New York Yankees and Their Free Agent Philosophy


Just because they are the New York Yankees, they will always be connected to the big names available in the trade market and in free agency. During Brian Cashman’s tenure with the team, he has been known for being aggressive in the free agent market.

CC Sabathia was one of the bigger free agent acquisitions over the last twenty years for the Yankees. After finally hanging up the cleats following this season, Sabathia recently said enough money will put Gerrit Cole in pinstripes. With the new careful spending from the Yankees front office; the big money, long term contracts given out by the Yankees may have coincidentally come to an end the same year that Sabathia decided to hang them up.

This Year

This past year, we all heard about how the Yankees didn’t have the pitching to make it to the World Series. At the trade deadline, the New York Yankees held off and did not acquire a talented starting pitcher. The asking price was too high for their liking. Yet, when it came down to the ALCS, it was the hitting that failed the Yankees, not the pitching. The Astros batted an abysmal .179 against the Yankees in the ALCS. The Yankees’ bats still couldn’t get the job done.

Examining the Offseason

Two game changing, high profile pitchers are free agents this year. It seems that the Yankees are once again connected the big names of Stephen Strasburg and Gerrit Cole. Will the Yankees go back to their old ways of paying to get the big names in pinstripes or will they be more financially smart this offseason?

The Yankees may shy away from the big deals this offseason. The Yankees have Jacoby Ellsbury on the books through 2020 at $21 million and Giancarlo Stanton earning over $25 million each year for the next eight years. Some would argue that the Yankees spent big by taking on the Stanton contract two offseasons ago. Obviously, hindsight is 20/20, but at the time, inserting the violent bat of Stanton was too good to pass up. Especially for the price the Yankees had to pay Even if the strikeouts combined between he and Aaron Judge are scary, it was a decent move.

New Way of Doing Business

Last offseason the Yankees passed on Bryce Harper and Manny Machado. They both commanded massive money on the free agent market. It already seems as though the Yankees made the right move on them. This past season was not what was expected of the two big money free agents. It’s possible that the Yankees of old went after one of them and landed one of them. This showed restraint when it came to handing out big money contracts.

Both Cole and Strasburg could have big money, long term contracts coming their way and they might just be too rich for the current approach. Still, the Yankees will be in on both and at the very least do their due diligence to see what the price is. If the Yankees want Cole or Strasburg bad enough they may end up being a big spender. If they don’t, they’ll have to think outside the box and sign one to less years for more money annually. Let’s not forget the Yankees will still sooner or later have to pay their big name stars, which include Aaron Judge and Gleyber Torres. Time will tell how the New York Yankees attack this crucial offseason, but Yankee fans may need to prepare for the new age approach to the Yankees.


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