Brian Cashman’s career with the New York Yankees has been highlighted by numerous successful deals which have greatly improved the state of the organization. 

Since taking over as the Senior Vice President and General Manager of the New York Yankees in 1998, Brian Cashman has had his fair share of success. As a result of countless strategic moves, he has brought six pennants and four world championships to the Bronx over his 18-year tenure.

Many of his best tactical approaches have been taken place in the offseason, immediately bettering the team’s chances for the following season when fans expect it the least.

Whether it is a few days after the World Series concludes, the winter meetings, or even after pitchers and catchers have reported, Cashman knows how to swing a deal — usually benefitting his side in the long run.

Negotiating while putting all cards on the table is an area in which he truly thrives.

With that said, some of his offseason swaps have impacted the club far more than others. Elite Sports NY took the time to sort out the abundance of transactions.

Here are Brian Cashman’s top winter moves since taking the executive reigns of the most successful franchise in sports.


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