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.