record and a 3.40 ERA.  The win-loss record was deceiving, as the rest of his metrics were good that season but not great.

The Yankees looked to improve by bringing in Weaver. He ended that season with the Yankees with a 5-3 win-loss record with a 4.04 ERA with significantly worse metrics than Lilly.

Not to be outdone by Lilly, Weaver gave up his own signature home run in the 2003 World Series, getting walked off by Alex Gonzalez.

The Yankees had the player they needed in house, but sent that player out for someone they thought was better. When Weaver didn’t pan out, they made another trade to get an effective starter.

8. Kevin Brown Acquired for Jeff Weaver, Brandon Weeden, Yhency Brazoban and Cash, 2003

Realizing Jeff Weaver was not the consistent starter they longed for, the Yankees traded Weaver and others to the Los Angeles Dodgers for Kevin Brown. This made a bad situation worse.

Brown had pitched the previous five seasons with the Dodgers. ending 2003 with a 2.39 ERA. But the good performances were rumored to have been helped by performance enhancing drugs.

In fact, the famous Mitchell Report named Kevin Brown as a user of PEDs during his time in with the Dodgers.

His performance with the Yankees showed that report to be accurate. In his final year in Los Angeles, hitters had a .236 batting average against Brown. This number rose to .262 in 2004 and .341 in 2005 with the Yankees. Of course, his 2004 season was marred by a shattered hand after Brown punched a dugout phone, which is always what you want to see in a major acquisition, as well as the Game 7 bomb he dropped in a last-ditch attempt to hold off the charging Red Sox.

Another interesting player in this trade was Brandon Weeden. Weeden eventually retired from baseball and became a quarterback for Oklahoma State University. He was then drafted by the Cleveland Browns 22nd overall. He turned 30 before his rookie season in the NFL. Sadly, he lacked the basic fundamentals necessary to compete in the NFL. His signature moment for the Browns was getting caught under the American flag pregame.

Weeden did ultimately escape from under the flag, but his career never recovered. The Yankees did find a redeeming moment in this trade by shipping him out.  But the next trade on our list was so horrific that it should have been a crime.

6. Mike Lowell traded for Todd Noel, Mark Johnson and Ed Yarnall, 1999

Scott Brosius was a free agent signing in 1998. That same year, little-known prospect Mike Lowell appeared in eight games with 15 plate appearances for the Yankees. Lowell’s path to the major leagues was blocked by Brosius, so he was traded to the Florida Marlins.

With the Marlins, Lowell put up solid hitting numbers that were better than Brosius. He even went on to help the Marlins defeat the Yankees in the 2003 World Series.

To make matters worse, he was then traded the Boston Red Sox where he was a staple in their lineup for five seasons.

Fred McGriff being traded due to Don Mattingly is understandable. But the Mike Lowell trade is not. The Yankees signed an aging third baseman, then traded away any insurance against Brosius’ regression.

The Yankees are a win now organization. But sometimes winning now means developing and using the talent when it is ready. Trading Lowell instead of holding him for 2001-02 was shortsighted.

Of the three players acquired in the deal, only Ed Yarnall played for the Yankees. That was only for 20 innings. The next player traded played for 13 seasons.

5. Rich Scheid, Dean Wilkins and Bob Tewksbury for Steve Trout, 1987

Bob “Rat” Tewksbury was yet another example of the Yankees trading a cheaper, younger and better in-house option for a temporary quick fix. It seems the Yankees were once again mastered by the urgency of the moment, making moves designed to win now as opposed to building a sustainable winner.

The 1987 season was a typical season under then-owner George Steinbrenner. The Yankees were a middling team struggling to stay in the pennant race. As middlers, teams must decide to go all in or fold a prepare for next year. I think we all know what Steinbrenner was going to do.

On July 13, 1987, the Yankees traded Tewksbury and others for Steve Trout. In the Yankees’ defense, Trout had a won loss record of 6-3 with three complete games, two of those being shutouts. So, at the time, it looked like the Yankees were getting a stud.

Instead, they got a dud. In New York, Trout had a won-loss record of 0-4 with a 6.60 ERA. Not only did he not help the Yankees win the pennant, but his pitching also actually made their chances worse. At the end of the season, he left for the greener pastures of Seattle and was out of the league in two seasons.

Meanwhile, Tewksbury would go on to pitch for another 12 seasons in the major leagues, amassing 110 wins. He finished his career with 3.92 ERA. He had double-digit wins in six seasons. He was an All-Star for the St. Louis Cardinals in 1992, the same year he placed third in the Cy Young award voting.

The Yankees had given up in the trade exactly what they needed to win. If only they could think long-term. But the Yankees have a long history of giving up young pitching, including the next player we will discuss.

4. Doug Drabek, Logan Easley and Brian Fisher for Pat Clements, Cecilio Guante and Rick Rhoden, 1987

That same 1987 season that saw Tewksbury traded also saw a future Cy Young award-winning pitcher shipped out. At the center of the trade was Rick Rhoden. Rhoden was brought in the help the Yankees to become a contender.

To his credit, Rhoden played the part. Coming off a season with the Pittsburgh Pirates that saw him win 15 games and finish fifth in the Cy Young voting, Rhoden continued his success with the Yankees. The other two players acquired served as solid options in the bullpen. On the surface, this trade looked like a win for the Yankees — at least, it did in 1987.

Little did the Yankees know that pitcher Doug Drabek would embark on a run of six straight seasons of double-digit wins. In fact, he would have double-digit wins in nine of his next 12 seasons. He would win the Cy Young award in 1990, also placing eighth in the MVP voting. He would finish fifth and fourth in the Cy Young voting in 1992 and 1994, respectively.

Drabek made the playoffs three consecutive years with the Pittsburgh Pirates from 1990-1992. He pitched well in the playoffs, posting a 2.05 ERA, but he was the pitcher of record for three losses to the Atlanta Braves in 1992. This speaks more to the pitching staff of the Braves at that time than Drabek.

But Drabek was only traded by the Yankees once. The next player was not lucky enough to have that distinction. In fact, he was traded to the same opposing team twice in the same season.

3. The Many Trades of Ron Hassey

December 4, 1984: Ron Hassey traded from Chicago Cubs to Yankees

December 12, 1985: Ron Hassey traded by Yankees to Chicago White Sox

February 13, 1986: Ron Hassey traded from the Chicago White Sox to the Yankees

July 30, 1986: Ron Hassey traded by the Yankees to the Chicago White Sox

Ron Hassey had to be feeling like weatherman Phil Connors. Connors, portrayed by Bill Murray in the movie Groundhog Day, relives the same day over and over. This hilarious movie finally ends when Connors is able to overcome his narcissistic self and win the love of producer Rita Hanson, played by Andie MacDowell.

Like Phil Conners having Ned Ryerson harass him to buy insurance, Hassey must have gotten sick of seeing then-owner George Steinbrenner approaching with the news that he was traded to the White Sox, again.

Hassey’s Groundhog Day nightmare before and during the 1986 season never seemed to end. Does he play for the Chicago White Sox or the New York Yankees? It seems both sides were tossing him back and forth like a hot potato. The White Sox ended up the winner or loser of that game, depending on how you look at it, as they kept Hassey when it was all said and done.

Hassey witnessed a lot of baseball history during his 14-year career. He is the only player to have caught two perfect games. He was even behind the plate when Los Angeles Dodgers outfielder Kirk Gibson hit is iconic home run in 1988.

The 1986 and 1987 were wild times for the trading Yankees. They shipped out good young pitchers and could not make up their mind about Hassey.

But Hassey was not the only player they made multiple deals to acquire.

2. Javier Vazquez pitches poorly twice for Yankees, 2003/2009

December 16, 2003: Traded by the Montreal Expos to the New York Yankees for Randy Choate, Nick Johnson and Juan Rivera.

December 22, 2009: Traded by the Atlanta Braves with Boone Logan to the New York Yankees for Melky Cabrera, Mike Dunn, Arodys Vizcaino and cash.

The Yankees thought Javier Vazquez was so nice that they traded for him twice. And twice, he let them down. The first time is shame on you. The second time is shame on me.

The Yankees have to own this one.

In 2003, Vazquez was acquired from the then-Montreal Expos. The first half of the 2004 season was gangbusters, with Vazquez going 10-5 before the All-Star break. He made his first and only All-Star game appearance that season.

But it all fell apart after that. The self-destruction of Vazquez saw him go 4-5 in the second half. He started one game in the postseason, in which he surrendered five earned runs in five innings pitched to the Minnesota Twins, a game the Yankees actually won. The second series went about the same; he surrendered seven earned runs in 6.1 innings across two outings in the ALCS against the Red Sox. As you’ll recall, he was on the mound to surrender Kevin Brown’s runs in Game 7, getting rocked for the death-knell grand slam.

Having seen enough, the Yankees cried, “No mas!”. They then traded him and others to the Arizona Diamondbacks for pitcher Randy “The Big Unit” Johnson.

Round two was just as dramatic. In December of 2009, the Yankees acquired Vazquez from the Atlanta Braves in preparation for the 2010 season. At the time, the deal was considered a steal by the Yankees.  After all, Vazquez was very good for Atlanta during the 2009 season. He pitched well enough to place fourth in the Cy Young voting.

But then the meltdown began immediately. Vazquez was unable to regain the form he had in Atlanta. He was 10-10 in 2010 with a 5.32 ERA. When the playoffs rolled around, he was banished to the black hole of the bullpen.

He was never to be seen nor heard from in a Yankee uniform again. Kind of like the last player on our list. Once he was gone, he was gone.

1. Jay Buhner: What Could Have Been?

It was the trade so bad that even fictional television characters got upset. Frank Costanza, the man who brought us Festivus, spoke for all Yankee fans when he berated the fictional George Steinbrenner, played by Larry David, on the television show Seinfeld.

Frank was right to be upset about the Jay Buhner trade. The trade occurred back in the ugly 1980’s when the Yankees seemed to trade away all their prospects in an attempt to win now. It was a strategy that ultimately saw them trade away outfielder Willie McGee to the St. Louis Cardinals as well (another bad one!). So, nobody can blame Frank Costanza for losing it.

It reminds me of some great advice I was once given: Never let the millionaires ruin your day. As fans, we get so excited and involved. Baseball is our religion. But for the players, this is a job. It’s what they do for a living. They have to separate their work life from their home life. So don’t let the millionaires ruin your home life. Enjoy baseball for what it is, the national pastime.

Nonetheless, should you choose to not heed this great advice, no one will blame you for being upset about the Jay Buhner trade. Buhner went on to play 13 seasons with the Seattle Mariners, hitting over 300 home runs in his career.

In return, the Yankees got, well, Ken Phelps. Phelps was in his early thirties at the time. His decline was inevitable. Yankee fans got a front row view of his decline while Mariner fans got to see Buhner’s rise to stardom.

This concludes our list. You may be wondering why I only gave Willie McGee a cursory mention. Trading McGee was terrible. I wanted to include it but couldn’t find a way. As Yankee fans, we know that not everything works out. On this day, I choose not to let the overlooking of a millionaire from yesteryear ruin my article. Will you?